Information on EC 1.13.11.33 - arachidonate 15-lipoxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
1.13.11.33
-
RECOMMENDED NAME
GeneOntology No.
arachidonate 15-lipoxygenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
arachidonate + O2 = (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dioxygenation
-
-
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
-
-
arachidonic acid metabolism
-
-
Linoleic acid metabolism
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 15-oxidoreductase
The product is rapidly reduced to the corresponding 15S-hydroxy compound.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
12/15 lipoxygenase
-
-
12/15-lipoxygenase
-
-
12/15-lipoxygenase
P16050
-
12/15-lipoxygenase
Mus musculus C57BL/6, Mus musculus C57BL6, Mus musculus DBA/2J
-
-
-
12/15-lipoxygenase
-
-
12/15-lipoxygenase
-
-
12/15-LO
-
-
12/15-LO
P16050
-
12/15-LO
Mus musculus C57BL/6, Mus musculus DBA/2J
-
-
-
12/15-LO
-
-
12/15-LOX
Mus musculus C57BL/6
-
;
-
12/15LO
-
-
12/15LO
-
-
12/15LO
Mus musculus C57BL6
-
-
-
12/15LO
-
-
15(S)-lipoxygenase-1
-
-
15-hLO-1
-
-
15-hLO-2
-
-
15-lipoxygenase
-
-
-
-
15-lipoxygenase
-
-
15-lipoxygenase
Q8K4F2
-
15-lipoxygenase
Sarcolobus globosus
-
-
15-lipoxygenase
-
-
15-lipoxygenase 1
-
-
15-lipoxygenase 1
-
-
15-lipoxygenase 2
-
-
15-lipoxygenase 2
O15296
-
15-lipoxygenase type 1
-
-
15-lipoxygenase type 2
-
-
15-lipoxygenase type-1
-
-
15-lipoxygenase-1
-
-
15-lipoxygenase-1
-
-
15-lipoxygenase-1
-
-
15-lipoxygenase-1
-
-
15-lipoxygenase-I
-
-
15-LO
Sarcolobus globosus
-
-
15-LO-1
-
-
15-LO-2
-
-
15-LOX
-
-
-
-
15-LOX
-
-
15-LOX
-
-
15-LOX-2
Q8K4F2
-
15-LOX-A
-
-
15-LOX2
-
-
15-LOX2
O15296
-
15-sLO
-
-
15S-lipoxygenase
-
-
Alox15
-
-
ALOX15-2
-
-
ALOX15B
-
-
arachidonate 15-lipoxygenase
-
-
arachidonate 15-lipoxygenase-1
-
-
arachidonic acid 15-lipoxygenase
-
-
-
-
arachidonic acid 15-lipoxygenase
-
-
endothelial 15-lipoxygenase-1
-
-
epidermis-type 15-LOX
-
-
human prostate epithelial 15-lipoxygenase-2
-
-
linoleic acid omega-6-lipoxygenase
-
-
-
-
lipoxygenase L-1
-
-
lipoxygenase-1
-
-
LO-1
-
-
LOX-1
-
-
LOX2
Cyanothece sp.
B7JX99
-
LOX2
B7JX99
-
-
LOX2:Hv:1
P93184
-
omega-6 lipoxygenase
-
-
-
-
oxygenase, arachidonate 15-lip-
-
-
-
-
reticulocyte 15-lipoxygenase-1
-
-
reticulocyte 15-LOX
-
-
reticulocyte-type 15-human lipoxygenase
-
-
reticulocyte-type 15-lipoxygenase
-
-
reticulocyte-type of 15-LOX-1
-
-
soybean 15-lipoxygenase
-
-
soybean lipoxygenase-3
-
-
additional information
-
cf. EC 1.13.11.12
additional information
-
cf. EC 1.13.11.12
CAS REGISTRY NUMBER
COMMENTARY
82249-77-2
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Cyanothece sp.
-
UniProt
Manually annotated by BRENDA team
gene ALOX15
UniProt
Manually annotated by BRENDA team
isozyme 15-LO-1
-
-
Manually annotated by BRENDA team
isozymes 15-hLO-1 and 15-hLO-2
-
-
Manually annotated by BRENDA team
isozymes 15-HLOa and 15-HLOb
-
-
Manually annotated by BRENDA team
two human isozymes: platelet 12-hLO, reticulocyte 15-hLO-1, and epithelial 15-hLO-2
-
-
Manually annotated by BRENDA team
cv. Salome
SwissProt
Manually annotated by BRENDA team
C57BL/6 mice
-
-
Manually annotated by BRENDA team
C57Bl6 mice
-
-
Manually annotated by BRENDA team
DBA/2J mice
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
-
-
Manually annotated by BRENDA team
Mus musculus C57BL6
C57Bl6 mice
-
-
Manually annotated by BRENDA team
Mus musculus DBA/2J
DBA/2J mice
-
-
Manually annotated by BRENDA team
PCC73102
SwissProt
Manually annotated by BRENDA team
Nostoc punctiforme PCC73102
PCC73102
SwissProt
Manually annotated by BRENDA team
Sarcolobus globosus
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
when 15-LOX-1 activity is knocked down by siRNA, the induction of MIP-1alpha, RANTES, and IP-10 is significantly attenuated
metabolism
-
shifting linoleic acid metabolism from 15-LOX-1 to COX-2 is procarcinogenic
physiological function
-
12/15-LOX is a critical mediator of the chronic type 1 inflammatory response. Evolution of the immune response to Toxoplasma gondii is accompanied by an increasing requirement for 12/15-LOX mediated signaling. Although 12/15-LOX deficient mice are resistant to acute Toxoplasma gondii infection, 80% of 12/15-LOX-deficient mice die during chronic toxoplasmosis, compared to no deaths in wild-type controls. The enhanced susceptibility of 12/15-LOX-deficient mice to chronic toxoplasmosis is associated with reduced production of IL-12 and gamma interferon (IFN-gamma) that is not evident during acute infection. Ex vivo IFN-gamma production by 12/15-LOX-deficient splenocytes can be rescued by the addition of recombinant IL-12. 12/15-LOX does not play a role in macrophage killing of Toxoplasma gondii in vitro
physiological function
-
12/15LO activity in the vessel wall contributes to atherogenesis by impairing the macrophage ATP-binding cassette transporter G1 cholesterol efflux pathway. 12/15LO activity reduces high density lipoprotein-mediated cholesterol efflux, ATP-binding cassette transporter G1 cellular expression. 12/15LO activity does not affect ATP-binding cassette transporter G1 mRNA expression
physiological function
-
12/15LO expression increases chemokine production. 12/15LO mediates early stages of adipose tissue inflammation and whole body insulin resistance induced by high fat feeding. Adipose tissue from high fat diet-fed 12/15LO KO mice is not infiltrated by macrophages and does not display any increase in the inflammatory markers compared to adipose tissue from normal chow-fed mice. 12/15LO KO mice exhibit no high fat diet-induced change in insulin-stimulated glucose disposal rate or hepatic glucose output. Insulin-stimulated Akt phosphorylation in muscle tissue from high fat diet-fed mice is significantly greater in 12/15LO KO mice than in wild-type mice
physiological function
-
15-lipoxygenases may have chondroprotective properties by reducing metalloproteinase-1 and -13 expression. Their respective metabolites, 13(S)-hydroxy octadecadienoic and 15(S)-hydroxyeicosatetraenoic acids, suppress interleukin-1beta-induced metalloproteinase-1 and -13 expression in a PPARgamma-dependent pathway
physiological function
-
15-LO-1 plays active roles in vascular remodeling, the progression of atherosclerosis and angiogenesis. The PC-3 prostate cancer cell line, which overexpresses 15-LO-1, secretes high levels of vascular endothelial growth factor and enhances tumor growth and angiogenesis as compared with the parental PC-3 cell lines. Angiogenesis and tumor formation is inhibited in transgenic mice overexpressing 15-LO-1 in endothelial cells under the control of preproendothelin promoter. Potential role of 15-LO-1 in regulating endothelium-derived NO, the expression level and activity of 15-LO-1 in endothelial cells may act as a potential NO barometer by modulating the level of eNOS enzyme and bioactive free NO in endothelial cells. 15-LO-1 in human endothelial cells can inhibit angiogenesis and vascular permeability by removing free NO, and its activity can in turn be modulated by the cytoplasmic NO level
physiological function
-
15-LOX metabolites (15(S)-hydroxyeicosatetraenoic acid, 15-hydroxyeicosatrienoic acid or 13(S)-hydroxyoctadecadienoic acid) can inhibit insulin-like growth factor II-induced 12-LOX expression and keratinocytes proliferation
physiological function
-
15-LOX-1 induces chemokine expression in A549 cells. Increased expression and activity of 15-LOX-1 in lung epithelial cells is a proinflammatory event in the pathogenesis of asthma and other inflammatory lung disorders. 15-LOX-1 overexpression results in upregulation of MIP-1alpha, MIP11beta, and RANTES, in increased migration of immature dendritic cells and of activated T cells and increases chemotaxis of mast cells. 15-LOX-1 ectopic expression upregulates NF-kappaB activity
physiological function
-
15-LOX-1 induces phosphorylation of tumor suppressor p53 independent of enzymatic activity. HCT-116 cells transiently transfected with either native or mutant 15-LOX-1 show an increase in p53 phosphorylation and an increase in the expression of downstream genes. 15-LOX-1 interacts with, and binds to, DNA-dependent protein kinase, which causes an approximate 3fold enhancement in kinase activity, resulting in increased p53 phosphorylation at Ser15
physiological function
-
15-LOX-1 promotes mitogenic response to epidermal growth factor in fibroblasts and NaBT-induced apoptosis in colon cancer cells. Non-steroidal anti-inflammatory drugs-induced apoptosis mediated by 15-LOX-1/GATA-6 in colon cancer
physiological function
-
15-LOX-2 increases cell cycle arrest at G0/G1 phase. Injected into athymic nu/nu mice, prostate cancer cells with 15-LOX-2 expression can still form palpable tumors without significant changes in tumorigenicity. But, the tumors with 15-LOX-2 expression grow significantly slower than those derived from vector controls and are kept dormant for a long period of time. Increase in cell death in tumors derived from prostate cancer cells with 15- LOX-2 expression. 15-LOX-2 suppresses vascular endothelial growth factor A gene expression and sustains tumor dormancy in prostate cancer
physiological function
-
endogenous 12/15-LOX defines the resident peritoneal macrophage population and regulates both the recruitment of monocytes/peritoneal macrophage and cytokine response to bacterial products in vivo
physiological function
-
high degree of motional flexibility and a high membrane binding affinity
physiological function
-
high levels of 15LO1 activity can contribute to the increases of MUC5AC observed in asthma
physiological function
-
inhibits tumour growth and metastasis. Enzyme promotes atherosclerosis and can inhibit growth and spread of lung (Lewis lung carcinoma model) and breast (mouse mammary adenocarcinoma model) cancer cells
physiological function
-
is a regulator of angiogenesis, antiangiogenic action in skeletal muscle system. 15-LO-1 significantly decreases all angiogenic effects induced by vascular endothelial growth factor-A and placental growth factor, including capillary perfusion, vascular permeability, vasodilatation, and the increase in capillary number
physiological function
-
lower degree of motional flexibility in aqueous solutions than mammalian isozymes
physiological function
-
macrophages that overexpress 15-LOX-2 show increased secretion of chemokine ligands CXCL10 and CCL2 after 24h incubation. Preconditioned medium from 15-LOX-2-overexpressing cells increases T cell migration, the expression of T cell activation marker CD69 and surface expression of chemokine receptor CXCR3, the CXCL10 chemokine ligand. Increased expression of 15-LOX-2 induced by hypoxia may participate in T cell recruitment in diseases such as atherosclerosis
physiological function
-
overexpression of human 15-LO-1 in RAW macrophages promotes reverse cholesterol transport through increased cholesteryl ester hydrolysis and ABCA1-mediated cholesterol efflux
physiological function
-
pathophysiological role of the enzyme in airway inflammation and atherosclerosis. Role in cell differentiation and importance for maturation of erythrocytes and degradation of cell organells. Role in neoplasia such as prostate cancer and colon carcinoma cells
physiological function
-
pathophysiological role of the enzyme in respiratory inflammation. Mice deficient of 12/15-LO have an attenuated allergic airway inflammation compared to wild type controls
physiological function
-
radiation-induced upregulation of 15-LOX-2 results in significant induction of apoptosis in head-and-neck cancer cells and and enhances killing effect of radiotherapy in head-and-neck cancer. The enzyme inhibits tumor growth through the effect of its main metabolite 15(S)-hydroxyeicosatetranoic acid on PPARgamma signaling pathway
physiological function
-
the expression of 15-lipoxygenase-1 and the putative formation of eoxins by Hodgkin Reed-Sternberg cells in vivo are likely to contribute to the inflammatory features of Hodgkin lymphoma
physiological function
-
high levels of 15LO1 interact with PEBP1 to displace Raf-1 and sustain MAPK/ERK activation
physiological function
Mus musculus C57BL/6
-
12/15-LOX is a critical mediator of the chronic type 1 inflammatory response. Evolution of the immune response to Toxoplasma gondii is accompanied by an increasing requirement for 12/15-LOX mediated signaling. Although 12/15-LOX deficient mice are resistant to acute Toxoplasma gondii infection, 80% of 12/15-LOX-deficient mice die during chronic toxoplasmosis, compared to no deaths in wild-type controls. The enhanced susceptibility of 12/15-LOX-deficient mice to chronic toxoplasmosis is associated with reduced production of IL-12 and gamma interferon (IFN-gamma) that is not evident during acute infection. Ex vivo IFN-gamma production by 12/15-LOX-deficient splenocytes can be rescued by the addition of recombinant IL-12. 12/15-LOX does not play a role in macrophage killing of Toxoplasma gondii in vitro, endogenous 12/15-LOX defines the resident peritoneal macrophage population and regulates both the recruitment of monocytes/peritoneal macrophage and cytokine response to bacterial products in vivo
-
physiological function
Mus musculus C57BL6
-
12/15LO expression increases chemokine production. 12/15LO mediates early stages of adipose tissue inflammation and whole body insulin resistance induced by high fat feeding. Adipose tissue from high fat diet-fed 12/15LO KO mice is not infiltrated by macrophages and does not display any increase in the inflammatory markers compared to adipose tissue from normal chow-fed mice. 12/15LO KO mice exhibit no high fat diet-induced change in insulin-stimulated glucose disposal rate or hepatic glucose output. Insulin-stimulated Akt phosphorylation in muscle tissue from high fat diet-fed mice is significantly greater in 12/15LO KO mice than in wild-type mice
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(16(R),5Z,8Z,11Z,14Z)-16-fluoroeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
P12530
-
wild-type enzyme: 78% of the 15,16(R) product and 22% of the 12,16(R) product
-
?
(16(R),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
P12530
-
wild-type enzyme and mutant enzyme I593A prouce small amounts of unspecific products. Mutant enzyme F353L produces 6% of 15,16(R) product and 94% of the 12,16(R) product
-
?
(16(S),5Z,8Z,11Z,14Z)-16-fluoroeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
P12530
-
wild-type enzyme: 69% of the 15,16(S) product and 31% of the 12,16(S) product
-
?
(16(S)5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
P12530
-
wild-type enzyme: 93% of the 15,16(S) product and 7% of the 12,16(S) product
-
?
(17(R),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
P12530
-
wild-type enzyme: 1% of the 15,17(R) product and 99% of the 12,17(R) product
-
?
(17(S),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
P12530
-
wild-type enzyme: 3% of the 15,17(S) product and 97% of the 12,17(S) product
-
?
(18(R),5Z,8Z,11Z,14Z)-18-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
P12530
oxygenation proceeds with little if any enantioselectivity
-
-
?
(18(S),5Z,8Z,11Z,14Z)-18-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
P12530
oxygenation proceeds with little if any enantioselectivity
-
-
?
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
15-hydroperoxy-11,13,17-eicosatrienoic acid
show the reaction diagram
-
-
-
?
2 arachidonate + 2 O2 + H+
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate + H2O
show the reaction diagram
-
-
(5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate slightly increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but more potent by 12(S)-hydroxyeicosatetranoic acid, overview, i.e. 15(S)-HPETE and 15(S)-HETE, the first is the predominant product
-
?
2 arachidonate + 2 O2 + H+
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate + H2O
show the reaction diagram
Mus musculus C57BL/6
-
-
(5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate slightly increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but more potent by 12(S)-hydroxyeicosatetranoic acid, overview, i.e. 15(S)-HPETE and 15(S)-HETE, the first is the predominant product
-
?
8,11,14-eicosatrienoic acid + O2
15-hydroperoxy-8,11,13-eicosatrienoic acid
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
O15296
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
Q8K4F2
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
Sarcolobus globosus
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
and small amounts of (5Z,8Z,10E,14Z)-12-hydro(pero)xy-5,8,10,14-icosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
15-hydroperoxy-5,8,11,13-eicosatetraenoic acid + 15-hydroxy-5,8,11,13-eicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
formation of 15S-hydroxyeicosatetraenoic acid and 12S-hydroxyeicosatetraenoic acid in a ratio of 12:1, double oxygenation products 14R,15S-dihydroxyeicosatetraenoic acid and various 8,15-dihydroxyeicosatetraenoic acids are also produced
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
and nonenzymatic production of 15-hydroxy-5,8,11,13-eicosatetraenoic acid, 15-keto-5,8,11,13-eicosatetraenoic acid, 13-hydroxy-14,15-epoxy-5,8,11-eicosatrienoic acid and 11,14,15-trihydroxy-5,8,12-eicosatrienoic acid
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
ratio of 15-lipoxygenation to 12-lipoxygenation is 9:1 for the wild-type enzyme and the mutant enzymes V104I, L397M and Q431R. The ratio of 15-lipoxygenation to 12-lipoxygenation is 1:1 for the mutant enzymes V104/L397M/M418V/Q431R, L397M/M418V/Q431R, L397M/M418V and M418V
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
15-hydroxyeicosatetraenoic acid and 12-hydroxyeicosatetraenoic acid in a ratio of 8.6:1
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
further metabolized to (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate, 15-HETE, has no effect on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
is further metabolized by hydroperoxide isomerase to the acid-sensitive metabolite 15(S)-hydroxy-11,12-epoxyeicosatrienoic acid, which is hydrolyzed to 11,12,15-trihydroxyeicosatrienoic acid, by a soluble epoxid hydrolase, causing endothelium-dependent smooth muscle hyperpolarization and relaxations, mass spectrometrical metabolite analysis and pathway, overview
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
the bifunctional enzyme also forms (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate, the product of 12-LO activity, EC 1.13.11.31, in a ratio of 9:1 15(S)-HPETE to 12(S)-HPETE, further reduced to the correspondent (S)-hydroxy fatty acids, in eosinophils, overview, the bifunctional enzyme also forms (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate, the product of 12-LO activity, EC 1.13.11.31, in a ratio of 9:1 15(S)-HPETE to 12(S)HPETE
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
is further metabolized to (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate, i.e. 15(S)-HETE
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
the enzyme is regulated pretranslational, translational and posttranslational
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
induction of experimental anemia leads to a systemic up-regulation of 12/15-lipoxygenases expression
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
O15296
15-lipoxygenase 2 is a negative cell cycle regulator in normal prostate epithelial cells, it could be a suppressor of prostate cancer development, which functions by restricting cell cycle progression
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
catalyzes enzymatic lipid peroxidation in complex biological structures via direct dioxygenation of phospholipids and cholesterol esters of biomembranes and plasma lipoproteins
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
the enzyme is implicated in inflammatory disorders, 15-lipoxygenase is induced in atherosclerosis and can oxidize low-density lipoprotein to its atherogenic form
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
first step in biotransformation of arachidonic acid to the 15-series of leukotrienes, reaction is involved in inactivation of slow-reacting substrances of anaphylaxis
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
alternative splicing of 15S-lipoxygenase provides a further level of regulation of fatty acid metabolism
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
12/15LO protein levels and activity are increased in pathologically affected regions of Alzheimers disease brains, enzyme inhibition causes a decrease in amyloid-beta protein, 12/15LO influences amyloid-beta protein precursor protein metabolism, overview
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
15-lipoxygenase type-1 is a prooxidant enzyme, which is expressed in asthmatic lungs leading to formation of pro- and anti-inflammatory mediators, overview
the product is further metabolized to 15(S)-hydroxyeicosatetranoic acid and 15-ketoeicosatetraenoic acid, the latter is the main product, pathway and mechanism, overview
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
15-LOX2 in NHP cells is positively regulated by Sp1 and negatively regulated by Sp3, but 15-LOX2 expression in NHP cells is not directly regulated by androgen/androgen receptor, overview
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
arachidonic acid is metabolized by the 15-lipoxygenase-1 pathway to the vasodilatory eicosanoids hydroxyepoxyeicosatrienoic acid and trihydroxyeicosatrienoic acid
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
arachidonic acid metabolization by lipoxygenases, overview
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
the enzyme is involved in acetylsalicylic acid-triggered production of 15(S)-hydroxyeicosatetranoic acid, 15(S)-HETE, in sensitive asthmatic patients, acetylsalicylate-tolerant asthma patients show reduced 15-LO activity
is metabolized to 15(S)-hydroxyeicosatetranoic, i.e. 15(S)-HETE
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
the enzyme modifies high density lipoprotein 3, the major and most antiatherogenic HDL subfraction, and impairs anti-inflammatory activity of the lipoprotein, which, after modification, fails to inhibit TNFalpha-mediated mRNA and protein induction of adhesion molecules and monocyte chemoattractant protein-1, MCP-1, in endothelial cells, overview
is metabolized to 15(S)-hydroxyeicosatetranoic, i.e. 15(S)-HETE
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
high oxygen affinity is important for effective catalysis, L367 is involved in oxygen access, channel structure, overview, arachidonic acid closes the substrate-binding pocket for oxygen diffusion but opens a fourth oxygen access channel
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
immunohistochemic assay
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
preferred substrate of isozyme 15-hLO-2, reaction of EC 1.13.11.33
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
regioselective oxidation is achieved through control over the position of hydrogen atom abstraction by the geometry and size of the enzyme active site and through control by the protein over the interaction of molecular oxygen with the generated delocalized substrate radical, analysis of catalytic mechanisms of lipoxygenases using 10,10-dideuterated arachidonic acid, 13,13-dideuterated arachidonic acid, and 0,10,13,13-d4-AA, overview
isozymes 15-hLO-1 and 15-hLO-2 also form small amounts of 11-HPETE, 8-HPETE, and 12-HPETE, the rate of 8/12-HPETE production by isozyme 15-hLO-1 with 13,13-dideuterated arachidonic acid as substrate is exeptionally high with 75% of overall production, overview
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
B2IZG6
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
12/15LO eicosanoid products reduce cholesterol efflux to high density lipoproteins, regulate ATP-binding cassette transporter G1 expression and enhance ATP-binding cassette transporter G1 degradation and ATP-binding cassette transporter G1 serine phosphorylation
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
15-H(p)ETE is the major reaction product independent of the pH
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
15-H(p)ETE is the major reaction product of 15-LOX-2 and 12/15-LOX independent of the pH
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
main product is 12(S)-hydroxyeicosatetranoic acid
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
product ratio is 9 to 1
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
5fold higher affinity for arachidonic acid than for linoleic acid for 15-hLO-1
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
both 15-LOX-1 and -2
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
Mus musculus C57BL/6
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
P93184
-
ratio of (5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate to (5Z,8Z,11Z,13E,15R)-15-hydroperoxyicosa-5,8,11,13-tetraenoate is 92:8
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
show the reaction diagram
-
-
the mutant enzyme A416G converts arachidonic acid to (11R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid and (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid in a 1.5:1 ratio
-
?
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
show the reaction diagram
-
an atomic-level study of the binding modes of linoleic acid to rabbit reticulocyte 15-rLO-1 is presented. Results are compared with binding of arachidonic acid to 15-rLO-1. Linoleic acid seems to adapt more easily to the enzyme structure and differs from arachidonic acid on some dynamical aspects that could introduce kinetic differences, as observed experimentally
-
-
?
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid + (12S,5Z,8Z,10E,14Z)-12-hydroperoxyeicosa-5,8,10,14-tetraenoic acid
show the reaction diagram
P12530
-
93% (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid and 7% (12S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
-
?
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid + (12S,5Z,8Z,10E,14Z)-12-hydroperoxyeicosa-5,8,10,14-tetraenoic acid
show the reaction diagram
-
-
the ratio of (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid to (12S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid is 20 for the wild-type enzyme
-
?
arachidonic acid + O2
15S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
?
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
13-hydroperoxyeicosatetraenoic acid + (5Z,8Z,11R,12E,14Z)-11-hydroperoxyicosa-5,8,12,14-tetraenoic acid + (5Z,8E,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
show the reaction diagram
Cyanothece sp., Cyanothece sp. PCC 8801
B7JX99
-
-
-
?
diarachidonylglycerophosphatidylcholine + O2
?
show the reaction diagram
Cyanothece sp., Cyanothece sp. PCC 8801
B7JX99
-
-
-
?
dilinoleoyl phosphatidic acid + O2
(S)-hydroperoxy dilinoleoyl phosphatidic acid
show the reaction diagram
-
i.e. dilinoleoylPA
-
-
?
dilinoleoyl phosphatidylcholine + O2
(S)-hydroperoxy dilinoleoyl phosphatidylcholine
show the reaction diagram
-
i.e. dilinoleoylPC
-
-
?
eicosapentaenoic acid + O2
15-hydroxyeicosapentaenoic acid
show the reaction diagram
-
-
-
-
?
eicosatrienoic acid + O2
?
show the reaction diagram
-
-
-
-
?
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
-
-
-
-
?
linoleate + O2
(9Z,11R,12Z)-11-hydroperoxyoctadeca-9,12-dienoate + (9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate + (9R,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate
show the reaction diagram
Cyanothece sp., Cyanothece sp. PCC 8801
B7JX99
-
(9Z,11R,12Z)-11-hydroperoxyoctadeca-9,12-dienoate is the primary product
-
?
linoleate + O2
?
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
4% of the activity with arachidonate
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
reaction of EC 1.13.11.12
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
an atomic-level study of the binding modes of linoleic acid to rabbit reticulocyte 15-rLO-1 is presented. Results are compared with binding of arachidonic acid to 15-rLO-1. Linoleic acid seems to adapt more easily to the enzyme structure and differs from arachidonic acid on some dynamical aspects that could introduce kinetic differences, as observed experimentally
-
-
?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
-
-
-
?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
-
-
-
?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
-
-
-
?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
-
-
-
?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
-
-
13-hydroperoxy-9,11-octadecadienoic acid + 13-hydroxy-9,11-octadecadienoic acid
?
linoleic acid + O2
13-hydroperoxy-(9Z,11E)-linoleic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
13-hydroxyoctadecadienoic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
show the reaction diagram
-
preferred substrate of isozyme 15-hLO-1, reaction of EC 1.13.11.12
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
show the reaction diagram
-
reaction of EC 1.13.11.12
-
-
?
linoleic acid + O2
13(S)-hydroxyoctadecadienoic acid
show the reaction diagram
-
-
12/15LO eicosanoid products reduce cholesterol efflux to high density lipoproteins, regulate ATP-binding cassette transporter G1 expression and enhance ATP-binding cassette transporter G1 degradation and ATP-binding cassette transporter G1 serine phosphorylation
-
?
linoleic acid + O2
13-S-hydroxyoctadecadienoic acid
show the reaction diagram
-
both 15-LOX-1, 15-LOX-2 reacts with linoleic acid poorly
-
-
?
linolenate + O2
11-hydroperoxyoctadecatrienoic acid + 9-hydroperoxyoctadecatrienoic acid + 13-hydroperoxyoctadecatrienoic acid
show the reaction diagram
Cyanothece sp., Cyanothece sp. PCC 8801
B7JX99
-
-
-
?
additional information
?
-
-
15-lipoxygenase is capable of disrupting the pH gradient maintained by mitochondria in living cells without additional factors specific for red blood cell development. Ectopic expression of 15-lipoxygenase leads to the collaps of the mitochondrial pH gradient in nonerythroid cells
-
-
-
additional information
?
-
-
15-LOX2 and 15-LOX2sv-b suppress prostate tumor development, and the tumor-suppressive functions apparently do not necessarily depend on arachidonic acid-metabolizing activity and nuclear localization
-
-
-
additional information
?
-
-
activation of the enzyme at the protein and product levels and increased sensitivity to constriction of pulmonary arteries by the product 15S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid may contribute to pulmonary hypoxic vasoconstriction in neonatal rabbits
-
-
-
additional information
?
-
-
production of antiinflammatory lipid mediators by the enzyme may be a general strategy by which pathogens regulate the host-pathogen relationship
-
-
-
additional information
?
-
-
the enzyme may be involved in the development of atherosclerosis
-
-
-
additional information
?
-
-
trans-10,cis-12-conjugated linoleic acid is not a substrate for 15-LOX-1
-
-
-
additional information
?
-
-
15-LOX2 is a functional tumor suppressor that regulates prostate epithelial cell differentiation, senescence, and growth size, overview
-
-
-
additional information
?
-
-
eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in eosinophils and mast cells, metabolism of 14,15-leukotrienes in eosinophils, overview
-
-
-
additional information
?
-
P16050
a bifunctional enzyme exhibiting 12-LO and 15-LO activity
-
-
-
additional information
?
-
-
a bifunctional enzyme exhibiting 12-LO and 15-LO activity, the enzyme is also able to catalyze stereoselective oxidation of linoleic acid at position 13 over 9 to preferentially form 13(S)-hydroperoxyoctadienoic acid, which enhances MCP-1 expression, overview
-
-
-
additional information
?
-
-
a bifunctional enzyme exhibiting 15-lipoxygenase and 12-lipoxygenase, EC 1.13.11.31, activities
-
-
-
additional information
?
-
-
conjugated linoleic acids are no substrates for 15-LO-1 in vitro, overview
-
-
-
additional information
?
-
-
product distributions of lipoxygenases under various conditions, overview
-
-
-
additional information
?
-
-
stereo-selectivity in LOX-catalyzed oxygenation of lysophospholipids, overview
-
-
-
additional information
?
-
-
substrate specificity of 15-hLO isozymes, the specific activity is affected by cholate and lipoxygenation reaction products, e.g. 13-hydroperoxyoctadienoic acid changes the (kcat/Km)AA/(kcat/Km)LA ratio more than 5fold for 15-hLO-1 and 3fold for 15-hLO-2, while 12-(S)-hydroperoxyeicosatetraenoic acid affects only the ratio of 15-hLO-1 more than 5fold. In addition, 13-(S)-hydroxyoctadecadienoic acid and 12-(S)-hydroxyeicosatetraenoic acid also affect substrate specificity, indicating that iron oxidation is not responsible for the change in the (kcat/Km)AA/(kcat/Km)LA ratio, residues R402, F414, F352, I417, and M418 are located at the active site and involved in catalysis, presence of a product-activated, allosteric regulatory site for both 15-hLO isozymes, competitive substrate capture experiments, overview
-
-
-
additional information
?
-
-
the bifunctional enzyme also forms (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate, the product of 12-LO activity, EC 1.13.11.31, in a ratio of 9:1 15(S)-HPETE to 12(S)HPETE
-
-
-
additional information
?
-
-
12/15-LO can catalyse the formation of EXC4
-
-
-
additional information
?
-
-
15-LOX-2 does not oxygenate (5Z,8Z,11Z,14Z)-nonadeca-5,8,11,14-tetraene-1,19-dioic acid at various pH
-
-
-
additional information
?
-
P93184
the enzyme also converts linoleate to (9Z,11E,13S)-13-hydroperoxy-11,13-octadecadienoate
-
-
-
additional information
?
-
B2IZG6
the enzyme also converts linoleate to (9Z,11E,13S)-13-hydroperoxy-11,13-octadecadienoate, alpha-linolenate to (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate and gamma-linolenate to (6Z,9Z,11E,13S)-13-hydroperoxy-6,9,11-octadecatrienoate
-
-
-
additional information
?
-
Cyanothece sp.
B7JX99
incubation of the enzyme with [(11S)-2H]-linoleic acid leads to the formation of hydroperoxides that have lost the deuterium label, thus suggesting that LOX2 catalyzes antarafacial oxygenation as opposed to the mechanism of manganese lipoxygenase
-
-
-
additional information
?
-
-
15LO1 interacts with PEBP1 (phosphatidylethanolamine-binding protein)
-
-
-
additional information
?
-
Mus musculus C57BL/6
-
a bifunctional enzyme exhibiting 12-LO and 15-LO activity, the enzyme is also able to catalyze stereoselective oxidation of linoleic acid at position 13 over 9 to preferentially form 13(S)-hydroperoxyoctadienoic acid, which enhances MCP-1 expression, overview
-
-
-
additional information
?
-
Nostoc punctiforme PCC73102
B2IZG6
the enzyme also converts linoleate to (9Z,11E,13S)-13-hydroperoxy-11,13-octadecadienoate, alpha-linolenate to (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate and gamma-linolenate to (6Z,9Z,11E,13S)-13-hydroperoxy-6,9,11-octadecatrienoate
-
-
-
additional information
?
-
B7JX99
incubation of the enzyme with [(11S)-2H]-linoleic acid leads to the formation of hydroperoxides that have lost the deuterium label, thus suggesting that LOX2 catalyzes antarafacial oxygenation as opposed to the mechanism of manganese lipoxygenase
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2 arachidonate + 2 O2 + H+
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate + H2O
show the reaction diagram
Mus musculus, Mus musculus C57BL/6
-
-
(5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate slightly increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but more potent by 12(S)-hydroxyeicosatetranoic acid, overview
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
further metabolized to (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate, 15-HETE, has no effect on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
is further metabolized by hydroperoxide isomerase to the acid-sensitive metabolite 15(S)-hydroxy-11,12-epoxyeicosatrienoic acid, which is hydrolyzed to 11,12,15-trihydroxyeicosatrienoic acid, by a soluble epoxid hydrolase, causing endothelium-dependent smooth muscle hyperpolarization and relaxations, mass spectrometrical metabolite analysis and pathway, overview
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
the bifunctional enzyme also forms (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate, the product of 12-LO activity, EC 1.13.11.31, in a ratio of 9:1 15(S)-HPETE to 12(S)-HPETE, further reduced to the correspondent (S)-hydroxy fatty acids, in eosinophils, overview
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
the enzyme is regulated pretranslational, translational and posttranslational
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
induction of experimental anemia leads to a systemic up-regulation of 12/15-lipoxygenases expression
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
O15296
15-lipoxygenase 2 is a negative cell cycle regulator in normal prostate epithelial cells, it could be a suppressor of prostate cancer development, which functions by restricting cell cycle progression
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
catalyzes enzymatic lipid peroxidation in complex biological structures via direct dioxygenation of phospholipids and cholesterol esters of biomembranes and plasma lipoproteins
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
the enzyme is implicated in inflammatory disorders, 15-lipoxygenase is induced in atherosclerosis and can oxidize low-density lipoprotein to its atherogenic form
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
first step in biotransformation of arachidonic acid to the 15-series of leukotrienes, reaction is involved in inactivation of slow-reacting substrances of anaphylaxis
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
alternative splicing of 15S-lipoxygenase provides a further level of regulation of fatty acid metabolism
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
12/15LO protein levels and activity are increased in pathologically affected regions of Alzheimers disease brains, enzyme inhibition causes a decrease in amyloid-beta protein, 12/15LO influences amyloid-beta protein precursor protein metabolism, overview
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
15-lipoxygenase type-1 is a prooxidant enzyme, which is expressed in asthmatic lungs leading to formation of pro- and anti-inflammatory mediators, overview
the product is further metabolized to 15(S)-hydroxyeicosatetranoic acid and 15-ketoeicosatetraenoic acid, the latter is the main product, pathway and mechanism, overview
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
15-LOX2 in NHP cells is positively regulated by Sp1 and negatively regulated by Sp3, but 15-LOX2 expression in NHP cells is not directly regulated by androgen/androgen receptor, overview
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
arachidonic acid is metabolized by the 15-lipoxygenase-1 pathway to the vasodilatory eicosanoids hydroxyepoxyeicosatrienoic acid and trihydroxyeicosatrienoic acid
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
arachidonic acid metabolization by lipoxygenases, overview
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
the enzyme is involved in acetylsalicylic acid-triggered production of 15(S)-hydroxyeicosatetranoic acid, 15(S)-HETE, in sensitive asthmatic patients, acetylsalicylate-tolerant asthma patients show reduced 15-LO activity
is metabolized to 15(S)-hydroxyeicosatetranoic, i.e. 15(S)-HETE
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
the enzyme modifies high density lipoprotein 3, the major and most antiatherogenic HDL subfraction, and impairs anti-inflammatory activity of the lipoprotein, which, after modification, fails to inhibit TNFalpha-mediated mRNA and protein induction of adhesion molecules and monocyte chemoattractant protein-1, MCP-1, in endothelial cells, overview
is metabolized to 15(S)-hydroxyeicosatetranoic, i.e. 15(S)-HETE
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
15-lipoxygenase is capable of disrupting the pH gradient maintained by mitochondria in living cells without additional factors specific for red blood cell development. Ectopic expression of 15-lipoxygenase leads to the collaps of the mitochondrial pH gradient in nonerythroid cells
-
-
-
additional information
?
-
-
15-LOX2 and 15-LOX2sv-b suppress prostate tumor development, and the tumor-suppressive functions apparently do not necessarily depend on arachidonic acid-metabolizing activity and nuclear localization
-
-
-
additional information
?
-
-
activation of the enzyme at the protein and product levels and increased sensitivity to constriction of pulmonary arteries by the product 15S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid may contribute to pulmonary hypoxic vasoconstriction in neonatal rabbits
-
-
-
additional information
?
-
-
production of antiinflammatory lipid mediators by the enzyme may be a general strategy by which pathogens regulate the host-pathogen relationship
-
-
-
additional information
?
-
-
the enzyme may be involved in the development of atherosclerosis
-
-
-
additional information
?
-
-
15-LOX2 is a functional tumor suppressor that regulates prostate epithelial cell differentiation, senescence, and growth size, overview
-
-
-
additional information
?
-
-
eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in eosinophils and mast cells, metabolism of 14,15-leukotrienes in eosinophils, overview
-
-
-
additional information
?
-
-
15LO1 interacts with PEBP1 (phosphatidylethanolamine-binding protein)
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
-
enhances activity, reversible by EGTA, inhibited by phosphatidyl serine and phosphatidyl choline
Ca2+
-
optimal activity at 2 mM or above
Ca2+
-
50% of maximal activity at 0.1 mM Ca2+ in presence of 5 mM EGTA
Ca2+
-
activates reaction with crude extract
Ca2+
-
-
Ca2+
-
for maximal intracellular activity, 12/15-lipoxygenases require a rise in cytosolic calcium concentration inducing a translocation of the enzyme from the cytosol to cellular membranes
Ca2+
-
at 0.005-0.05 mM is required for efficient membrane binding
Ca2+
-
1 mM
Ca2+
-
assay in presence of Ca2+
Ca2+
-
in the presence of Ca2+, with or without calcium ionophore, the majority of 15-LO-1 is found in the membrane fraction, although significant amounts are also detected in the supernatant fraction
Fe
-
iron-containing metalloenzyme
Fe2+
-
addition in a molar excess, more than 50:1 purified protein:Fe2+, leads to a 3fold increase in the specific activity
Fe2+
-
required for the catalytic cycle of fatty acid oxidation by lipoxygenase, overview
Fe2+
-
required, iron content of the 15-hLO isozymes determined with a Finnigan inductively coupled plasma mass spectrometer, ICP-MS, using cobalt-EDTA as an internal standard
Fe2+
-
iron-containing metalloenzyme
Fe2+
Cyanothece sp.
B7JX99
LOX2 contains iron with an iron to protein ratio of 45%
Iron
-
-
Iron
-
contains iron
Iron
-
contains 1.76 mol of iron per mol of enzyme
Iron
-
contains 1 mol of non-heme iron per mol of enzyme
Iron
-
contains 0.95 mol of iron per mol of enzyme
Iron
-
the recombinant enzyme contains a variable amount of iron, often as low as 0.2 mol per mol of enzyme
Iron
-
nonheme iron dioxygenase
Iron
-
the iron is liganded by four histidines at positions 361, 366, 541 and 545 asell as the C-terminal isoleucine
Mg2+
-
activates reaction with crude extract
Mg2+
-
in the presence of Mg2+, with or without calcium ionophore, the majority of 15-LO-1 is found in the membrane fraction, although significant amounts are also detected in the supernatant fraction
Mn2+
-
activates reaction with crude extract
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(-)-5,7-O-diacetyl-3',4',5'-O-triacetylepigallocatechin-3-O-(3'',4'',5''-O-triacetyl)gallate
-
IC50: 0.061 mM
(-)-5,7-O-dibutyryl-3',4',5'-O-tributyrylepigallocatechin-3-O-(3'',4'',5''-O-tributyryl) gallate
-
IC50: 0.033 mM
(-)-5,7-O-dimethyl-3',4',5'-O-trimethylepigallocatechin-3-O-(3'',4'',5''-O-trimethyl) gallate
-
IC50: 0.03 mM
(-)-5,7-O-dipropionyl-3',4',5'-O-tripropionylepigallocatechin-3-O-(3'',4'',5''-O-tripropionyl) gallate
-
IC50: 0.031 mM
(-)-epigallocatechin-3-gallate
-
IC50: 0.1 mM
(-)-jaspic acid
-
IC50: 0.0014 mM
(Z)-9-octadecenyl sulfate
-
allosteric inhibition
1,2,3-triphenylindolizine-7-carbonitrile
-
IC50: 0.028 mM
1-(((2,4,6-trimethylphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.017 mM
1-(((2,4-dimethoxyphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.027 mM
1-(((2,5-dimethoxyphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.015 mM
1-(((2-methyl)ethylsulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.042 mM
1-(((2-methyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.022 mM
1-(((2-thienyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.021 mM
1-(((3,4-dimethoxyphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.019 mM
1-(((3-thienyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.023 mM
1-(((4-(2-methylethyl)phenl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.016 mM
1-(((4-chlorophenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.022 mM
1-(((4-methoxyphenyl)sulfonyl)oxy)-2,3-bis(4-methylphenyl)-7-indolizinecarbonitrile
-
IC50: 0.025 mM
1-(((4-methoxyphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.025 mM
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-bis(4-chlorophenyl)-7-indolizinecarbonitrile
-
IC50: 0.2 mM
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-bis(4-fluorophenyl)-7-indolizinecarbonitrile
-
IC50: 0.22 mM
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-bis(4-methoxyphenyl)-7-indolizinecarbonitrile
-
IC50: 0.024 mM
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-bis(4-methylphenyl)-7-indolizinecarbonitrile
-
IC50: 0.2 mM
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-dibutyl-7-indolizinecarbonitrile
-
IC50: 0.03 mM
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-diethyl-7-indolizinecarbonitrile
-
IC50: 0.029 mM
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarboxaldehyde
-
IC50: 0.02 mM
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinylethanone
-
IC50: 0.023 mM
1-(((4-methysulfonyllphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.024 mM
1-(((4-trifluoromethylphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.023 mM
1-((4-methylphenyl)sulfonyl)2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.029 mM
1-((butylsulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.028 mM
1-((methylsulfonyl)oxy)-2,3-diphenyl-7-indolizine-carbonitrile
-
IC50: 0.022 mM
1-((N,N-dimethylaminosulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.025 mM
1-((phenylsulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.024 mM
1-(1,3-dibenzyloxy-2-propyloxy)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.031 mM
1-(1-Hydroxy-1-phenyl-ethyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.017 mM
1-(1-hydroxyethyl)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.026 mM
1-(2-furyl)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.024 mM
1-(2-Methoxy-phenyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.02 mM
1-(2-methoxyphenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.029 mM
1-(3-chlorophenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.031 mM
1-(3-Methoxy-phenyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.02 mM
1-(4-chlorophenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.031 mM
1-(4-fluorophenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.035 mM
1-(4-Methoxy-phenyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.02 mM
1-(4-Methoxy-phenyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.037mM
1-(4-methoxyphenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.032 mM
1-(4-methylphenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.037 mM
1-(Cyclohexyl-hydroxy-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.023 mM
1-(Hydroxy-p-tolyl-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.022 mM
1-(Hydroxy-phenyl-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.035 mM
1-(Hydroxy-phenyl-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.048 mM
1-(hydroxymethyl)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.026 mM
1-(hydroxymethyl)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.034 mM
1-(Methoxy-phenyl-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.021 mM
1-(methoxymethoxy)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.031 mM
1-(methoxymethoxy)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.075 mM
1-acetyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.023 mM
1-acetyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.044 mM
1-benzoyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.023 mM
1-benzoyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.043 mM
1-benzyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.027 mM
1-benzyloxymethoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.027 mM
1-benzyloxymethoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.039 mM
1-formyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.029 mM
1-formyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.061 mM
1-methoxy-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.033 mM
1-methoxy-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.077 mM
1-methyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.027 mM
1-methyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.046 mM
1-phenylmethoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.031 mM
1-[(4-Chloro-phenyl)-hydroxy-methyl]-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.023 mM
1-[Hydroxy-(4-methoxy-phenyl)-methyl]-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.017 mM
11-hydroxytephrosin
Sarcolobus globosus
-
IC50: 0.071 mM
11-thialinoleic acid
-
is a noncompetitive inhibitor of 15-lipoxygenase-1 with respect to arachidonate or linoleic acid as substrates. Presence of inhibitor does not alter the product distribution for 15-lipoxygenase-1. It does not change the regioselectivity of 15-lipoxygenase-1
12alpha-hydroxydeguelin
Sarcolobus globosus
-
IC50: 0.018 mM
12alpha-hydroxyrotenone
Sarcolobus globosus
-
IC50: 0.102 mM
13S-hydroperoxy-9E,11E-octadecydienoic acid
-
rapidly inactivates
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
-
IC50: 0.007 mM
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
-
IC50: 0.0018 mM
2,3,4,5-tetrabromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
-
IC50: 0.00079 mM
2,3,5-tribromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
-
IC50: 0.0022 mM
2,3-bis(4-chlorophenyl)-7-indolizinecarbonitrile
-
IC50: 0.033 mM
2,3-bis(4-fluorophenyl)-7-indolizinecarbonitrile
-
IC50: 0.03 mM
2,3-bis(4-methylphenyl)-7-indolizinecarbonitrile
-
IC50: 0.027 mM
2,3-Dihydroxybenzoic acid
-
47.7% inhibition at 0.015 mM, active site binding structure
2,3-diphenyl-1-(2-thienyl)indolizine-7-carbonitrile
-
IC50: 0.02 mM
2,3-diphenyl-1-(3-thienyl)indolizine-7-carbonitrile
-
IC50: 0.019 mM
2,3-diphenyl-1-indolizinol tosylate
-
IC50: 0.025 mM
2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.03 mM
2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.051 mM
2,4-dibromo-6-(2,4-dibromo-6-methoxyphenoxy)phenol
-
IC50: 0.01 mM
2,4-Dibromophenol
-
IC50: 0.034 mM
2,4-dihydroxybenzoic acid
-
49.9% inhibition at 0.015 mM, active site binding structure
2,5-dihydroxybenzoic acid
-
21.2% inhibition at 0.015 mM, active site binding structure
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
-
IC50: 0.005 mM
2-(1H-indol-3-yl)-N-[(4-pentylphenyl)sulfonyl]acetamide
-
-
2-(4-ethylpiperazin-1-yl)4-methylpyrimido[4,5-b][1,4]benzothiazine
-
-
2-(4-ethylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
2-(4-methylpiperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
2-(morpholin-4-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
2-(piperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
2-(pyrrolidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
2-([4-[(4-fluorobenzyl)oxy]butyl]sulfanyl)-5-(naphthalen-1-yl)-1,3,4-oxadiazole
-
-
2-alkyl benzopyran-4-ones
-
weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
2-alkyl-6-hydroxy-4-H-benzopyran-4-one
-
weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
2-hydroxybenzoic acid
-
46.0% inhibition at 0.015 mM, active site binding structure
2-[2-(1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione
-
-
2-[2-(2-bromo-1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione
-
-
2-[2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione
-
-
2-[3-(1H-indol-3-yl)propyl]-1H-isoindole-1,3(2H)-dione
-
-
3'-chloro-7,8-dihydroxyisoflavone
-
weak inhibition of isozyme 15-hLO-2
3,4,5-Trihydroxybenzoic acid
-
60.5% inhibition at 0.015 mM, active site binding structure
3,4,6,8-tetrabromooxanthren-1-ol
-
IC50: 0.0009 mM
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
-
IC50: 0.009 mM
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
-
IC50: 0.005 mM
3,4-dibromo-2-(5-bromo-2-hydroxyphenoxy)phenol
-
IC50: 0.011 mM
3,4-dihydroxybenzoic acid
-
51.6% inhibition at 0.015 mM, active site binding structure; 73.3% inhibition at 0.015 mM, active site binding structure
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
-
IC50: 0.05 mM
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
-
IC50: 0.015 mM
3,5-Dihydroxybenzoic acid
-
58.1% inhibition at 0.015 mM, active site binding structure
3,6,8-tribromooxanthren-1-ol
-
IC50: 0.0008 mM
3-(2-[[(4-pentylphenyl)sulfonyl]amino]ethyl)-1H-indole-6-carboxylic acid
-
-
3-hydroxy-H-benzopyran-4-one derivatives
-
weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
3-Hydroxybenzoic acid
-
47.6% inhibition at 0.015 mM, active site binding structure
3-[1-[(4-pentylphenyl)sulfonyl]pyrrolidin-3-yl]-1H-indole
-
-
3-[3-bromo-5-(2,6-dibromo-4-{2-[2-(3-bromo-4-hydroxy-phenyl)-ethylcarbamoyl]-2-[(E)-hydroxyimino]-ethyl}-phenoxy)-4-methyl-phenyl]-N-[(E)-2-(3,5-dibromo-4-hydroxy-phenyl)-vinyl]-2-[(E)-hydroxyimino]-propionamide
-
IC50: 0.059 mM
4',6,7-trihydroxyisoflavan
-
-
4',6,7-trihydroxyisoflavanone
-
weak inhibition of isozyme 15-hLO-2
4',6,7-trihydroxyisoflavone
-
weak inhibition of isozyme 15-hLO-2
4'-butyl-N-[2-(1H-indol-3-yl)ethyl]biphenyl-4-sulfonamide
-
IC50: 0.00053 mM in the presence of arachidonate, IC50: 0.0002 mM in the presence of linoleic acid
4'-chloro-7,8-dihydroxyisoflavone
-
weak inhibition of isozyme 15-hLO-2
4'-ethyl-N-[2-(1H-indol-3-yl)ethyl]biphenyl-4-sulfonamide
-
IC50: 0.00026 mM in the presence of arachidonate, IC50: 0.00047 mM in the presence of linoleic acid
4'-tert-butyl-N-[2-(1H-indol-3-yl)ethyl]biphenyl-4-sulfonamide
-
IC50: 0.00027 mM in the presence of arachidonate, IC50: 0.00023 mM in the presence of linoleic acid
4,4'-propane-2,2-diylbis(2,6-dibromophenol)
-
IC50: 0.004 mM
4,5-bis(4-chlorophenyl)-1H-imidazole-2-thiol
-
-
4,5-bis(4-fluorophenyl)-1H-imidazole-2-thiol
-
-
4,5-bis(4-methoxyphenyl)-1H-imidazole-2-thiol
-
-
4,5-diphenyl-1H-imidazole-2-thiol
-
-
4,7,10,13-eicosatetraenoic acid
-
-
4-((5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)butyl)-4-fluorobenzoate
-
-
-
4-((5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)methyl)-benzyl-4-fluorobenzoate
-
-
-
4-(2-chlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
-
4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
-
4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
-
4-(4-chlorophenyl)-5-phenyl-1H-imidazole-2-thiol
-
-
4-(4-methoxyphenyl)-5-phenyl-1H-imidazole-2-thiol
-
-
4-(5-(1H-indol-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(2-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(3-hydroxynaphthalen-2-yl)-1,3,4-oxadiazol-2-ylthio)-but-2-ynyl-4-fluorobenzoate
-
low solubility
-
4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(furan-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylamino)but-2-ynyl-thiophene-2-carboxylate
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-yn-1-ol
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-1H-indole-4-carboxylate
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-chlorobenzoate
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-methoxybenzoate
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-benzofuran-2-carboxylate
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-thiophene-2-carboxylate
-
-
-
4-(5-(naphthalen-1-yl)-1,3,4-thiadiazol-2-ylthio)but-2-ynyl-thiophene-2-carboxylate
-
low solubility
-
4-(5-(quinolin-5-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-(5-phenyl-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
-
-
4-([2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]sulfamoyl)-N-(3-hydroxypropyl)benzamide
-
-
4-([2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]sulfamoyl)-N-(4-methoxyphenyl)benzamide
-
-
4-([2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]sulfamoyl)-N-butylbenzamide
-
-
4-([2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]sulfamoyl)-N-cyclohexylbenzamide
-
-
4-([2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]sulfamoyl)-N-phenylbenzamide
-
-
4-([2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]sulfamoyl)-N-[3-(dimethylamino)propyl]benzamide
-
-
4-([2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethyl]sulfamoyl)benzoic acid
-
-
4-allyl-2-methoxyphenyl 1-adamantanecarboxylate
-
-
4-allyl-2-methoxyphenyl 1-cyclohexanecarboxylate
-
-
4-allyl-2-methoxyphenyl 2-chlorobenzoate
-
-
4-allyl-2-methoxyphenyl 2-fluorobenzoate
-
-
4-allyl-2-methoxyphenyl 2-methylbenzoate
-
-
4-allyl-2-methoxyphenyl 2-pyridinecarboxylate
-
-
4-allyl-2-methoxyphenyl 3-chlorobenzoate
-
-
4-allyl-2-methoxyphenyl 3-fluorobenzoate
-
-
4-allyl-2-methoxyphenyl 3-methoxybenzoate
-
-
4-allyl-2-methoxyphenyl 3-methylbenzoate
-
-
4-allyl-2-methoxyphenyl 4-chlorobenzoate
-
-
4-allyl-2-methoxyphenyl 4-fluorobenzoate
-
-
4-allyl-2-methoxyphenyl 4-methoxybenzoate
-
-
4-allyl-2-methoxyphenyl 4-methylbenzoate
-
-
4-allyl-2-methoxyphenyl benzoate
-
-
4-allyl-2-methoxyphenyl isonicotinate
-
-
4-allyl-2-methoxyphenyl nicotinate
-
-
4-bromo-N-[2-(1H-indol-3-yl)ethyl]benzenesulfonamide
-
-
4-Bromophenol
-
IC50: 0.048 mM
4-Bromophenol
-
IC50: 0.055 mM
4-butyl-N-[2-(1H-indol-3-yl)ethyl]benzenesulfonamide
-
IC50: 0.00307 mM in the presence of arachidonate, IC50: 0.004 mM in the presence of linoleic acid
4-butyl-N-[2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethyl]benzenesulfonamide
-
-
4-butyl-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
-
4-ethyl-N-[2-(1H-indol-3-yl)ethyl]benzenesulfonamide
-
IC50: 0.01 mM in the presence of arachidonate, IC50: 0.01 mM in the presence of linoleic acid
4-hydroxy-3-methoxybenzoic acid
-
45.4% inhibition at 0.015 mM, active site binding structure
4-hydroxybenzoic acid
-
47.0% inhibition at 0.015 mM, active site binding structure
4-methyl-2-(4-ethylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
4-methyl-2-(4-hydroxypiperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
4-methyl-2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
4-methyl-2-(4-methylpiperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
4-methyl-2-(4-phenylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
4-methyl-2-(morpholin-4-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
4-methyl-2-(piperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
4-methyl-2-(pyrrolidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
-
4-nitrocatechol
-
IC50: 0.0046 mM
4-pentyl-N-(2-[2-phenyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-4-yl]ethyl)benzenesulfonamide
-
-
4-pentyl-N-(2-[2-[4-(trifluoromethyl)phenyl]-1H-indol-3-yl]ethyl)benzenesulfonamide
-
-
4-pentyl-N-[2-(2-phenyl-1H-indol-3-yl)ethyl]benzenesulfonamide
-
-
4-pentyl-N-[2-(2-quinolin-3-yl-1H-indol-3-yl)ethyl]benzenesulfonamide
-
-
4-pentyl-N-[2-(5-phenyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
-
4-pentyl-N-[2-(5-phenyl-2-pyrazin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
-
4-pentyl-N-[2-(5-phenyl-2-pyridin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
-
4-pentyl-N-[2-(5-phenyl-2-pyridin-3-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
-
4-pentyl-N-[2-(5-phenyl-2-pyridin-4-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
-
4-pentyl-N-[2-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
-
4-pentyl-N-[2-[5-(1H-pyrrol-2-yl)-1H-indol-3-yl]ethyl]benzenesulfonamide
-
-
4-pentyl-N-[3-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)propyl]benzenesulfonamide
-
-
4-[4-(dimethylamino)phenyl]-5-(4-methoxyphenyl)-1H-imidazole-2-thiol
-
-
4-[4-(methylsulfanyl)phenyl]-5-phenyl-1H-imidazole-2-thiol
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1-benzothiophene-2-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1-benzothiophene-3-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1H-imidazole-4-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2,4-difluorobenzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2-fluorobenzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2-fluoropyridine-3-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2-methoxybenzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4,5-trichlorothiophene-2-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4,5-trifluorobenzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4-difluorobenzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-(trifluoromethyl)benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-chloro-1-benzothiophene-2-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-chlorothiophene-2-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-fluorobenzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(difluoromethoxy)benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(methylsulfonyl)benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(triazan-2-yl)benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(trifluoromethoxy)benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(trifluoromethyl)benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-bromobenzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-chloro-3-(trifluoromethyl)benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-[(trifluoromethyl)sulfanyl]benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl benzoate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl cyclobutanecarboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl cyclopentanecarboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl cyclopropanecarboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl furan-2-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl naphthalene-2-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl thiophene-3-carboxylate
-
-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]butyl 4-fluorobenzoate
-
-
4-[[5-(naphthalen-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-fluorobenzoate
-
-
5,8,11,14,17-eicosapentaenoic acid
-
-
5,8,11,14-eicosatetraenoic acid
-
-
5,8,11,14-eicosatetraenoic acid
-
-
5,8,11,14-eicosatetraenoic acid
-
IC50: 0.00012 mM
5,8,11,14-Eicosatetraynoic acid
-
0.0009 mM, 50% inhibition
5,8,11,14-Eicosatetraynoic acid
-
-
5,8,11,14-Eicosatetraynoic acid
-
inhibits reaction of linoleic acid
5,8,11,14-Eicosatetraynoic acid
-
-
5-(4-chlorophenyl)-4-(4-methoxyphenyl)-1H-imidazole-2-thiol
-
-
5-(4-chlorophenyl)-4-(4-methoxyphenyl)-2-(methylsulfanyl)-1H-imidazole
-
-
5-(4-chlorophenyl)-4-[4-(dimethylamino)phenyl]-1H-imidazole-2-thiol
-
-
5-(4-chlorophenyl)-4-[4-(methylsulfanyl)phenyl]-1H-imidazole-2-thiol
-
-
5-(4-fluorophenyl)-4-(4-methoxyphenyl)-1H-imidazole-2-thiol
-
-
5-(4-fluorophenyl)-4-[4-(methylsulfanyl)phenyl]-1H-imidazole-2-thiol
-
-
5-(methoxymethoxy)-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.032 mM
5-(methoxymethoxy)-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.059 mM
5-ethoxy-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.028 mM
5-methoxy-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.029 mM
5-methoxy-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.059 mM
6,11-dihydro[1]benzothiopyrano[4,3-b]indole
-
PD146176
6,7-dihydroxy-2-t-butylbenzopyran-4-one
-
weak inhibition of isozyme 15-hLO-2
6,7-dihydroxy-3',4'-methylenedioxyisoflavan
-
-
6,7-dihydroxy-3'-methylisoflavan
-
-
6,7-dihydroxy-3'-methylisoflavanone
-
weak inhibition of isozyme 15-hLO-2
6,7-dihydroxy-4'-methoxyisoflavan
-
-
6,7-dihydroxy-4'-methoxyisoflavanone
-
weak inhibition of isozyme 15-hLO-2
6,7-dihydroxyisoflavones
-
weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
6,7-dimethoxy-2,3-dihydrochromone
Sarcolobus globosus
-
IC50: 0.137 mM
6,7-diphenylpyrrolo[1,2-a]pyrimidin-8-ol tosylate
-
IC50: 0.015 mM
6,7-diphenylpyrrolo[1,2-b]pyridazin-5-yl trifluoromethanesulfonate
-
IC50: 0.043 mM
6,7-diphenylpyrrolo[1,2-c]pyrimidin-5-ol tosylate
-
IC50: 0.022 mM
6-hydroxy-2-pentyl-4H-benzopyran-4-one
-
weak inhibition of isozyme 15-hLO-2
6-oxo-6alpha,12alpha-dehydrodeguelin
Sarcolobus globosus
-
-
6-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]-1-phenylhexan-1-one
-
low solubility
6alpha,12alpha-12alpha-hydroxyelliptone
Sarcolobus globosus
-
IC50: 0.062 mM
6alpha,12alpha-dehydrodeguelin
Sarcolobus globosus
-
IC50: 0.071 mM
7,10,13-eicosatrienoic acid
-
-
7,8-dihydroxy-3',4'-dimethoxyisoflavan
-
-
7,8-dihydroxy-3'-methylisoflavone
-
weak inhibition of isozyme 15-hLO-2
7,8-dihydroxy-3'-trifluoromethylisoflavone
-
weak inhibition of isozyme 15-hLO-2
7,8-dihydroxy-4'-methoxyisoflavan
-
-
7,8-dihydroxy-4'-methylisoflavan
-
-
7,8-dihydroxy-4'-methylisoflavone
-
weak inhibition of isozyme 15-hLO-2
7,8-dihydroxyisoflavone
-
weak inhibition of isozyme 15-hLO-2
7-(1,1-dimethylethyl)-2,3-diphenyl-1-indolizinol tosylate
-
IC50: 0.022 mM
7-cyano-2,3-diphenylindolizin-1-yl 2-methoxybenzoate
-
IC50: 0.03 mM
7-cyano-2,3-diphenylindolizin-1-yl 3-methoxybenzoate
-
IC50: 0.028 mM
7-cyano-2,3-diphenylindolizin-1-yl 4-methoxybenzoate
-
IC50: 0.028 mM
7-cyano-2,3-diphenylindolizin-1-yl trifluoromethanesulfonate
-
IC50: 0.046 mM
7-cyano-2,3-diphenylindolizin-1-yl trifluoromethanesulfonate
-
IC50: 0.059 mM
7-hydroxy-H-benzopyran-4-one derivatives
-
weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
8,11,14-Eicosatrienoic acid
-
-
AAAKKAAK
-
64.2% inhibition at 0.25 mM
alpha-mangostin
-
NSC30552, a natural product, caspase-3 pathway inhibitor, performs selective inhibition of 12-LO
anthraquinone
-
-
apigenin
-
IC50: 0.5 mM
apigenin
-
IC50: 0.18 mM
apigenin
-
IC50: 0.0034 mM without Triton X-100, IC50: 0.0003 mM in the presence of 0.01% Triton X-100
arachidonic acid
-
autoinactivates 15-hLO-1 to a much greater extent than linoleic acid at high substrate concentrations. No autoinactivation at low substrate concentrations
baicalein
-
IC50: 0.035 mM
baicalein
-
IC50: 0.001 mM
baicalein
-
potent inhibitor, IC50: 0.0016 mM without Triton X-100, IC50: 0.038 mM in the presence of 0.01% Triton X-100
baicalein
-
-
barbigerone
Sarcolobus globosus
-
IC50: 0.063 mM
Benzoic acid
-
48.4% inhibition at 0.015 mM, active site binding structure
bestatin
-
IC50: 0.027 mM
bestatin 7
-
IC50: 0.027 mM
beta-casein
-
11.7% inhibition at 0.025 mM
-
BODIPY-D3825
-
competes with the substrate fatty acid for binding at the active site
caffeic acid
-
36.2% inhibition at 0.015 mM
caffeic acid
-
specific inhibition of 15-LO
caffeic acid
-
specific inhibitor of 15-LOX-1
chrysin
-
IC50: 1 mM
cinnamyl 3,4-dihydroxy-cyanocinnamate
-
CDC
cinnamyl-3,4-dihydroxy-a-cyanocinnamate
-
-
conjugated linoleic acids
-
conjugated linoleic acids may function as inhibitors of 15-LO-1 activity in macrophages/in vivo, overview
-
daidzein
-
IC50: 0.25 mM
daidzein
-
IC50: 0.43 mM
dansyl tryptamine
-
IC50: 0.00373 mM
decyl gallate
-
-
dysidenin
-
-
ebselen
-
i.e. 2-phenyl-1,2-benzisoselenazol-3(2H)-one, irreversible inhibition, IC50: 0.00006 mM
eicosatetraynoic acid
-
-
epicatechin
-
IC50: 0.06 mM
esculetin
-
-
ethyl gallate
-
-
fisetin
-
IC50: 0.0035 mM
fisetin
-
IC50: 0.0018 mM
flavone
-
IC50: 0.7 mM
flavone
-
IC50: 0.32 mM
galangin
-
IC50: 0.2 mM
galangin
-
IC50: 0.045 mM
GATA-6
-
inhibits non-steroidal anti-inflammatory drugs-induced transcription of 15-LOX-1 in colorectal cancer cells
-
genistein
-
IC50: 1 mM
genistein
-
IC50: 0.018 mM
genistein
Sarcolobus globosus
-
IC50: above 0.167 mM
genistin
Sarcolobus globosus
-
IC50: above 0.167 mM
glucocorticoid
-
inhibits induction in monocytes
-
glucosyringic acid
Sarcolobus globosus
-
IC50: above 0.167 mM
hesperetin
-
IC50: 0.09 mM
interferon-gamma
-
inhibits induction in monocytes
-
iodoacetamide
-
1.0 mM, 30% inhibition
IRKEIKKN
-
33.9% inhibition at 0.25 mM
isotachioside
Sarcolobus globosus
-
IC50: above 0.167 mM
jaspaquinol
-
IC50: 0.0003 mM
L-carnosine
-
3.6% inhibition at 0.25 mM
linoleic acid
-
-
linoleic acid
-
autoinactivates 15-hLO-1 to a much greater extent than linoleic acid at high substrate concentrations. No autoinactivation at low substrate concentrations
linoleic acid
-
fully deuterated, the mode of inhibition, in the presence of 13-(S)-hydroxyoctadecadienoic acid, changes from mixed-type inhibition to competitive inhibition
luteolin
-
IC50: 0.003 mM
luteolin
-
IC50: 0.0006 mM
methyl 3-(2-[[(4-pentylphenyl)sulfonyl]amino]ethyl)-1H-indole-6-carboxylate
-
-
methyl gallate
-
-
morin
-
IC50: 0.018 mM
morin
-
IC50: 0.006 mM
myricetin
-
IC50: 0.006 mM
myricetin
-
IC50: 0.018 mM
N'-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
-
N'-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3S)-1-phenoxypyrrolidin-3-yl]sulfamide
-
-
N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
-
N-(4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol)-2-ylthio)but-2-ynyl-thiophene-2-carboxamide
-
-
-
n-butyl gallate
-
-
N-ethyl-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-[(3R)-1-(1-methyl-1-phenylethyl)pyrrolidin-3-yl]sulfamide
-
-
N-ethyl-N-[(3R)-1-[1-(4-fluorophenyl)ethyl]pyrrolidin-3-yl]-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]sulfamide
-
-
n-propyl gallate
-
-
n-tetradecyl gallate
-
-
N-[(3R)-1-(3,4-dichlorobenzyl)pyrrolidin-3-yl]-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-methylsulfamide
-
-
N-[2-(1H-indol-3-yl)-1-methylethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(1H-indol-3-yl)ethyl]-2'-methylbiphenyl-4-sulfonamide
-
IC50: 0.00092 mM in the presence of arachidonate, IC50: 0.00046 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-3'-methylbiphenyl-4-sulfonamide
-
IC50: 0.00045 mM in the presence of arachidonate, IC50: 0.00032 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-4'-(1-methylethyl)biphenyl-4-sulfonamide
-
IC50: 0.00028 mM in the presence of arachidonate, IC50: 0.00014 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-4'-(2-methylpropyl)biphenyl-4-sulfonamide
-
IC50: 0.00091 mM in the presence of arachidonate, IC50: 0.00017 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-4'-methoxybiphenyl-4-sulfonamide
-
IC50: 0.0015 mM in the presence of arachidonate, IC50: 0.00109 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-4'-methylbiphenyl-4-sulfonamide
-
IC50: 0.00047 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-4-methylbenzenesulfonamide
-
IC50: 0.01 mM in the presence of arachidonate, IC50: 0.01 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-4-pentylbenzenesulfonamide
-
IC50: 0.00042 mM in the presence of arachidonate, IC50: 0.00102 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-4-propylbenzenesulfonamide
-
IC50: 0.00313 mM in the presence of arachidonate, IC50: 0.0032 mM in the presence of linoleic acid
N-[2-(1H-indol-3-yl)ethyl]-N-methyl-4-pentylbenzenesulfonamide
-
-
N-[2-(1H-indol-3-yl)ethyl]biphenyl-4-sulfonamide
-
IC50: 0.0034 mM in the presence of arachidonate, IC50: 0.0042 mM in the presence of linoleic acid
N-[2-(2,5-diphenyl-1H-imidazol-4-yl)ethyl]-4-methylbenzenesulfonamide
-
-
N-[2-(2,5-diphenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(2-cyclopropyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(2-dibenzo[b,d]furan-2-yl-1H-indol-3-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(2-methyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(2-tert-butyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(5-fluoro-1H-indol-3-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(5-methyl-1H-indol-3-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(6-fluoro-1H-indol-3-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-(7-methyl-1H-indol-3-yl)ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(1-benzofuran-2-yl)-1-methyl-1H-indol-3-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]-4-(hydrazinocarbonyl)benzenesulfonamide
-
-
N-[2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]-4-bromobenzenesulfonamide
-
-
N-[2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]-4-methylbenzenesulfonamide
-
-
N-[2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]ethyl]-4-pyridin-4-ylbenzenesulfonamide
-
-
N-[2-[2-(2,5-dimethoxyphenyl)-1H-indol-3-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(2-methyl-1,3-thiazol-4-yl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(4-chlorophenyl)-1H-indol-3-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(4-chlorophenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(4-ethoxyphenyl)-1H-indol-3-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethyl]-4-methylbenzenesulfonamide
-
-
N-[2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(4-methoxyphenyl)-1H-indol-3-yl]ethyl]biphenyl-4-sulfonamide
-
-
N-[2-[2-(4-methoxyphenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[2-(4-methylphenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[5-(3-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[5-(4-fluorophenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-phenylpiperazine-1-sulfonamide
-
-
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N'-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
-
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N'-[(3S)-1-phenoxypyrrolidin-3-yl]sulfamide
-
-
N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-4-pentylpiperazine-1-sulfonamide
-
-
N-[3-(1H-indol-3-yl)propyl]-4-pentylbenzenesulfonamide
-
-
N-[3-(2,5-diphenyl-1H-imidazol-4-yl)propyl]-4-pentylbenzenesulfonamide
-
-
N-[3-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]propyl]-4-pentylbenzenesulfonamide
-
-
N-[3-[2-(1-benzofuran-2-yl)-1H-indol-3-yl]propyl]biphenyl-4-sulfonamide
-
-
N-[4-(1H-indol-3-yl)butyl]-4-pentylbenzenesulfonamide
-
-
Naringenin
-
IC50: 0.25 mM
neodysidenin
-
natural product from marine sponge Dysidea herbacea from Papua New Guinea, extraction and purification, overview, steady-state inhibition kinetics, competitive mode of inhibition, selective for 12-LO
nor-dihydro-guaiaretic acid
-
-
nordihydroguaiaretic acid
-
0.002 mM, 50% inhibition
nordihydroguaiaretic acid
-
IC50: 0.0005 mM
nordihydroguaiaretic acid
-
IC50: 0.0018 mM
nordihydroguaiaretic acid
-
IC50: 0.00011 mM
nordihydroguaiaretic acid
-
-
nordihydroguaiaretic acid
-
IC50: 0.00011 mM
nordihydroguaiaretic acid
-
0.0001-0.001 mM
nordihydroguaiaretic acid
-
-
NSC172033
-
a synthetic compound from the NCI library
NSC292213
-
a synthetic compound from the NCI library
NSC617570
-
a synthetic compound from the NCI library
NVPGEIVE
-
65.0% inhibition at 0.25 mM
octyl gallate
-
-
PCMB
-
0.1 mM, 30% inhibition
PD 146 176
-
IC50: 0.00038 mM
PD-146176
-
IC50: 0.00381 mM
PD146176
-
-
PD146176
-
selective inhibitor of 12/15-LOX, macrophages treated with PD146176 elaborate reduced levels of interleukin-12 in response to Toxoplasma gondii antigen
PKYPVEPFTE
-
74.6% inhibition at 0.25 mM
poly-Lys
-
KKKKKKKK
propyl gallate
-
96% inhibition at 0.05 mM
quercetin
-
IC50: 0.0045 mM
quercetin
-
IC50: 0.004 mM
quercetin
Sarcolobus globosus
-
IC50: 0.029 mM
quercetin
-
-
RINKKIEK
-
68.1% inhibition at 0.25 mM, a beta-casein-derived octapeptide
RINKKIPK
-
57.7% inhibition at 0.25 mM
rutin
-
IC50: 1 mM
salicylhydroxymic acid
-
IC50: 0.057 mM
-
sarcolobin
Sarcolobus globosus
-
IC50: 0.06 mM
siRNA
-
cholesterol-tagged siRNAs targeting mouse leukocyte 12/15-LO reduce 12/15-LO expression in the kidney and confer beneficial effects on diabetes-induced changes in glomerular structure and ECM accumulation
-
siRNA
-
-
-
siRNA
-
knockdown of 15-LOX-2 expression, decreases chemokine ligand CXCL10 secretion from hypoxic macrophages and reduces T cell migration and CD69 expression
-
SITRINKK
-
65.3% inhibition at 0.25 mM
squalene
-
IC50 is 0.0012 mM
tachioside
Sarcolobus globosus
-
IC50: above 0.167 mM
taxifolin
-
IC50: 1 mM
taxifolin
-
IC50: 0.025 mM
tephrosin
Sarcolobus globosus
-
IC50: 0.064 mM
tert-butylhydroxyanisol
-
IC50: 0.16 mM
Toluene-4-sulfonic acid 6,7-diphenyl-pyrrolo[1,2-b]pyridazin-5-yl ester
-
IC50: 0.017 mM
Toluene-4-sulfonic acid 6,7-diphenyl-pyrrolo[1,2-b]pyridazin-5-yl ester
-
IC50: 0.028 mM
toluene-4-sulfonic acid 7-cyano-2,3-diphenyl-indolizin-1-yl ester
-
IC50: 0.017mM
toluene-4-sulfonic acid 7-cyano-2,3-diphenyl-indolizin-1-yl ester
-
IC50: 0.025 mM
vanillic acid 4-O-beta-D-glucoside
Sarcolobus globosus
-
IC50: 0.161 mM
villosinol
Sarcolobus globosus
-
-
michellamine B
-
NSC661755, potent but non-selective inhibitor, a natural anti-viral agent
additional information
-
the enzyme undergoes suicidal inactivation, during fatty acid oxygenation
-
additional information
-
IC50 above 0.1 mM: compound 1a, compound 1b, compound 1d, compound 1e, compound 1g
-
additional information
-
docking experiments and qualitative structure-activity relationship, QSAR, data, overview
-
additional information
-
development of an assay method for high throughput screening of libraries for platelet-type 12-hLO selective inhibitors, four organo-mercurial compounds with NCI library IDs NSC20410, NSC268879, NSC321237, and NSC321239, are also found to be selectively inhibitory, but not pursued further due to their potentially toxic side effects, overview
-
additional information
-
comparison of structural requirements for flavonoid inhibitory potency and selectivity against platelet 12-hLO, EC 1.13.11.31, and reticulocyte 15-hLO-1 and prostate epithelial 15-hLO-2, overview, catechols are essential for high potency, isoflavones and isoflavanones tend to select against 12-hLO, isoflavans tend to select against isozyme 15-hLO-1, but few flavonoids target isozyme 15-hLO-2, molecular modeling analysis, overview
-
additional information
-
no inhibition by 2,6-dihydroxybenzoic acid
-
additional information
-
quantitative structure activity relationship analysis using crystal structure, PDB ID 1IK3, EC 1.13.11.12, of the enzyme in complex with 13(S)-hydroperoxy-9(Z)-2,11(E)-octadecadienoic acid, docking studies, inhibitor binding structures, overview
-
additional information
-
docking studies, inhibitor binding structures, overview
-
additional information
-
synthesis and evaluation of 2,4,5-tri-substituted imidazoles, which show highly potent inhibition of 15-lipoxygenase with excellent selectivity over the lipoxygenases 5-LO, EC 1.13.11.34, and platelet 12-LO, EC 1.13.11.31
-
additional information
-
sulproston, misoprostol, and ONO-AE-248 inhibit acetylsalicylic acid-induced 15(S)-HETE production
-
additional information
-
docking experiments and structure activity relationship, comparative studies, comparison with the crystal structure with PDB entry: 1IK3, EC 1.13.11.12, overview
-
additional information
-
enzyme inhibition causes a decrease in amyloid-beta protein
-
additional information
-
inhibitory and LOX binding abilities of diverse RINKKIEK peptide derivatives, overview
-
additional information
-
15-LOX2 in NHP cells is negatively regulated by Sp3
-
additional information
-
intraarticular glucocorticoid treatment does not influence the 15-LO-1 enzyme in rheumatoid arthritis tissue
-
additional information
-
physico-chemical state of the substrate and the complex equilibrium between fatty acid monomers, acid soaps and micelles may impact the reaction specificity of LOX-isoforms
-
additional information
-
pH alterations in the near physiological range impact the iron content of LOX and thus the catalytic activity
-
additional information
-
15-LOX-1 can be inactivated by epigenetic silencing, hypermethylation of the CpG islands of the 15-LOX-1 promoter results in its reduced transcription in cancers, e.g. lymphomas, lung, prostate and cervix cancers. Brominated phenol esters are potent 15-LOX-1 inhibitors
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
12(S)-hydroperoxyeicosatetraenoic acid
-
reduces the kinetic lag phase
13(S)-hydroperoxyoctadecadienoic acid
-
activates 15-hLO-1 and removes the kinetic lag phase
13-(S)-hydroxyoctadecadienoic acid
-
allosteric effector, which changes the conformation of 15-hLO-2 such that substrate affinity toward linoleic acid is significantly increased
13-hydroperoxy-octadecadienoic acid
-
-
15(S)-hydroperoxyeicosatetraenoic acid
-
activates 15-hLO-1 and removes the kinetic lag phase
Acetylsalicylic acid
-
ASA, 40% activation of 15(S)-HETE production at 0.02 mM in ASA-sensitive asthmatic patients
phosphatidylcholine
-
stimulates
phosphatidylinositol-3,4-bisphosphate
-
0.02 mM, 3fold activity increase, in the presence of Ca2+
phosphatidylinositol-4,5-bisphosphate
-
0.02 mM, 3fold activity increase, in the presence of Ca2+
mannitol
-
osmotic activation of nasal tissue with mannitol activates 15-LO-1 leading to increased amounts of 15(S)-hydroxyeicosatetranoic acid in nasal lavage, and the levels of 15(S)-hydroxyeicosatetranoic acid are associated with nasal symptoms
additional information
-
interleukin-4 induces the expression of 15-LO-1 in cord blood derived mast cells, CBMC
-
additional information
-
linoleic acid induces 15-LO-1 expression 2.6fold
-
additional information
-
15-LOX2 in NHP cells is positively regulated by Sp1, the enzyme is induced in cell senescence
-
additional information
-
under cellular conditions (low fatty acid and low oxygen concentrations), the allosteric binding of 12(S)-hydroxyeicosatetraenoic acid to 15-hLO-1 can increase the substrate specificity of 15-hLO-1 toward arachidonic acid over linoleic acid significantly, tunneling mechanism
-
additional information
-
positional specificity of wild-type 15-LOX-2 does hardly depend on the pH of the reaction buffer. The pH sensitivity can be induced by introduction of a His at the active site
-
additional information
-
radiation-induced upregulation of 15-LOX-2 and 15(S)-hydroxyeicosatetranoic acid by a dose of 4 Gy in head-and-neck cancer cells
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0289
(16(R),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, wild-type enzyme
0.136
(16(R),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, mutant enzyme F353L
0.0227
(16(S),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, mutant enzyme F353L
0.0236
(16(S),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, wild-type enzyme
0.0368
(17(R),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, mutant enzyme L353L
0.293
(17(R),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, wild-type enzyme
0.0313
(17(S),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, mutant enzyme L353L
0.236
(17(S),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, wild-type enzyme
0.0083
1-linoleoyl lysophosphatidic acid
-
pH 7.4, 25C
0.0175
1-linoleoyl lysophosphatidylcholine
-
pH 7.4, 25C
0.0022
arachidonate
-
in HEPES buffer at 23C
0.005
arachidonate
-
-
0.0025
arachidonic acid
-
13,13-dideuterated arachidonic acid, pH 7.5, 25C, recombinant isozyme 15-hLO-1
0.0028
arachidonic acid
-
10,10,13,13-tetradeuterated arachidonic acid, pH 7.5, 25C, recombinant isozyme 15-hLO-1
0.00301
arachidonic acid
-
pH 7.4, wild-type enzyme
0.0034
arachidonic acid
-
10,10-dideuterated arachidonic acid, pH 7.5, 25C, recombinant isozyme 15-hLO-1
0.0037
arachidonic acid
-
unlabeled substrate, pH 7.5, 25C, recombinant isozyme 15-hLO-1
0.0038
arachidonic acid
-
-
0.0087
arachidonic acid
-
pH 7.4, mutant enzyme F353L
0.0106
arachidonic acid
-
-
0.012
arachidonic acid
-
-
0.025
arachidonic acid
-
-
0.025
arachidonic acid
-
splice variant 15-LOb1
0.028
arachidonic acid
-
-
0.0631
arachidonic acid
-
-
0.068
arachidonic acid
-
-
1.1
arachidonic acid
-
splice variant 15-LOb2
0.09
dilinoleoyl phosphatidic acid
-
pH 7.4, 25C
0.0717
dilinoleoyl phosphatidylcholine
-
pH 7.4, 25C
0.003
linoleic acid
-
-
0.0062
linoleic acid
-
-
0.0095
linoleic acid
-
-
0.0121
linoleic acid
-
pH 7.4, 25C
0.0235
linoleic acid
-
in HEPES buffer at 23C
0.0772
linoleic acid
-
-
0.0052
O2
-
pH 7.4, wild-type enzyme, with substrate linoleic acid
0.007
O2
-
pH 7.4, mutant L367W, with substrate linoleic acid
0.009
O2
-
pH 7.4, mutant L367E, with substrate linoleic acid; pH 7.4, mutant L367K, with substrate linoleic acid
0.0096
O2
-
with linoleic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C
0.015
O2
-
with arachidonic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C, in the presence of 12(S)-hydroperoxyeicosatetraenoic acid
0.022
O2
-
with linoleic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C, in the presence of 12(S)-hydroperoxyeicosatetraenoic acid
0.024
O2
-
with arachidonic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C
0.0401
O2
-
pH 7.4, mutant L367F, with substrate linoleic acid
4.2
O2
-
-
0.01
lipoic acid
-
splice variant 15-LOb1
additional information
additional information
-
steady-state kinetics of isozymes 15-hLO-1 and 15-hLO-2 with arachidonate and linoleic acid in presence or absence of 0.2% sodium cholate, or of oxygenated fatty acids, overview
-
additional information
additional information
-
kinetics with lysophospholipid substrates
-
additional information
additional information
-
free-energy distribution for oxygen inside the substrate-free rabbit 12/15-LOX, containing four nested free-energy isosurfaces with different energy levels, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.08
(16(R),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, mutant enzyme F353L
0.2
(16(S),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, mutant enzyme F353L
0.51
(16(S),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, wild-type enzyme
0.18
(17(R),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, wild-type enzyme
0.2
(17(R),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, mutant enzyme L353L
0.24
(17(S),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, mutant enzyme L353L
1.24
(17(S),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
-
pH 7.4, wild-type enzyme
3
arachidonate
-
mutant enzyme A416G
14
arachidonate
-
wild-type enzyme
0.57
arachidonic acid
-
at 15C, normalized to iron content
0.62
arachidonic acid
-
at pH 7
0.74
arachidonic acid
-
at pH 8
0.75
arachidonic acid
-
at 22C, normalized to iron content; at pH 7.5
1
arachidonic acid
-
10,10,13,13-tetradeuterated arachidonic acid, pH 7.5, 25C, recombinant isozyme 15-hLO-1
1.04
arachidonic acid
-
at 30C, normalized to iron content
1.38
arachidonic acid
-
at 37C, normalized to iron content
2.49
arachidonic acid
-
13,13-dideuterated arachidonic acid, pH 7.5, 25C, recombinant isozyme 15-hLO-1
6.02
arachidonic acid
-
pH 7.4, mutant enzyme F353L
8.16
arachidonic acid
-
pH 7.4, wild-type enzyme
9.26
arachidonic acid
-
10,10-dideuterated arachidonic acid, pH 7.5, 25C, recombinant isozyme 15-hLO-1
9.93
arachidonic acid
-
unlabeled substrate, pH 7.5, 25C, recombinant isozyme 15-hLO-1
97
arachidonic acid
-
-
4
linoleic acid
-
recombinant enzyme
10.2
linoleic acid
-
pH 7.5, 20C
17.8
linoleic acid
-
pH 7.5, 30C
0.3
O2
-
pH 7.4, mutant L367K, with substrate linoleic acid
2.2
O2
-
pH 7.4, mutant L367E, with substrate linoleic acid
4.4
O2
-
pH 7.4, mutant L367W, with substrate linoleic acid
5.1
O2
-
with arachidonic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C, in the presence of 12(S)-hydroperoxyeicosatetraenoic acid
5.2
O2
-
-
5.6
O2
-
pH 7.4, mutant L367F, with substrate linoleic acid
5.6
O2
-
with arachidonic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C
7
O2
-
with linoleic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C, in the presence of 12(S)-hydroperoxyeicosatetraenoic acid
7.6
O2
-
with linoleic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C
13.7
O2
-
pH 7.4, wild-type enzyme, with substrate linoleic acid
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00005
arachidonic acid
-
at 15C, normalized to iron content
290
0.00015
arachidonic acid
-
at 22C, normalized to iron content; at pH 7.5
290
0.00024
arachidonic acid
-
at pH 7
290
0.00028
arachidonic acid
-
at pH 8
290
0.00046
arachidonic acid
-
at 30C, normalized to iron content
290
0.00075
arachidonic acid
-
at 37C, normalized to iron content
290
8
arachidonic acid
-
-
290
240
O2
-
with arachidonic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C
9
320
O2
-
with linoleic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C, in the presence of 12(S)-hydroperoxyeicosatetraenoic acid
9
340
O2
-
with arachidonic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C, in the presence of 12(S)-hydroperoxyeicosatetraenoic acid
9
790
O2
-
with linoleic acid as substrate, in 25 mM Hepes buffer, pH 7.5, 25C
9
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.1
2-([4-[(4-fluorobenzyl)oxy]butyl]sulfanyl)-5-(naphthalen-1-yl)-1,3,4-oxadiazole
-
Ki above 0.1 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.0006
4-((5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)butyl)-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.07
4-((5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)methyl)-benzyl-4-fluorobenzoate
-
apparent value, Ki above 0.07 mM, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000023
4-(5-(1H-indol-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000057
4-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000043
4-(5-(2-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000081
4-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.00001
4-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate, 4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate, 4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, Ki above 0.00001 mM, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.001
4-(5-(furan-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.0013
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylamino)but-2-ynyl-thiophene-2-carboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.0035
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-yn-1-ol
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000076
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-1H-indole-4-carboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.00001
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-chlorobenzoate, 4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate, 4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-methoxybenzoate
-
apparent value, Ki above 0.00001 mM, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000015
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-benzofuran-2-carboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000019
4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-thiophene-2-carboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.00014
4-(5-(quinolin-5-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000082
4-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.000026
4-(5-phenyl-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1-benzothiophene-2-carboxylate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1-benzothiophene-3-carboxylate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.0014
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1H-imidazole-4-carboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2,4-difluorobenzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2-fluorobenzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2-fluoropyridine-3-carboxylate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00047
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2-methoxybenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4,5-trichlorothiophene-2-carboxylate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.000016
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4,5-trifluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4-difluorobenzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.000027
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-(trifluoromethyl)benzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.000031
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-chloro-1-benzothiophene-2-carboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-chlorothiophene-2-carboxylate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-fluorobenzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(difluoromethoxy)benzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.000033
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(methylsulfonyl)benzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.000015
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(triazan-2-yl)benzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(trifluoromethoxy)benzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(trifluoromethyl)benzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-bromobenzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.0001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-chloro-3-(trifluoromethyl)benzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-[(trifluoromethyl)sulfanyl]benzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl benzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.000085
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl cyclobutanecarboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl cyclopentanecarboxylate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00027
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl cyclopropanecarboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00017
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl furan-2-carboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.000022
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl naphthalene-2-carboxylate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl thiophene-3-carboxylate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.000026
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]butyl 4-fluorobenzoate
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.00001
4-[[5-(naphthalen-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-fluorobenzoate
-
Ki less than 0.00001 mM, apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
0.002
apigenin
-
-
0.00018
baicalein
-
-
0.0011
baicalein
-
in the presence of 0.01% Triton X-100
0.001
BODIPY-D3825
-
-
0.009
BODIPY-D3825
-
-
0.008
dysidenin
-
above, pH 7.5, recombinant isozyme 15-hLO-1
0.0041
linoleic acid
-
-
0.005
linoleic acid
-
fully deuterated, in the presence of 13-(S)-hydroxyoctadecadienoic acid
0.002
N-(4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol)-2-ylthio)but-2-ynyl-thiophene-2-carboxamide
-
apparent value, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23C
-
0.5
neodysidenin
-
above, pH 7.5, recombinant isozyme 15-hLO-1
0.017
linoleic acid
-
fully deuterated
additional information
additional information
-
-
-
additional information
additional information
-
docking experiments and structure activity relationship comparative studies, estimated inhibition constants, calculated in autodock, overview
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.061
(-)-5,7-O-diacetyl-3',4',5'-O-triacetylepigallocatechin-3-O-(3'',4'',5''-O-triacetyl)gallate
-
IC50: 0.061 mM
0.033
(-)-5,7-O-dibutyryl-3',4',5'-O-tributyrylepigallocatechin-3-O-(3'',4'',5''-O-tributyryl) gallate
-
IC50: 0.033 mM
0.03
(-)-5,7-O-dimethyl-3',4',5'-O-trimethylepigallocatechin-3-O-(3'',4'',5''-O-trimethyl) gallate
-
IC50: 0.03 mM
0.031
(-)-5,7-O-dipropionyl-3',4',5'-O-tripropionylepigallocatechin-3-O-(3'',4'',5''-O-tripropionyl) gallate
-
IC50: 0.031 mM
0.1
(-)-epigallocatechin-3-gallate
-
IC50: 0.1 mM
0.0014
(-)-jaspic acid
-
IC50: 0.0014 mM
0.028
1,2,3-triphenylindolizine-7-carbonitrile
-
IC50: 0.028 mM
0.017
1-(((2,4,6-trimethylphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.017 mM
0.027
1-(((2,4-dimethoxyphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.027 mM
0.015
1-(((2,5-dimethoxyphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.015 mM
0.042
1-(((2-methyl)ethylsulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.042 mM
0.022
1-(((2-methyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.022 mM
0.021
1-(((2-thienyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.021 mM
0.019
1-(((3,4-dimethoxyphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.019 mM
0.023
1-(((3-thienyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.023 mM
0.016
1-(((4-(2-methylethyl)phenl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.016 mM
0.022
1-(((4-chlorophenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.022 mM
0.025
1-(((4-methoxyphenyl)sulfonyl)oxy)-2,3-bis(4-methylphenyl)-7-indolizinecarbonitrile
-
IC50: 0.025 mM
0.025
1-(((4-methoxyphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.025 mM
0.2
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-bis(4-chlorophenyl)-7-indolizinecarbonitrile
-
IC50: 0.2 mM
0.22
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-bis(4-fluorophenyl)-7-indolizinecarbonitrile
-
IC50: 0.22 mM
0.024
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-bis(4-methoxyphenyl)-7-indolizinecarbonitrile
-
IC50: 0.024 mM
0.2
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-bis(4-methylphenyl)-7-indolizinecarbonitrile
-
IC50: 0.2 mM
0.03
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-dibutyl-7-indolizinecarbonitrile
-
IC50: 0.03 mM
0.029
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-diethyl-7-indolizinecarbonitrile
-
IC50: 0.029 mM
0.02
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarboxaldehyde
-
IC50: 0.02 mM
0.023
1-(((4-methylphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinylethanone
-
IC50: 0.023 mM
0.024
1-(((4-methysulfonyllphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.024 mM
0.023
1-(((4-trifluoromethylphenyl)sulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.023 mM
0.029
1-((4-methylphenyl)sulfonyl)2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.029 mM
0.028
1-((butylsulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.028 mM
0.022
1-((methylsulfonyl)oxy)-2,3-diphenyl-7-indolizine-carbonitrile
-
IC50: 0.022 mM
0.025
1-((N,N-dimethylaminosulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.025 mM
0.024
1-((phenylsulfonyl)oxy)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.024 mM
0.031
1-(1,3-dibenzyloxy-2-propyloxy)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.031 mM
0.017
1-(1-Hydroxy-1-phenyl-ethyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.017 mM
0.026
1-(1-hydroxyethyl)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.026 mM
0.024
1-(2-furyl)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.024 mM
0.02
1-(2-Methoxy-phenyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.02 mM
0.029
1-(2-methoxyphenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.029 mM
0.031
1-(3-chlorophenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.031 mM
0.02
1-(3-Methoxy-phenyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.02 mM
0.031
1-(4-chlorophenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.031 mM
0.035
1-(4-fluorophenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.035 mM
0.02
1-(4-Methoxy-phenyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.02 mM
0.037
1-(4-Methoxy-phenyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.037mM
0.032
1-(4-methoxyphenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.032 mM
0.037
1-(4-methylphenyl)methoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.037 mM
0.023
1-(Cyclohexyl-hydroxy-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.023 mM
0.022
1-(Hydroxy-p-tolyl-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.022 mM
0.035
1-(Hydroxy-phenyl-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.035 mM
0.048
1-(Hydroxy-phenyl-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.048 mM
0.026
1-(hydroxymethyl)-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.026 mM
0.034
1-(hydroxymethyl)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.034 mM
0.021
1-(Methoxy-phenyl-methyl)-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.021 mM
0.031
1-(methoxymethoxy)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.031 mM
0.075
1-(methoxymethoxy)-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.075 mM
0.023
1-acetyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.023 mM
0.044
1-acetyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.044 mM
0.023
1-benzoyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.023 mM
0.043
1-benzoyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.043 mM
0.027
1-benzyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.027 mM
0.027
1-benzyloxymethoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.027 mM
0.039
1-benzyloxymethoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.039 mM
0.029
1-formyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.029 mM
0.061
1-formyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.061 mM
0.033
1-methoxy-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.033 mM
0.077
1-methoxy-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.077 mM
0.027
1-methyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.027 mM
0.046
1-methyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.046 mM
0.031
1-phenylmethoxy-2,3-diphenyl-7-indolizinecarbonitrile
-
IC50: 0.031 mM
0.023
1-[(4-Chloro-phenyl)-hydroxy-methyl]-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.023 mM
0.017
1-[Hydroxy-(4-methoxy-phenyl)-methyl]-2,3-diphenyl-indolizine-7-carbonitrile
-
IC50: 0.017 mM
0.071
11-hydroxytephrosin
Sarcolobus globosus
-
IC50: 0.071 mM
0.018
12alpha-hydroxydeguelin
Sarcolobus globosus
-
IC50: 0.018 mM
0.102
12alpha-hydroxyrotenone
Sarcolobus globosus
-
IC50: 0.102 mM
0.0018
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
-
IC50: 0.0018 mM
0.007
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
-
IC50: 0.007 mM
0.00079
2,3,4,5-tetrabromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
-
IC50: 0.00079 mM
0.0022
2,3,5-tribromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
-
IC50: 0.0022 mM
0.033
2,3-bis(4-chlorophenyl)-7-indolizinecarbonitrile
-
IC50: 0.033 mM
0.03
2,3-bis(4-fluorophenyl)-7-indolizinecarbonitrile
-
IC50: 0.03 mM
0.027
2,3-bis(4-methylphenyl)-7-indolizinecarbonitrile
-
IC50: 0.027 mM
0.02
2,3-diphenyl-1-(2-thienyl)indolizine-7-carbonitrile
-
IC50: 0.02 mM
0.019
2,3-diphenyl-1-(3-thienyl)indolizine-7-carbonitrile
-
IC50: 0.019 mM
0.025
2,3-diphenyl-1-indolizinol tosylate
-
IC50: 0.025 mM
0.03
2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.03 mM
0.051
2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.051 mM
0.01
2,4-dibromo-6-(2,4-dibromo-6-methoxyphenoxy)phenol
-
IC50: 0.01 mM
0.034
2,4-Dibromophenol
-
IC50: 0.034 mM
0.005
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
-
IC50: 0.005 mM
0.034
2-(4-ethylpiperazin-1-yl)4-methylpyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.235
2-(4-ethylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.267
2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.18
2-(4-methylpiperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.14
2-(morpholin-4-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.146
2-(piperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.216
2-(pyrrolidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.0062
3'-chloro-7,8-dihydroxyisoflavone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.0009
3,4,6,8-tetrabromooxanthren-1-ol
-
IC50: 0.0009 mM
0.005
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
-
IC50: 0.005 mM
0.009
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
-
IC50: 0.009 mM
0.011
3,4-dibromo-2-(5-bromo-2-hydroxyphenoxy)phenol
-
IC50: 0.011 mM
0.015
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
-
IC50: 0.015 mM
0.05
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
-
IC50: 0.05 mM
0.0008
3,6,8-tribromooxanthren-1-ol
-
IC50: 0.0008 mM
0.059
3-[3-bromo-5-(2,6-dibromo-4-{2-[2-(3-bromo-4-hydroxy-phenyl)-ethylcarbamoyl]-2-[(E)-hydroxyimino]-ethyl}-phenoxy)-4-methyl-phenyl]-N-[(E)-2-(3,5-dibromo-4-hydroxy-phenyl)-vinyl]-2-[(E)-hydroxyimino]-propionamide
-
IC50: 0.059 mM
0.00051
4',6,7-trihydroxyisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-1
0.071
4',6,7-trihydroxyisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-2
0.0038
4',6,7-trihydroxyisoflavanone
-
pH 7.5, 22C, isozyme 15-hLO-2
0.1
4',6,7-trihydroxyisoflavanone
-
above, pH 7.5, 22C, isozyme 15-hLO-1
0.049
4',6,7-trihydroxyisoflavone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.0002
4'-butyl-N-[2-(1H-indol-3-yl)ethyl]biphenyl-4-sulfonamide
-
IC50: 0.00053 mM in the presence of arachidonate, IC50: 0.0002 mM in the presence of linoleic acid
0.009
4'-chloro-7,8-dihydroxyisoflavone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.00047
4'-ethyl-N-[2-(1H-indol-3-yl)ethyl]biphenyl-4-sulfonamide
-
IC50: 0.00026 mM in the presence of arachidonate, IC50: 0.00047 mM in the presence of linoleic acid
0.00023
4'-tert-butyl-N-[2-(1H-indol-3-yl)ethyl]biphenyl-4-sulfonamide
-
IC50: 0.00027 mM in the presence of arachidonate, IC50: 0.00023 mM in the presence of linoleic acid
0.004
4,4'-propane-2,2-diylbis(2,6-dibromophenol)
-
IC50: 0.004 mM
0.062
4,5-bis(4-chlorophenyl)-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.0234
4,5-bis(4-fluorophenyl)-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.0147
4,5-bis(4-methoxyphenyl)-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.0152
4,5-diphenyl-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.045
4-(2-chlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
versus substrate linoleic acid
0.132
4-(2-chlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
versus substrate arachidonic acid
0.055
4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
versus substrate linoleic acid
0.378
4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
versus substrate arachidonic acid
0.036
4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
versus substrate linoleic acid
0.133
4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
versus substrate arachidonic acid
0.0249
4-(4-chlorophenyl)-5-phenyl-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.0137
4-(4-methoxyphenyl)-5-phenyl-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.000017
4-allyl-2-methoxyphenyl 1-adamantanecarboxylate
-
-
0.0022
4-allyl-2-methoxyphenyl 1-cyclohexanecarboxylate
-
-
0.168
4-allyl-2-methoxyphenyl 2-chlorobenzoate
-
-
0.0067
4-allyl-2-methoxyphenyl 2-fluorobenzoate
-
-
0.0772
4-allyl-2-methoxyphenyl 2-methylbenzoate
-
-
0.0333
4-allyl-2-methoxyphenyl 2-pyridinecarboxylate
-
-
0.0052
4-allyl-2-methoxyphenyl 3-chlorobenzoate
-
-
0.0021
4-allyl-2-methoxyphenyl 3-fluorobenzoate
-
-
0.023
4-allyl-2-methoxyphenyl 3-methoxybenzoate
-
-
0.0114
4-allyl-2-methoxyphenyl 3-methylbenzoate
-
-
0.1343
4-allyl-2-methoxyphenyl 4-chlorobenzoate
-
-
0.0072
4-allyl-2-methoxyphenyl 4-fluorobenzoate
-
-
0.019
4-allyl-2-methoxyphenyl 4-methoxybenzoate
-
-
0.0146
4-allyl-2-methoxyphenyl 4-methylbenzoate
-
-
0.0044
4-allyl-2-methoxyphenyl benzoate
-
-
0.0023
4-allyl-2-methoxyphenyl isonicotinate
-
-
0.0017
4-allyl-2-methoxyphenyl nicotinate
-
-
0.048
4-Bromophenol
-
IC50: 0.048 mM
0.055
4-Bromophenol
-
IC50: 0.055 mM
0.004
4-butyl-N-[2-(1H-indol-3-yl)ethyl]benzenesulfonamide
-
IC50: 0.00307 mM in the presence of arachidonate, IC50: 0.004 mM in the presence of linoleic acid
0.014
4-butyl-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
versus substrate linoleic acid
0.05
4-butyl-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
-
versus substrate arachidonic acid
0.01
4-ethyl-N-[2-(1H-indol-3-yl)ethyl]benzenesulfonamide
-
IC50: 0.01 mM in the presence of arachidonate, IC50: 0.01 mM in the presence of linoleic acid
0.036
4-methyl-2-(4-ethylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.2
4-methyl-2-(4-hydroxypiperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
above, pH 9.0, 20C
0.018
4-methyl-2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.076
4-methyl-2-(4-methylpiperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.2
4-methyl-2-(4-phenylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
above, pH 9.0, 20C
0.053
4-methyl-2-(morpholin-4-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.058
4-methyl-2-(morpholin-4-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.058
4-methyl-2-(piperidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.048
4-methyl-2-(pyrrolidin-1-yl)pyrimido[4,5-b][1,4]benzothiazine
-
pH 9.0, 20C
0.0046
4-nitrocatechol
-
IC50: 0.0046 mM
0.000072
4-pentyl-N-(2-[2-phenyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-4-yl]ethyl)benzenesulfonamide
-
versus substrate linoleic acid
0.000372
4-pentyl-N-(2-[2-phenyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-4-yl]ethyl)benzenesulfonamide
-
versus substrate arachidonic acid
0.01
4-pentyl-N-[2-(5-phenyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
above, versus substrate linoleic acid
0.00281
4-pentyl-N-[2-(5-phenyl-2-pyrazin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
versus substrate linoleic acid
0.00097
4-pentyl-N-[2-(5-phenyl-2-pyridin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
versus substrate linoleic acid
5.321
4-pentyl-N-[2-(5-phenyl-2-pyridin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
versus substrate arachidonic acid
0.00056
4-pentyl-N-[2-(5-phenyl-2-pyridin-3-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
versus substrate linoleic acid
0.000087
4-pentyl-N-[2-(5-phenyl-2-pyridin-4-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
versus substrate linoleic acid
3.211
4-pentyl-N-[2-(5-phenyl-2-pyridin-4-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
versus substrate arachidonic acid
0.000006
4-pentyl-N-[2-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
versus substrate linoleic acid
0.000013
4-pentyl-N-[2-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
-
versus substrate arachidonic acid
0.000053
4-pentyl-N-[3-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)propyl]benzenesulfonamide
-
versus substrate linoleic acid
0.000396
4-pentyl-N-[3-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)propyl]benzenesulfonamide
-
versus substrate arachidonic acid
0.0094
4-[4-(dimethylamino)phenyl]-5-(4-methoxyphenyl)-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.0057
4-[4-(methylsulfanyl)phenyl]-5-phenyl-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.00012
5,8,11,14-eicosatetraenoic acid
-
IC50: 0.00012 mM
0.0047
5-(4-chlorophenyl)-4-(4-methoxyphenyl)-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.25
5-(4-chlorophenyl)-4-(4-methoxyphenyl)-2-(methylsulfanyl)-1H-imidazole
-
value above, pH 7.0, temperature not specified in the publication
0.0223
5-(4-chlorophenyl)-4-[4-(dimethylamino)phenyl]-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.0197
5-(4-chlorophenyl)-4-[4-(methylsulfanyl)phenyl]-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.011
5-(4-fluorophenyl)-4-(4-methoxyphenyl)-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.136
5-(4-fluorophenyl)-4-[4-(methylsulfanyl)phenyl]-1H-imidazole-2-thiol
-
pH 7.0, temperature not specified in the publication
0.032
5-(methoxymethoxy)-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.032 mM
0.059
5-(methoxymethoxy)-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.059 mM
0.028
5-ethoxy-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.028 mM
0.029
5-methoxy-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.029 mM
0.059
5-methoxy-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.059 mM
0.018
6,7-dihydroxy-2-t-butylbenzopyran-4-one
-
pH 7.5, 22C, isozyme 15-hLO-1
0.00035
6,7-dihydroxy-3',4'-methylenedioxyisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-1
0.016
6,7-dihydroxy-3',4'-methylenedioxyisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-2
0.00021
6,7-dihydroxy-3'-methylisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-1
0.0083
6,7-dihydroxy-3'-methylisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-2
0.00021
6,7-dihydroxy-3'-methylisoflavanone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.014
6,7-dihydroxy-3'-methylisoflavanone
-
pH 7.5, 22C, isozyme 15-hLO-2
0.00015
6,7-dihydroxy-4'-methoxyisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-1
0.1
6,7-dihydroxy-4'-methoxyisoflavan
-
above, pH 7.5, 22C, isozyme 15-hLO-2
0.0016
6,7-dihydroxy-4'-methoxyisoflavanone
-
pH 7.5, 22C, isozyme 15-hLO-2
0.019
6,7-dihydroxy-4'-methoxyisoflavanone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.137
6,7-dimethoxy-2,3-dihydrochromone
Sarcolobus globosus
-
IC50: 0.137 mM
0.015
6,7-diphenylpyrrolo[1,2-a]pyrimidin-8-ol tosylate
-
IC50: 0.015 mM
0.043
6,7-diphenylpyrrolo[1,2-b]pyridazin-5-yl trifluoromethanesulfonate
-
IC50: 0.043 mM
0.022
6,7-diphenylpyrrolo[1,2-c]pyrimidin-5-ol tosylate
-
IC50: 0.022 mM
0.038
6-hydroxy-2-pentyl-4H-benzopyran-4-one
-
pH 7.5, 22C, isozyme 15-hLO-1
0.062
6alpha,12alpha-12alpha-hydroxyelliptone
Sarcolobus globosus
-
IC50: 0.062 mM
0.071
6alpha,12alpha-dehydrodeguelin
Sarcolobus globosus
-
IC50: 0.071 mM
0.1
7,8-dihydroxy-3',4'-dimethoxyisoflavan
-
above, pH 7.5, 22C, isozyme 15-hLO-1; above, pH 7.5, 22C, isozyme 15-hLO-2
0.011
7,8-dihydroxy-3'-methylisoflavone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.0083
7,8-dihydroxy-3'-trifluoromethylisoflavone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.0037
7,8-dihydroxy-4'-methoxyisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-1
0.1
7,8-dihydroxy-4'-methoxyisoflavan
-
above, pH 7.5, 22C, isozyme 15-hLO-2
0.0057
7,8-dihydroxy-4'-methylisoflavan
-
pH 7.5, 22C, isozyme 15-hLO-1
0.1
7,8-dihydroxy-4'-methylisoflavan
-
above, pH 7.5, 22C, isozyme 15-hLO-2
0.0078
7,8-dihydroxy-4'-methylisoflavone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.013
7,8-dihydroxyisoflavone
-
pH 7.5, 22C, isozyme 15-hLO-1
0.022
7-(1,1-dimethylethyl)-2,3-diphenyl-1-indolizinol tosylate
-
IC50: 0.022 mM
0.03
7-cyano-2,3-diphenylindolizin-1-yl 2-methoxybenzoate
-
IC50: 0.03 mM
0.028
7-cyano-2,3-diphenylindolizin-1-yl 3-methoxybenzoate
-
IC50: 0.028 mM
0.028
7-cyano-2,3-diphenylindolizin-1-yl 4-methoxybenzoate
-
IC50: 0.028 mM
0.046
7-cyano-2,3-diphenylindolizin-1-yl trifluoromethanesulfonate
-
IC50: 0.046 mM
0.059
7-cyano-2,3-diphenylindolizin-1-yl trifluoromethanesulfonate
-
IC50: 0.059 mM
0.0031
alpha-mangostin
-
pH 7.5, recombinant isozyme 15-hLO-1
0.05
alpha-mangostin
-
above, pH 7.5, recombinant isozyme 15-hLO-2
0.0003 - 100
apigenin
-
IC50: 0.0034 mM without Triton X-100, IC50: 0.0003 mM in the presence of 0.01% Triton X-100
0.18
apigenin
-
IC50: 0.18 mM
0.5
apigenin
-
IC50: 0.5 mM
0.001
baicalein
-
IC50: 0.001 mM
0.035
baicalein
-
IC50: 0.035 mM
0.038 - 100
baicalein
-
potent inhibitor, IC50: 0.0016 mM without Triton X-100, IC50: 0.038 mM in the presence of 0.01% Triton X-100
0.063
barbigerone
Sarcolobus globosus
-
IC50: 0.063 mM
0.027
bestatin
-
IC50: 0.027 mM
0.027
bestatin 7
-
IC50: 0.027 mM
1
chrysin
-
IC50: 1 mM
0.25
daidzein
-
IC50: 0.25 mM
0.43
daidzein
-
IC50: 0.43 mM
0.00373
dansyl tryptamine
-
IC50: 0.00373 mM
0.00006
ebselen
-
i.e. 2-phenyl-1,2-benzisoselenazol-3(2H)-one, irreversible inhibition, IC50: 0.00006 mM
0.06
epicatechin
-
IC50: 0.06 mM
0.0018
fisetin
-
IC50: 0.0018 mM
0.0035
fisetin
-
IC50: 0.0035 mM
0.32
flavone
-
IC50: 0.32 mM
0.7
flavone
-
IC50: 0.7 mM
0.045
galangin
-
IC50: 0.045 mM
0.2
galangin
-
IC50: 0.2 mM
0.018
genistein
-
IC50: 0.018 mM
0.167
genistein
Sarcolobus globosus
-
IC50: above 0.167 mM
1
genistein
-
IC50: 1 mM
0.167
genistin
Sarcolobus globosus
-
IC50: above 0.167 mM
0.167
glucosyringic acid
Sarcolobus globosus
-
IC50: above 0.167 mM
0.09
hesperetin
-
IC50: 0.09 mM
0.167
isotachioside
Sarcolobus globosus
-
IC50: above 0.167 mM
0.0003
jaspaquinol
-
IC50: 0.0003 mM
0.0076
michellamine B
-
pH 7.5, recombinant isozyme 15-hLO-1
0.006
morin
-
IC50: 0.006 mM
0.018
morin
-
IC50: 0.018 mM
0.006
myricetin
-
IC50: 0.006 mM
0.018
myricetin
-
IC50: 0.018 mM
0.031
N'-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate linoleic acid
0.186
N'-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate arachidonic acid
0.08
N'-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3S)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate linoleic acid
0.822
N'-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3S)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate arachidonic acid
0.038
N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate linoleic acid
0.375
N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate arachidonic acid
0.01
N-ethyl-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-[(3R)-1-(1-methyl-1-phenylethyl)pyrrolidin-3-yl]sulfamide
-
versus substrate linoleic acid
0.132
N-ethyl-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-[(3R)-1-(1-methyl-1-phenylethyl)pyrrolidin-3-yl]sulfamide
-
versus substrate arachidonic acid
0.003
N-ethyl-N-[(3R)-1-[1-(4-fluorophenyl)ethyl]pyrrolidin-3-yl]-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]sulfamide
-
versus substrate linoleic acid
0.75
N-ethyl-N-[(3R)-1-[1-(4-fluorophenyl)ethyl]pyrrolidin-3-yl]-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]sulfamide
-
versus substrate arachidonic acid
0.011
N-[(3R)-1-(3,4-dichlorobenzyl)pyrrolidin-3-yl]-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-methylsulfamide
-
versus substrate linoleic acid
0.083
N-[(3R)-1-(3,4-dichlorobenzyl)pyrrolidin-3-yl]-N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-methylsulfamide
-
versus substrate arachidonic acid
0.00046
N-[2-(1H-indol-3-yl)ethyl]-2'-methylbiphenyl-4-sulfonamide
-
IC50: 0.00092 mM in the presence of arachidonate, IC50: 0.00046 mM in the presence of linoleic acid
0.00032
N-[2-(1H-indol-3-yl)ethyl]-3'-methylbiphenyl-4-sulfonamide
-
IC50: 0.00045 mM in the presence of arachidonate, IC50: 0.00032 mM in the presence of linoleic acid
0.00014
N-[2-(1H-indol-3-yl)ethyl]-4'-(1-methylethyl)biphenyl-4-sulfonamide
-
IC50: 0.00028 mM in the presence of arachidonate, IC50: 0.00014 mM in the presence of linoleic acid
0.00017
N-[2-(1H-indol-3-yl)ethyl]-4'-(2-methylpropyl)biphenyl-4-sulfonamide
-
IC50: 0.00091 mM in the presence of arachidonate, IC50: 0.00017 mM in the presence of linoleic acid
0.00109
N-[2-(1H-indol-3-yl)ethyl]-4'-methoxybiphenyl-4-sulfonamide
-
IC50: 0.0015 mM in the presence of arachidonate, IC50: 0.00109 mM in the presence of linoleic acid
0.00047
N-[2-(1H-indol-3-yl)ethyl]-4'-methylbiphenyl-4-sulfonamide
-
IC50: 0.00047 mM in the presence of linoleic acid
0.01
N-[2-(1H-indol-3-yl)ethyl]-4-methylbenzenesulfonamide
-
IC50: 0.01 mM in the presence of arachidonate, IC50: 0.01 mM in the presence of linoleic acid
0.00102
N-[2-(1H-indol-3-yl)ethyl]-4-pentylbenzenesulfonamide
-
IC50: 0.00042 mM in the presence of arachidonate, IC50: 0.00102 mM in the presence of linoleic acid
0.0032
N-[2-(1H-indol-3-yl)ethyl]-4-propylbenzenesulfonamide
-
IC50: 0.00313 mM in the presence of arachidonate, IC50: 0.0032 mM in the presence of linoleic acid
0.0042
N-[2-(1H-indol-3-yl)ethyl]biphenyl-4-sulfonamide
-
IC50: 0.0034 mM in the presence of arachidonate, IC50: 0.0042 mM in the presence of linoleic acid
0.000364
N-[2-(2,5-diphenyl-1H-imidazol-4-yl)ethyl]-4-methylbenzenesulfonamide
-
versus substrate linoleic acid
0.0028
N-[2-(2,5-diphenyl-1H-imidazol-4-yl)ethyl]-4-methylbenzenesulfonamide
-
versus substrate arachidonic acid
0.000033
N-[2-(2,5-diphenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.000162
N-[2-(2,5-diphenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
versus substrate arachidonic acid
0.01
N-[2-(2-cyclopropyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
above, versus substrate arachidonic acid; above, versus substrate linoleic acid
0.01
N-[2-(2-methyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
above, versus substrate linoleic acid
0.00192
N-[2-(2-tert-butyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.01
N-[2-(2-tert-butyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
-
above, versus substrate arachidonic acid
0.00072
N-[2-[2-(2-methyl-1,3-thiazol-4-yl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.000099
N-[2-[2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.0011
N-[2-[2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate arachidonic acid
0.000021
N-[2-[2-(4-chlorophenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.0011
N-[2-[2-(4-chlorophenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate arachidonic acid
0.01
N-[2-[2-(4-methoxyphenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
above, versus substrate linoleic acid
0.003
N-[2-[2-(4-methylphenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.000082
N-[2-[5-(3-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.000531
N-[2-[5-(3-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate arachidonic acid
0.000059
N-[2-[5-(4-fluorophenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.000261
N-[2-[5-(4-fluorophenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate arachidonic acid
0.000014
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.00005
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
versus substrate arachidonic acid
0.212
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-phenylpiperazine-1-sulfonamide
-
versus substrate linoleic acid
3.45
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-phenylpiperazine-1-sulfonamide
-
versus substrate arachidonic acid
0.083
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N'-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate linoleic acid
0.719
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N'-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate arachidonic acid
0.272
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N'-[(3S)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate linoleic acid
2.41
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N'-[(3S)-1-phenoxypyrrolidin-3-yl]sulfamide
-
versus substrate arachidonic acid
0.091
N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-4-pentylpiperazine-1-sulfonamide
-
versus substrate linoleic acid
0.646
N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-4-pentylpiperazine-1-sulfonamide
-
versus substrate arachidonic acid
0.00014
N-[3-(2,5-diphenyl-1H-imidazol-4-yl)propyl]-4-pentylbenzenesulfonamide
-
versus substrate linoleic acid
0.000914
N-[3-(2,5-diphenyl-1H-imidazol-4-yl)propyl]-4-pentylbenzenesulfonamide
-
versus substrate arachidonic acid
0.25
Naringenin
-
IC50: 0.25 mM
0.5
neodysidenin
-
above, pH 7.5, recombinant isozyme 15-hLO-1
0.00011
nordihydroguaiaretic acid
-
IC50: 0.00011 mM
0.00011
nordihydroguaiaretic acid
-
IC50: 0.00011 mM
0.0005
nordihydroguaiaretic acid
-
IC50: 0.0005 mM
0.0018
nordihydroguaiaretic acid
-
IC50: 0.0018 mM
0.0094
NSC172033
-
pH 7.5, recombinant isozyme 15-hLO-1
0.05
NSC172033
-
above, pH 7.5, recombinant isozyme 15-hLO-2
0.025
NSC292213
-
pH 7.5, recombinant isozyme 15-hLO-1
0.05
NSC292213
-
above, pH 7.5, recombinant isozyme 15-hLO-2
0.05
NSC617570
-
above, pH 7.5, recombinant isozyme 15-hLO-2
0.5
NSC617570
-
above, pH 7.5, recombinant isozyme 15-hLO-1
0.00038
PD 146 176
-
IC50: 0.00038 mM
0.00381
PD-146176
-
IC50: 0.00381 mM
0.004
quercetin
-
IC50: 0.004 mM
0.0045
quercetin
-
IC50: 0.0045 mM
0.029
quercetin
Sarcolobus globosus
-
IC50: 0.029 mM
1
rutin
-
IC50: 1 mM
0.057
salicylhydroxymic acid
-
IC50: 0.057 mM
-
0.06
sarcolobin
Sarcolobus globosus
-
IC50: 0.06 mM
0.0012
squalene
-
IC50 is 0.0012 mM
0.167
tachioside
Sarcolobus globosus
-
IC50: above 0.167 mM
0.025
taxifolin
-
IC50: 0.025 mM
1
taxifolin
-
IC50: 1 mM
0.064
tephrosin
Sarcolobus globosus
-
IC50: 0.064 mM
0.16
tert-butylhydroxyanisol
-
IC50: 0.16 mM
0.017
Toluene-4-sulfonic acid 6,7-diphenyl-pyrrolo[1,2-b]pyridazin-5-yl ester
-
IC50: 0.017 mM
0.028
Toluene-4-sulfonic acid 6,7-diphenyl-pyrrolo[1,2-b]pyridazin-5-yl ester
-
IC50: 0.028 mM
0.017
toluene-4-sulfonic acid 7-cyano-2,3-diphenyl-indolizin-1-yl ester
-
IC50: 0.017mM
0.025
toluene-4-sulfonic acid 7-cyano-2,3-diphenyl-indolizin-1-yl ester
-
IC50: 0.025 mM
0.161
vanillic acid 4-O-beta-D-glucoside
Sarcolobus globosus
-
IC50: 0.161 mM
0.05
michellamine B
-
above, pH 7.5, recombinant isozyme 15-hLO-2
0.1
additional information
-
IC50 above 0.1 mM: compound 1a, compound 1b, compound 1d, compound 1e, compound 1g
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.668
-
commercial preparation
2.125
-
-
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.7 - 7.3
-
-
6.8 - 7.2
-
-
7 - 8.5
-
-
7
P93184
-
8 - 9
-
pH-optimum of 15-LOX-2 for arachidonic acid oxygenation
9
-
assay at
9.3
Cyanothece sp.
B7JX99
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6 - 10
Cyanothece sp.
B7JX99
-
6 - 9.5
-
pH 6 about 50% of maximal activity, pH 9.5 about 60% of maximal activity
7 - 8
-
approximately level between pH 7 and 8
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20
-
assay at
22
-
assay at
22
-
assay at room temperature
25
-
assay at
25
P93184
assay at
25
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
epidermoid carcinoma of the submandibular gland
Manually annotated by BRENDA team
-
12/15-LOX is selectively enhanced in the periphery, 12/15-LOX-expressing myeloid cells are enriched in the brain during chronic toxoplasmosis
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
12/15-LOX is selectively enhanced in the periphery, 12/15-LOX-expressing myeloid cells are enriched in the brain during chronic toxoplasmosis
-
Manually annotated by BRENDA team
-
breast carcinoma BT-20 cells
Manually annotated by BRENDA team
-
express both 15-LOX-1 and -2
Manually annotated by BRENDA team
-
15-LOX-1 but not 15-LOX-2
Manually annotated by BRENDA team
-
15-LOX-2 is the predominant isoform in cytoplasm
Manually annotated by BRENDA team
-
medium expression
Manually annotated by BRENDA team
-
endothelial 15-LO-1 isozyme
Manually annotated by BRENDA team
-
human umbilical vein endothelial cells, HUVEC
Manually annotated by BRENDA team
-
CD31+ cell, rheumatoid arthritis tissue
Manually annotated by BRENDA team
-
high expression
Manually annotated by BRENDA team
-
peak-I 15 lipoxygenase is the predominant enzyme form
Manually annotated by BRENDA team
-
eosinophil 15-lipoxygenase is a leukotriene A4 synthase
Manually annotated by BRENDA team
-
15-lipoxygenase activity is 100fold greater in eosinophils than in neutrophils
Manually annotated by BRENDA team
-
airway epithelial cell
Manually annotated by BRENDA team
-
airway, high expression in airway epithelial cells, medium expression in cornea epithelial cells
Manually annotated by BRENDA team
-
in airway epithelial cells, 15LO1 expression increases with asthma severity and correlates with MUC5AC expression
Manually annotated by BRENDA team
-
isozyme 15-hLO-2
Manually annotated by BRENDA team
-
of the tracheobronchial tree, 15-LOX-1
Manually annotated by BRENDA team
-
hypopharyngeal carcinoma
Manually annotated by BRENDA team
-
low expression
Manually annotated by BRENDA team
-
rheumatoid arthritis tissue
Manually annotated by BRENDA team
Mus musculus DBA/2J
-
-
-
Manually annotated by BRENDA team
-
macrophage cell line
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
macrophage cell line
-
Manually annotated by BRENDA team
-
epidermal carcinoma of the mouth
Manually annotated by BRENDA team
-
neonatal foreskin cultured keratinocytes
Manually annotated by BRENDA team
Mus musculus DBA/2J
-
-
-
Manually annotated by BRENDA team
-
expression, but no activity of 15-LOX in leukemic blasts induced by a Ca2+ ionophore, from acute myeloid leukemic and acute lymphoid leukemic patients, overview, quantitative expression analysis
Manually annotated by BRENDA team
-
2 isoenzymes detected in leukocytes, the minor isoenzyme is enriched in leukocytes from an eosinophilic patient
Manually annotated by BRENDA team
-
eosinophil-enriched leukocytes
Manually annotated by BRENDA team
-
peritoneal polymorphonuclear leukocytes
Manually annotated by BRENDA team
-
from healthy individuals, quantitative expression analysis
Manually annotated by BRENDA team
Mus musculus DBA/2J
-
-
-
Manually annotated by BRENDA team
Mus musculus DBA/2J
-
-
-
Manually annotated by BRENDA team
-
15-LOX-2
Manually annotated by BRENDA team
-
isozyme 15-LO-1, differentiated monocytes obtained from human venous blood, CD14+
Manually annotated by BRENDA team
-
12/15-LOX is a macrophage-selective regulator of interleukin-12 production
Manually annotated by BRENDA team
-
12/15-LOX is expressed by 95% of resident peritoneal CD11bhigh cells, with the remaining 5% being 12/15-LOX-. 12/15-LOX+ cells are phenotypically defined by high F4/80, SR-A, and Siglec1 expression, and enhanced IL-10 and G-CSF generation. In contrast, 12/15-LOX- cells are a dendritic cell population. Resident peritoneal macrophage numbers are significantly increased in 12/15-LOX-/- mice, suggesting alterations in migratory trafficking or cell differentiation in vivo
Manually annotated by BRENDA team
-
rheumatoid arthritis tissue
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
12/15-LOX is a macrophage-selective regulator of interleukin-12 production, 12/15-LOX is expressed by 95% of resident peritoneal CD11bhigh cells, with the remaining 5% being 12/15-LOX-. 12/15-LOX+ cells are phenotypically defined by high F4/80, SR-A, and Siglec1 expression, and enhanced IL-10 and G-CSF generation. In contrast, 12/15-LOX- cells are a dendritic cell population. Resident peritoneal macrophage numbers are significantly increased in 12/15-LOX-/- mice, suggesting alterations in migratory trafficking or cell differentiation in vivo, peritoneal
-
Manually annotated by BRENDA team
-
medium expression
Manually annotated by BRENDA team
-
from lungs of asthma patients, and from skin and cord blood
Manually annotated by BRENDA team
-
carcinoma of the retromolar trigone region
Manually annotated by BRENDA team
-
low expression
Manually annotated by BRENDA team
-
peak-II 15 lipoxygenase is the predominant enzyme form
Manually annotated by BRENDA team
-
neutrophils do not express 15-lipoxygenase
Manually annotated by BRENDA team
-
15-lipoxygenase 2, 15-LOX2, is down-regulated in prostate cancers compared with normal and benign prostate tissues
Manually annotated by BRENDA team
-
epithelial cells, 15-LOX2 has multiple alternatively spliced isoforms and is a negative cell-cycle regulator in normal prostate epithelial cells, 15-LOX2 is positively regulated by Sp1 and negatively regulated by Sp3, overview
Manually annotated by BRENDA team
-
epithelium, isozyme 15-hLO-2
Manually annotated by BRENDA team
-
reticulocyte-rich anaemic blood cells
Manually annotated by BRENDA team
-
medium expression
Manually annotated by BRENDA team
-
higher expression of 15-LO-1 compared with ostheoarthritis synovial tissue
Manually annotated by BRENDA team
-
15-LOX-1 and 15-LOX-2
Manually annotated by BRENDA team
Mus musculus DBA/2J
-
-
-
Manually annotated by BRENDA team
-
low expression
Manually annotated by BRENDA team
-
low expression of 15-LO-1 in ostheoarthritis synovial tissue
Manually annotated by BRENDA team
-
squamous cell carcinoma of retromolar trigone
Manually annotated by BRENDA team
-
laryngeal carcinoma
Manually annotated by BRENDA team
-
squamous cell carcinoma of floor mouth
Manually annotated by BRENDA team
additional information
-
stroma-free hemolysis supernatant of a reticulocyte-rich blood cell suspension
Manually annotated by BRENDA team
additional information
-
15-LOX2 expression is decreased or lost in high-grade prostate intraepithelial neoplasia and prostate cancer PCa cells
Manually annotated by BRENDA team
additional information
-
the enzyme is overexpressed in atherosclerotic lesions
Manually annotated by BRENDA team
additional information
-
15-LOX-1 and -2 are preferentially expressed in normal tissue, present in HTB-38 cells
Manually annotated by BRENDA team
additional information
-
15-LOX-2 is almost undetectable in parental head-and-neck cancer cell lines FaDu and UMSCC-1
Manually annotated by BRENDA team
additional information
-
high expression in L-1236 cells (Hodgkin Reed-Sternberg cells), present in HDLM2 cells and KMH2 cells
Manually annotated by BRENDA team
additional information
-
high expression in L-1236 cells (Hodgkin ReedSternberg cells), low expression in seminal fluid
Manually annotated by BRENDA team
additional information
-
is absent in prostate cancer cells
Manually annotated by BRENDA team
additional information
-
is preferentially expressed in normal tissue
Manually annotated by BRENDA team
additional information
-
present in SF cells of rheumatoid arthritis tissue, absent in CD3+ T cells or in CD20+ B cells of rheumatoid arthritis tissue
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
15-LOX-1 is only detected in, 15-LOX-2 is expressed in both the cytoplasm and the nucleus
Manually annotated by BRENDA team
-
15-LOX-1, in epithelial cells within the tumour and surrounding normal tissue
Manually annotated by BRENDA team
-
main distribution
Manually annotated by BRENDA team
-
a significant fraction of the active protein is secreted extracellularly by an Xcp-dependent process
-
Manually annotated by BRENDA team
-
the enzyme associates to biomembranes primarily via hydrophobic interactions between surface-exposed apolar amino acid side chains and membrane lipids. Calcium supports membrane binding probably by forming salt bridges between the negatively charged head groups of membrane phospholipids and acidic surface amino acids of the membrane
Manually annotated by BRENDA team
-
enzyme is translocated to the membrane upon calcium challenge
Manually annotated by BRENDA team
-
15-LOX-2 is expressed in both the cytoplasm and the nucleus
Manually annotated by BRENDA team
-
the 15-LOX2 clones express 15-LOX2 in the nuclei and possess robust enzymatic activity, whereas 15-LOX2sc-b clones show neither nuclear protein localization nor arachidonic acid-metabolizing activity
Manually annotated by BRENDA team
-
predominantly localized in
-
Manually annotated by BRENDA team
-
the enzyme translocates to the membrane upon calcium challenge. In the presence of Ca2+/Mg2+, with or without calcium ionophore, the majority of 15-LO-1 is present in the membrane fraction
Manually annotated by BRENDA team
additional information
-
15-LOX-1, in the stroma of fibroblasts
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
61000
-
gel filtration
639253
65000
Cyanothece sp.
B7JX99
SDS-PAGE
712421
70000
-
gel filtration
639242
75000
-
SDS-PAGE
671247
75000
-
SDS-PAGE
671670
76000
-
SDS-PAGE
677239
78000
-
sucrose density gradient centrifugation, analytical ultracentrifugation
639251
81000
-
SDS-PAGE
677081
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 72000, SDS-PAGE
?
-
x * 70000, SDS-PAGE
?
-
x * 74000, SDS-PAGE
?
-
x * 75000, SDS-PAGE
?
-
x * 74727, electrospray mass spectrometry
?
P93184
x * 106000, calculated from sequence
?
B2IZG6
x * 70891, calculated from sequence
?
Nostoc punctiforme PCC73102
-
x * 70891, calculated from sequence
-
additional information
-
structural modeling, overview
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
-
-
glycoprotein
-
contains 5% carbohydrate
glycoprotein
-
-
glycoprotein
-
contains 4.6% neutral sugar
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure of 15S-LOX1 in complex with inhibitor determined with a resolution of 2.4 A under PDB ID 1lox, reinterpretation of the crystallographic data, structure analysis and modelling, overview
-
crystals are grown by vapor diffusion method from concentrated solutions of the protein in sodium phosphate buffer, pH 7.0
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7
-
24 h, 30% loss of activity
639253
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
-
structural alterations induced by increasing the temperature to 30C are completely reversible, loss of reversibility at 35C, aggregates between 45-50C. The enzyme is thermolabile and requires the presence of a lipid environment to be stabilized at higher temperatures
702247
45
-
structural alterations induced by increasing the temperature to 45C are completely reversible, loss of reversibility above 45C, aggregates at 60C. The enzyme is structurally stable and its membrane binding properties are hardly affected by temperature alterations
702247
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
frozen at -70C and thawed with recovery of activity
-
repeated freeze thawing especially in the absence of gylcerol results in 60% reduction of specific activity
-
severe autoinactivation is observed at high substrate concentrations if the substrate is not HPLC-purified and stored at -80C
-
repeated freezing and thawing causes a considerable loss of activity
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, 5% glycerol, stable for more than 6 months
-
-80C, 10% glycerol
-
-80C, 10-20% glycerol
-
-80C, 10% glycerol
-
-40C, 1 month, 60% loss of activity
-
-80C, 10% glycerol
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
HisTrap column chromatography, gel filtration
Cyanothece sp.
B7JX99
by sequential ammonium sulfate precipitation, both cationic and anionic exchange chromatography and a fast protein liquid chromatography apparatus
-
by one step Ni2+ affinity chromatography, more than 90% pure
-
on Ni column
-
partial
-
recombinant His-tagged enzyme from Escherichia coli coli by nickel affinity and anion exchange chromatography
-
recombinant His-tagged isozyme 15-hLO-1 by nickel affinity chromatography, recombinant untagged isozyme 15-hLO-2 by ion exchange chromatography
-
recombinant isozyme 15-hLO-2 from Spodoptera frugiperda Sf9 cells by anion exchange chromatography, recombinant His-tagged isozyme 15-hLO-1
-
Resource-Q 5 column chromatography
-
to greater than 90% purity
-
two enzyme forms
-
using Ni-NTA chromatography
-
without a His6-tag, more than 90% pure
-
on Ni column
-
by sequential fractionated ammonium sulfate precipitation, hydrophobic interaction chromatography and anion exchange chromatography
-
on Ni column
-
three isoenzymes
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21 Star cells
Cyanothece sp.
B7JX99
15-LO-1 expressed in Sf 9 cells
-
15-LOX-1 cDNA fragment without 3'-UTR inserted into pLP-IRESneo, overexpression of 15-LOX-1 in A549 cells
-
15-LOX2 has at least six alternatively spliced isoforms
-
expressed as a fusion protein with GFP (pEGFP-15LOX-2) in DU145 and PC-3 cells
-
expressed in CV-1 cells
-
expressed in Escherichia coli as a His-tagged fusion protein
-
expressed in Mus musculus C57BL/6
-
expressed in Mus musculus C57BL/6 prostate
-
expressed in rabbit aorta endothelium
-
expressed in Sf9 cells
-
expressed with hexa-His tags
-
expression in a human osteosarcoma cell line, expression of a CheY-15-lipoxygenase fusion protein in Escherichia coli
-
expression in CHO and in neuro-2 A neuroblastoma cells both stably expressing human APP carrying the K670N/M671L Swedish mutation, expression analysis
-
expression in Escherichia coli
-
expression of His-tagged isozyme 15-hLO-1, expression of isozyme 15-hLO-2 in Spodoptera frugiperda Sf9 cells using the baculovirus transfection system
-
expression of isozyme 15-hLO-1 as His-tagged enzyme, and of untagged isozyme 15-hLO-2
-
expression of isozyme 15-hLO-2 in Spodoptera frugiperda Sf9 cells using the baculovirus transfection system, expression of N-terminally His6-tagged 15-hLO-1
-
expression to high levels, approximately 20% of cellular protein, in a baculovirus/insect cell expression system
-
gene ALOX15, DNA and amino acid sequence determination and analysis of wild-type and mutant T560M, promoter sequence analysis, genotyping, overview, expression of wild-type and mutant enzymes in Escherichia coli and HEK-297 cells, the mutant shows a low expression level in both systems compared to the wild-type enzyme
P16050
HCT-116 and LoVo cells transfected with 15-LOX-1 vector
-
isoenzyme 15S-LOb and a splice variant of 15-LOb, baculovirus/insect cell expression system
-
LOX isoforms ligated into the pQE-9 plasmid and expressed as N-terminal His-tag fusion protein in Escherichia coli (XL-1 Blue)
-
overexpressed as N-terminally, His6-tagged protein
-
overexpression of 15-LOX-2 in human macrophages by adenovirus-mediated gene delivery
-
overexpression of His-tagged enzyme in Escherichia coli
-
overexpression of isozyme 15-LO-1 in Oryctolagus cuniculus via adenovirus transfection method, the expression is restricted to aortic endothelial cells, overview
-
Pca cell clones stably expressing 15-LOX2 or splice variant 15-LOX2sc-b are estabilished. The 15-LOX2 clones express 15-LOX2 in the nuclei and possess robust enzymatic activity, whereas 15-LOX2sc-b clones show neither nuclear protein localization nor arachidonic acid-metabolizing activity
-
pcDNA3.1(1) vector carrying native or mutant 15-LOX-1 expressed in HCT-116 cells
-
radiation-inducible 15-LOX-2 expression vector in which the full-length 15-LOX-2 cDNA is inserted downstream the recombinant Egr-1 promoter (pEgr-LOX2-GFP) and transfected in head-and-neck cancer cells
-
RAW 267.4 murine macrophages stably transfected to overexpress 15-LO-1
-
transgenic mice overexpressing 15-LO-1
-
without a His6-tag
-
expression in Escherichia coli
P93184
ligated into the pQE-9 plasmid and expressed as N-terminal His-tag fusion protein in Escherichia coli (XL-1 Blue)
-
transgenic mice models overexpressing 15-LOX in endothelial cells
-
expression in Escherichia coli
-
expression in the baculovirus/insect cell system, expression as intracellular enzyme and after fusion with a signal peptide as export protein in High Five cells
-
ligated into the pQE-9 plasmid and expressed as N-terminal His-tag fusion protein in Escherichia coli (XL-1 Blue)
-
the recombinant wild-type enzyme and various mutants are expressed in Escherichia coli as His-tagged fusion proteins
-
12/15LO stably overexpressed in mouse J774 macrophages
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
demethylation of DNA in some cell lines increases 15-LOX-1 expression. Increased levels of 15-LOX-1 are associated with downregulation of GATA-6 in Caco-2 colon cancer cells treated with sodium butyrate to induce cell differentiation and apoptosis. Activation of the cGMP-PKG system can induce the cellular expression of 15-LOX-1 in SW-480 colon cancer cells. 5-aza-2-deoxycytidine increases 15-LOX-1 expression. Interleukin-4 upregulates the 15-LOX-1 gene in HTB-38 and Caco-2 human colorectal cancer cell lines. Interleukin-13 upregulates the 15-LOX-1 gene in HTB-38 and Caco-2 human colorectal cancer cell lines
-
increased expression and activity of 15-LO-1 in the respiratory tissue from asthma patients. Patients with chronic obstructive pulmonary disease also display an increased expression of 15-LO-1 in bronchial biopsies. Interleukin-4 and interleukin-13 are inducers
-
induction by interleukin-4 and interleukin-13
-
interleukin-13 induces 15LO1 expression and production of intracellular 15-hydroxyeicosatetraenoic acid conjugated to phosphotidylethanolamine in vitro. 15-hydroxyeicosatetraenoic acid enhances interleukin-13 induced MUC5AC expression in vitro
-
interleukin-4 increases the expression of 15-LOX-1 and of downstream targets of p53
-
level of 15-LOX expression is dose-dependently induced by UVA and UVB-irradiation. Psoralen plus ultraviolet A, UVA-photochemotherapy significantly increases 15-LOX expression
-
normal human airway epithelial cells treated with interleukin-4 express higher levels of 15-LOX-1 than transfected A549 cells
-
15LO1 is highly expressed in fresh epithelial cells from severe asthmatic patients
-
hypoxia increases ALOX15 in human muscle cells
-
ischemia of the heart leads to increased expression of ALOX15
-
12/15-LOX activity is enhanced during chronic, but not acute, toxoplasmosis
-
allergen challenge up-regulates the expression of 12/15-LO in airway epithelial cells in mice. Interleukin-4 and interleukin-13 are inducers
-
12/15-LOX activity is enhanced during chronic, but not acute, toxoplasmosis
Mus musculus C57BL/6
-
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A416T
-
inactive mutant protein
A416V
-
inactive mutant protein
A417G
-
the mutant enzyme converts arachidonic acid to (11R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid and (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid in a 1.5:1 ratio. The wild.type enzyme converts arachidonic acid exlusively (15S)-Hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid. Turnover number for arachidonic acid is 4.6fold lower than that of the wild-type enzyme, no significant change in Km-value
D602Y
-
15-LOX-2 mutant shows a similar pH-profile as the wild-type enzyme
D602Y/V603H
-
a strong shift of the pH profile of 15-LOX-2 mutant towards more acidic values
H361L
-
is devoid of enzymatic activity, can induce phosphorylation of p53 as the wild-type
L397M
-
ratio of 15-lipoxygenation to 12-lipoxygenation is 9:1 for the wild-type enzyme and the mutant enzymes V104I, L397M and Q431R
L397M/M418V
-
the ratio of 15-lipoxygenation to 12-lipoxygenation is 1:1 for the mutant enzymes V104/L397M/M418V/Q431R, L397M/M418V/Q431R, L397M/M418V and M418V, compared to 9:1 for the wild-type enzyme
L397M/M418V/Q431R
-
the ratio of 15-lipoxygenation to 12-lipoxygenation is 1:1 for the mutant enzymes V104/L397M/M418V/Q431R, L397M/M418V/Q431R, L397M/M418V and M418V, compared to 9:1 for the wild-type enzyme
N287D
-
relative catalytic activity: 1.1% compared to wild-type 100%
N287L
-
relative catalytic activity: 0.5% compared to wild-type 100%
N287Q
-
relative catalytic activity: 3.9% compared to wild-type 100%
Q294L
-
relative catalytic activity: 0.6% compared to wild-type 100%
Q431R
-
ratio of 15-lipoxygenation to 12-lipoxygenation is 9:1 for the wild-type enzyme and the mutant enzymes V104I, L397M and Q431R
T560A
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mutant shows strongly impaired catalytic activity, relative catalytic activity: 16.6% compared to wild-type 100%
T560M
P16050
naturally occurring enzyme mutant, the mutant shows 20fold reduced catalytic activity, genotyping using 12974 samples, the haplotypes show increased risk of coronary artery disease compared to non-carriers, overview
T560M
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mutant shows strongly impaired catalytic activity, relative catalytic activity: 3.8% compared to wild-type 100%
T560S
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enzyme retains activity, relative catalytic activity: 70.7% compared to wild-type 100%
V104/L397M/M418V/Q431R
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the ratio of 15-lipoxygenation to 12-lipoxygenation is 1:1 for the mutant enzymes V104/L397M/M418V/Q431R, L397M/M418V/Q431R, L397M/M418V and M418V, compared to 9:1 for the wild-type enzyme
V104I
-
ratio of 15-lipoxygenation to 12-lipoxygenation is 9:1 for the wild-type enzyme and the mutant enzymes V104I, L397M and Q431R
F353L
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the ratio of turnover-number to KM-value is 4fold lower than the value for the wild-type enzyme. The mutation strongly alters the positional specificity of the oxygenation of most substrates in favor of 12-lipoxygenation except from (16(S),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
F412E
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mutation slightly impairs membrane binding, mutant enzyme shows 29% of the arachidonic acid oxygenase activity of the wild-type enzyme
F70H
-
mutation impairs membrane binding, mutant enzyme shows 53% of the arachidonic acid oxygenase activity of the wild-type enzyme
I593A
-
mutation induces alterations in the stereochemical characteristics of hydroxy fatty acid oxygenation
L195E
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mutation impairs membrane binding, mutant enzyme shows 42% of the arachidonic acid oxygenase activity of the wild-type enzyme
L367E
-
site-directed mutagenesis, site-directed mutagenesis, the mutant shows reduced activity with O2 compared to the wild-type enzyme, L367 is involved in oxygen access, overview
L367F
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site-directed mutagenesis, site-directed mutagenesis, the mutant shows reduced activity with O2 compared to the wild-type enzyme, in silico mutagenesis and structural modeling, L367 is involved in oxygen access, overview
L367K
-
site-directed mutagenesis, site-directed mutagenesis, the mutant shows reduced activity with O2 compared to the wild-type enzyme, L367 is involved in oxygen access, overview
L367W
-
site-directed mutagenesis, site-directed mutagenesis, the mutant shows reduced activity with O2 compared to the wild-type enzyme, L367 is involved in oxygen access, overview
L71K
-
mutation impairs membrane binding, mutant enzyme shows 50% of the arachidonic acid oxygenase activity of the wild-type enzyme
W181E
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mutation strongly impairs membrane binding, mutant enzyme shows 34% of the arachidonic acid oxygenase activity of the wild-type enzyme
Y15E
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mutation impairs membrane binding, mutant enzyme shows 61% of the arachidonic acid oxygenase activity of the wild-type enzyme
Y292E
-
mutation slightly impairs membrane binding, mutant enzyme shows 112% of the arachidonic acid oxygenase activity of the wild-type enzyme
M418V
-
the ratio of 15-lipoxygenation to 12-lipoxygenation is 1:1 for the mutant enzymes V104/L397M/M418V/Q431R, L397M/M418V/Q431R, L397M/M418V and M418V, compared to 9:1 for the wild-type enzyme
additional information
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endothelial 15-lipoxygenase-1 overexpression in Oryctolagus cuniculus aortic endothelial cells increases acetylcholine-induced hypotension and vasorelaxation, overview
V603H
-
a strong shift of the pH profile of 15-LOX-2 mutant towards more acidic values. 15-H(p)ETE is the major oxygenation product at pH 8
additional information
-
12/15-LO knockout mice show reduced monocyte chemoattractant protein MCP-1 expression
additional information
Mus musculus C57BL/6
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12/15-LO knockout mice show reduced monocyte chemoattractant protein MCP-1 expression
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug development
-
15-LO-1 is an attractive pharmacological target for treatment of inflammatory respiratory diseases like asthma, rhinitis and chronic obstructive pulmonary disease
drug development
-
trials of 15LO1 pathway inhibitors in asthma may be a promising treatment strategy
medicine
-
tumorigenesis
medicine
-
15-LOX-1 and its metabolites (13-S-hydroxyoctadecadienoic acid and 15-S-hydroxyeicosatetraenoic acid) have anti-carcinogenic effects in colorectal cancer. 15-LOX-1 is possibly of prognostic value in stage IV colon cancer survival
medicine
-
15-LOX-2 is a negative regulator of tumor growth via downregulating angiogenesis
medicine
-
15-LOX-2 may be a potential target in radiation-targeted therapy of head-and-neck cancer
medicine
-
interruption of 12-LOX catalytic activity and the 12-hydroxyeicosatetraenoic acid signaling pathway by increasing 15-LOX metabolites may be a promising target for psoriasis therapies
medicine
-
pro-tumorigenic feedback loop for 13-(S)-hydroxyoctadecadienoic acid against 15-hLO-2
medicine
-
under cellular conditions (low fatty acid and low oxygen concentrations), the allosteric binding of 12(S)-hydroxyeicosatetraenoic acid to 15-hLO-1 can increase the substrate specificity of 15-hLO-1 toward arachidonic acid over linoleic acid significantlysignificantly, which may have important implications in cancer progression
drug development
-
systemic delivery of cholesterol-tagged siRNAs targeting 12/15-LO has renoprotective effects under diabetic conditions and therefore can be a novel therapeutic approach for diabetic nephropathy
medicine
-
has anti-carcinogenic effects in colorectal cancer
drug development
Mus musculus DBA/2J
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systemic delivery of cholesterol-tagged siRNAs targeting 12/15-LO has renoprotective effects under diabetic conditions and therefore can be a novel therapeutic approach for diabetic nephropathy
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