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 hide
1.13.11.33
-
RECOMMENDED NAME
GeneOntology No.
arachidonate 15-lipoxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
arachidonate + O2 = (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dioxygenation
-
-
-
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oxidation
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-
-
-
redox reaction
-
-
-
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
arachidonic acid metabolism
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Arachidonic acid metabolism
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Linoleic acid metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 15-oxidoreductase
The product is rapidly reduced to the corresponding 15S-hydroxy compound.
CAS REGISTRY NUMBER
COMMENTARY hide
82249-77-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
Cyanothece sp.
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
cv. Salome
SwissProt
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
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-
Manually annotated by BRENDA team
Mus musculus C57BL6
C57Bl6 mice
-
-
Manually annotated by BRENDA team
Mus musculus DBA/2J
DBA/2J mice
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-
Manually annotated by BRENDA team
PCC73102
SwissProt
Manually annotated by BRENDA team
PCC73102
SwissProt
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Sarcolobus globosus
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-
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
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
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
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
-
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
-
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
-
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
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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
-
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
-
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
oxygenation proceeds with little if any enantioselectivity
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-
?
(18(S),5Z,8Z,11Z,14Z)-18-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
show the reaction diagram
oxygenation proceeds with little if any enantioselectivity
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-
?
1,2-diarachidonoylglycerophosphocholine + O2
?
show the reaction diagram
1-linoleoyl lysophosphatidic acid + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidic acid
show the reaction diagram
-
i.e. linoleoyl-lysoPA
major product
-
?
1-linoleoyl lysophosphatidylcholine + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidylcholine
show the reaction diagram
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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
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
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-
-
-
?
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-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
-
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
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?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
show the reaction diagram
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?
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 + (12S,5Z,8Z,10E,14Z)-12-hydroperoxyeicosa-5,8,10,14-tetraenoic acid
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
arachidonic acid + O2
15S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
show the reaction diagram
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-
-
-
?
arachidonic acid + O2
?
show the reaction diagram
-
-
-
-
?
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
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-
?
eicosapentaenoic acid + O2
15-hydroxyeicosapentaenoic acid
show the reaction diagram
-
-
-
-
?
eicosatrienoic acid + O2
?
show the reaction diagram
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-
-
?
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
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-
?
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
linoleate + O2
?
show the reaction diagram
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-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxy-octadeca-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(S)-hydroxyoctadecadienoic acid
show the reaction diagram
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-
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
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?
linoleic acid + O2
13-hydroperoxy-(9Z,11E)-linoleic acid
show the reaction diagram
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
linoleic acid + O2
13-hydroxyoctadecadienoic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
13-S-hydroxyoctadecadienoic acid
show the reaction diagram
-
both 15-LOX-1, 15-LOX-2 reacts with linoleic acid poorly
-
-
?
linoleic acid + O2
?
show the reaction diagram
linolenate + O2
11-hydroperoxyoctadecatrienoic acid + 9-hydroperoxyoctadecatrienoic acid + 13-hydroperoxyoctadecatrienoic acid
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
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
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
show the reaction diagram
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
show the reaction diagram
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-
-
-
?
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mn2+
-
activates reaction with crude extract
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(-)-5,7-O-diacetyl-3',4',5'-O-triacetylepigallocatechin-3-O-(3'',4'',5''-O-triacetyl)gallate
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IC50: 0.061 mM
(-)-5,7-O-dibutyryl-3',4',5'-O-tributyrylepigallocatechin-3-O-(3'',4'',5''-O-tributyryl) gallate
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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
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IC50: 0.031 mM
(-)-epigallocatechin-3-gallate
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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
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
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
1-acetyl-2,3-diphenylindolizine-7-carbonitrile
1-benzoyl-2,3-diphenylindolizine-7-carbonitrile
1-benzyl-2,3-diphenylindolizine-7-carbonitrile
-
IC50: 0.027 mM
1-benzyloxymethoxy-2,3-diphenyl-7-indolizinecarbonitrile
1-formyl-2,3-diphenylindolizine-7-carbonitrile
1-methoxy-2,3-diphenylindolizine-7-carbonitrile
1-methyl-2,3-diphenylindolizine-7-carbonitrile
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
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
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
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
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
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
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-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
5-ethoxy-6,7-diphenylpyrrolo[1,2-b]pyridazine
-
IC50: 0.028 mM
5-methoxy-6,7-diphenylpyrrolo[1,2-b]pyridazine
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
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
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
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
caffeic acid
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
dansyl tryptamine
-
IC50: 0.00373 mM
decyl gallate
-
-
dysidenin
-
-
ebselen
eicosatetraynoic acid
-
-
epicatechin
-
IC50: 0.06 mM
esculetin
-
-
ethyl gallate
-
-
fisetin
flavone
galangin
GATA-6
-
inhibits non-steroidal anti-inflammatory drugs-induced transcription of 15-LOX-1 in colorectal cancer cells
-
genistein
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
luteolin
methyl 3-(2-[[(4-pentylphenyl)sulfonyl]amino]ethyl)-1H-indole-6-carboxylate
-
-
methyl gallate
-
-
michellamine B
-
NSC661755, potent but non-selective inhibitor, a natural anti-viral agent
myricetin
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
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
PKYPVEPFTE
-
74.6% inhibition at 0.25 mM
poly-Lys
-
KKKKKKKK
propyl gallate
-
96% inhibition at 0.05 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
SITRINKK
-
65.3% inhibition at 0.25 mM
squalene
-
IC50 is 0.0012 mM
tachioside
Sarcolobus globosus
-
IC50: above 0.167 mM
taxifolin
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
toluene-4-sulfonic acid 7-cyano-2,3-diphenyl-indolizin-1-yl ester
vanillic acid 4-O-beta-D-glucoside
Sarcolobus globosus
-
IC50: 0.161 mM
villosinol
Sarcolobus globosus
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
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
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
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+
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0289 - 0.136
(16(R),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
0.0227 - 0.0236
(16(S),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
0.0368 - 0.293
(17(R),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
0.0313 - 0.236
(17(S),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
0.0083
1-linoleoyl lysophosphatidic acid
-
pH 7.4, 25C
0.0175
1-linoleoyl lysophosphatidylcholine
-
pH 7.4, 25C
0.0022 - 0.005
arachidonate
0.0025 - 1.1
arachidonic acid
0.09
dilinoleoyl phosphatidic acid
-
pH 7.4, 25C
0.0717
dilinoleoyl phosphatidylcholine
-
pH 7.4, 25C
0.003 - 0.0772
linoleic acid
0.01
lipoic acid
-
splice variant 15-LOb1
0.0052 - 4.2
O2
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.08
(16(R),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
Oryctolagus cuniculus
-
pH 7.4, mutant enzyme F353L
0.2 - 0.51
(16(S),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid
0.18 - 0.2
(17(R),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
0.24 - 1.24
(17(S),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid
3 - 14
arachidonate
0.57 - 97
arachidonic acid
4 - 17.8
linoleic acid
0.3 - 13.7
O2
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00005 - 8
arachidonic acid
240 - 790
O2
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
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