Information on EC 1.13.11.33 - arachidonate 15-lipoxygenase and Organism(s) Homo sapiens

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


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EC NUMBER
COMMENTARY hide
1.13.11.33
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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
the reaction proceeds via hydrogen abstraction, peroxide cleavage, radical rearrangement, and epoxide formation. To initiate the reaction the ferrous LOX is first activated by peroxide-dependent oxidation to a ferric form. The lipohydroperoxidase activity is initiatedwhen a lipid hydroperoxide (ROOH) is bound at the active site of the enzyme. The enzyme then catalyzes a homolytic cleavage of the hydroperoxy bond, which leads to the formation of an oxygen-centered alkoxy radical, a hydroxyl and oxidizes the ferrous iron to a ferric form. Then the enzyme binds a linoleic acid molecule (or an alterative reductant such as guaiacol) and releases a carbon-centered linoleic radical. This reaction reduces the ferric LOX back to its ferrous form to start the next catalytic cycle. The released radical intermediates may then initiate free radical secondary reactions leading to the formation of mixed oxygenated and non-oxygenated linoleic acid dimer
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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
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
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shifting linoleic acid metabolism from 15-LOX-1 to COX-2 is procarcinogenic
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
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
(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
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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
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?
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
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?
eicosapentaenoic acid + O2
15-hydroxyeicosapentaenoic acid
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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?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
show the reaction diagram
linoleic acid + O2
13-hydroperoxy-(9Z,11E)-linoleic acid
show the reaction diagram
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?
linoleic acid + O2
13-hydroxylinoleic acid
show the reaction diagram
linoleic acid + O2
13-S-hydroxyoctadecadienoic acid
show the reaction diagram
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both 15-LOX-1, 15-LOX-2 reacts with linoleic acid poorly
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?
linoleic acid + O2
?
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
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
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
Mg2+
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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
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(Z)-9-octadecenyl sulfate
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allosteric inhibition
1-(3-chlorobenzoyl)-N-(2-chlorophenyl)-1H-pyrazole-3-carboxamide
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1-acetyl-N-(3,4-dichlorophenyl)-1H-pyrazole-3-carboxamide
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1-benzyl-N-(2-chlorophenyl)-1H-pyrazole-3-carboxamide
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1-[(2H-1,3-benzodioxol-5-yl)carbamothioyl]-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
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11-thialinoleic acid
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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
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
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IC50: 0.0018 mM
2,3,4,5-tetrabromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
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IC50: 0.00079 mM
2,3,5-tribromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
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IC50: 0.0022 mM
2,4-dibromo-6-(2,4-dibromo-6-methoxyphenoxy)phenol
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IC50: 0.01 mM
2,4-Dibromophenol
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IC50: 0.034 mM
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
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IC50: 0.005 mM
2-(1H-pyrazol-3-yl)-1,3-benzoxazole
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2-([4-[(4-fluorobenzyl)oxy]butyl]sulfanyl)-5-(naphthalen-1-yl)-1,3,4-oxadiazole
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2-alkyl benzopyran-4-ones
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weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
2-alkyl-6-hydroxy-4-H-benzopyran-4-one
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weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
3'-chloro-7,8-dihydroxyisoflavone
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weak inhibition of isozyme 15-hLO-2
3,4,6,8-tetrabromooxanthren-1-ol
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IC50: 0.0009 mM
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
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IC50: 0.005 mM
3,4-dibromo-2-(5-bromo-2-hydroxyphenoxy)phenol
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IC50: 0.011 mM
3,6,8-tribromooxanthren-1-ol
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IC50: 0.0008 mM
3-(4-bromophenyl)-6-(4-chlorophenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[2,1-b][1,3]thiazol-5-amine
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3-(4-bromophenyl)-6-(4-chlorophenyl)-N-cyclohexylimidazo[2,1-b][1,3]thiazol-5-amine
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3-(4-bromophenyl)-N-cyclohexyl-6-(2-nitrophenyl)imidazo[2,1-b][1,3]thiazol-5-amine
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3-(4-methoxyphenyl)-6-phenyl-N-(2,4,4-trimethylpentan-2-yl)imidazo[2,1-b][1,3]thiazol-5-amine
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protective activity of compound 5i against H2O2-induced cell death in differentiated PC12 cells
3-hydroxy-H-benzopyran-4-one derivatives
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weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
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
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IC50: 0.059 mM
4',6,7-trihydroxyisoflavan
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4',6,7-trihydroxyisoflavanone
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weak inhibition of isozyme 15-hLO-2
4',6,7-trihydroxyisoflavone
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weak inhibition of isozyme 15-hLO-2
4'-chloro-7,8-dihydroxyisoflavone
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weak inhibition of isozyme 15-hLO-2
4,4'-propane-2,2-diylbis(2,6-dibromophenol)
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IC50: 0.004 mM
4,5-dichloro-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
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4-((5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)butyl)-4-fluorobenzoate
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4-((5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)methyl)-benzyl-4-fluorobenzoate
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4-(2-benzoylhydrazinyl)benzene-1-sulfonamide
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10% inhibition
4-(2-chlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
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4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
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4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
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4-(5-(1H-indol-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(2-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(3-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(3-hydroxynaphthalen-2-yl)-1,3,4-oxadiazol-2-ylthio)-but-2-ynyl-4-fluorobenzoate
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low solubility
4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(furan-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylamino)but-2-ynyl-thiophene-2-carboxylate
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4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-yn-1-ol
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4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-1H-indole-4-carboxylate
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4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-benzofuran-2-carboxylate
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4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-thiophene-2-carboxylate
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4-(5-(naphthalen-1-yl)-1,3,4-thiadiazol-2-ylthio)but-2-ynyl-thiophene-2-carboxylate
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low solubility
4-(5-(quinolin-5-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-(5-phenyl-1,3,4-oxadiazol-2-ylthio)but-2-ynyl-4-fluorobenzoate
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4-allyl-2-methoxyphenyl 1-adamantanecarboxylate
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4-allyl-2-methoxyphenyl 1-cyclohexanecarboxylate
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4-allyl-2-methoxyphenyl 2-chlorobenzoate
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4-allyl-2-methoxyphenyl 2-fluorobenzoate
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4-allyl-2-methoxyphenyl 2-methylbenzoate
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4-allyl-2-methoxyphenyl 2-pyridinecarboxylate
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4-allyl-2-methoxyphenyl 3-chlorobenzoate
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4-allyl-2-methoxyphenyl 3-fluorobenzoate
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4-allyl-2-methoxyphenyl 3-methoxybenzoate
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4-allyl-2-methoxyphenyl 3-methylbenzoate
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4-allyl-2-methoxyphenyl 4-chlorobenzoate
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4-allyl-2-methoxyphenyl 4-fluorobenzoate
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4-allyl-2-methoxyphenyl 4-methoxybenzoate
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4-allyl-2-methoxyphenyl 4-methylbenzoate
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4-allyl-2-methoxyphenyl benzoate
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4-allyl-2-methoxyphenyl isonicotinate
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4-allyl-2-methoxyphenyl nicotinate
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4-amino-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
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4-bromo-5-chloro-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
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4-bromo-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
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4-Bromophenol
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IC50: 0.055 mM
4-butyl-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
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4-butyl-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
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4-chloro-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
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4-chloro-N-(2-chloro-4-fluorophenyl)-5-(difluoromethyl)-1H-pyrazole-3-carboxamide
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4-chloro-N-(2-chloro-4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide
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4-chlorophenyl 3-[(2-chlorophenyl)carbamoyl]-1H-pyrazole-1-carboxylate
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4-pentyl-N-(2-[2-phenyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-4-yl]ethyl)benzenesulfonamide
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4-pentyl-N-[2-(5-phenyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
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4-pentyl-N-[2-(5-phenyl-2-pyrazin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
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4-pentyl-N-[2-(5-phenyl-2-pyridin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
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4-pentyl-N-[2-(5-phenyl-2-pyridin-3-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
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4-pentyl-N-[2-(5-phenyl-2-pyridin-4-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
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4-pentyl-N-[2-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
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4-pentyl-N-[3-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)propyl]benzenesulfonamide
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4-[(E)-benzoyldiazenyl]benzene-1-sulfonamide
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4-[(E)-benzoyldiazenyl]benzonitrile
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80% inhibition, competitive
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1-benzothiophene-2-carboxylate
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4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1-benzothiophene-3-carboxylate
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4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 1H-imidazole-4-carboxylate
-
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4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 2,4-difluorobenzoate
-
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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
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-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4,5-trichlorothiophene-2-carboxylate
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-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4,5-trifluorobenzoate
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4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3,4-difluorobenzoate
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4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 3-(trifluoromethyl)benzoate
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-
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
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-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl 4-(methylsulfonyl)benzoate
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-
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
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-
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl furan-2-carboxylate
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-
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
-
-
4-{[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}but-2-yn-1-yl 4-chlorobenzoate
-
-
4-{[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}but-2-yn-1-yl 4-fluorobenzoate
-
-
4-{[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}but-2-yn-1-yl 4-methoxybenzoate
-
-
5,8,11,14-Eicosatetraynoic acid
5-amino-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
-
5-butyl-N3-(2-chloro-4-fluorophenyl)-N1-hexyl-1H-pyrazole-1,3-dicarboxamide
-
-
5-chloro-2-(1H-pyrazol-3-yl)-1,3-benzoxazole
-
-
5-chloro-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
-
5-fluoro-2-(1H-pyrazol-3-yl)-1,3-benzoxazole
-
-
5-tert-butyl-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
-
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-(2-bromophenyl)-N-cyclohexyl-3-phenylimidazo[2,1-b][1,3]thiazol-5-amine
-
-
6-(2-nitrophenyl)-3-phenyl-N-(2,4,4-trimethylpentan-2-yl)imidazo[2,1-b][1,3]thiazol-5-amine
-
-
6-(4-nitrophenyl)-3-phenyl-N-(2,4,4-trimethylpentan-2-yl)imidazo[2,1-b][1,3]thiazol-5-amine
-
-
6-chloro-2-(1H-pyrazol-3-yl)-1,3-benzoxazole
-
-
6-chloro-2-(4,5-dichloro-1H-pyrazol-3-yl)-1,3-benzoxazole
-
-
6-chloro-2-(5-chloro-1H-pyrazol-3-yl)-1,3-benzoxazole
-
-
6-fluoro-2-(1H-pyrazol-3-yl)-1,3-benzoxazole
-
-
6-hydroxy-2-pentyl-4H-benzopyran-4-one
-
weak inhibition of isozyme 15-hLO-2
6-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]-1-phenylhexan-1-one
-
low solubility
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-hydroxy-H-benzopyran-4-one derivatives
-
weak inhibition of isozymes 15-hLO-1 and 15-hLO-2
AA-861
-
-
alpha-mangostin
-
NSC30552, a natural product, caspase-3 pathway inhibitor, performs selective inhibition of 12-LO
anthraquinone
-
-
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
bestatin 7
-
IC50: 0.027 mM
caffeic acid
CDC
-
CAS-No. 132465-11-3
-
cinnamyl 3,4-dihydroxy-cyanocinnamate
-
CDC
conjugated linoleic acids
-
conjugated linoleic acids may function as inhibitors of 15-LO-1 activity in macrophages/in vivo, overview
-
dysidenin
-
-
eicosatetraynoic acid
-
-
esculetin
-
-
ethyl 6-([3-[(2-chloro-4-fluorophenyl)carbamoyl]-1H-pyrazole-1-carbonyl]amino)hexanoate
-
-
gallic acid
-
-
GATA-6
-
inhibits non-steroidal anti-inflammatory drugs-induced transcription of 15-LOX-1 in colorectal cancer cells
-
glucocorticoid
-
inhibits induction in monocytes
-
interferon-gamma
-
inhibits induction in monocytes
-
linoleic acid
michellamine B
-
NSC661755, potent but non-selective inhibitor, a natural anti-viral agent
N'-(4-bromophenyl)benzohydrazide
-
28% inhibition
N'-(4-cyanophenyl)benzohydrazide
-
9% inhibition
N'-(4-methoxyphenyl)benzohydrazide
-
73% inhibition
N'-(4-methylphenyl)benzohydrazide
-
93% inhibition, competitive
N'-(4-nitrophenyl)benzohydrazide
-
17% inhibition
N'-phenylbenzohydrazide
-
33% inhibition
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-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxamide
-
-
N-(2,5-dichlorophenyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-1-(dimethylsulfamoyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-1-(phenylacetyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-1-methyl-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-1-[3-(trifluoromethyl)benzene-1-sulfonyl]-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4,5-bis(trifluoromethyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4-(trifluoromethyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4-fluoro-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4-iodo-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4-methyl-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4-methyl-5-(trimethylsilyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4-nitro-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4-phenyl-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-4-[(methanesulfonyl)amino]-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-5-(difluoromethyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-5-iodo-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-5-methyl-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-5-nitro-1H-pyrazole-3-carboxamide
-
-
N-(2-chloro-4-fluorophenyl)-5-[(methanesulfonyl)amino]-1H-pyrazole-3-carboxamide
-
-
N-(2-chlorophenyl)-1H-pyrazole-3-carboxamide
-
-
N-(2-chlorophenyl)-N-methyl-1H-pyrazole-3-carboxamide
-
-
N-(3,4-dichlorophenyl)-1H-pyrazole-3-carboxamide
-
-
N-(4-(5-(naphthalen-1-yl)-1,3,4-oxadiazol)-2-ylthio)but-2-ynyl-thiophene-2-carboxamide
-
-
N-(4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
-
N-(5-chloro-1,3-thiazol-2-yl)-1H-pyrazole-3-carboxamide
-
-
N-(5-chloropyridin-2-yl)-1H-pyrazole-3-carboxamide
-
-
N-(5-fluoropyridin-2-yl)-1H-pyrazole-3-carboxamide
-
-
N-(7-fluoroquinolin-3-yl)-1H-pyrazole-3-carboxamide
-
-
N-(isoquinolin-3-yl)-1H-pyrazole-3-carboxamide
-
-
N-(pyridin-2-yl)-1H-pyrazole-3-carboxamide
-
-
N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide
-
-
N-(pyridin-4-yl)-1H-pyrazole-3-carboxamide
-
-
N-(quinolin-2-yl)-1H-pyrazole-3-carboxamide
-
-
N-(quinolin-3-yl)-1H-pyrazole-3-carboxamide
-
-
N-(quinolin-6-yl)-1H-pyrazole-3-carboxamide
-
-
N-(tert-butyl)-3-phenyl-6-(p-tolyl)imidazo[2,1-b]thiazol-5-amine
-
-
N-(tert-butyl)-6-(4-chlorophenyl)-3-phenylimidazo[2,1-b]thiazol-5-amine
-
-
N-(tert-butyl)-6-(4-methoxyphenyl)-3-phenylimidazo[2,1-b]thiazol-5-amine
-
-
N-(tert-butyl)-6-(4-nitrophenyl)-3-phenylimidazo[2,1-b]thiazol-5-amine
-
-
N-benzyl-1H-pyrazole-3-carboxamide
-
-
N-cyclohexyl-6-(2-fluorophenyl)-3-phenylimidazo[2,1-b][1,3]thiazol-5-amine
-
-
N-cyclohexyl-6-(4-methoxyphenyl)-3-phenylimidazo[2,1-b][1,3]thiazol-5-amine
-
-
N-cyclohexyl-6-(4-nitrophenyl)-3-phenylimidazo[2,1-b][1,3]thiazol-5-amine
-
-
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-phenyl-1H-pyrazole-3-carboxamide
-
-
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-(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-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-[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)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
-
-
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-(2,5-diphenyl-1H-imidazol-4-yl)propyl]-4-pentylbenzenesulfonamide
-
-
N-[4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carboxamide
-
-
N-[4-fluoro-2-(trifluoromethyl)phenyl]-1H-pyrazole-3-carboxamide
-
-
N1-(2H-1,3-benzodioxol-5-yl)-N-3-(2-chloro-4-fluorophenyl)-1H-pyrazole-1,3-dicarboxamide
-
-
N1-butyl-N3-(2-chlorophenyl)-N3-methyl-1H-pyrazole-1,3-dicarboxamide
-
-
N3-(2,2-difluoro-2H-1,3-benzodioxol-4-yl)-N1-hexyl-5-methyl-1H-pyrazole-1,3-dicarboxamide
-
-
N3-(2-chloro-4-fluorophenyl)-N1-hexyl-4-methyl-1H-pyrazole-1,3-dicarboxamide
-
-
N3-(2-chloro-4-fluorophenyl)-N1-pentyl-1H-pyrazole-1,3-dicarboxamide
-
-
N3-(2-chlorophenyl)-N1,N1-dimethyl-1H-pyrazole-1,3-dicarboxamide
-
-
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
PD146176
-
-
phenyl[(E)-phenyldiazenyl]methanone
-
87% inhibition
quercetin
-
-
siRNA
-
[(E)-(4-bromophenyl)diazenyl](phenyl)methanone
-
44% inhibition
[(E)-(4-methoxyphenyl)diazenyl](phenyl)methanone
-
19% inhibition
[(E)-(4-methylphenyl)diazenyl](phenyl)methanone
-
44% inhibition
[(E)-(4-nitrophenyl)diazenyl](phenyl)methanone
-
34% inhibition
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
0.005
arachidonate
-
-
0.0025 - 1.1
arachidonic acid
0.003 - 0.0772
linoleic acid
0.01
lipoic acid
-
splice variant 15-LOb1
0.0096 - 4.2
O2
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
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3 - 14
arachidonate
0.57 - 9.93
arachidonic acid
4 - 17.8
linoleic acid
5.1 - 7.6
O2
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00005 - 0.00075
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
0.00001
4-(5-(3-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 23°C
0.00001
4-(5-(4-chlorophenyl)-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 23°C
0.00001
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
0.00398
4-[(E)-benzoyldiazenyl]benzonitrile
-
pH and temperature not specified in the publication
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
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 23°C
0.00001
4-{[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}but-2-yn-1-yl 4-chlorobenzoate
-
apparent value, Ki above 0.00001 mM, in 25 mM HEPES buffer (pH 7.5), 0.01% (v/v) Triton X-100, at 23°C
0.00001
4-{[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}but-2-yn-1-yl 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 23°C
0.00001
4-{[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}but-2-yn-1-yl 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 23°C
0.002
apigenin
-
-
0.00018 - 0.0011
baicalein
0.008
dysidenin
-
above, pH 7.5, recombinant isozyme 15-hLO-1
0.005 - 0.017
linoleic acid
0.00081
N'-(4-methylphenyl)benzohydrazide
-
pH and temperature not specified in the publication
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 23°C
0.5
neodysidenin
-
above, pH 7.5, recombinant isozyme 15-hLO-1
additional information
additional information
-
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0018
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
Homo sapiens
-
IC50: 0.0018 mM
0.00079
2,3,4,5-tetrabromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
Homo sapiens
-
IC50: 0.00079 mM
0.0022
2,3,5-tribromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol
Homo sapiens
-
IC50: 0.0022 mM
0.01
2,4-dibromo-6-(2,4-dibromo-6-methoxyphenoxy)phenol
Homo sapiens
-
IC50: 0.01 mM
0.034
2,4-Dibromophenol
Homo sapiens
-
IC50: 0.034 mM
0.005
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
Homo sapiens
-
IC50: 0.005 mM
0.0062
3'-chloro-7,8-dihydroxyisoflavone
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.0009
3,4,6,8-tetrabromooxanthren-1-ol
Homo sapiens
-
IC50: 0.0009 mM
0.005
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
Homo sapiens
-
IC50: 0.005 mM
0.011
3,4-dibromo-2-(5-bromo-2-hydroxyphenoxy)phenol
Homo sapiens
-
IC50: 0.011 mM
0.0008
3,6,8-tribromooxanthren-1-ol
Homo sapiens
-
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
Homo sapiens
-
IC50: 0.059 mM
0.00051 - 0.071
4',6,7-trihydroxyisoflavan
0.0038 - 0.1
4',6,7-trihydroxyisoflavanone
0.049
4',6,7-trihydroxyisoflavone
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.009
4'-chloro-7,8-dihydroxyisoflavone
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.004
4,4'-propane-2,2-diylbis(2,6-dibromophenol)
Homo sapiens
-
IC50: 0.004 mM
0.045 - 0.132
4-(2-chlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
0.055 - 0.378
4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
0.036 - 0.133
4-(3,4-dichlorophenyl)-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
0.055
4-Bromophenol
Homo sapiens
-
IC50: 0.055 mM
0.014 - 0.05
4-butyl-N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]piperazine-1-sulfonamide
0.000072 - 0.000372
4-pentyl-N-(2-[2-phenyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-4-yl]ethyl)benzenesulfonamide
0.01
4-pentyl-N-[2-(5-phenyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
Homo sapiens
-
above, versus substrate linoleic acid
0.00281
4-pentyl-N-[2-(5-phenyl-2-pyrazin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
Homo sapiens
-
versus substrate linoleic acid
0.00097 - 5.321
4-pentyl-N-[2-(5-phenyl-2-pyridin-2-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
0.00056
4-pentyl-N-[2-(5-phenyl-2-pyridin-3-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
Homo sapiens
-
versus substrate linoleic acid
0.000087 - 3.211
4-pentyl-N-[2-(5-phenyl-2-pyridin-4-yl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
0.000006 - 0.000013
4-pentyl-N-[2-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)ethyl]benzenesulfonamide
0.000053 - 0.000396
4-pentyl-N-[3-(5-phenyl-2-thioformyl-1H-imidazol-4-yl)propyl]benzenesulfonamide
0.00978
4-[(E)-benzoyldiazenyl]benzonitrile
Homo sapiens
-
pH and temperature not specified in the publication
0.018
6,7-dihydroxy-2-t-butylbenzopyran-4-one
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.00035 - 0.016
6,7-dihydroxy-3',4'-methylenedioxyisoflavan
0.00021 - 0.0083
6,7-dihydroxy-3'-methylisoflavan
0.00021 - 0.014
6,7-dihydroxy-3'-methylisoflavanone
0.00015 - 0.1
6,7-dihydroxy-4'-methoxyisoflavan
0.0016 - 0.019
6,7-dihydroxy-4'-methoxyisoflavanone
0.038
6-hydroxy-2-pentyl-4H-benzopyran-4-one
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.1
7,8-dihydroxy-3',4'-dimethoxyisoflavan
Homo sapiens
-
above, pH 7.5, 22°C, isozyme 15-hLO-1; above, pH 7.5, 22°C, isozyme 15-hLO-2
0.011
7,8-dihydroxy-3'-methylisoflavone
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.0083
7,8-dihydroxy-3'-trifluoromethylisoflavone
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.0037 - 0.1
7,8-dihydroxy-4'-methoxyisoflavan
0.0057 - 0.1
7,8-dihydroxy-4'-methylisoflavan
0.0078
7,8-dihydroxy-4'-methylisoflavone
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.013
7,8-dihydroxyisoflavone
Homo sapiens
-
pH 7.5, 22°C, isozyme 15-hLO-1
0.0031 - 0.05
alpha-mangostin
0.0003 - 100
apigenin
Homo sapiens
-
IC50: 0.0034 mM without Triton X-100, IC50: 0.0003 mM in the presence of 0.01% Triton X-100
0.038 - 100
baicalein
Homo sapiens
-
potent inhibitor, IC50: 0.0016 mM without Triton X-100, IC50: 0.038 mM in the presence of 0.01% Triton X-100
0.027
bestatin 7
Homo sapiens
-
IC50: 0.027 mM
0.0076 - 0.05
michellamine B
0.00535
N'-(4-methylphenyl)benzohydrazide
Homo sapiens
-
pH and temperature not specified in the publication
0.031 - 0.186
N'-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
0.08 - 0.822
N'-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3S)-1-phenoxypyrrolidin-3-yl]sulfamide
0.038 - 0.375
N'-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-N-methyl-N-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
0.01 - 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
0.003 - 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
0.011 - 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
0.000364 - 0.0028
N-[2-(2,5-diphenyl-1H-imidazol-4-yl)ethyl]-4-methylbenzenesulfonamide
0.000033 - 0.000162
N-[2-(2,5-diphenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
0.01
N-[2-(2-cyclopropyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
Homo sapiens
-
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
Homo sapiens
-
above, versus substrate linoleic acid
0.00192 - 0.01
N-[2-(2-tert-butyl-5-phenyl-1H-imidazol-4-yl)ethyl]-4-pentylbenzenesulfonamide
0.00072
N-[2-[2-(2-methyl-1,3-thiazol-4-yl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
Homo sapiens
-
versus substrate linoleic acid
0.000099 - 0.0011
N-[2-[2-(3-nitrophenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
0.000021 - 0.0011
N-[2-[2-(4-chlorophenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
0.01
N-[2-[2-(4-methoxyphenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
Homo sapiens
-
above, versus substrate linoleic acid
0.003
N-[2-[2-(4-methylphenyl)-5-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
Homo sapiens
-
versus substrate linoleic acid
0.000082 - 0.000531
N-[2-[5-(3-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
0.000059 - 0.000261
N-[2-[5-(4-fluorophenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
0.000014 - 0.00005
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-pentylbenzenesulfonamide
0.212 - 3.45
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-4-phenylpiperazine-1-sulfonamide
0.083 - 0.719
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N'-[(3R)-1-phenoxypyrrolidin-3-yl]sulfamide
0.272 - 2.41
N-[2-[5-(4-methoxyphenyl)-2-phenyl-1H-imidazol-4-yl]ethyl]-N'-[(3S)-1-phenoxypyrrolidin-3-yl]sulfamide
0.091 - 0.646
N-[2-[5-(4-methoxyphenyl)-2-thioformyl-1H-imidazol-4-yl]ethyl]-4-pentylpiperazine-1-sulfonamide
0.00014 - 0.000914
N-[3-(2,5-diphenyl-1H-imidazol-4-yl)propyl]-4-pentylbenzenesulfonamide
0.5
neodysidenin
Homo sapiens
-
above, pH 7.5, recombinant isozyme 15-hLO-1
0.00011
nordihydroguaiaretic acid
Homo sapiens
-
IC50: 0.00011 mM
0.0094 - 0.05
NSC172033
0.025 - 0.05
NSC292213
0.05 - 0.5
NSC617570
0.00697
phenyl[(E)-phenyldiazenyl]methanone
Homo sapiens
-
pH and temperature not specified in the publication
0.1
additional information
Homo sapiens
-
IC50 above 0.1 mM: compound 1a, compound 1b, compound 1d, compound 1e, compound 1g
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.125
-
-
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.7 - 7.3
-
-
6.8 - 7.2
-
-
7 - 8.5
-
-
8 - 9
-
pH-optimum of 15-LOX-2 for arachidonic acid oxygenation
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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 hide
LITERATURE
25
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
epidermoid carcinoma of the submandibular gland
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
-
visceral adipose tissue
Manually annotated by BRENDA team
-
medium expression
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
-
immature
Manually annotated by BRENDA team
-
hypopharyngeal carcinoma
Manually annotated by BRENDA team
-
epidermal carcinoma of the mouth
Manually annotated by BRENDA team
-
carcinoma of the retromolar trigone region
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
-
CD14+
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
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
-
15-LOX-1, in the stroma of fibroblasts
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70000
-
x * 70000, SDS-PAGE
72000
-
x * 72000, SDS-PAGE
74000
-
x * 74000, SDS-PAGE
74727
-
x * 74727, electrospray mass spectrometry
76000
-
SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
frozen at -70°C and thawed with recovery of activity
-
repeated freeze thawing especially in the absence of gylcerol results in 60% reduction of specific activity
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severe autoinactivation is observed at high substrate concentrations if the substrate is not HPLC-purified and stored at -80°C
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70°C, 5% glycerol, stable for more than 6 months
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-80°C, 10% glycerol
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-80°C, 10-20% glycerol
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by one step Ni2+ affinity chromatography, more than 90% pure
-
on Ni column
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partial
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recombinant His-tagged enzyme from Escherichia coli coli by nickel affinity and anion exchange chromatography
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recombinant His-tagged isozyme 15-hLO-1 by nickel affinity chromatography, recombinant untagged isozyme 15-hLO-2 by ion exchange chromatography
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recombinant His6-tagged isozyme 15-LOX-2 from Escherichia coli strain Rossetta 2 (DE3) by cobalt affinity chromatography, ultrafiltration, and gel filtration
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recombinant isozyme 15-hLO-2 from Spodoptera frugiperda Sf9 cells by anion exchange chromatography, recombinant His-tagged isozyme 15-hLO-1
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Resource-Q 5 column chromatography
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to greater than 90% purity
-
two enzyme forms
-
using Ni-NTA chromatography
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without a His6-tag, more than 90% pure
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
15-LO-1 expressed in Sf 9 cells
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15-LOX-1 cDNA fragment without 3'-UTR inserted into pLP-IRESneo, overexpression of 15-LOX-1 in A549 cells
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15-LOX2 has at least six alternatively spliced isoforms
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expressed as a fusion protein with GFP (pEGFP-15LOX-2) in DU145 and PC-3 cells
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expressed in CV-1 cells
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expressed in Escherichia coli as a His-tagged fusion protein
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expressed in Mus musculus C57BL/6
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expressed in Mus musculus C57BL/6 prostate
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expressed in rabbit aorta endothelium
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expressed in Sf9 cells
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expressed with hexa-His tags
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expression in a human osteosarcoma cell line, expression of a CheY-15-lipoxygenase fusion protein in Escherichia coli
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expression in CHO and in neuro-2 A neuroblastoma cells both stably expressing human APP carrying the K670N/M671L Swedish mutation, expression analysis
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expression in Escherichia coli
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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
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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
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expression to high levels, approximately 20% of cellular protein, in a baculovirus/insect cell expression system
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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
gene ALOX15, located on the short arm of chromosome 17
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HCT-116 and LoVo cells transfected with 15-LOX-1 vector
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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)
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overexpressed as N-terminally, His6-tagged protein
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overexpression of 15-LOX-2 in human macrophages by adenovirus-mediated gene delivery
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overexpression of His-tagged enzyme in Escherichia coli
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overexpression of isozyme 15-LO-1 in Oryctolagus cuniculus via adenovirus transfection method, the expression is restricted to aortic endothelial cells, overview
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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
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pcDNA3.1(1) vector carrying native or mutant 15-LOX-1 expressed in HCT-116 cells
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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
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RAW 267.4 murine macrophages stably transfected to overexpress 15-LO-1
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recombinant expression of 15-LOX-1 in Spodoptera frugiperda SF9 cells
-
recombinant expression of His6-tagged isozyme 15-LOX-2 in Escherichia coli strain Rossetta 2 (DE3), coexpression with Escherichia coli YjgD protein
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sequence comparisons and phylogenetic analysis
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transgenic mice overexpressing 15-LO-1
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without a His6-tag
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
12/15-LO is upregulated in white adipose tissue in the obese state. The potent vasoconstricting and pro-inflammatory hormone angiotensin II (Ang II) led to increases in leukocyte-type 12-LO mRNA and protein levels, as well as increased enzyme activity
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15LO1 is highly expressed in fresh epithelial cells from severe asthmatic patients
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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
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hypoxia increases ALOX15 in human muscle cells; ischemia of the heart leads to increased expression of ALOX15
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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
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induction by interleukin-4 and interleukin-13
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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
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interleukin-4 increases the expression of 15-LOX-1 and of downstream targets of p53
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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
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normal human airway epithelial cells treated with interleukin-4 express higher levels of 15-LOX-1 than transfected A549 cells
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
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
I417A
-
naturally occuring mutation, the mutant produces 94% 12-hydroperoxyicosatetraenoate and 6% 15-hydroperoxyicosatetraenoate, in contrast to the wild-type, that produces 15% 12-hydroperoxyicosatetraenoate and 85% 15-hydroperoxyicosatetraenoate
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
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
M419T
-
naturally occuring mutation, the mutant produces more 12-hydroperoxyicosatetraenoate compared to 15-hydroperoxyicosatetraenoate, incontrast to the wild-type, inversed substrate specificity
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
-
mutant shows strongly impaired catalytic activity, relative catalytic activity: 16.6% compared to wild-type 100%
T560S
-
enzyme retains activity, relative catalytic activity: 70.7% compared to wild-type 100%
T594V
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naturally occuring mutation, the mutant produces more 12-hydroperoxyicosatetraenoate compared to 15-hydroperoxyicosatetraenoate, incontrast to the wild-type, inversed substrate specificity
V104/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
V104I
-
ratio of 15-lipoxygenation to 12-lipoxygenation is 9:1 for the wild-type enzyme and the mutant enzymes V104I, L397M and Q431R
V603H
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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
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endothelial 15-lipoxygenase-1 overexpression in Oryctolagus cuniculus aortic endothelial cells increases acetylcholine-induced hypotension and vasorelaxation, overview