Information on EC 1.13.11.34 - arachidonate 5-lipoxygenase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY
1.13.11.34
-
RECOMMENDED NAME
GeneOntology No.
arachidonate 5-lipoxygenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate = leukotriene A4 + H2O
show the reaction diagram
(1b)
-
-
-
arachidonate + O2 = (6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
(1a)
-
-
-
arachidonate + O2 = leukotriene A4 + H2O
show the reaction diagram
overall reaction
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dioxygenation
-
-
-
-
oxidation
-
-
-
-
oxidation
-
the enzyme catalyzes the formation of 5(S)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid, 5(S)-hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid, and 5(S)-trans-5,6-oxido-7,9-trans-11,14-cis eicosatetraenoic acid
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
-
-
arachidonic acid metabolism
-
-
lipoxin biosynthesis
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 5-oxidoreductase
-
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5-lipoxygenase
P09917
-
5-lipoxygenase
-
-
5-lipoxygenase
P48999
-
5-lipoxygenase
Mus musculus C57BL/6
P48999
-
-
5-lipoxygenase
P12527
-
5-lipoxygenase
-
-
5-LO
-
-
-
-
5-LO
P09917
-
5-LO
P48999
-
5-LO
Mus musculus C57BL/6, Mus musculus C57BL/6J
P48999
-
-
5-LOX
-
-
5-LOX
P12527
-
5-LOX
-
-
5DELTA-lipoxygenase
-
-
-
-
5LOX-1
-
-
ALOX5
-
-
arachidonate 5-LO
-
-
arachidonate:oxygen oxidoreductase
-
-
arachidonic 5-lipoxygenase
-
-
-
-
arachidonic acid 5-lipoxygenase
-
-
-
-
C-5-lipoxygenase
-
-
-
-
DELTA5-lipoxygenase
-
-
-
-
H5-LO
-
-
leukotriene A4 synthase
-
-
-
-
leukotriene-A4 synthase
-
-
-
-
lipoxygenase 15
-
-
lipoxygenase 5
-
-
lipoxygenase-1
-
-
LO-1
-
-
LOX-5
-
-
LTA synthase
-
-
-
-
LTA4 synthase
-
-
LTA4 synthase
P09917
-
oxygenase, arachidonate, 5-lip-
-
-
-
-
PMNL 5-lipoxygenase
-
-
CAS REGISTRY NUMBER
COMMENTARY
80619-02-9
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
C57BL/6 mice
-
-
Manually annotated by BRENDA team
C57BL/6 mice
UniProt
Manually annotated by BRENDA team
C57BL/6, 129Sv mice
-
-
Manually annotated by BRENDA team
C57BL/6J mice
UniProt
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
UniProt
Manually annotated by BRENDA team
Mus musculus C57BL/6J
C57BL/6J mice
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
5-LO-/- infected with Trypanosoma cruzi, are more susceptible than C57BL/6 and wild-type 129Sv, showing higher parasitemia and mortality
malfunction
-
blockade of 5-LOX signaling results in downregulation of cyclin D1, matrix metalloproteinase (MMP-7, -9), urokinase plasminogen activator and its receptor, and pro-apoptotic proteins
malfunction
-
Trypanosoma cruzi infection in mice deficient in 5-lipoxygenase (5-LO) results in transiently increased parasitemia, and improved survival rate compared with wild type mice. Myocardia from 5-LO-deficient mice exhibit reduced inflammation, collagen deposition, and migration of CD4+, CD8+, and interferon-gamma-producer cells compared with wild type littermates. Moreover, decreased amounts of tumor necrosis factor-alpha, interferon-gamma, and nitric oxide synthase are found in the hearts of 5-LO-deficient mice
metabolism
-
5-lipoxygenase is a key enzyme in leukotriene biosynthesis
metabolism
-
5-lipoxygenase is involved in the production of matrix metalloproteinase-9
metabolism
-
5-LO has a central role in leukotriene biosynthesis
physiological function
-
5-lipoxygenase products may not only play a major role in controlling heart tissue parasitism, i.e., host resistance to acute infection with Trypanosoma cruzi in vivo, but in the event of an infection also play an important part in erythrocyte oxidative stress, an NO-dependent effect. 5-lipoxygenase metabolites increase lipid peroxidation levels in erythrocytes during the early phase of murine Trypanosoma cruzi infection, but do not participate in the development of anemia, thrombocytopenia or leukopenia in Trypanosoma cruzi-infected mice
physiological function
-
5-lipoxygenase-derived lipid hydroperoxide is responsible for endogenous DNA-adduct formation. 5-lipoxygenase is responsible for the generation of the heptanone-etheno-2'-deoxyguanosine DNA-adduct in CESS cells
physiological function
-
5-lipoxygenase/5-lipoxygenase activating protein interaction, which may serve as a feed-back control point for leukotriene C4 biosynthesis
physiological function
-
catalyzes two steps in biosynthesis of leukotrienes, a group of lipid mediators of inflammation derived from arachidonic acid, which are used as antagonists in treatment of asthma. A potential role also in atherosclerosis
physiological function
-
role of the 5-lipoxygenase pathway in B cells before the cells finally differentiate to plasma cells
physiological function
-
5-lipoxygenase is a key determinant of acute myocardial inflammation and mortality during Trypanosoma cruzi infection
physiological function
-
5-lipoxygenase plays a pivotal role in atherogenesis and is involved in plaque stability
physiological function
-
5-LO products significantly contribute to tumour cell proliferation
physiological function
-
activation of 5-LOX modulates the G1/S phase transition regulatory proteins and causes cell proliferation
physiological function
-
several arachidonic acid metabolites formed via the 5-LO pathway (5-HETE, 5-oxo-ETE, leukotriene B4, leukotriene D4) can promote proliferationof cancer cells
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(12S)hydroperoxy-5,8-cis-10-trans-13-cis-eicosatetraenoic acid + O2
(5S,12S)-dihydroperoxy-5,8-cis-10-trans-13-cis-eicosatetraenoic acid
show the reaction diagram
-
22% of the activity with arachidonic acid
-
?
(15S)-hydroperoxy-5,8,11-cis-13-trans-eicosatetraenoic acid + O2
(5S,15S)-dihydroperoxy-5,8,11-cis-13-trans-eicosatetraenoic acid
show the reaction diagram
-
30% of the activity with arachidonic acid
-
?
(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P12527
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P48999
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P09917
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P09917
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P12527
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P48999
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4 via stereospecific hydration by LTA4 hydrolase, LTA4 induces VEGF transcription in malignant mesothelial cells, the enzyme is upregulated in cancer cells and is pro-angiogenic
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4, has no effect on on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
stereospecific removal of the pro-R hydrogen at C10 resulting in epoxide formation
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
efficient LTA4 formation of 5LO requires both phosphatidyl choline and coactosin-like protein
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
Mus musculus C57BL/6
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
Mus musculus C57BL/6
P48999
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
Mus musculus C57BL/6J
P48999
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate + O2
leukotriene A4
show the reaction diagram
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate + O2
leukotriene A4
show the reaction diagram
-
-
-
?
1-linoleoyl lysophosphatidic acid + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidic acid
show the reaction diagram
-
i.e. linoleoyl-lysoPA
major product
-
?
1-linoleoyl lysophosphatidylcholine + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidylcholine
show the reaction diagram
-
i.e. linoleoyl-lysoPC
major product
-
?
11,14,17-eicosatrienoic acid + O2
?
show the reaction diagram
-
-
-
-
?
2',7'-dichlorodihydrofluorescein diacetate + O2
?
show the reaction diagram
-
development of a fluorescence assay for 5-LOX, overview
-
-
?
2',7'-dichlorodihydrofluorescein diacetate + O2
2',7'-dichlorofluorescein
show the reaction diagram
-
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
5,8,11-eicosatrienoic acid + O2
?
show the reaction diagram
-
almost as active as arachidonic acid
-
-
?
5-hydroperoxyeicosatetraenoic acid
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
8,11,14-eicosatrienoic acid + O2
?
show the reaction diagram
-
-
-
-
?
8,11,14-eicosatrienoic acid + O2
?
show the reaction diagram
-
-
-
-
?
8,11,14-eicosatrienoic acid + O2
?
show the reaction diagram
-
4% of the activity with 5,8,11,14,17-eicosapentaenoic acid
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
72% of the activity with 5,8,11,14,17-eicosapentaenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
(5S,6R)-dihydroperoxy-7,9,11,14-eicosatetraenoic acid is produced as major product especially when the incubation is performed on ice rather than at room temperature, 6R-oxygenase activity
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ minor products: 5-hydroxy-6,8,11,14-eicosatetraenoic acid, 6-trans-leukotriene B4 and 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
5-hydroperoxyeicosatetraenoic acid + 11(S)-hydroperoxyeicosatetraenoic acid + 15-hydroperoxyeicosatetraenoic acid + 5(S),12(S)-dihydroperoxy-6,8,10,14-eicosatetraenoic acid + 6-trans-leukotriene B4 + 12-epi-6-trans-leukotiene B4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ leukotriene A4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
5(S)-hydroperoxyeicosatetraenoic acid is the most abundant primary oxygenation product, representing 60% of the total hydroperoxyeicosatetraenoic acids, followed by 8(S)-hydroperoxyeicosatetraenoic acid, 9-hydroperoxyeicosatetraenoic acid, 11(S)-hydroperoxyeicosatetraenoic acid, 12-hydroperoxyeicosatetraenoic acid, and 15-hydroperoxyeicosatetraenoic acid in decreasing order of abundance, all possible diH(P)ETEs are detected
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
the enzyme is rather specific for the insertion of O2 at the fifth carbon on arachidonic acid
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
+ minor amounts of the double oxygenation products
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
formation of leukotriene A4 without release of the intermediate (6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
i.e. 5,8,11,14-eicosatetraenoic acid
5(S)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid + 6-trans-leukotriene B4 + 12-epi-6-trans-leukotriene B4
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
higher affinity of arachidonate than linoleic acid for the ferrous form of lipoxygenase-1. Hydrogen abstraction step displays high kinetic isotope effects on kcat due to tunneling contributions. Lack of solvent-dependent rate-limiting steps at lower temperatures with arachidonate as substrate
-
-
?
arachidonate + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
P12527
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
P48999
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
P09917
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
first committed step in the synthesis of leukotrienes
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
stereospecific abstraction of the pro-S hydrogen at C7, followed by insertion of molecular O2 at C5
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
Mus musculus C57BL/6
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
Mus musculus C57BL/6
P48999
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
Mus musculus C57BL/6J
P48999
-
-
-
?
arachidonic acid + O2
5-hydroperoxyeicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(5S,6E,8Z,11Z,14Z)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
bishomo-gamma-linolenic acid + O2
?
show the reaction diagram
-
-
-
-
?
docosahexaenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
homo-gamma-linolenic acid + O2
8-L-hydroxy-9,11,14-eicosatrienoic acid
show the reaction diagram
-
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
lower affinity of linoleic acid than arachidonic acid for the ferrous form of lipoxygenase-1. Hydrogen abstraction step displays high kinetic isotope effects on kcat due to tunneling contributions
-
-
?
linoleic acid + O2
9-hydroperoxyoctadecadienoic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
9-hydroperoxyoctadecadienoic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
9-hydroperoxyoctadecadienoic acid
show the reaction diagram
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
the purified protein expresses both 5-oxygenase and leukotriene A4 synthase activities in the ratio of 6:1
-
-
-
additional information
?
-
-
the enzyme exhibits 6R-oxygenase activity with (5S)-hydroxy and (5S)-hydroperoxy acids as substrates
-
-
-
additional information
?
-
-
arachidonate 5-lipoxygenase and leukotriene A5 synthase are identical
-
-
-
additional information
?
-
-
the enzyme is involved in lipoxin synthesis from 5,15-dihydroxyperoxyeicosatetraenoic acid via 5,6-epoxide
-
-
-
additional information
?
-
-
enzyme of leukotriene biosynthetic pathway
-
-
-
additional information
?
-
-
key enzyme in leukotriene metabolism, in human mast cells glucocorticoids effectively and selectively upregulate the expression
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in the biosynthesis of proinflammatory leukotrienes
-
-
-
additional information
?
-
-
5-lipoxygenase/cyclooxygenase-2 cross-talk through cysteinyl leukotriene receptor 2 in endothelial cells, overview
-
-
-
additional information
?
-
P48999
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
-
additional information
?
-
P12527
5-LOX is the key enzyme in the biosynthesis of leukotrienes through catalyzing the initial two steps in conversion of arachidonic acid to leukotrienes
-
-
-
additional information
?
-
-
ALOX5-derived lipid mediators leukotrienes and lipoxins have regulatory functions in inflammation by modulating activities of immune cells and cytokine production, host control of Mycobacterium tuberculosis is regulated by 5-lipoxygenase
-
-
-
additional information
?
-
P48999
inhibition of 5-lipoxygenase does not affect cardiac ischemia-reperfusion injury but the post-ischemic inflammatory response, overview
-
-
-
additional information
?
-
-
inhibition of COX pathways does not increase the transformation of arachidonic acid by the 5-LOX pathway
-
-
-
additional information
?
-
-
key enzyme in biosynthesis of leukotrienes, overview. Upon cell activation, cytosolic and nuclear enzyme translocates the nuclear envelope, where it interacts with phospholipase A2, making free arachidonate available for 5-LO, and with 5-LO activating protein, i.e. FLAP. 5-LO regulates cancer cell survival and interferes with the mechanismtumor suppression, and increases cancer cell chemoresistance, overview
-
-
-
additional information
?
-
-
key enzyme in the leukotriene biosynthesis, pathway overview, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
P09917
key enzyme in the leukotriene biosynthesis, pathway overview, the 5-LO pathway is linked to the development of cardiovascular disease and other diseases, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
-
no significant effect of LTB4, 12-hydroperoxyeicosatetraenoic acid or 15-hydroperoxyeicosatetraenoic acid on leukemic blast growth and on their apoptose rate, overview
-
-
-
additional information
?
-
-
the enzyme is involved in survival of Epstein-Barr virus-converted B lymphoma cells via function of 5-hydroperoxyeicosatetraenoic acid, overview
-
-
-
additional information
?
-
-
the enzyme is the key enzyme in biosynthesis of biologically active leukotrienes
-
-
-
additional information
?
-
-
the enzyme, catalyzing the key step in leukotriene biosynthesis, interacts with methyl jasmonate, which is probably involved in the anticarcinogenic activity of methyl jasmonate inducing apoptosis, overview
-
-
-
additional information
?
-
-
stereo-selectivity in LOX-catalyzed oxygenation of lysophospholipids, overview
-
-
-
additional information
?
-
-
5-lipoxygenase has a two-domain structure, the small N-terminal beta-barrel domain and a larger catalytic domain containing a single atom of non-heme iron coordinating with His525, His530, His716 and Ile864
-
-
-
additional information
?
-
Mus musculus C57BL/6J
P48999
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid + O2
?
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P09917
-
a conjugated epoxide intermediate in leukotriene biosynthesis, is unstable and enzymatically metabolized to leukotriene B4 or by spontaneous hydrolysis
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P12527
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
P48999
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4 via stereospecific hydration by LTA4 hydrolase, LTA4 induces VEGF transcription in malignant mesothelial cells, the enzyme is upregulated in cancer cells and is pro-angiogenic
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4, has no effect on on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
-
efficient LTA4 formation of 5LO requires both phosphatidyl choline and coactosin-like protein
-
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
Mus musculus C57BL/6
-
-
is unstable and metabolized to leukotriene B4 by leukotriene A4 hydrolase, which binds to its specific receptor
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
Mus musculus C57BL/6
P48999
-
is unstable and metabolized to leukotriene B4
-
?
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
leukotriene A4 + H2O
show the reaction diagram
Mus musculus C57BL/6J
P48999
-
is unstable and metabolized to leukotriene B4
-
?
5-hydroperoxyeicosatetraenoic acid
leukotriene A4 + H2O
show the reaction diagram
-
-
is unstable and metabolized to leukotriene B4
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
P12527
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
P48999
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
P09917
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
first committed step in the synthesis of leukotrienes
-
-
?
arachidonic acid + O2
5-hydroperoxyeicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
Mus musculus C57BL/6
-
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
Mus musculus C57BL/6
P48999
-
-
-
?
arachidonic acid + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyeicosa-6,8,11,14-tetraenoate
show the reaction diagram
Mus musculus C57BL/6J
P48999
-
-
-
?
additional information
?
-
-
the enzyme is involved in lipoxin synthesis from 5,15-dihydroxyperoxyeicosatetraenoic acid via 5,6-epoxide
-
-
-
additional information
?
-
-
enzyme of leukotriene biosynthetic pathway
-
-
-
additional information
?
-
-
key enzyme in leukotriene metabolism, in human mast cells glucocorticoids effectively and selectively upregulate the expression
-
-
-
additional information
?
-
-
key enzyme in leukotriene biosynthesis, catalyzes the initial steps in the conversion of arachidonic acid to biologically active leukotrienes. Leukotrienes are considered as potent mediators of inflammatory and allergic reactions
-
-
-
additional information
?
-
-
key enzyme in the biosynthesis of proinflammatory leukotrienes
-
-
-
additional information
?
-
-
5-lipoxygenase/cyclooxygenase-2 cross-talk through cysteinyl leukotriene receptor 2 in endothelial cells, overview
-
-
-
additional information
?
-
P48999
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
-
additional information
?
-
P12527
5-LOX is the key enzyme in the biosynthesis of leukotrienes through catalyzing the initial two steps in conversion of arachidonic acid to leukotrienes
-
-
-
additional information
?
-
-
ALOX5-derived lipid mediators leukotrienes and lipoxins have regulatory functions in inflammation by modulating activities of immune cells and cytokine production, host control of Mycobacterium tuberculosis is regulated by 5-lipoxygenase
-
-
-
additional information
?
-
P48999
inhibition of 5-lipoxygenase does not affect cardiac ischemia-reperfusion injury but the post-ischemic inflammatory response, overview
-
-
-
additional information
?
-
-
inhibition of COX pathways does not increase the transformation of arachidonic acid by the 5-LOX pathway
-
-
-
additional information
?
-
-
key enzyme in biosynthesis of leukotrienes, overview. Upon cell activation, cytosolic and nuclear enzyme translocates the nuclear envelope, where it interacts with phospholipase A2, making free arachidonate available for 5-LO, and with 5-LO activating protein, i.e. FLAP. 5-LO regulates cancer cell survival and interferes with the mechanismtumor suppression, and increases cancer cell chemoresistance, overview
-
-
-
additional information
?
-
-
key enzyme in the leukotriene biosynthesis, pathway overview, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
P09917
key enzyme in the leukotriene biosynthesis, pathway overview, the 5-LO pathway is linked to the development of cardiovascular disease and other diseases, regulatory mechanisms underlying the expression and control of 5-LO activity, overview
-
-
-
additional information
?
-
-
no significant effect of LTB4, 12-hydroperoxyeicosatetraenoic acid or 15-hydroperoxyeicosatetraenoic acid on leukemic blast growth and on their apoptose rate, overview
-
-
-
additional information
?
-
-
the enzyme is involved in survival of Epstein-Barr virus-converted B lymphoma cells via function of 5-hydroperoxyeicosatetraenoic acid, overview
-
-
-
additional information
?
-
-
the enzyme is the key enzyme in biosynthesis of biologically active leukotrienes
-
-
-
additional information
?
-
-
the enzyme, catalyzing the key step in leukotriene biosynthesis, interacts with methyl jasmonate, which is probably involved in the anticarcinogenic activity of methyl jasmonate inducing apoptosis, overview
-
-
-
additional information
?
-
Mus musculus C57BL/6J
P48999
5-LO inhibition in obese mice downregulates genes involved in hepatic fatty acid uptake, i.e. L-FABP and FAT/CD36, and normalizes PPARalpha and acyl-CoA oxidase expression, whereas the expression of lipogenic genes, i.e. FASN and SREBP-1c, remains unaltered. The 5-LO inhibition restores hepatic microsomal triglyceride transfer protein, MTP, activity in parallel with a stimulation of hepatic VLDL-TG and ApoB secretion in obese mice, overview
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
1-Oleoyl-2-acetyl-sn-glycerol
P09917
both Ca2+ and glyceride, e.g. 1-oleoyl-2-acetyl-sn-glycerol, might decrease the concentration of lipid hydroperoxide needed for activation of 5-LO, enabling cellular 5-LO product formation at a low redox tone
1-Oleoyl-2-acetyl-sn-glycerol
-
both Ca2+ and glyceride, e.g. 1-oleoyl-2-acetyl-sn-glycerol, might decrease the concentration of lipid hydroperoxide needed for activation of 5-LO, enabling cellular 5-LO product formation at a low redox tone
Ba2+
-
45% of the activation with Ca2+
Ca2+
-
above 0.1 mM, required for maximal activity
Ca2+
-
required
Ca2+
-
optimal concentration is 2 mM
Ca2+
-
required
Ca2+
-
half-maximal activation around 0.03 mM
Ca2+
-
required
Ca2+
-
required
Ca2+
-
half-maximal activity at 0.1 mM; required
Ca2+
-
half-maximal activity at 0.02 mM; required
Ca2+
-
stimulates
Ca2+
-
stimulates
Ca2+
-
stimulates
Ca2+
-
stimulates
Ca2+
-
the enzyme is activated by a Ca2+-mediated translocation to membranes
Ca2+
-
5-lipoxygenase product formation in arachidonic acid-stimulated polymorphonuclear leukocytes is independent of Ca2+. Ca2+ and 5-lipoxygenase phosphorylation seem to be required for arachidonic acid-induced 5-lipoxygenase product formation
Ca2+
-
5-lipoxygenase product formation in arachidonic acid-stimulated polymorphonuclear leukocytes is independent of Ca2+
Ca2+
-
0.1 mM
Ca2+
-
activates, Ca2+ induces the translocation of 5-LO from a soluble compartment to nuclear structures, where 5-LO co-localizes with 5-LO activating protein, FLAP
Ca2+
P09917
binds at the C2-like domain, stimulates and induces enzyme translocation from the nuclear soluble to the envelope fraction, both Ca2+ and glyceride might decrease the concentration of lipid hydroperoxide needed for activation of 5-LO, enabling cellular 5-LO product formation at a low redox tone
Ca2+
-
binds at the C2-like domain, stimulates and induces enzyme translocation from the nuclear soluble to the envelope fraction, both Ca2+ and glyceride might decrease the concentration of lipid hydroperoxide needed for activation of 5-LO, enabling cellular 5-LO product formation at a low redox tone
Ca2+
-
upon stimulation with calcium ionophore, GFP-5-lipoxygenase translocates to the nuclear envelope allowing it to interact with 5-lipoxygenase activating protein (FLAP) and leukotriene C4 synthase
Ca2+
-
stimulation with calcium ionophore
Ca2+
-
Ca2+ is required for 5LO activity, the enzyme contains two Ca2+, full activation is reached at 0.004-0.01 mM Ca2+
Ca2+
-
activates
Ca2+
-
Ca2+ stimulates enzyme activity
Ca2+
-
addition of Ca2+ increases catalytic activity of wild-type nzyme by 50%
Fe
-
the iron acts as electron acceptor and donor, during hydrogen abstraction and peroxide formation
Fe2+
-
isoflavones reduce active state iron to ferrous state and prevent the activation of the resting enzyme
Fe2+
-
Asn720 is present in the fifth coordination position of iron
Fe2+
-
-
Fe2+
-
ferrous form of LO-1
Fe3+
P09917
because catalysis by 5-LO requires oxidation of Fe2+ to the active Fe3+ state by lipid hydroperoxides, the redox tone is an important parameter of cellular 5-LO activity
Fe3+
-
because catalysis by 5-LO requires oxidation of Fe2+ to the active Fe3+ state by lipid hydroperoxides, the redox tone is an important parameter of cellular 5-LO activity
Iron
-
contains one iron atom per molecule, the native enzyme is in a pseudo-axial high-spin ferric state
Iron
-
wild-type enzyme contains 0.65 mol of iron per mol of enzyme, H372 and H550 constitute two of the iron ligands
Mg2+
-
5 mM activates 5LO in vitro in the presence of PC
Mg2+
-
-
Mg2+
-
activates
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(-)-epicatechin
-
-
(1-difluoromethyl-2-oxo-1,2-dihydropyridin-3-yl)acetic acid
-
-
-
(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)acetic acid
-
-
-
(10E,12E)-octadeca-10,12-dien-8-ynoic acid
-
-
(11E)-octadec-11-en-9-ynoic acid
-
-
(15S)-hydroperoxy-5,8,11,13-eicosatetraenoyl lysophosphatidylcholine
-
-
(17S)-hydroperoxy-4,7,10,13,15,19-docosahexaenoyl lysophosphatidylcholine
-
-
(1E)-1-((1-[(1Z)-prop-1-en-1-yldisulfanyl]propyl)sulfinyl)prop-1-ene
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[3-methoxy-4-(3-phenoxypropoxy)phenyl]prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(morpholin-4-ylcarbonyl)phenyl]prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(piperidin-1-ylcarbonyl)phenyl]prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(pyrrolidin-1-ylcarbonyl)phenyl]prop-2-en-1-one
-
-
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-[(4-methylpiperazin-1-yl)carbonyl]phenyl]prop-2-en-1-one
-
-
(2E)-3-(3,4-dihydroxyphenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
-
-
(2E)-3-[3-(2-ethoxyethoxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(2-ethoxyethoxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(3-ethoxypropoxy)-3-methoxyphenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(benzyloxy)-3-bromo-5-methoxyphenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E)-3-[4-(benzyloxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
-
(2E,2'E)-(1,1'-(2,2-bis((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
potent inhibition by 92%
(2E,2'E)-(1,1'-(2,2-bis((4-(cinnamoyloxymethyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-phenylacrylate)
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
(2E,2'E)-(1,1'-(2-((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
potent inhibition by 91%
(2E,2'E)-(1,1'-(2-((4-(cinnamoyloxymethyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-phenylacrylate)
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
(2E,2'E)-2,2'-(4,4'-(2,2-bis(((1-(2-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)propane-1,3-diyl)bis(oxy)bis(methylene)bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
-
(2E,2'E)-2,2'-(4,4'-(2,2-bis(((1-(2-(cinnamoyloxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)propane-1,3-diyl)bis(oxy)bis(methylene)bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl) bis(3-phenylacrylate)
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
(2E,5E)-5-[(2E)-3-(furan-2-yl)prop-2-en-1-ylidene]-3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one
-
-
(2Z)-2-[4-(acetylamino)phenyl]-3-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
-
(5E)-2-(3-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(3-fluorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-aminophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-chlorophenyl)-5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-chlorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-hydroxyphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-2-(4-methylphenyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(2,4-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3,5-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(3-chlorobenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-hydroxy-3-methoxy-5-nitrobenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-methoxybenzylidene)-2-(4-methoxyphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-tert-butylbenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(4-[(methylperoxy)acetyl]benzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(5-chloro-2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-(anthracen-9-ylmethylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
-
(5E)-5-4-[(methylperoxy)acetyl]benzylidene
-
-
(5E)-5-benzylidene-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
-
(5E)-5-[4-(dimethylamino)benzylidene]-2-(piperidin-1-yl)-1,3-thiazol-4(5H)-one
-
-
(5Z)-2-(cyclohexylamino)-5-(4-propoxybenzylidene)-1,3-thiazol-4(5H)-one
-
-
(5Z)-5-(4-methoxybenzylidene)-2-(pyrrolidin-1-yl)-1,3-thiazol-4(5H)-one
-
-
(5Z)-5-(4-methylbenzylidene)-2-(naphthalen-2-ylamino)-1,3-thiazol-4(5H)-one
-
-
(5Z)-5-benzylidene-2-(phenylamino)-1,3-thiazol-4(5H)-one
-
-
(6E,8Z,11Z,14Z)-(5S)-hydroperoxyicosa-6,8,11,14-tetraenoate
-
inhibits reaction with arachidonate
(E)-N-hydroxy-N-(3-(3-phenoxyphenyl)-allyl)acetamide
-
BWA4C
([3-chloro-5-(2,3-dihydro-1H-inden-4-ylamino)phenyl]sulfanyl)acetic acid
-
-
([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)(naphthalen-1-yl)acetic acid
-
-
1,10-phenanthroline
-
0.01 mM, 34% inhibition
1,4a-dimethyl-7-(propan-2-yl)-1-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene (non-preferred name)
-
-
1-(2,4-difluorophenyl)-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
-
1-(2,4-dihydroxyphenyl)-2-(naphthalen-2-yl)ethanone
-
-
1-(3,4-dichlorobenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
P12527
82% inhibition at 0.005 mM
1-(3,4-dichlorobenzyl)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
P12527
38.5% inhibition at 0.005 mM
1-(3,4-difluorophenyl)-1,2,4-triazinan-3-one
-
-
1-(3-bromophenyl)-1,2,4-triazinan-3-one
-
-
1-(3-chlorophenyl)-1,2,4-triazinan-3-one
-
-
1-(3-ethylphenyl)-1,2,4-triazinan-3-one
-
-
1-(3-hydroxyphenyl)-3-[4-(methylsulfonyl)phenyl]prop-2-yn-1-one
-
-
1-(3-hydroxyphenyl)-3-[4-(methylsulfonyl)phenyl]prop-2-yn-1-one
-
-
1-(4-aminosulfonylphenyl)-5-(2-chloropyridin-4-yl)-3-trifluoromethyl-1H-pyrazole
-
-
1-(4-aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole
-
-
1-(4-chlorobenzyl)-2-[2,2-dimethyl-3-(1H-tetrazol-5-yl)propyl]-4-methyl-6-[2-(5-phenylpyridin-2-yl)ethyl]-2,2a,4,5-tetrahydro-1H-thiopyrano[2,3,4-cd]indole
-
-
1-(4-chlorophenoxy)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
P12527
22% inhibition at 0.005 mM
1-(4-chlorophenoxy)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
P12527
26% inhibition at 0.005 mM
1-(4-chlorophenoxy)-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
70% inhibition at 0.005 mM
1-(4-methanesulfonylphenyl)-5-(2-chloropyridin-4-yl)-3-trifluoromethyl-1H-pyrazole
-
-
1-(4-methanesulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole
-
-
1-(4-methylbenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
P12527
35% inhibition at 0.005 mM
1-(4-methylbenzyl)-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
P12527
55% inhibition at 0.005 mM
1-(6-methylpyridin-2-yl)-1,2,4-triazinan-3-one
-
-
1-(7-tert-butyl-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)butan-1-one
-
-
1-(8-tert-butyl-4,4-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-cyclopropylbutan-1-one
-
-
1-(benzyloxy)hept-2-yn-4-ol
-
forms three hydrogen bonds with 5-lipoxygenase
1-(difluoromethyl)-5-[[2-(methylsulfonyl)phenyl]ethynyl]pyridin-2(1H)-one
-
-
1-benzyl-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
P12527
41% inhibition at 0.005 mM
1-benzyl-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
-
1-benzyl-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
P12527
64% inhibition at 0.005 mM
1-benzyl-3-(4-morpholin-4-ylbutyl)-1H-indole
P12527
42% inhibition at 0.005 mM
1-benzyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
P12527
95% inhibition at 0.005 mM
1-benzyl-3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
P12527
32% inhibition at 0.005 mM
1-benzyl-3-[3-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]propyl]-5-methoxy-2-methyl-1H-indole
P12527
46.5% inhibition at 0.005 mM
1-benzyl-5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
80% inhibition at 0.005 mM
1-benzyl-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
54% inhibition at 0.005 mM
1-benzyl-5-methoxy-2-methyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
P12527
65% inhibition at 0.005 mM
1-hydroxy-1-[1-(5-methoxy-1-methyl-1H-indol-2-yl)ethyl]urea
-
-
1-O-dodecyl 2,3-O-isopropylidene-5,6-dideoxy-5-N-[4-(2-hydroxy-2-oxoethyl) phenylaminocarbonyl] amino-beta-L-gulofuranoside sodium salt
-
competitive inhibitior, IC50: 0.0035 mM with recombinant enzyme, IC50: 0.005 mM with native enzyme
1-phenyl-5-(propan-2-yl)-1,2,4-triazinan-3-one
-
-
1-[(4methylbenzyl)oxy]hept-2-yn-4-ol
-
is more potent than 1-(benzyloxy)hept-2-yn-4-ol to 5-lipoxygenase
1-[1-(6-tert-butyl-1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
-
-
1-[3-(benzyloxy)phenyl]-1,2,4-triazinan-3-one
-
-
1-[3-(methylsulfanyl)phenyl]-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
-
1-[4-([3-fluoro-5-[4-(methylsulfinyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
-
-
1-[4-([3-fluoro-5-[4-(methylsulfonyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
-
-
10,17(S)-dihydroxydocosahexaenoic acid
-
IC50: 0.017 mM
11,14,17-Eicosatrienoic acid
-
IC50: 0.015 mM
11,14,17-Eicosatrienoic acid
-
substrate inhibition
11alpha,13-dihydrohelenalin acetate
-
enzyme from polymorphonuclear leukocyte
15-hydroperoxy-6,8,11,13-eicosatetraenoic acid
-
IC50: 0.0048 mM
2,3,4',5-tetrahydroxystilbene-2-O-D-glucoside
-
polymorphonuclear leukocyte
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-3-yl)propanoic acid
-
-
-
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
micromolar 5-LOX inhibitory activity
-
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)propanoic acid
-
-
-
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-5-yl)acetic acid
-
-
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-5-yl)propanoic acid
-
-
-
2-(2,2-dimethyl-6-(4-nitrophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
2-(2,2-dimethyl-7-phenyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
2-(2,4-dihydroxyphenyl)-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one
-
-
2-(2-methoxyphenyl)-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)acetamide
-
-
2-(2-[ethyl(hydroxy)amino]ethyl)dibenzo[b,e]oxepin-11(6H)-one
-
-
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
-
-
2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
-
-
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
-
-
2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c]chromene-3,6,9-triol
-
-
2-(3-[hydroxy(methyl)amino]propyl)dibenzo[b,e]oxepin-11(6H)-one
-
-
2-(4-(biphenyl-4-ylamino)-6-chloropyrimidine-2-ylthio)octanoic acid
-
-
2-(4-(biphenyl-4-ylmethylamino)-6-chloropyrimidin-2-ylthio)octanoic acid
-
-
2-(4-chloro-6-(2,3-dimethylphenylamino)pyrimidin-2-ylthio)acetic acid
-
-
2-(4-chloro-6-(4'-cyanobiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
-
2-(4-chloro-6-(5-methoxy-2-methylbiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
-
2-(4-methylphenyl)-5-(2-phenylethenylidene)-1,3-thiazol-4(5H)-one
-
-
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(5-methyl-1,3-thiazol-2-yl)propanamide
-
-
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-1,3-thiazol-2-ylpropanamide
-
-
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
-
-
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-thiophen-3-ylpropanamide
-
-
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-(methylsulfonyl)acetamide
-
-
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-(phenylsulfonyl)acetamide
-
-
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-tosylacetamide
-
-
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1Hpyrrolizin-5-yl)-N-tosylpropanamide
-
-
2-(6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
2-(6-(4-tert-butylphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(thiophen-2-ylmethyl)propanamide
-
-
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-1,3-thiazol-2-ylpropanamide
-
-
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
-
-
2-(dibenzo[b,d]furan-3-yl)-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2-([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)octanoic acid
-
-
2-benzyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2-hexyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2-hydroxy-5-(3-nitrophenyl)cyclohexa-2,5-diene-1,4-dione
-
-
2-hydroxy-5-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
-
-
2-hydroxy-5-methoxy-3-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
-
-
2-methoxy-5-(naphthalen-2-yloxy)cyclohexa-2,5-diene-1,4-dione
-
-
2-[(1-hydroxy-6-oxo-1,6-dihydropyridin-3-yl)ethynyl]benzenesulfonamide
-
-
2-[(4-[[3,5-bis(2,2,2-trifluoroethoxy)phenyl]amino]-6-chloropyrimidin-2-yl)sulfanyl]octanoic acid
-
-
2-[2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
micromolar 5-LOX inhibitory activity
-
2-[3-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
micromolar 5-LOX inhibitory activity
-
2-[4'-(iso-propylphenyl)-amino]-5,6-dimethyl-1,4-benzoquinone
-
potent inhibitor, IC50: 0.006 mM
2-[4-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
micromolar 5-LOX inhibitory activity
-
2-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
-
2-[5,8-dimethyl-7-(2-morpholin-4-ylethoxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-N-1,3-thiazol-2-ylpropanamide
-
-
2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
-
-
2-[7-[2-(dimethylamino)ethoxy]-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]-N-1,3-thiazol-2-ylpropanamide
-
-
2-[7-[2-(dimethylamino)ethoxy]-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]-N-pyridin-2-ylpropanamide
-
-
3'-nitrobiphenyl-2,4-diol
-
-
3,4,5-trimethoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
-
-
3-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
micromolar 5-LOX inhibitory activity
-
3-(2-(2-[(4-chlorophenyl)sulfanyl]ethoxy)-3-methoxy-5-[5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-2-yl]benzyl)-1-hydroxy-1-methylurea
-
-
3-(2-morpholin-4-yl-2-oxoethyl)-1-phenoxy-1H-indole
P12527
21% inhibition at 0.005 mM
3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
P12527
16% inhibition at 0.005 mM
3-(3-morpholin-4-yl-3-oxopropyl)-1-phenoxy-1H-indole
P12527
23% inhibition at 0.005 mM
3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
P12527
33% inhibition at 0.005 mM
3-(4,5-dihydroxy-2-methyl-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-1-yl)-2-hydroxy-4,6-dimethoxybenzoic acid
-
-
3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
62% inhibition at 0.005 mM
3-(6-(4-chlorphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)propionic acid
-
-
3-(cyclohexylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
-
-
3-(decahydronaphthalen-2-ylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
-
-
3-benzyl-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
-
-
3-ethoxy-11-oxours-12-en-23-oic acid
-
-
3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
P12527
64% inhibition at 0.005 mM
3-[4-(methylsulfonyl)phenyl]-1-[4-(propan-2-yl)phenyl]prop-2-yn-1-one
-
-
3-[5-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
-
-
3-[[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]methyl]-1-[4-(methylsulfonyl)phenyl]-5-phenyl-1H-pyrazole
-
-
4,4'-(2,3-dimethyl)-1,4-butanediylbis-1,2-benzenediol
-
-
4,5-bis(4-chlorophenyl)-1,2-selenazole
-
44% inhibition at 0.01 mM
4,5-bis(4-methoxyphenyl)-1,2-selenazole
-
58% inhibition at 0.01 mM
4,7,10,13,16,19-docosahexaenoic acid
-
IC50: 0.0013 mM
4,9-dimethoxy-3-methyl-9,10-dihydrophenanthrene-2,7-diol
-
-
4-((3,4-dichlorobenzyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
P12527
27% inhibition at 0.005 mM
4-((4-chlorobenzoyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
P12527
32% inhibition at 0.005 mM
4-(1-(4-methylbenzyl)-1H-indol-3-yl)-1-morpholinobutan-1-one
P12527
34% inhibition at 0.005 mM
4-(1-benzothiophen-3-yl)benzene-1,3-diol
-
-
4-(1-benzoyl-1H-indol-3-yl)-1-morpholinobutan-1-one
P12527
58% inhibition at 0.005 mM
4-(1-benzyl-1H-indol-3-yl)-1-morpholinobutan-1-one
P12527
26% inhibition at 0.005 mM
4-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
micromolar 5-LOX inhibitory activity
-
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)-N-methyltetrahydro-2H-pyran-4-carboxamide
-
-
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-ol
-
-
4-(3-fluoro-5[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-carboxylic acid
-
-
4-(4-chlorophenyl)-5-(4-methoxyphenyl)-1,2-selenazole
-
53% inhibition at 0.01 mM
4-(4-chlorophenyl)-5-p-tolyl-1,2-selenazole
-
45% inhibition at 0.01 mM
4-(4-chlorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-2H-chromen-2-one
-
IC50: 180 nM
4-(4-fluorophenyl)-5-(4-(methylsulfonyl)phenyl)-1,2-selenazole
-
60% inhibition at 0.01 mM
4-(4-fluorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenoxy]methyl)-2H-chromen-2-one
-
IC50: 55 nM
4-(4-fluorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-2H-chromen-2-one
-
IC50: 27 nM
4-(6-methoxynaphthalen-2-yl)butan-2-one
-
-
4-(acetyloxy)-2-[4-(acetyloxy)-6-methylhept-5-en-2-yl]cyclohexyl (2Z)-2-methylbut-2-enoate
-
-
4-(dibenzo[b,d]furan-3-yl)benzene-1,3-diol
-
-
4-(furan-3-yl)-7-[[2-(tetrahydro-2H-pyran-4-yl)pyridin-4-yl]methoxy]naphthalene-2-carbonitrile
-
-
4-(furan-3-yl)-7-[[6-(4-hydroxytetrahydro-2H-pyran-4-yl)pyridin-2-yl]methoxy]naphthalene-2-carbonitrile
-
-
4-(furan-3-yl)-7-[[7-(tetrahydro-2H-pyran-4-yl)-1,2,3,4-tetrahydroquinolin-2-yl]oxy]naphthalene-2-carbonitrile
-
-
4-(naphthalen-2-ylmethyl)benzene-1,3-diol
-
-
4-(thianthren-2-yl)benzene-1,3-diol
-
-
4-benzylbenzene-1,3-diol
-
-
4-chloro-N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00042 mM
4-chloro-N-([4-[(2E)-3-phenylprop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00083 mM
4-hexylbenzene-1,3-diol
-
-
4-methoxy-4-[3-(naphthalen-2-ylmethoxy)phenyl]tetrahydro-2H-pyran
-
-
4-methoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
-
-
4-methyl-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,2,3-thiadiazole-5-carboxamide
-
-
4-methyl-N-([4-[(2E)-3-(2,3,4-trimethylphenyl)prop-2 enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00045 mM
4-methyl-N-([4-[(2E)-3-phenylprop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00089 mM
4-methylesculetin
-
polymorphonuclear leukocyte
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-hydroxy-5-nitrophenyl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-hydroxyphenyl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-methoxyphenyl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-phenylethyl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(propan-2-yl)benzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-methyl-N-phenylbenzamide
-
-
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-propylbenzamide
-
-
4-[1-(4-chlorobenzyl)-4-methyl-6-[(5-phenylpyridin-2-yl)methoxy]-2,2a,4,5-tetrahydro-1H-thiopyrano[2,3,4-cd]indol-2-yl]-3,3-dimethyl-N-(methylsulfonyl)butanamide
-
-
4-[4-(4-fluoro-phenyl)-thiazol-2-ylamino]-2,6-dimethylphenol
-
KR-33749, the compound exhibits a more than 1000fold selectivity for 5-LO against 12-LO and 15-LO
-
4-[5-(1H-indol-3-yl)-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide
-
-
4-[5-(1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-5 by 41%
4-[5-(1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-15 by 31%
4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
-
-
4-[5-(6-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-5 by 51%
4-[5-(6-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-15 by 36%
4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-5 by 94%
4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-15 by 36%
5,5'-di(prop-2-en-1-yl)biphenyl-2,2'-diol
-
-
5,5-dimethyl-1-phenyl-1,2,4-triazinan-3-one
-
-
5,6-Dehydroarachidonate
-
irreversible
5,6-Methano-leukotriene A4
-
-
5,8,11,13-eicosatetraynoic acid
-
IC50: 0.028 mM
5,8,11,14,17-eicosapentaenoic acid
-
-
5-(2-[[3-(trifluoromethyl)phenyl]amino]phenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
5-(3,5-di-tert-butyl-4-hydroxybenzylidene)thiazolidin-2,4-dione
-
effective inhibitor of 5-LOX in vivo
-
5-(4-chlorophenyl)-4-(4-methoxyphenyl)-1,2-selenazole
-
42% inhibition at 0.01 mM
5-(4-chlorophenyl)-4-p-tolyl-1,2-selenazole
-
67% inhibition at 0.01 mM
5-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole
-
-
5-(4-methoxyphenyl)-4-p-tolyl-1,2-selenazole
-
64% inhibition at 0.01 mM
5-(7-tert-butyl-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-5-oxopentanenitrile
-
-
5-butyl-1-phenyl-1,2,4-triazinan-3-one
-
-
5-chloro-1-(4-chlorophenoxy)-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
38% inhibition at 0.005 mM
5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
71% inhibition at 0.005 mM
5-ethyl-1-phenyl-1,2,4-triazinan-3-one
-
-
5-hydroperoxy-6,8,11,14-eicosatetraenoic acid
-
-
5-methoxy-2-methyl-1-(4-methylbenzyl)-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
26% inhibition at 0.005 mM
5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
73% inhibition at 0.005 mM
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
-
-
6-(trideca-1,4,7-triene-1-sulfinyl)-hex-5-enoic acid
-
-
6-ethenesulfinyl-hex-5-enoic acid
-
-
6-ethenesulfinyl-hex-5-enoic acid amide
-
-
6-hept-1-ene-1-sulfinyl-hex-5-enoic acid
-
-
6-hept-1-enylsulfanyl-hex-5-enoic acid
-
-
6-vinylsulfanyl-hex-5-enoic acid
-
-
6-vinylsulfanyl-hex-5-enoic acid amide
-
-
6-[(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]naphthalene-2-carboxylic acid
-
-
6-[[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]methyl]-1-methylquinolin-2(1H)-one
-
-
7,17(S)-dihydroxydocosahexaenoic acid
-
IC50: 0.007 mM
7,8-dihydroxy-2H-chromen-2-one
-
-
7-(4-methylphenyl)-6-[4-(methylsulfonyl)phenyl]-2,3-dihydro-1H-pyrrolizine
-
-
7-([3-fluoro-5-[(1R)-1-hydroxy-1-pyridin-2-ylpropyl]phenoxy]methyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 175 nM
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-(4-fluorophenyl)-2H-chromen-2-one
-
-
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 200 nM
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-phenyl-2H-chromen-2-one
-
IC50: 300 nM
7-([3-fluoro-5-[(1S)-1-hydroxy-1-(1,3-thiazol-2-yl)propyl]phenoxy]methyl)-4-(4-fluorophenyl)-2H-chromen-2-one
-
IC50: 175 nM
7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 9 nM
7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-4-phenyl-2H-chromen-2-one
-
IC50: 26 nM
7-tert-butyl-N-ethyl-N,3,3-trimethyl-2,3-dihydro-1-benzofuran-5-carboxamide
-
-
7-thiaarachidonic acid
-
-
7-[[3-(1-ethyl-1-hydroxypropyl)-5-fluorophenoxy]methyl]-4-furan-3-yl-2H-chromen-2-one
-
IC50: 15 nM
7-[[3-(4-methoxytetrahydro-2H-pyran-4-yl)benzyl]oxy]-4-phenylnaphtho[2,3-c]furan-1(3H)-one
-
-
7-[[3-fluoro-5-(3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl)phenoxy]methyl]-4-(furan-3-yl)quinoline-2-carbonitrile
-
-
8,11,13-cis-icosatrienoic acid
-
-
8,11,14-Eicosatrienoic acid
-
IC50: 0.00219 mM
8,11,14-Eicosatrienoic acid
-
substrate inhibition
8-hydroxyquinoline
-
0.01 mM, 59% inhibition
A-53162
-
-
-
AA-861
-
competitive 5-LO inhibitor
AA861
-
i.e. 2-(12-hydroxydodeca-5,10-diynyl)-3,5,6-trimethyl-1,4-benzoquinone, IC50: 0.004-0.01 mM
AA861
-
-
AA861
-
-
AA861
-
IC50: 0.0026 mM
AA861
-
specific inhibition
ABT 761
-
CAS: 154355-76-7
ABT-761
-
-
acetonylacetone bisphenylhydrazone
-
IC50 for reaction with linoleic acid: 0.015 mM, IC50 for reaction with arachidonic acid: 0.0039 mM
arachidonic acid
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00023 mM; substrate inhibition
arachidonic acid
-
substrate inhibition above 0.045-0.05 mM
arachidonic acid
-
substrate inhibition
arachidonic acid
-
competitive inhibitor of linoleic acid oxidation
arachidonoyl lysophosphatidylcholine
-
-
baicalein
-
IC50: 0.0012 mM
benzaldehyde phenylhydrazone
-
IC50 for reaction with linoleic acid: 0.0345 mM, IC50 for reaction with arachidonic acid: 0.0014 mM
benzyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
benzyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
beta-hydroxyacteoside
-
enzyme from polymorphonuclear leukocyte
biphenyl-2,4-diol
-
-
BW755C
-
CAS: 66000-40-6; i.e. 3-amino-1-[3-(trifluoromethyl)phenyl]-2-pyrazoline, IC50: 0.013 mM
BW755C
-
CAS: 66000-40-6; IC50: 0.004-0.015 mM
BW755C
-
CAS: 66000-40-6
BW755C
-
CAS: 66000-40-6; IC50: 0.53 MM
caffeic acid
-
IC50: 0.046 mM
caffeic acid
-
-
caffeic acid
-
-
caffeic acid
-
micromolar 5-LOX inhibitory activity
cannabidiol
-
-
capsaicin
-
enzyme from polymorphonuclear leukocyte
catechol
-
IC50: 0.062 mM
celecoxib
-
-
celecoxib
-
-
celecoxib
-
0.01 mM inhibits LOX-5 by 89%
celecoxib
-
0.01 mM inhibits LOX-15 by 22%
CGP28238
-
-
cholesterol
-
addition to a membrane preperation in vitro reduces 5-lipoxygenase activity by half. Cholesterol sulfate can inhibit 5-lipoxygenase in intact cells
Cirsiliol
-
-
Cirsiliol
-
IC50: 0.098 mM
CJ-13,610
-
-
CJ-13610
-
-
Cox-189
-
-
daidzein
-
noncompetitive
daphnetin
-
polymorphonuclear leukocyte
delphinidin 3-O-galactoside
-
from Vaccinium myrtillus berries, strong inhibitor, in a concentration-dependent manner
delphinidin 3-O-glucoside
-
from Vaccinium myrtillus berries, strong inhibitor, in a concentration-dependent manner
diclofenac
-
-
diphenyldisulfide
-
IC50: 0.002-0.005
docosahexaenoic acid
-
substrate inhibition
ebselen
-
54% inhibition at 0.01 mM
eicosapentaenoic acid
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00065 mM; substrate inhibition
eicosapentaenoic acid
-
substrate inhibition
eltenac
-
-
epinephrine
-
IC50: 0.98 mM
ER-34122
-
-
esculetin
-
IC50: 0.0045 mM
esculetin
-
polymorphonuclear leukocyte
ethyl 1-benzyl-2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(3-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
prevents leukotriene B4 production in pleural exudates of carrageenan-treated rats, associated with reduced severity of pleurisy. Significantly reduces the inflammatory reaction measured as exudate volume (77%), inflammatory cell numbers (40%), and leukotriene B4 levels (49%) in the pleural exudates
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-pyrrolo[2,3-f]quinoline-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-hydroxy-6-phenyl-1H-indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-5-phenyl-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(3-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-(4-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-(4-trifluoromethylbenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
-
ethyl 2-[[4-chloro-6-(quinolin-6-ylamino)pyrimidin-2-yl]sulfanyl]octanoate
-
-
ethyl 5-benzoyloxy-2-(3-chlorobenzyl)-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 5-hydroxy-2-phenylethyl-1H-indole-3-carboxylate
-
-
ethyl 5-hydroxy-2-phenylpropyl-1H-benzo[g]indole-3-carboxylate
-
-
ethyl 6-biphenyl-4-yl-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
-
etoricoxib
-
-
Eugenol
-
non-competitive, reversible inhibitor, IC50: 0.026 mM
eupatilin
-
IC50: 0.098 mM
falcarindiol
-
-
forsythiaside
-
enzyme from polymorphonuclear leukocyte
forsythiaside
-
polymorphonuclear leukocyte
fraxetin
-
polymorphonuclear leukocyte
genistein
-
noncompetitive
gingerdione
-
enzyme from polymorphonuclear leukocyte
glutathione
-
inhibition is increased in presence of glutathione peroxidase
glutathione
P09917
efficiency of non-redox-type 5-LO inhibitors depends on the presence of glutathione peroxidase activity leading to low hydroperoxide concentration
glutathione
-
efficiency of non-redox-type 5-LO inhibitors depends on the presence of glutathione peroxidase activity leading to low hydroperoxide concentration
helenalin
-
enzyme from polymorphonuclear leukocyte
hyperforin
-
-
indomethacin
-
IC50: 0.36 mM
iodoacetamide
-
0.01 mM, 20% inhibition
isoriccardin C
-
-
L-651,392
-
i.e. 4-bromo-2,7-dimethoxy-3H-phenothiazin-3-one, + 1 mM NADH, IV50: 0.0003-0.0005 mM
L-651,896
-
i.e. 2,3-dihydro-6-[3-(2-hydroxymethyl)-phenyl-2-propenyl]-5-benzofuranol, IC50: 0.0003-0.0004 mM
L-656,224
-
i.e. 7-chloro-2-[(4-methoxyphenyl)-methyl]-3-methyl-5-propyl-4-benzofuranol, IC50: 0.0008 mM
L-656,224
-
IC50: 0.0003-0.0004 mM
L-670,630
-
IC50: 0.0004 mM
L-689,065
-
IC50: 0.0003 mM
L-697,198
-
IC50: 0.00002 mM
-
L-702,590
-
-
-
L-702,701
-
IC50: 0.0015 mM
-
L-739,010
-
-
L-746,530
-
IC50: 27 nM
L705,302
-
IC50: 0.00002 mM
-
leucocyanidol
-
polymorphonuclear leukocyte
licofelone
-
formerly termed ML-3000
licofelone
-
-
licofelone
-
dual COX-2?5-LO inhibitor
marchantin A
-
-
marchantin B
-
-
marchantin D
-
-
marchantin E
-
-
meloxicam
-
-
methanol
-
complete inhibition at 50% v/v
methyl (4-[(5E)-5-(4-methoxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]phenoxy)acetate
-
-
methyl 2-(allylamino)-1H-indole-3-carboxylate
-
-
methyl 2-(benzylamino)-1H-indole-3-carboxylate
-
-
methyl 2-(diallylamino)-1H-indole-3-carboxylate
-
-
methyl 2-[(2-chlorophenyl)amino]-1H-indole-3-carboxylate
-
-
methyl 2-[(3-bromophenyl)amino]-1H-indole-3-carboxylate
-
-
methyl 2-[(3-chlorophenyl)amino]-1H-indole-3-carboxylate
-
-
methyl 2-[(3-chlorophenyl)amino]-5-chloro-1H-indole-3-carboxylate
-
-
methyl 2-[(3-fluorophenyl)amino]-1H-indole-3-carboxylate
-
-
methyl 2-[(4-chlorophenyl)amino]-1H-indole-3-carboxylate
-
-
miogadial
-
potent inhibitor, IC50: 0.004 mM
miogatrial
-
potent inhibitor, IC50: 0.0075 mM
mithramycin
-
reduces endogenous 5-lipoxygenase in Mono Mac 6 cell, which blocks GC-boxes in the proximal part of the 5-lipoxygenase gene promoter
MK 886
-
i.e. CAS: 118414-82-7, inhibition of 5-lipoxygenase in prostate cancer cells blocks production of 5-hydroxyeicosatetraenoic acid and induces massive apoptosisin both hormone-responsive and hormone-nonresponsive prostate cancer cells
MK-886
-
competitive 5-LO inhibitor
MK886
-
a specific FLAP inhibitor
MK886
-
specific inhibitor of 5-hydroperoxyeicosatetraenoic acid synthesis by the enzyme
MK886
-
5-LOX activating protein inhibitor
myrtol
-
enzyme from RBL-1 cell
-
N-(2,4-dimethylphenyl)-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
-
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,3-benzodioxole-5-carboxamide
-
-
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)cyclopentanecarboxamide
-
-
N-(3-phenoxycinnamyl)-acetohydroxamic acid
-
-
N-(4-chlorophenyl)-N-hydroxy-N'-(3-chlorophenyl)urea
-
IC50: 0.0001 mM
N-(furan-2-ylmethyl)-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
-
N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)-4-methylbenzenesulfonamide
-
IC50: 0.00045 mM
N-benzyl-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
-
N-cyclopentyl-2-[7-(2-methoxyethoxy)-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide
-
-
N-dodecyl-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
-
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
-
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
-
N-hydroxy-N-[1-(1-methyl-1H-indol-2-yl)ethyl]acetamide
-
-
N-methyl-2[4-(2,4,6-trimethylphenyl)phenyl]-propenehydroxamic acid
-
IC50: 0.0005 mM
N-tert-butyl-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
-
N-[2-(cyclohexyloxy)-4-nitrophenyl]methanesulfonamide
-
-
N-[5-(4-fluorophenoxy)thiophen-2-yl]methanesulfonamide
-
-
NEM
-
0.01 mM, 75% inhibition
nimesulide
-
-
nordihydroguaiaretic acid
-
IC50: 0.0023 mg/ml
nordihydroguaiaretic acid
-
IC50: 5 ppm
nordihydroguaiaretic acid
-
-
nordihydroguaiaretic acid
-
NDGA
nordihydroguaiaretic acid
-
-
nordihydroguaiaretic acid
-
reduces oxidative damage of erythrocytes in C57BL/6 Trypanosoma cruzi-infected mice but not in C57BL/6 iNOS-/- infected mice
nordihydroguaiaretic acid
-
is more potent inhibitor of 5-lipoxygenase than 1-(benzyloxy)hept-2-yn-4-ol
nordihydroguiaraetic acid
-
IC50 for reaction with linoleic acid: 0.17 mM, IC50 for reaction with arachidonic acid: 0.0365 mM
nordihydroguiaraetic acid
-
IC50: 0.00021 mM
norepinephrine
-
IC50: 0.49 mM
ochnaflavone
-
IC50: 0.0656 mM
oroxindin
-
polymorphonuclear leukocyte
paleatin B
-
-
panaxynol
-
-
parecoxib
-
-
perrottetin D
-
-
Phenidone
-
IC50: 0.005-0.01 mM
piceid
-
polymorphonuclear leukocyte
polygodial
-
strong inhibitory activity, IC50: 0.0086 mM
quercetagetin-7-O-beta-D-glucoside
-
polymorphonuclear leukocyte
quercetin
-
IC50: 0.0003-0.0005 mM
quercetin
-
IC50: 0.0021 mM
radulanin H
-
-
resveratrol
-
polymorphonuclear leukocyte
Rev-5901
-
competitive 5-LO inhibitor
-
rofecoxib
-
-
rofecoxib
-
0.01 mM inhibits LOX-5 by 11%
rofecoxib
-
0.01 mM inhibits LOX-15 by 6%
rutin
-
IC50: 0.033 mM
RWJ-63556
-
-
S-2474
-
-
SC-560
-
-
SC-756
-
-
shogaol
-
enzyme from polymorphonuclear leukocyte
sideritoflavone
-
polymorphonuclear leukocyte
sulindac sulfide
-
5-LO-selective inhibitor
sulindac sulfide
-
-
suspensaside
-
enzyme from polymorphonuclear leukocyte
suspensaside
-
polymorphonuclear leukocyte
tambuletin
-
polymorphonuclear leukocyte
tepoxalin
-
-
tert-butyl 4-[4-(1-benzyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
P12527
38% inhibition at 0.005 mM
tert-butyl 4-[4-(1-benzyl-5-methoxy-2-methyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
P12527
51.5% inhibition at 0.005 mM
tert-butyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
P12527
84% inhibition at 0.005 mM
tert-butyl 4-[4-(5-methoxy-2-methyl-1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
P12527
71% inhibition at 0.005 mM
thioctic acid
-
-
valdecoxib
-
-
verbascoside
-
enzyme from polymorphonuclear leukocyte
verbascoside
-
polymorphonuclear leukocyte
YS121
-
-
ZD 2138
-
i.e. CAS: 140841-32-3, IC50: 0.0003 mM
ZD-2138
-
-
ZD-2138
P12527
-
Zileutin
-
-
zileuton
-
IC50: 0.01
zileuton
-
IC50: 0.0038 mM with recombinant enzyme, IC50: 0.0011 mM with native enzyme
zileuton
P12527
87% inhibition at 0.005 mM
zileuton
-
reduces exudate formation (77%), cell infiltration (41%), and leukotriene B4 exudate levels (66%)
ZM 230,486
-
IC50: 0.00009 mM
ZM230487
-
-
[1-(2-[[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
-
[1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
-
[1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-phenylprop-2-enoate
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
[1-(3-[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2-[(3-[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2,2-bis[[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propoxy)methyl]-2-[[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
incorporation of additional caffeoyl units in hexamer results in less potent inhibition
[1-(3-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2-[(3-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2,2-bis[[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propoxy)methyl]-2-[[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-phenylprop-2-enoate
-
shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety
[2-[(1S,8aR)-2-formyl-5,5,8a-trimethyldecahydronaphthalen-1-yl]ethylidene]propanedial
-
-
ML-3000
-
i.e. licofelone, ML-3000 has no effect on 5-LOX product synthesis in whole-blood assay, inhibition of COX pathways does not increase the transformation of arachidonic acid by the 5-LOX pathway
additional information
-
classes of 5-lipoxygenase inhibitors: 1. compounds that inhibit the enzyme via antioxidant mechanism - NGDA, BW755c, AA-861, ICI-207968, and A-53612. High toxicity, unacceptable for clinical development. 2. compounds that interact with the non-heme iron moiety of the enzyme - BW-A4A, and ABT-761 both effective in asthma and zileuton. 3. nonredox competitive inhibitors - ZD-2138 and L-697198
-
additional information
-
-
-
additional information
-
classes of 5-lipoxygenase inhibitors: 1. compounds that inhibit the enzyme via antioxidant mechanism - NGDA, BW755c, AA-861, ICI-207968, and A-53612. High toxicity, unacceptable for clinical development. 2. compounds that interact with the non-heme iron moiety of the enzyme - BW-A4A, and ABT-761 both effective in asthma and zileuton. 3. nonredox competitive inhibitors - ZD-2138 and L-697198
-
additional information
-
overview: inhibitors and perspectives for future drug development
-
additional information
-
zinc inhibits leukotriene B4 formation due to a direct or indirect inhibitory effect on 5-lipoxygenase
-
additional information
-
selenium-induced apoptosis in prostate cancer cells may be mediated through inhibition of the activity of arachidonate 5-lipoxygenase. The anti-cancer effects of selenium may be substantially compromised by consumption of high-fat diets rich in arachidonic acid or its precursor fatty acids
-
additional information
-
plant extracts with inhibitory activity on arachidonate 5-lipoxygenase, inhibition of the 5-lipoxygenase pathway is considered to be interesting in the treatment of a variety of inflammatory diseases
-
additional information
-
plant extracts with inhibitory activity on arachidonate 5-lipoxygenase, inhibition of the 5-lipoxygenase pathway is considered to be interesting in the treatment of a variety of inflammatory diseases.
-
additional information
-
no inhibition by galanal A, galanal B and 8beta(17)-epoxy-15-hydroxy-12(E)-labden-16-al
-
additional information
-
95% ethanol extract of Glycine tomentella inhibits tilapia thrombocyte 5-LOX with IC50 of 0.00043 mg/ml
-
additional information
-
enzyme activity is inhibited by essential oil from Ballota africana (IC50: 29.99 ppm), methanol extract from Croton sylvaticus (IC50: 25.64 ppm), aqueous extract from Croton sylvaticus (IC50: 60.9 ppm), methanol extract from Melianthus comosus (IC50: 55.05 ppm), aqueous extract from Melianthus comosus (IC50: 13.84 ppm), methanol extract from Pentanisia prunelloides (IC50: 32.7 ppm), and methanol extract from Warburgia salutaris (IC50: 32.11 ppm)
-
additional information
-
isoflavones reduce active state iron to ferrous state and prevent the activation of the resting enzyme, model for the inhibition of lipoxygenase by isoflavones, overview
-
additional information
P12527
inhibitor design, synthesis, biological evaluation, and molecular modeling, overview
-
additional information
-
docking and molecular modeling studies, overview
-
additional information
-
no inhibition by 1-linoleoyl lysophosphatidylcholine and (13S)-hydroperoxy-9,11-octadecadienoyl lysophosphatidylcholine
-
additional information
-
virtual inhbitor screening, structure-function relationship analysis, overview
-
additional information
-
class of dual microsomal PGE2 synthase-1/5-lipoxygenase inhibitors based on the structure of pirinixic acid. Target oriented structural modification of pirinixic acid, particularly R substitution with extended n-alkyl or bulky aryl substituents and concomitant replacement of the 2,3-dimethylaniline by a biphenyl-4-yl-methane-amino residue, results in potent suppression of mPGES-1 and 5-lipoxygenase activity. Is not inhibited by 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-isopropyl-1H-indol-2-yl)-2,2-dimethylpropanoic acid
-
additional information
-
5-lipoxygenase may be inhibited either by the direct interaction with an inhibitor or by the binding of an inhibitor to the 5-lipoxygenase activating protein (FLAP), e.g., the clinically effective MK-0591. Highly potent FLAP inhibitors are 2,2-bisaryl-bicycloheptanes
-
additional information
-
[(hept-2-yn-1-ylsulfanyl)methyl]benzene is no inhibitor, there are no strong interactions to stabilize the compound in the 5-lipoxygenase active site
-
additional information
-
class of 1-(4-methanesulfonylphenyl and 4-aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazoles as potent dual 5-LOX and COX-1/COX-2 isozyme inhibitors of inflammation
-
additional information
-
sulindac sulfone and sulindac do not inhibit 5-LO
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(13S)-hydroperoxy-9,11-octadecadienoic acid
-
-
(13S)-hydroperoxy-9,11-octadecadienoyl lysophosphatidylcholine
-
50% activation concentration AC50 is 0.0015 mM
1,25(OH)2D3
-
gives a strong (100fold) upregulation of 5-lipoxygenase protein in differentiating Mono Mac 6 cells
5,8,11,14,17-eicosapentaenoic acid
-
competitive inhibition of oxygenation of arachidonic acid
5-lipoxygenase activating protein
-
5-lipoxygenase activating protein is crucial for conversion of endogenous substrate by 5LO 5-lipoxygenase activating protein also stimulates the utilization of exogenous arachidonic acid, and greatly (190fold) stimulates utilization of (5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
-
5-lipoxygenase-activating protein
-
a 18000 Da integral membrane protein required, in peripheral cells, for the activation of 5-lipoxygenase
-
5-lipoxygenase-activating protein
-
functional 5-LOX requires binding to 5-lipoxygenase-activating protein which helps 5-LOX binding to arachidonic acid at the nuclear membrane and enhances the efficiency of leukotriene synthesis
-
5-LO activating protein
-
i.e. FLAP, Ca2+ induces the translocation of 5-LO from a soluble compartment to nuclear structures, where 5-LO co-localizes with 5-LO activating protein
-
5-LO-activating protein
-
i.e. FLAP, a small permanently membrane-bound protein that is essential for the biosynthesis of leukotrienes from endogenous arachidonic acid. FLAP binds arachidonic acid and is thought to assist in the provision of substrate to 5-LO
-
5-LOX activating protein
-
-
-
7-thiaarachidonic acid
-
-
adenosine
-
stimulates at 0.01 mM or lower
adenosine
-
58% of the activation with ATP
adenosine
-
slight stimulation
Adenosine 5'-O-(2-thiodiphosphate)
-
stimulates at 0.01 mM or lower
ADP
-
about half as active as ATP
ADP
-
74% of the activation with ATP
ADP
-
stimulation
ADP-beta-S
-
82% of the activation with ATP
AMP
-
about half as active as ATP
AMP
-
68% of the activation with ATP
AMP
-
stimulation
AMP-4-nitrophenylphosphate
-
77% of the activation with ATP
ATP
-
required
ATP
-
half-maximal activity at 0.02 mM; stimulates
ATP
-
half-maximal stimulation at 0.031 mM
ATP
-
required
ATP
-
stimulates
ATP
-
stimulates
ATP
-
stimulates
ATP
P09917
upregulation of 5-LO through the C2-like domain
ATP
-
upregulation of 5-LO through the C2-like domain
ATP-alphaS
-
118% of the activation with ATP
ATP-gammaS
-
80% of the activation with ATP
cAMP
-
stimulation
CLP
-
can upregulate and modulate the 5-lipoxygenase pathway in vitro
-
coactosin-like protein
-
stoichiometry 1:1
-
coactosin-like protein
-
binds 5-LO and promotes leukotriene formation, coactosin-like protein prevents heat-inactivation of 5-LO
-
coactosin-like protein
-
functions as a 5-LO chaperone
-
CTP
-
about half as active as ATP
FLAP
P09917
5-LO-activating protein, a small permanently membrane-bound protein that is essential for the biosynthesis of leukotrienes from endogenous arachidonic acid. FLAP binds arachidonic acid and is thought to assist in the provision of substrate to 5-LO
-
GTP
-
stimulation
Guanosine 5'-O-(2-thiodiphosphate)
-
stimulates at 0.01 mM or lower
Nicotine
-
treatment with 0.01 mM nicotine activates 5-lipoxygenase gastric cancer cell lines from 36-72 h
phosphatidyl choline
-
addition increases catalytic activity of wild-type nzyme by 50%
phosphatidylcholine
-
stimulates
phosphatidylcholine
-
enzyme activity is supported by phosphatidylcholine more than by any other lipid tested, except for a cationic lipid, which is more stimulatory than phosphatidylcholine
phosphatidylcholine
-
-
protein factors from human leukocyte
-
stimulates
-
protein factors from human leukocyte
-
characterization of the membrane-associated stimulating factor
-
transforming growth factor beta
-
gives a strong (100fold) upregulation of 5-lipoxygenase protein in differentiating Mono Mac 6 cells
-
UTP
-
stimulation
guanosine 5'-O-(3-thiotriphosphate)
-
10fold stimulation of arachidonic acid oxidation at 0.0005-0.001 mM
additional information
-
the enzym eis upregulated in Epstein-Barr virus infected cells
-
additional information
P09917
coactosin-like protein, i.e. CLP, can bind to 5-LO and supports Ca2+-induced 5-LO enzyme activity. CLP seems to function as a chaperone or scaffold for 5-LO. About 100fold induction of 5-LO mRNA, protein and activity is found after differentiation of HL-60 and human monocytic Mono Mac 6 cells with TGF-beta and 1,25(OH)2D3, upregulation of 5-LO through the C2-like domain. Factors like cell stress and phorbol ester activate MAPK kinases, which phosphorylate the enzyme and enhance its activity and induce nuclear translocation, overview
-
additional information
-
coactosin-like protein, i.e. CLP, can bind to 5-LO and supports Ca2+-induced 5-LO enzyme activity. CLP seems to function as a chaperone or scaffold for 5-LO, upregulation of 5-LO through the C2-like domain
-
additional information
-
Ca2+-ionophore A23187
-
additional information
-
calcium ionophore A23187 increases concentrations of 5(S)-hydroxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid from 0.07 to 45.5 pmol/10000000 cells
-
additional information
-
in the mouse 5-lipoxygenase gene there are no GC-boxes in tandem, the core promoter contains only one Sp1/3 binding site
-
additional information
-
stimulated with Ca-ionophore A 23187
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.002
1-linoleoyl lysophosphatidic acid
-
pH 6.3, 25C
0.003
1-linoleoyl lysophosphatidylcholine
-
pH 6.3, 25C
0.013
5,8,11,14,17-eicosapentaenoic acid
-
-
0.024
5,8,11,14,17-eicosapentaenoic acid
-
-
0.032
5,8,11-eicosatrienoic acid
-
-
0.09
8,11,14-Eicosatrienoic acid
-
-
0.0051
arachidonate
-
reaction mixture contains 1 mM DTT, 1 mM ATP, 2 mM CaCl2, and 0.01 mM indomethacin in phosphate buffered saline, at 37C
0.02
arachidonate
-
wild-type, pH and temperature not specified in the publication
0.06
arachidonate
-
mutant DELTA1-114, pH and temperature not specified in the publication
0.012
arachidonic acid
-
-
0.015
arachidonic acid
-
-
0.017
arachidonic acid
-
-
0.019
arachidonic acid
-
-
0.022
arachidonic acid
-
-
0.0258
arachidonic acid
-
-
0.03
arachidonic acid
-
-
0.033
arachidonic acid
-
-
0.038
arachidonic acid
-
-
0.182
arachidonic acid
-
-
0.05
bishomo-gamma-linolenic acid
-
-
0.004
linoleic acid
-
pH 6.3, 25C
0.039
linoleic acid
-
-
0.039
linoleic acid
-
-
0.2
linoleic acid
-
-
additional information
additional information
-
kinetics with lysophospholipid substrates
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
25
arachidonic acid
-
-
138
linoleic acid
-
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
31000
arachidonic acid
-
at 25C
290
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0019
(17S)-hydroperoxy-4,7,10,13,15,19-docosahexaenoyl lysophosphatidylcholine
-
pH 6.3, 25C
0.025
5,8,11,14,17-eicosapentaenoic acid
-
-
0.0005
5-hydroperoxy-6,8,11,14-eicosatetraenoic acid
-
-
0.15
8,11,13-cis-icosatrienoic acid
-
-
0.0137
arachidonic acid
-
-
0.02
arachidonic acid
-
-
0.00038
arachidonoyl lysophosphatidylcholine
-
pH 6.3, 25C
additional information
additional information
-
inhibition kinetics, overview
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00077
(1-difluoromethyl-2-oxo-1,2-dihydropyridin-3-yl)acetic acid
-
pH and temperature not specified in the publication
-
0.00044
(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)acetic acid
-
pH and temperature not specified in the publication
-
0.005
(10E,12E)-octadeca-10,12-dien-8-ynoic acid
-
pH and temperature not specified in the publication
0.06
(11E)-octadec-11-en-9-ynoic acid
-
pH and temperature not specified in the publication
0.0241
(17S)-hydroperoxy-4,7,10,13,15,19-docosahexaenoyl lysophosphatidylcholine
-
pH 6.3, 25C
0.0005
(1E)-1-((1-[(1Z)-prop-1-en-1-yldisulfanyl]propyl)sulfinyl)prop-1-ene
-
pH and temperature not specified in the publication
0.0141
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0103
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.03
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0159
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0358
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.013
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[3-methoxy-4-(3-phenoxypropoxy)phenyl]prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0061
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(morpholin-4-ylcarbonyl)phenyl]prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0068
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(piperidin-1-ylcarbonyl)phenyl]prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0105
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-(pyrrolidin-1-ylcarbonyl)phenyl]prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0079
(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-[4-[(4-methylpiperazin-1-yl)carbonyl]phenyl]prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.00004
(2E)-3-(3,4-dihydroxyphenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.003
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
-
pH and temperature not specified in the publication
0.016
(2E)-3-[3-(2-ethoxyethoxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0097
(2E)-3-[4-(2-ethoxyethoxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0124
(2E)-3-[4-(3-ethoxypropoxy)-3-methoxyphenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.011
(2E)-3-[4-(benzyloxy)-3-bromo-5-methoxyphenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.0102
(2E)-3-[4-(benzyloxy)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
-
pH 7.4, temperature not specified in the publication
0.00066
(2E,2'E)-(1,1'-(2,2-bis((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
-
0.00246
(2E,2'E)-(1,1'-(2,2-bis((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
per number of caffeic acid moieties
0.00079
(2E,2'E)-(1,1'-(2-((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
-
0.00237
(2E,2'E)-(1,1'-(2-((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
per number of caffeic acid moieties
0.03
(2E,5E)-5-[(2E)-3-(furan-2-yl)prop-2-en-1-ylidene]-3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication; a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00011
(2Z)-2-[4-(acetylamino)phenyl]-3-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.00013
(5E)-2-(3-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00038
(5E)-2-(3-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00012
(5E)-2-(3-fluorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00024
(5E)-2-(3-fluorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00011
(5E)-2-(4-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00055
(5E)-2-(4-acetylphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00063
(5E)-2-(4-aminophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00193
(5E)-2-(4-aminophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00011
(5E)-2-(4-chlorophenyl)-5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.0004
(5E)-2-(4-chlorophenyl)-5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00009
(5E)-2-(4-chlorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00028
(5E)-2-(4-chlorophenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00065
(5E)-2-(4-hydroxyphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00169
(5E)-2-(4-hydroxyphenyl)-5-(4-methoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0004
(5E)-2-(4-methylphenyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00245
(5E)-2-(4-methylphenyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00098
(5E)-5-(2,4-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00202
(5E)-5-(2,4-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0008
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0013
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00048
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00054
(5E)-5-(2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00013
(5E)-5-(3,5-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00035
(5E)-5-(3,5-dimethoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0027
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.01
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.003
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.0095
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00125
(5E)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.0029
(5E)-5-(3-chloro-5-ethoxy-4-hydroxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0003
(5E)-5-(3-chlorobenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00058
(5E)-5-(3-chlorobenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.003
(5E)-5-(4-hydroxy-3-methoxy-5-nitrobenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.0044
(5E)-5-(4-hydroxy-3-methoxy-5-nitrobenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00032
(5E)-5-(4-methoxybenzylidene)-2-(4-methoxyphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.004
(5E)-5-(4-methoxybenzylidene)-2-(4-methoxyphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.0003
(5E)-5-(4-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00066
(5E)-5-(4-methoxybenzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00015
(5E)-5-(4-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.0005
(5E)-5-(4-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00053
(5E)-5-(4-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.002
(5E)-5-(4-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0003
(5E)-5-(4-tert-butylbenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00091
(5E)-5-(4-tert-butylbenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00019
(5E)-5-(4-[(methylperoxy)acetyl]benzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00211
(5E)-5-(4-[(methylperoxy)acetyl]benzylidene)-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0003
(5E)-5-(5-chloro-2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00065
(5E)-5-(5-chloro-2-hydroxy-3-methoxybenzylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0003
(5E)-5-(anthracen-9-ylmethylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.004
(5E)-5-(anthracen-9-ylmethylidene)-2-phenyl-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00035
(5E)-5-benzylidene-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00073
(5E)-5-benzylidene-2-(4-methylphenyl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.02
(5E)-5-[4-(dimethylamino)benzylidene]-2-(piperidin-1-yl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.03
(5E)-5-[4-(dimethylamino)benzylidene]-2-(piperidin-1-yl)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.012
(5Z)-2-(cyclohexylamino)-5-(4-propoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.014
(5Z)-2-(cyclohexylamino)-5-(4-propoxybenzylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.03
(5Z)-5-(4-methoxybenzylidene)-2-(pyrrolidin-1-yl)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication; a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.03
(5Z)-5-(4-methylbenzylidene)-2-(naphthalen-2-ylamino)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication; a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.03
(5Z)-5-benzylidene-2-(phenylamino)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication; a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.0039
([3-chloro-5-(2,3-dihydro-1H-inden-4-ylamino)phenyl]sulfanyl)acetic acid
-
pH and temperature not specified in the publication
0.005
([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)(naphthalen-1-yl)acetic acid
-
in intact polymorphonuclear leukocytes
0.029
1,4a-dimethyl-7-(propan-2-yl)-1-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene (non-preferred name)
-
pH and temperature not specified in the publication
0.0006
1-(2,4-difluorophenyl)-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
37C, partially purified enzyme
0.007
1-(2,4-difluorophenyl)-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
37C, intact polymorphonuclear leukocytes
0.0068
1-(2,4-dihydroxyphenyl)-2-(naphthalen-2-yl)ethanone
-
pH not specified in the publication, 37C, cell-based test system
0.01
1-(2,4-dihydroxyphenyl)-2-(naphthalen-2-yl)ethanone
-
value above, pH not specified in the publication, 37C, cell-free based test system
0.00087
1-(3,4-dichlorobenzyl)-3-(2-morpholin-4-yl-2-oxoethyl)-1H-indole
P12527
-
0.0028
1-(3,4-difluorophenyl)-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.0021
1-(3-bromophenyl)-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.0035
1-(3-chlorophenyl)-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.0066
1-(3-ethylphenyl)-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.0003
1-(3-hydroxyphenyl)-3-[4-(methylsulfonyl)phenyl]prop-2-yn-1-one
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.3
1-(3-hydroxyphenyl)-3-[4-(methylsulfonyl)phenyl]prop-2-yn-1-one
-
pH and temperature not specified in the publication
0.00039
1-(4-aminosulfonylphenyl)-5-(2-chloropyridin-4-yl)-3-trifluoromethyl-1H-pyrazole
-
-
0.005
1-(4-aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole
-
-
0.000016
1-(4-chlorobenzyl)-2-[2,2-dimethyl-3-(1H-tetrazol-5-yl)propyl]-4-methyl-6-[2-(5-phenylpyridin-2-yl)ethyl]-2,2a,4,5-tetrahydro-1H-thiopyrano[2,3,4-cd]indole
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.00225
1-(4-chlorophenoxy)-5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
-
0.00047
1-(4-methanesulfonylphenyl)-5-(2-chloropyridin-4-yl)-3-trifluoromethyl-1H-pyrazole
-
-
0.0044
1-(4-methanesulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole
-
-
0.0039
1-(6-methylpyridin-2-yl)-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.0085
1-(7-tert-butyl-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)butan-1-one
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.008
1-(8-tert-butyl-4,4-dimethyl-3,4-dihydro-2H-chromen-6-yl)-4-cyclopropylbutan-1-one
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.76
1-(benzyloxy)hept-2-yn-4-ol
-
-
0.0034
1-(difluoromethyl)-5-[[2-(methylsulfonyl)phenyl]ethynyl]pyridin-2(1H)-one
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.003
1-benzyl-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
37C, intact polymorphonuclear leukocytes
0.01
1-benzyl-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
above, 37C, partially purified enzyme
0.00317
1-benzyl-3-(3-morpholin-4-yl-3-oxopropyl)-1H-indole
P12527
-
0.00085
1-benzyl-3-(4-oxo-4-piperazin-1-ylbutyl)-1H-indole
P12527
-
0.00095
1-benzyl-5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
-
0.0038
1-hydroxy-1-[1-(5-methoxy-1-methyl-1H-indol-2-yl)ethyl]urea
-
pH and temperature not specified in the publication
0.005
1-O-dodecyl 2,3-O-isopropylidene-5,6-dideoxy-5-N-[4-(2-hydroxy-2-oxoethyl) phenylaminocarbonyl] amino-beta-L-gulofuranoside sodium salt
-
competitive inhibitior, IC50: 0.0035 mM with recombinant enzyme, IC50: 0.005 mM with native enzyme
0.0039
1-phenyl-5-(propan-2-yl)-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.045
1-[(4methylbenzyl)oxy]hept-2-yn-4-ol
-
-
0.0056
1-[1-(6-tert-butyl-1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
-
pH and temperature not specified in the publication
0.0049
1-[3-(benzyloxy)phenyl]-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.001
1-[3-(methylsulfanyl)phenyl]-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
37C, partially purified enzyme
0.004
1-[3-(methylsulfanyl)phenyl]-3-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)urea
-
37C, intact polymorphonuclear leukocytes
0.00034
1-[4-([3-fluoro-5-[4-(methylsulfinyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
-
pH and temperature not specified in the publication
0.000195
1-[4-([3-fluoro-5-[4-(methylsulfonyl)tetrahydro-2H-pyran-4-yl]phenoxy]methyl)phenyl]-2-methyl-1H-imidazole
-
pH and temperature not specified in the publication
0.017
10,17(S)-dihydroxydocosahexaenoic acid
-
IC50: 0.017 mM
0.015
11,14,17-Eicosatrienoic acid
-
IC50: 0.015 mM
0.0048
15-hydroperoxy-6,8,11,13-eicosatetraenoic acid
-
IC50: 0.0048 mM
0.0037
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-3-yl)propanoic acid
-
pH and temperature not specified in the publication
-
0.0002
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
pH and temperature not specified in the publication
-
0.00025
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)propanoic acid
-
pH and temperature not specified in the publication
-
0.00046
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-5-yl)acetic acid
-
pH and temperature not specified in the publication
0.003
2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-5-yl)propanoic acid
-
pH and temperature not specified in the publication
-
0.0015
2-(2,2-dimethyl-6-(4-nitrophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
0.00031
2-(2,2-dimethyl-7-phenyl-6-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
0.1
2-(2,4-dihydroxyphenyl)-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one
-
pH and temperature not specified in the publication
0.004
2-(2-methoxyphenyl)-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)acetamide
-
37C, intact polymorphonuclear leukocytes
0.01
2-(2-methoxyphenyl)-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)acetamide
-
above, 37C, partially purified enzyme
0.0055
2-(2-[ethyl(hydroxy)amino]ethyl)dibenzo[b,e]oxepin-11(6H)-one
-
pH and temperature not specified in the publication
0.03
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
-
pH and temperature not specified in the publication
0.02 - 2
2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
-
pH and temperature not specified in the publication
0.0032
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
-
pH and temperature not specified in the publication
0.0036
2-(3-methylbut-2-en-1-yl)-6H-[1]benzofuro[3,2-c]chromene-3,6,9-triol
-
pH and temperature not specified in the publication
0.0049
2-(3-[hydroxy(methyl)amino]propyl)dibenzo[b,e]oxepin-11(6H)-one
-
pH and temperature not specified in the publication
0.0007
2-(4-(biphenyl-4-ylamino)-6-chloropyrimidine-2-ylthio)octanoic acid
-
in intact polymorphonuclear leukocytes
0.0015
2-(4-(biphenyl-4-ylamino)-6-chloropyrimidine-2-ylthio)octanoic acid
-
purified 5-lipoxygenase
0.001
2-(4-(biphenyl-4-ylmethylamino)-6-chloropyrimidin-2-ylthio)octanoic acid
-
in intact polymorphonuclear leukocytes
0.002
2-(4-(biphenyl-4-ylmethylamino)-6-chloropyrimidin-2-ylthio)octanoic acid
-
purified 5-lipoxygenase
0.0004
2-(4-chloro-6-(4'-cyanobiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
in intact polymorphonuclear leukocytes
0.0015
2-(4-chloro-6-(4'-cyanobiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
purified 5-lipoxygenase
0.0005
2-(4-chloro-6-(5-methoxy-2-methylbiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
in intact polymorphonuclear leukocytes
0.002
2-(4-chloro-6-(5-methoxy-2-methylbiphenyl-4-ylamino)pyrimidin-2-ylthio)octanoic acid
-
purified 5-lipoxygenase
0.00023
2-(4-methylphenyl)-5-(2-phenylethenylidene)-1,3-thiazol-4(5H)-one
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.0004
2-(4-methylphenyl)-5-(2-phenylethenylidene)-1,3-thiazol-4(5H)-one
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.0008
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(5-methyl-1,3-thiazol-2-yl)propanamide
-
37C, partially purified enzyme
0.001
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(5-methyl-1,3-thiazol-2-yl)propanamide
-
37C, intact polymorphonuclear leukocytes
0.0008
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-1,3-thiazol-2-ylpropanamide
-
37C, in intact polymorphonuclear leukocytes
0.001
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-1,3-thiazol-2-ylpropanamide
-
37C, partially purified enzyme
0.0009
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
-
37C, intact polymorphonuclear leukocytes
0.006
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
-
37C, partially purified enzyme
0.003
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-thiophen-3-ylpropanamide
-
37C, partially purified enzyme
0.008
2-(5,8-dimethyl-7-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-thiophen-3-ylpropanamide
-
37C, intact polymorphonuclear leukocytes
0.00023
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-(methylsulfonyl)acetamide
-
-
0.00025
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-(phenylsulfonyl)acetamide
-
-
0.00026
2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-N-tosylacetamide
-
-
0.0016
2-(6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
0.00018
2-(6-(4-tert-butylphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid
-
-
0.008
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(thiophen-2-ylmethyl)propanamide
-
37C, intact polymorphonuclear leukocytes
0.01
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-(thiophen-2-ylmethyl)propanamide
-
37C, partially purified enzyme
0.0008
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
-
37C, partially purified enzyme
0.005
2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-pyridin-2-ylpropanamide
-
37C, intact polymorphonuclear leukocytes
0.0008
2-(dibenzo[b,d]furan-3-yl)-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-free based test system
0.01
2-(dibenzo[b,d]furan-3-yl)-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
value above, pH not specified in the publication, 37C, cell-based test system
0.0041
2-([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)octanoic acid
-
in intact polymorphonuclear leukocytes
0.0065
2-([4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl]sulfanyl)octanoic acid
-
purified 5-lipoxygenase
0.01
2-benzyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
value above, pH not specified in the publication, 37C, cell-based test system; value above, pH not specified in the publication, 37C, cell-free based test system
0.0014
2-hexyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-free based test system
0.003
2-hexyl-5-hydroxycyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-based test system
0.0046
2-hydroxy-5-(3-nitrophenyl)cyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-free based test system
0.01
2-hydroxy-5-(3-nitrophenyl)cyclohexa-2,5-diene-1,4-dione
-
value above, pH not specified in the publication, 37C, cell-based test system
0.00078
2-hydroxy-5-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-free based test system
0.0023
2-hydroxy-5-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
-
value above, pH not specified in the publication, 37C, cell-based test system
0.01
2-hydroxy-5-methoxy-3-(naphthalen-2-ylmethyl)cyclohexa-2,5-diene-1,4-dione
-
value above, pH not specified in the publication, 37C, cell-based test system; value above, pH not specified in the publication, 37C, cell-free based test system
0.00028
2-methoxy-5-(naphthalen-2-yloxy)cyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-free based test system
0.0067
2-methoxy-5-(naphthalen-2-yloxy)cyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-based test system
0.01
2-[(1-hydroxy-6-oxo-1,6-dihydropyridin-3-yl)ethynyl]benzenesulfonamide
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.0015
2-[(4-[[3,5-bis(2,2,2-trifluoroethoxy)phenyl]amino]-6-chloropyrimidin-2-yl)sulfanyl]octanoic acid
-
in intact polymorphonuclear leukocytes
0.003
2-[(4-[[3,5-bis(2,2,2-trifluoroethoxy)phenyl]amino]-6-chloropyrimidin-2-yl)sulfanyl]octanoic acid
-
purified 5-lipoxygenase
0.002
2-[2-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
pH and temperature not specified in the publication
-
0.00037
2-[3-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
pH and temperature not specified in the publication
-
0.006
2-[4'-(iso-propylphenyl)-amino]-5,6-dimethyl-1,4-benzoquinone
-
potent inhibitor, IC50: 0.006 mM
0.003
2-[4-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]propanoic acid
-
pH and temperature not specified in the publication
-
0.00068
2-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
; per number of caffeic acid moieties
0.00018
2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
-
-
0.001
2-[7-[2-(dimethylamino)ethoxy]-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]-N-1,3-thiazol-2-ylpropanamide
-
37C, partially purified enzyme
0.01
2-[7-[2-(dimethylamino)ethoxy]-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]-N-1,3-thiazol-2-ylpropanamide
-
above, 37C, intact polymorphonuclear leukocytes
0.01
3'-nitrobiphenyl-2,4-diol
-
value above,pH not specified in the publication, 37C, cell-based test system; value above, pH not specified in the publication, 37C, cell-free based test system
0.0009
3,4,5-trimethoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
-
37C, in intact polymorphonuclear leukocytes
0.01
3,4,5-trimethoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
-
above, 37C, partially purified enzyme
0.00037
3-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
pH and temperature not specified in the publication
-
0.01
3-(2-(2-[(4-chlorophenyl)sulfanyl]ethoxy)-3-methoxy-5-[5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-2-yl]benzyl)-1-hydroxy-1-methylurea
-
pH and temperature not specified in the publication
0.0042
3-(4,5-dihydroxy-2-methyl-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-1-yl)-2-hydroxy-4,6-dimethoxybenzoic acid
-
pH and temperature not specified in the publication
0.00206
3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
-
0.01
3-(cyclohexylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
-
value above, pH not specified in the publication, 37C, cell-based test system; value above, pH not specified in the publication, 37C, cell-free based test system
0.00058
3-(decahydronaphthalen-2-ylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-based test system
0.011
3-(decahydronaphthalen-2-ylmethyl)-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
-
pH not specified in the publication, 37C, cell-free based test system
0.01
3-benzyl-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
-
value above, pH not specified in the publication, 37C, cell-based test system; value above, pH not specified in the publication, 37C, cell-free based test system
0.0015
3-ethoxy-11-oxours-12-en-23-oic acid
-
pH and temperature not specified in the publication
0.00238
3-[2-[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]ethyl]-1H-indole
P12527
-
0.32
3-[4-(methylsulfonyl)phenyl]-1-[4-(propan-2-yl)phenyl]prop-2-yn-1-one
-
pH and temperature not specified in the publication
0.0005
3-[5-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
-
pH and temperature not specified in the publication
0.000003
3-[[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]methyl]-1-[4-(methylsulfonyl)phenyl]-5-phenyl-1H-pyrazole
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.0013
4,7,10,13,16,19-docosahexaenoic acid
-
IC50: 0.0013 mM
0.0085
4,9-dimethoxy-3-methyl-9,10-dihydrophenanthrene-2,7-diol
-
pH and temperature not specified in the publication
0.01
4-(1-benzothiophen-3-yl)benzene-1,3-diol
-
value above, pH not specified in the publication, 37C, cell-based test system; value above, pH not specified in the publication, 37C, cell-free based test system
0.074
4-(1-benzyl-1H-indol-3-yl)-1-morpholinobutan-1-one
P12527
-
0.00347
4-(1-difluoromethyl-2-oxo-1,2-dihydropyridin-4-yl)phenylacetic acid
-
pH and temperature not specified in the publication
-
0.0068
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)-N-methyltetrahydro-2H-pyran-4-carboxamide
-
pH and temperature not specified in the publication
0.0006
4-(3-fluoro-5-[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-ol
-
pH and temperature not specified in the publication
0.00054
4-(3-fluoro-5[[4-(2-methyl-1H-imidazol-1-yl)benzyl]oxy]phenyl)tetrahydro-2H-pyran-4-carboxylic acid
-
pH and temperature not specified in the publication
0.00018
4-(4-chlorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-2H-chromen-2-one
-
IC50: 180 nM
0.008
4-(4-fluorophenyl)-5-(4-(methylsulfonyl)phenyl)-1,2-selenazole
-
-
0.000055
4-(4-fluorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenoxy]methyl)-2H-chromen-2-one
-
IC50: 55 nM
0.000027
4-(4-fluorophenyl)-7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-2H-chromen-2-one
-
IC50: 27 nM
0.003
4-(6-methoxynaphthalen-2-yl)butan-2-one
-
value above, pH and temperature not specified in the publication
0.0077
4-(acetyloxy)-2-[4-(acetyloxy)-6-methylhept-5-en-2-yl]cyclohexyl (2Z)-2-methylbut-2-enoate
-
pH and temperature not specified in the publication
0.0063
4-(dibenzo[b,d]furan-3-yl)benzene-1,3-diol
-
pH not specified in the publication, 37C, cell-free based test system
0.01
4-(dibenzo[b,d]furan-3-yl)benzene-1,3-diol
-
value above, pH not specified in the publication, 37C, cell-based test system
0.0055
4-(furan-3-yl)-7-[[2-(tetrahydro-2H-pyran-4-yl)pyridin-4-yl]methoxy]naphthalene-2-carbonitrile
-
pH and temperature not specified in the publication
0.000015
4-(furan-3-yl)-7-[[6-(4-hydroxytetrahydro-2H-pyran-4-yl)pyridin-2-yl]methoxy]naphthalene-2-carbonitrile
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.0038
4-(furan-3-yl)-7-[[7-(tetrahydro-2H-pyran-4-yl)-1,2,3,4-tetrahydroquinolin-2-yl]oxy]naphthalene-2-carbonitrile
-
pH and temperature not specified in the publication
0.0023
4-(naphthalen-2-ylmethyl)benzene-1,3-diol
-
value above, pH not specified in the publication, 37C, cell-based test system
0.0074
4-(naphthalen-2-ylmethyl)benzene-1,3-diol
-
pH not specified in the publication, 37C, cell-free based test system
0.0021
4-(thianthren-2-yl)benzene-1,3-diol
-
pH not specified in the publication, 37C, cell-based test system
0.0032
4-(thianthren-2-yl)benzene-1,3-diol
-
pH not specified in the publication, 37C, cell-free based test system
0.009
4-benzylbenzene-1,3-diol
-
pH not specified in the publication, 37C, cell-free based test system
0.01
4-benzylbenzene-1,3-diol
-
value above, pH not specified in the publication, 37C, cell-based test system
0.00042
4-chloro-N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00042 mM
0.00083
4-chloro-N-([4-[(2E)-3-phenylprop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00083 mM
0.0028
4-hexylbenzene-1,3-diol
-
value above, pH not specified in the publication, 37C, cell-based test system
0.0046
4-hexylbenzene-1,3-diol
-
pH not specified in the publication, 37C, cell-free based test system
0.00001
4-methoxy-4-[3-(naphthalen-2-ylmethoxy)phenyl]tetrahydro-2H-pyran
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.006
4-methoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
-
37C, intact polymorphonuclear leukocytes
0.01
4-methoxy-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)benzamide
-
above, 37C, partially purified enzyme
0.01
4-methyl-N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,2,3-thiadiazole-5-carboxamide
-
37C, intact polymorphonuclear leukocytes; above, 37C, partially purified enzyme
0.00045
4-methyl-N-([4-[(2E)-3-(2,3,4-trimethylphenyl)prop-2 enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00045 mM
0.00089
4-methyl-N-([4-[(2E)-3-phenylprop-2-enoyl]phenyl]carbamoyl)benzenesulfonamide
-
IC50: 0.00089 mM
0.0114
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-hydroxy-5-nitrophenyl)benzamide
-
pH 7.4, temperature not specified in the publication
0.0165
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-hydroxyphenyl)benzamide
-
pH 7.4, temperature not specified in the publication
0.0249
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-methoxyphenyl)benzamide
-
pH 7.4, temperature not specified in the publication
0.0142
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(2-phenylethyl)benzamide
-
pH 7.4, temperature not specified in the publication
0.0221
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-(propan-2-yl)benzamide
-
pH 7.4, temperature not specified in the publication
0.0204
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-methyl-N-phenylbenzamide
-
pH 7.4, temperature not specified in the publication
0.0129
4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]-N-propylbenzamide
-
pH 7.4, temperature not specified in the publication
0.000036
4-[1-(4-chlorobenzyl)-4-methyl-6-[(5-phenylpyridin-2-yl)methoxy]-2,2a,4,5-tetrahydro-1H-thiopyrano[2,3,4-cd]indol-2-yl]-3,3-dimethyl-N-(methylsulfonyl)butanamide
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.00007
4-[4-(4-fluoro-phenyl)-thiazol-2-ylamino]-2,6-dimethylphenol
-
in 50 mM Tris-HCl buffer (pH 7.4) containing 0.4 mM CaCl2+ , 0.024 mg/ml alpha-phosphatidylcholine and 0.02 mM ATP, at 22C
-
0.041
4-[5-(1H-indol-3-yl)-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.01
4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.002
5,5'-di(prop-2-en-1-yl)biphenyl-2,2'-diol
-
pH and temperature not specified in the publication
0.0048
5,5-dimethyl-1-phenyl-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.028
5,8,11,13-eicosatetraynoic acid
-
IC50: 0.028 mM
0.00077
5-(2-[[3-(trifluoromethyl)phenyl]amino]phenyl)-1,3,4-oxadiazole-2(3H)-thione
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.003
5-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole
-
value above, pH and temperature not specified in the publication
0.006
5-(7-tert-butyl-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-5-oxopentanenitrile
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.0084
5-butyl-1-phenyl-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.00133
5-chloro-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
-
0.006
5-ethyl-1-phenyl-1,2,4-triazinan-3-one
-
pH and temperature not specified in the publication
0.00316
5-methoxy-2-methyl-3-(4-morpholin-4-yl-4-oxobutyl)-1H-indole
P12527
-
0.00137
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
-
pH and temperature not specified in the publication
0.009
6-[(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]naphthalene-2-carboxylic acid
-
pH not specified in the publication, 37C, cell-free based test system
0.01
6-[(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]naphthalene-2-carboxylic acid
-
value above, pH not specified in the publication, 37C, cell-based test system
0.00033
6-[[3-fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenoxy]methyl]-1-methylquinolin-2(1H)-one
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.007
7,17(S)-dihydroxydocosahexaenoic acid
-
IC50: 0.007 mM
0.0069
7,8-dihydroxy-2H-chromen-2-one
-
pH and temperature not specified in the publication
0.01
7-(4-methylphenyl)-6-[4-(methylsulfonyl)phenyl]-2,3-dihydro-1H-pyrrolizine
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.000175
7-([3-fluoro-5-[(1R)-1-hydroxy-1-pyridin-2-ylpropyl]phenoxy]methyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 175 nM
0.0002
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 200 nM
0.0003
7-([3-fluoro-5-[(1R,3R,5S)-3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl]phenoxy]methyl)-4-phenyl-2H-chromen-2-one
-
IC50: 300 nM
0.000175
7-([3-fluoro-5-[(1S)-1-hydroxy-1-(1,3-thiazol-2-yl)propyl]phenoxy]methyl)-4-(4-fluorophenyl)-2H-chromen-2-one
-
IC50: 175 nM
0.000009
7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-4-furan-3-yl-2H-chromen-2-one
-
IC50: 9 nM
0.000026
7-([3-fluoro-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]sulfanyl)-4-phenyl-2H-chromen-2-one
-
IC50: 26 nM
0.022
7-tert-butyl-N-ethyl-N,3,3-trimethyl-2,3-dihydro-1-benzofuran-5-carboxamide
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.000015
7-[[3-(1-ethyl-1-hydroxypropyl)-5-fluorophenoxy]methyl]-4-furan-3-yl-2H-chromen-2-one
-
IC50: 15 nM
0.000014
7-[[3-(4-methoxytetrahydro-2H-pyran-4-yl)benzyl]oxy]-4-phenylnaphtho[2,3-c]furan-1(3H)-one
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.000027
7-[[3-fluoro-5-(3-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-yl)phenoxy]methyl]-4-(furan-3-yl)quinoline-2-carbonitrile
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.00219
8,11,14-Eicosatrienoic acid
-
IC50: 0.00219 mM
0.0026
AA861
-
IC50: 0.0026 mM
0.004 - 0.01
AA861
-
i.e. 2-(12-hydroxydodeca-5,10-diynyl)-3,5,6-trimethyl-1,4-benzoquinone, IC50: 0.004-0.01 mM
0.0039
acetonylacetone bisphenylhydrazone
-
IC50 for reaction with linoleic acid: 0.015 mM, IC50 for reaction with arachidonic acid: 0.0039 mM
0.00023
arachidonic acid
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00023 mM
0.0166
arachidonoyl lysophosphatidylcholine
-
pH 6.3, 25C
0.0012
baicalein
-
IC50: 0.0012 mM
0.0014
benzaldehyde phenylhydrazone
-
IC50 for reaction with linoleic acid: 0.0345 mM, IC50 for reaction with arachidonic acid: 0.0014 mM
0.00013
benzyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00035
benzyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.00017
benzyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00048
benzyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0028
biphenyl-2,4-diol
-
pH not specified in the publication, 37C, cell-free based test system
0.0042
biphenyl-2,4-diol
-
pH not specified in the publication, 37C, cell-based test system
0.004 - 0.015
BW755C
-
IC50: 0.004-0.015 mM
0.013
BW755C
-
i.e. 3-amino-1-[3-(trifluoromethyl)phenyl]-2-pyrazoline, IC50: 0.013 mM
0.53
BW755C
-
IC50: 0.53 mM
0.004
caffeic acid
-
-
0.004
caffeic acid
-
pH and temperature not specified in the publication
0.025
caffeic acid
-
-
0.046
caffeic acid
-
IC50: 0.046 mM
0.062
catechol
-
IC50: 0.062 mM
0.0195
celecoxib
-
37C, whole blood assay
0.098
Cirsiliol
-
IC50: 0.098 mM
0.00115 - 0.00155
CJ-13610
-
pH 7.5, 37C, dependent on assay method via fluorescence or UV measurement, kinetics, overview
0.157
daidzein
-
pH 7.4, 27C
0.0069
delphinidin 3-O-galactoside
-
-
0.00215
delphinidin 3-O-glucoside
-
-
0.002 - 0.005
diphenyldisulfide
-
IC50: 0.002-0.005 mM
0.00065
eicosapentaenoic acid
-
induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00065 mM
0.98
epinephrine
-
IC50: 0.98 mM
0.0045
esculetin
-
IC50: 0.0045 mM
0.00065
ethyl 1-benzyl-2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0018
ethyl 1-benzyl-2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.000097
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0012
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0016
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0017
ethyl 2-(2-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.00015
ethyl 2-(3-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00045
ethyl 2-(3-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.000086
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00023
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0017
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.002
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00058
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-pyrrolo[2,3-f]quinoline-3-carboxylate
-
recombinant 5-lipoxygenase
0.0043
ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-pyrrolo[2,3-f]quinoline-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0012
ethyl 2-(3-chlorobenzyl)-5-hydroxy-6-phenyl-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0057
ethyl 2-(3-chlorobenzyl)-5-hydroxy-6-phenyl-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.01
ethyl 2-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.03
ethyl 2-(3-chlorobenzyl)-5-methoxy-1-methyl-1H-benzo[g]-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.03
ethyl 2-(3-chlorobenzyl)-5-phenyl-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils; recombinant 5-lipoxygenase
0.007
ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.01
ethyl 2-(3-chlorobenzyl)-7,8-dimethoxy-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.000045
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00052
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0033
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0048
ethyl 2-(3-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00014
ethyl 2-(3-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00034
ethyl 2-(3-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.00013
ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00052
ethyl 2-(3-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.000095
ethyl 2-(4-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0006
ethyl 2-(4-bromobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.000084
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0012
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0007
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0012
ethyl 2-(4-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.000067
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00032
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.002
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0021
ethyl 2-(4-chlorophenyl)-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.000096
ethyl 2-(4-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0005
ethyl 2-(4-fluorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.00015
ethyl 2-(4-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00065
ethyl 2-(4-methoxybenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.00025
ethyl 2-(4-trifluoromethylbenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0017
ethyl 2-(4-trifluoromethylbenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0003
ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0024
ethyl 2-[(3-chlorophenyl)-amino]-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.000031
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00049
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0017
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0028
ethyl 2-[2-(3-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.000049
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0028
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0007
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0039
ethyl 2-[2-(4-chlorophenyl)ethyl]-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0006
ethyl 2-[[4-chloro-6-(quinolin-6-ylamino)pyrimidin-2-yl]sulfanyl]octanoate
-
in intact polymorphonuclear leukocytes
0.019
ethyl 2-[[4-chloro-6-(quinolin-6-ylamino)pyrimidin-2-yl]sulfanyl]octanoate
-
purified 5-lipoxygenase
0.0034
ethyl 5-benzoyloxy-2-(3-chlorobenzyl)-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.01
ethyl 5-benzoyloxy-2-(3-chlorobenzyl)-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0055
ethyl 5-hydroxy-2-phenylethyl-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0073
ethyl 5-hydroxy-2-phenylethyl-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00013
ethyl 5-hydroxy-2-phenylpropyl-1H-benzo[g]indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.00044
ethyl 5-hydroxy-2-phenylpropyl-1H-benzo[g]indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.00033
ethyl 6-biphenyl-4-yl-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0028
ethyl 6-biphenyl-4-yl-(3-chlorobenzyl)-5-hydroxy-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.026
Eugenol
-
non-competitive, reversible inhibitor, IC50: 0.026 mM
0.098
eupatilin
-
IC50: 0.098 mM
0.125
genistein
-
pH 7.4, 27C
0.36
indomethacin
-
IC50: 0.36 mM
0.0003 - 0.0004
L-651,896
-
i.e. 2,3-dihydro-6-[3-(2-hydroxymethyl)-phenyl-2-propenyl]-5-benzofuranol, IC50: 0.0003-0.0004 mM
0.0003 - 0.0004
L-656,224
-
IC50: 0.0003-0.0004 mM
0.0008
L-656,224
-
i.e. 7-chloro-2-[(4-methoxyphenyl)-methyl]-3-methyl-5-propyl-4-benzofuranol, IC50: 0.0008 mM
0.0004
L-670,630
-
IC50: 0.0004 mM
0.0003
L-689,065
-
IC50: 0.0003 mM
0.00002
L-697,198
-
IC50: 0.00002 mM
-
0.0015
L-702,701
-
IC50: 0.0015 mM
-
0.000027
L-746,530
-
IC50: 27 nM
0.00002
L705,302
-
IC50: 0.00002 mM
-
0.00058
methyl (4-[(5E)-5-(4-methoxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]phenoxy)acetate
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00086
methyl (4-[(5E)-5-(4-methoxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]phenoxy)acetate
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.03
methyl 2-(allylamino)-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils; recombinant 5-lipoxygenase
0.0034
methyl 2-(benzylamino)-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.004
methyl 2-(benzylamino)-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0069
methyl 2-(diallylamino)-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0125
methyl 2-(diallylamino)-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0098
methyl 2-[(2-chlorophenyl)amino]-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0102
methyl 2-[(2-chlorophenyl)amino]-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0035
methyl 2-[(3-bromophenyl)amino]-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0083
methyl 2-[(3-bromophenyl)amino]-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0065
methyl 2-[(3-chlorophenyl)amino]-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0081
methyl 2-[(3-chlorophenyl)amino]-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0035
methyl 2-[(3-chlorophenyl)amino]-5-chloro-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0055
methyl 2-[(3-chlorophenyl)amino]-5-chloro-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0079
methyl 2-[(3-fluorophenyl)amino]-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0134
methyl 2-[(3-fluorophenyl)amino]-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.0072
methyl 2-[(4-chlorophenyl)amino]-1H-indole-3-carboxylate
-
5-lipoxygenase inhibited in neutrophils
0.0098
methyl 2-[(4-chlorophenyl)amino]-1H-indole-3-carboxylate
-
recombinant 5-lipoxygenase
0.004
miogadial
-
potent inhibitor, IC50: 0.004 mM
0.0075
miogatrial
-
potent inhibitor, IC50: 0.0075 mM
0.0032
MK-886
-
37C, whole blood assay
0.0163
N-(2,4-dimethylphenyl)-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
pH 7.4, temperature not specified in the publication
0.002
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,3-benzodioxole-5-carboxamide
-
37C, intact polymorphonuclear leukocytes
0.01
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)-1,3-benzodioxole-5-carboxamide
-
above, 37C, partially purified enzyme
0.008
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)cyclopentanecarboxamide
-
37C, intact polymorphonuclear leukocytes
0.01
N-(3,5a,10-trimethyl-2-oxo-2,3,3a,4,5,5a,6,10,10a,10b-decahydrofuro[3',2':7,8]naphtho[2,3-d][1,3]thiazol-8-yl)cyclopentanecarboxamide
-
37C, partially purified enzyme
0.000038
N-(3-phenoxycinnamyl)-acetohydroxamic acid
-
recombinant 5-lipoxygenase
0.00016
N-(3-phenoxycinnamyl)-acetohydroxamic acid
-
5-lipoxygenase inhibited in neutrophils
0.0001
N-(4-chlorophenyl)-N-hydroxy-N'-(3-chlorophenyl)urea
-
IC50: 0.0001 mM
0.0009
N-(furan-2-ylmethyl)-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
37C, partially purified enzyme
0.01
N-(furan-2-ylmethyl)-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
above, 37C, intact polymorphonuclear leukocytes
0.00045
N-([4-[(2E)-3-(2,4-dichlorophenyl)prop-2-enoyl]phenyl]carbamoyl)-4-methylbenzenesulfonamide
-
IC50: 0.00045 mM
0.018
N-benzyl-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
pH 7.4, temperature not specified in the publication
0.01
N-cyclopentyl-2-[7-(2-methoxyethoxy)-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide
-
above, 37C, intact polymorphonuclear leukocytes; above, 37C, partially purified enzyme
0.0157
N-dodecyl-4-[(1E)-3-(2-hydroxy-4-methoxyphenyl)-3-oxoprop-1-en-1-yl]benzamide
-
pH 7.4, temperature not specified in the publication
0.00005
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
a cell-free assay utilizing the 100000g supernatant (S100) of human polymorphonuclear leukocytes (PMNL) homogenates is applied, pH and temperature not specified in the publication
0.00008
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
a cell-based test system using isolated human polymorphonuclear leukocytes is applied, pH and temperature not specified in the publication
0.00011
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
in intact polymorphonuclear leukocytes
0.00016
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
purified 5-lipoxygenase
0.15
N-hydroxy-N-[(2E)-3-(3-phenoxyphenyl)prop-2-en-1-yl]acetamide
-
pH and temperature not specified in the publication
0.00119
N-hydroxy-N-[1-(1-methyl-1H-indol-2-yl)ethyl]acetamide
-
pH and temperature not specified in the publication
0.0005
N-methyl-2[4-(2,4,6-trimethylphenyl)phenyl]-propenehydroxamic acid
-
IC50: 0.0005 mM
0.004
N-tert-butyl-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
37C, partially purified enzyme
0.01
N-tert-butyl-2-(7-methoxy-5,8-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
-
above, 37C, intact polymorphonuclear leukocytes
0.01
N-[2-(cyclohexyloxy)-4-nitrophenyl]methanesulfonamide
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.00013
N-[5-(4-fluorophenoxy)thiophen-2-yl]methanesulfonamide
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.00009
nordihydroguaiaretic acid
-
pH 7.5, 37C, assay method via fluorescence measurement
0.001
nordihydroguaiaretic acid
-
-
0.0015
nordihydroguaiaretic acid
-
-
0.00021
nordihydroguiaraetic acid
-
IC50: 0.00021 mM
0.0365
nordihydroguiaraetic acid
-
IC50 for reaction with linoleic acid: 0.17 mM, IC50 for reaction with arachidonic acid: 0.0365 mM
0.49
norepinephrine
-
IC50: 0.49 mM
0.0656
ochnaflavone
-
IC50: 0.0656 mM
0.005 - 0.01
Phenidone
-
IC50: 0.005-0.01 mM
0.0086
polygodial
-
strong inhibitory activity, IC50: 0.0086 mM
0.0003 - 0.0005
quercetin
-
IC50: 0.0003-0.0005 mM
0.0021
quercetin
-
IC50: 0.0021 mM
0.033
rutin
-
IC50: 0.033 mM
0.00013
SC-756
-
pH 7.5, 37C, assay method via fluorescence measurement
0.02
sulindac sulfide
-
pH and temperature not specified in the publication
0.00074
tert-butyl 4-[4-(1H-indol-3-yl)butanoyl]piperazine-1-carboxylate
P12527
-
0.0003
ZD 2138
-
i.e. CAS: 140841-32-3, IC50: 0.0003 mM
0.00011 - 0.00012
ZD-2138
-
pH 7.5, 37C, dependent on assay method via fluorescence or UV measurement
0.00012 - 0.00092
zileuton
-
pH 7.5, 37C, dependent on assay method via fluorescence or UV measurement
0.00028
zileuton
-
in 50 mM Tris-HCl buffer (pH 7.4) containing 0.4 mM CaCl2+ , 0.024 mg/ml alpha-phosphatidylcholine and 0.02 mM ATP, at 22C
0.0008
zileuton
-
recombinant 5-lipoxygenase
0.00083
zileuton
P12527
-
0.0009
zileuton
-
5-lipoxygenase inhibited in neutrophils
0.0011
zileuton
-
IC50: 0.0038 mM with recombinant enzyme, IC50: 0.0011 mM with native enzyme
0.01
zileuton
-
IC50: 0.01 mM
0.00009
ZM 230,486
-
IC50: 0.00009 mM
0.00074
[1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
-
0.00148
[1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
per number of caffeic acid moieties
0.0075
[2-[(1S,8aR)-2-formyl-5,5,8a-trimethyldecahydronaphthalen-1-yl]ethylidene]propanedial
-
in 100 mM phosphate buffer, pH 6.3, 25C
0.1
ML-3000
-
above, 37C, whole blood assay
additional information
additional information
-
enzyme inhibition in presence of inhibitor and glutathione peroxidase, overview
-
additional information
additional information
-
inhibitory activity in polymorphonuclear leukocytes, overview
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.006
-
-
0.0069
-
-
5.7
-
enzyme form L2
13.7
-
enzyme form L1
21.9
-
commercial prearation
additional information
-
assay methods
additional information
-
-
additional information
-
-
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
-
assay at
7.4
-
assay at
7.5 - 8
-
-
7.5
-
assay at
additional information
-
pH of the reaction has profound influence on the product profile
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
3.5 - 7
-
almost inactive at pH 3.5 and at pH 7.0
7 - 9
-
pH 7.0: 66% of maximal activity, pH 9.0: about 60% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
27
-
assay at
37
-
assay at
37
P48999
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
expression is not significantly different between diabetic and control rats. Activation of the 5-lipoxygenase previously reported in streptozotocin-induced diabetic rats can be explained by an augmented sensitivity to cysteinyl leukotrienes in the diabetic aorta
Manually annotated by BRENDA team
P48999
of young and old mice, comparison of enzyme expression and activity in brain regions, e.g. cortex, hippocampus and cerebellum, overview
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
of young and old mice, comparison of enzyme expression and activity in brain regions, e.g. cortex, hippocampus and cerebellum, overview
-
Manually annotated by BRENDA team
-
in healthy animals, 5-LOX expression is almost exclusively limited to the bronchiolar epithelial cells, while Metastrongylus spp.-parasitized pigs have greater 5-LOX-specific immunoreactivity involving a wide range of cell types within foci of granulomatous and eosinophilic bronchopneumonia
Manually annotated by BRENDA team
-
Epstein-Barr virus-converted B lymphoma cells
Manually annotated by BRENDA team
-
of diverse tissues, e.g. colon, lung breast, prostate, pancreas, bone, brain, and mesothelial cancer cells
Manually annotated by BRENDA team
-
high level of expression
Manually annotated by BRENDA team
P48999
highest expresion of the enzyme in brain
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
highest expresion of the enzyme in brain
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
-
osteoarthritic chondrocyte
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
atherosclerotic tissue
Manually annotated by BRENDA team
-
foam cell of human atherosclerotic tissue
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
Mus musculus C57BL/6J
-
-
-
Manually annotated by BRENDA team
-
high level of expression, colocalization of 5-lipoxygenase and 5-lipoxygenase-activating protein in CA1 pyramidal neurons
Manually annotated by BRENDA team
P48999
increased enzyme content in older rats, overview
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
increased enzyme content in older rats, overview
-
Manually annotated by BRENDA team
-
the 5-lipoxygenase core promoter is unmethylated, expression of 5-lipoxygenase protein upon differentiation
Manually annotated by BRENDA team
-
normal skin keratinocytes and a cell line of human keratinocytes, HaCaT
Manually annotated by BRENDA team
-
unstimulated basophilic leukemia cells
Manually annotated by BRENDA team
-
induced by a Ca2+ ionophore, from acute myeloid leukemic and acute lymphoid leukemic patients, upregulation of the enzyme, quantitative expression analysis
Manually annotated by BRENDA team
P12527
peritoneal
Manually annotated by BRENDA team
-
polymorphonuclear
Manually annotated by BRENDA team
-
polymorphonuclear
Manually annotated by BRENDA team
-
peritoneal polymorphonuclear
Manually annotated by BRENDA team
-
peritoneal polymorphonuclear
Manually annotated by BRENDA team
-
polymorphonuclear leukocyte
Manually annotated by BRENDA team
-
from healthy individuals, quantitative expression analysis
Manually annotated by BRENDA team
P48999
increased enzyme activity in obese mice compared to twild-type mice, overview
Manually annotated by BRENDA team
Mus musculus C57BL/6J
-
increased enzyme activity in obese mice compared to twild-type mice, overview
-
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
bone marrow-derived mast cell line PB-3c
Manually annotated by BRENDA team
-
mast cell line HMC-1
Manually annotated by BRENDA team
-
highest expression
Manually annotated by BRENDA team
P09917
a monocytic cell line
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
-
from peripheral venous blood
Manually annotated by BRENDA team
-
constitutive production of 5-hydroxyeicosatetraenoic acid
Manually annotated by BRENDA team
-
high enzyme expression level
Manually annotated by BRENDA team
-
basophilic leukemia cell
Manually annotated by BRENDA team
-
retinal blood vessels of wild-type and mutant mice, diabetic mice show increased expression of leukotriene B4 receptors
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
retinal blood vessels of wild-type and mutant mice, diabetic mice show increased expression of leukotriene B4 receptors
-
Manually annotated by BRENDA team
-
ungerminated
Manually annotated by BRENDA team
-
peripheral cells, including CD4, CD8, CD45RO, CD45RA, T helper type 2, T-cell receptor-alphabeta and -gammadelta expressing cells
Manually annotated by BRENDA team
-
high expression of 5-lipoxygenase in mantle zone B cells from tonsils, weak expression in germinal centre cells and no expression in plasma cells from tonsils. High expression in mantle B cell lymphoma and weak or no expression in follicular lymphoma. Primary leukemized mantle B cell lymphoma (B-prolymphocytic leukaemia cells) and mantle B cell lymphoma cell lines also expressed 5-lipoxygenase
Manually annotated by BRENDA team
-
contains at least 3 isoenzymes
Manually annotated by BRENDA team
-
5-lipoxygenase/cyclooxygenase-2 cross-talk through cysteinyl leukotriene receptor 2 in endothelial cells, overview
Manually annotated by BRENDA team
additional information
P09917
expression of 5-LO is much higher in differentiated myeloid cells and cell lines than in undifferentiated cells, cell lines HeLa, U-937 and HL-60TB do not express 5-LO protein
Manually annotated by BRENDA team
additional information
-
tissue specific expression analysis, overview
Manually annotated by BRENDA team
additional information
-
Granta 519 cell and JEKO-1 cell
Manually annotated by BRENDA team
additional information
-
PBML cells
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
polymorphonuclear leukocytes: translocation of cytosolic enzyme to the nuclear envelope where it interacts with 5-lipoxygenase-activating protein
Manually annotated by BRENDA team
-
in basophilic leukemia cells translocation of cytosolic enzyme and the soluble nuclear enzyme to the nuclear envelope where it interacts with 5-lipoxygenase-activating protein
Manually annotated by BRENDA team
-
Ca2+ induces the translocation of 5-LO from a soluble compartment to nuclear structures, where 5-LO co-localizes with 5-LO activating protein, FLAP
Manually annotated by BRENDA team
-
resides in the cytosol of resting neutrophils from females
Manually annotated by BRENDA team
-
in resting cells, 5LO resides either in the cytosol (e.g. in neutrophils, eosinophils, peritoneal macrophages) or in a nuclear soluble compartment associated with chromatin (e.g. in alveolar macrophages, Langerhans cells, basophilic leukemia cells)
Manually annotated by BRENDA team
-
when leukocytes are activated to produce leukotrienes, 5-LO moves from the cytosol to the perinuclear membrane
Manually annotated by BRENDA team
-
the enzyme is activated by a Ca2+-mediated translocation to membranes. The enzyme binds to membranes at a defined orientation with the symmetry axis of the putative N-terminal beta-barrel tilted about 45 from the membrane normal
Manually annotated by BRENDA team
-
polymorphonuclear leukocytes: translocation of cytosolic enzyme to the nuclear envelope where it interacts with 5-lipoxygenase-activating protein
Manually annotated by BRENDA team
-
in basophilic leukemia cells translocation of cytosolic enzyme and the soluble nuclear enzyme to the nuclear envelope where it interacts with 5-lipoxygenase-activating protein, alvelolar macrophages nuclear soluble enzyme moves to the nucear envelope where it interacts with 5-lipoxygenase-activating protein
Manually annotated by BRENDA team
-
when leukocytes are activated to produce leukotrienes, 5-LO moves from the cytosol to the perinuclear membrane
Manually annotated by BRENDA team
-
in basophilic leukemia cells translocation of cytosolic enzyme and the soluble nuclear enzyme to the nuclear envelope where it interacts with 5-lipoxygenase-activating protein, alvelolar macrophages nuclear soluble enzyme moves to the nucear envelope where it interacts with 5-lipoxygenase-activating protein
Manually annotated by BRENDA team
-
Ca2+ induces the translocation of 5-LO from a soluble compartment to nuclear structures, where 5-LO co-localizes with 5-LO activating protein, FLAP
Manually annotated by BRENDA team
-
soluble fraction, translocation to the nuclear envelope upon cell activation by Ca2+
Manually annotated by BRENDA team
P09917
soluble fraction, translocation to the nuclear envelope upon cell activation by Ca2+
Manually annotated by BRENDA team
-
in stimulated HEK293/T and COS-7 cells the activated 5-lipoxygenase appears mainly at the nuclear envelope
Manually annotated by BRENDA team
-
resides in a nuclear soluble compartment associated with chromatin
Manually annotated by BRENDA team
-
resides in a nuclear soluble compartment associated with chromatin. In male neutrophils, a substantial part of 5-lipoxygenase is located at the perinuclear region already in resting cells, only marginally redistributes upon stimulation
Manually annotated by BRENDA team
-
tonsillar polymorphonuclear granulocytes
Manually annotated by BRENDA team
-
5-LO associates with a nuclear fraction only when differentiated cells are primed with phorbol ester and stimulated with ionophore
Manually annotated by BRENDA team
-
in activated cells
Manually annotated by BRENDA team
-
translocates from the cytosol to the membrane upon stimulation in female neutrophils
Manually annotated by BRENDA team
additional information
-
localization of enzyme and reactions, and activation in the cell, overview
-
Manually annotated by BRENDA team
additional information
P09917
localization of enzyme and reactions, and activation in the cell, overview
-
Manually annotated by BRENDA team
additional information
-
upon cell activation, cytosolic and nuclear enzyme translocates the nuclear envelope, where it interacts with phospholipase A2, making free arachidonate available for 5-LO, and with 5-LO activating protein, i.e. FLAP
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
50000 - 55000
-
gel filtration
439458
78000
-
SDS-PAGE
711633
85000
-
enzyme form L1 and L2, gel filtration
439439
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 80000, SDS-PAGE
?
-
x * 72000, SDS-PAGE
?
-
x * 73000, SDS-PAGE
?
-
x * 75000, SDS-PAGE
?
-
x * 92000, SDS-PAGE
?
-
x * 35000, enzyme form L2, SDS-PAGE, x * 85000, enzyme form L2, SDS-PAGE
?
-
x * 83000, upon storage degraded into a lower molecular mass protein of 36000 Da, SDS-PAGE
?
-
x * 72000-80000
additional information
-
the L1 form is gradually transformed into the L2 form with a significant reduction in specific activity
additional information
-
residues 1-128 of the enzyme form the regulatory C2-like domain
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
phosphoprotein
-
Ca2+ and 5-lipoxygenase phosphorylation seem to be required for arachidonic acid-induced 5-lipoxygenase product formation
phosphoprotein
-
enzyme regulation by phosphorylation
phosphoprotein
P09917
the amino acid sequence of 5-LO contains several protein kinase motifs, e.g. at Ser271 and Ser663, 5-LO is phosphorylated in vitro by the protein kinases p38 MAPK-regulated MAPKAPK-2/3, ERK1/2, CaMKII and PKA. Conditions that activate MAPKAPKs and ERKs (e.g. cell stress, and phorbol esters) induce nuclear translocation of 5-LO and enhance product formation in intact cells, and this process is susceptible to kinase inhibitors. Phosphorylation on Ser523 by PKA directly suppresses 5-LO catalysis both in vitro and in the cell, and prevents nuclear localization of 5-LO by inhibiting the nuclear import function of a nuclear import sequence close to the kinase motif
phosphoprotein
-
5LO can be phosphorylated at three residues: Ser-271 (by MAP-KAP kinases), Ser-663 (by ERK2), and Ser-523 (by protein kinase A catalytic subunit)
phosphoprotein
-
cellular 5-LO activity is regulated by both divalent cations and by phosphorylation, mitogen-activatedprotein kinasesandproteinkinase A can phosphorylate 5-LO in the catalytic domain
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure analysis
P09917
crystal structure analysis
-
crystal structure analysis
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
2
-
half-life: 24 h
439442, 439456
24
-
1 h, 50% loss of activity
439456
37
-
half-life: 30 s
439450
40
-
5 min, stable up to
439466
60
-
5 min, most of the activity is lost
439466
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
coactosin-like protein functions as a stabilizing chaperone for 5-lipoxygenase (preventing non-turnover inactivation)
-
efficiently stabilized by 20% v/v glycerol
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, 1 month, 50% loss of activity
-
0-4C, 24 h, loss of more than half of its activity
-
0C, 30 h, about 70% loss of activity, in presence of 2 mM ATP only 30% loss of activity
-
-20C, stable for weeks
-
0-4C, 30 min, 40-60% loss of activity
-
4C, stable for days
-
4C, 48 h, no appreciable loss of activity
-
-20C, 40 mM potassium phosphate buffer, pH 6.3, 2 M (NH4)2SO4, enzyme form L1 is stable for months
-
4C, the L1 form is gradually transformed into the L2 form with a significant reduction in specific activity, the L2 form loses all of its activity over a few days and more rapid in absence of (NH4)2SO4
-
-70C, 1 week, no appreciable inactivation
-
-70C, appreciable loss of activity after several weeks
-
0-4C, 24 h, loss of more than half of its activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
MonoQ column chromatography
-
partially purified by sonication, centrifugation and gel filtration
-
recombinant enzyme
-
recombinant enzyme partially from Escherichia coli strain MV1190 by ammonium sulfate fractionation and ATP affinity chromatography
-
recombinant soluble MBP-regulatory C2-like domain fusion protein from Escherichia coli strain BL21(DE3) by amylose affinity chromatography, fusion protein cleavage by TEV protease, and further purification of the C2-like domain by hydrophobic interaction chromatography
-
native enzyme to homogeneity from ungerminated seed
-
using Ni-NTA chromatography
-
major isoenzyme L1
-
immunoaffinity purification
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5-lipoxygenase cDNA cloned into EGFP fusion protein vector (pEGFP-h5-LO) and expressed in HEK293/T or COS-7 cells, or into a pUC13 vector, full length 5-lipoxygenase cDNA subcloned into pGEX and pcDNA3, expressed in Escherichia coli Y1090
-
DNA and amino acid sequence analysis
-
Escherichia coli MV1190 transformed with pT3-5LO plasmid
-
expressed in Escherichia coli
-
expressed in Escherichia coli BL21 and MV1190 cells
-
expression in Escherichia coli
-
expression in Escherichia coli strain MV1190
-
expression in human osteosarcoma cell line 143.98.2
-
expression of regulatory C2-like domain of the enzyme, residues 1-128, containing a tobacco etch virus protease-cleavage site, in Escherichia coli strain BL21(DE3) as soluble maltose-binding-protein fusion protein
-
from adipose tissue, expression of the enzyme in Spodoptera frugiperda Sf9 cells using the baculovirus transfection system, subcloning and propagation of the virus in Escherichia coli strain DH10
-
genotyping of 1916 sputum-positive patients with pulmonary tuberculosis from Ghana and in 2269 exposed, apparently healthy control individuals, polymorphisms of a variable number of tandem repeats of the ALOX5 promoter and of the exonic non-synonymous variant g.760G>A are analyzed by fragment length determination and fluorescence resonance energy transfer, respectively, and DNA sequencing. ALOX5 gene expression depends on the copy number of the Sp1-binding sequences in the promoter, whereby the 5 allele, compared with the 3, 4 and 6 alleles, is associated with the highest degree of expression
-
HEK 293 cells stably transfected with a pcDNA3.1 vector expressing 5-lipoxygenase
-
high expression baculovirus system
-
the gene contains 14 exons, DNA methylation is responsible for suppression of 5-LO expression, the 5-LO core promoter is completely methylated in the cell lines U-937 and HL-60TB, which do not express 5-LO protein, regulation mechanisms, overview, expression in HeLa cells, which lack endogenous enzyme, for promoter analysis, the basal promoter undergoes DNA looping to distant gene regions
P09917
wild-type and mutant enzyme F359W/A424I/N425M/A603I, expression in Escherichia coli
-
expressed in Escherichia coli as a His-tagged fusion protein
-
expressed in Sf-21 insect cells
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
DNA methylation is responsible for suppression of 5-lipoxygenase expression in most cell types
-
aberrant methylation may lead to upregulated 5-lipoxygenase expression in tumor cells. The 5-lipoxygenase core promoter is completely methylated in cell lines U-937 and HL-60TB, which do not express 5-lipoxygenase. Treatment with the demethylating agent 5-aza-2'deoxycytidine restores 5-lipoxygenase expression
-
0.01 mM hydroxynonenal induces 5-LOX promoter activity significantly by 310% and 580% after 48 and 72 h of incubation, respectively. The addition of anti-transforming growth factor-beta1 antibody reduces hydroxynonenal-induced 5-LOX expression by 40%
-
methyl-DNA binding proteins MBD1, MBD2 and MeCP2 downregulate 5-LO mRNA expression in U-937 cells
-
stimulation of J774A.1 cells with 0.01 mM acrolein for 4-24 h leads to increased 5-LO expression through activation of the ERK pathway. Acrolein-induced 5-LO expression is inhibited in a dose-dependent manner by pretreatment with AG1478, but not by pretreatment with AG1295
-
5-LOX activity is quantitatively similar in normal versus Metastrongylus spp.-parasitized lung tissue samples
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
E254K
-
naturally occuring non-synonymous exonic variant g.760G/A is associated with tuberculosis, genotyping of 1916 sputum-positive patients with pulmonary tuberculosis from Ghana and in 2269 exposed, apparently healthy control individuals, polymorphisms of a variable number of tandem repeats of the ALOX5 promoter and of the exonic non-synonymous variant g.760G>A are analyzed by fragment length determination and fluorescence resonance energy transfer, respectively, and DNA sequencing. The association of the exonic variant is stronger in infections caused by the mycobacterial lineage Mycobacterium africanum West-African 2, overview, distribution of haplotypes, overview
F359W/A4241
-
8-lipoxygenating mutant
F359W/A424I/N425M/A603I
-
15-lipoxygenating mutant
F359W/A424I/N425M/A603I
-
produces only minor amounts of leukotriene A4
F359W/A424I/N425M/A603I
-
oxygenates polyenoic fatty acids containing C11=C12 and C14=C15 double bonds, C20:DELTA11,14,17, C20:DELTA11,14, C18:DELTA9,12, C18:DELTA6,9,12 and C18:DELTA9,12,15 which are not oxygenated by the wild-type enzyme. C20:DELTA5,8,11 that lacks the C11=C12 double bond is not oxygenated
H362Q
-
reduced enzyme activity, similar amounts of iron as non-mutated enzyme
H367N
-
inactive, contains 0.2 mol of iron per mol of protein, compared to 0.86 mol of iron per mol of protein for the wild-type enzyme
H367Q
-
inactive, contains 0.5 mol of iron per mol of protein, compared to 0.86 mol of iron per mol of protein for the wild-type enzyme
H367S
-
inactive, contains 0.5 mol of iron per mol of protein, compared to 0.86 mol of iron per mol of protein for the wild-type enzyme
H372Q
-
no detectable enzyme activity, practically devoid of iron
H390Q
-
reduced enzyme activity, similar amounts of iron as non-mutated enzyme
H399Q
-
reduced enzyme activity, similar amounts of iron as non-mutated enzyme
H550Q
-
no detectable enzyme activity, practically devoid of iron
S271A
P09917
site-directed mutagenesis, mutation of the phosphorylation site results in impaired cellular 5-LO product formation when transfected cells are selectively activated by arachidonic acid
S663A
P09917
site-directed mutagenesis, mutation of the phosphorylation site results in impaired cellular 5-LO product formation when transfected cells are selectively activated by arachidonic acid
W102A
-
the mutation prevents interaction with coactosin-like protein, the mutant shows barely detectable dioxygenase activity
W13/75/102A
-
triple mutant shows higher total activity than the wild type enzyme
W13A
-
the mutation upregulates leukotriene production, the enzyme activity of the mutant 5-LO at low concentrations of phosphatidylcholine (0.005 mg/ml) and arachidonic acid (0.02 mM) is reduced compared to the wild type enzyme
W75A
-
the mutation upregulates leukotriene production, the enzyme activity of the mutant 5-LO at low concentrations of phosphatidylcholine (0.005 mg/ml) and arachidonic acid (0.02 mM) is reduced compared to the wild type enzyme
DELTA1-114
-
D114 truncation mutant shows 6.8% residual activity compared to wild-type, Km (arachidonate) increased compared to wild-type. Vmax: 9.3% compared to wild-type (100%). Addition of phosphatidyl choline or Ca2+ increases catalytic activity only by 11% compared to 50% in wild-type. Truncated mutant exhibits impaired membrane binding properties
DELTA1-125
-
I125 truncation mutant shows 1.8% residual activity compared to wild-type, addition of phosphatidyl choline or Ca2+ increases catalytic activity only by 11% compared to 50% in wild-type. Truncated mutant exhibits impaired membrane binding properties
additional information
-
5-LO-deficient mice show an inhibition of diabetes-induced acellular capillary formation in retina, and show reduced leukostasis and superoxide generation, diabetic enzyme-deficient mice show suppression of NF-kappaB expression, overview
additional information
P48999
construction of enzyme-deficient knockout mice, 5-LOX deficient and wild-type mice show no significant difference in infarct size after 30 min of coronary artery ligation and 24 h of reperfusion, but neutrophil infiltration as well as tumor necrosis factor expression are increased in 5-lipoxygenase-deficient mice, overview
additional information
Mus musculus C57BL/6
-
5-LO-deficient mice show an inhibition of diabetes-induced acellular capillary formation in retina, and show reduced leukostasis and superoxide generation, diabetic enzyme-deficient mice show suppression of NF-kappaB expression, overview
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug development
-
the enzyme is a target in drug design for cancer therapy, inhibitors inclinical trials, overview
drug development
-
caffeoyl clusters are good lead compounds in the design and synthesis of more potent 5-lipoxygenase inhibitors
drug development
-
due to their high potency against 5-lipoxygenase and the marked efficacy in biological systems, benzo[g]indole-3-carboxylates may have potential as anti-inflammatory therapeutics
drug development
-
gender difference in biosynthesis of leukotrienes (inflammatory mediators) may lead to new possibilities regarding development and use of 5-lipoxygenase inhibitors
drug development
-
pirinixic acid derivatives constitute a novel class of dual mPGES-1/5-lipoxygenase inhibitors with a promising pharmacologial profile and a potential for therapeutic use
medicine
-
selenium -induced apoptosis in prostate cancer cells may be mediated thgroufgh inhibition of the activity of arachidonate 5-lipoxygenase. The anti-cancer effects of selenium may be substantially compromised by consumption of high-fat diets rich in arachidonic acid or its precursor fatty acids
medicine
-
powerful inhibitory properties of anthocyanins (delphinidin glycosides) towards lipoxygenases in relation to their currently known availability in human metabolism may in vivo prevent inflammatory diseases
medicine
-
direct 5-LO inhibitors are able to suppress the viability of various human tumour cells independently of 5-LO inhibition
drug development
P48999
the enzyme is an emerging target in obesity, insulin resistance, and artherosclerosis
drug development
Mus musculus C57BL/6J
-
the enzyme is an emerging target in obesity, insulin resistance, and artherosclerosis
-
drug development
-
due to their high potency against 5-lipoxygenase and the marked efficacy in biological systems, benzo[g]indole-3-carboxylates may have potential as anti-inflammatory therapeutics
synthesis
-
synthesis of 5-hydroperoxyeicosatetraenoic acid and 5(S),12(S)-dihydroxy-6,10-trans-8,14-cis-eicosatetraenoic acid