Information on EC 1.13.11.31 - arachidonate 12-lipoxygenase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
1.13.11.31
-
RECOMMENDED NAME
GeneOntology No.
arachidonate 12-lipoxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
arachidonate + O2 = (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dehydration
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-
-
-
dioxygenation
-
-
-
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oxidation
-
-
-
-
redox reaction
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-
-
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reduction
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
arachidonic acid metabolism
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Arachidonic acid metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 12-oxidoreductase
The product is rapidly reduced to the corresponding 12S-hydroxy compound.
CAS REGISTRY NUMBER
COMMENTARY hide
82391-43-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
soft coral
-
-
Manually annotated by BRENDA team
strain A/J
UniProt
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
-
-
Manually annotated by BRENDA team
Mus musculus C57BL6
C57Bl6 mice
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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
(Z,Z,Z,E)-5,8,11,13-eicosatetraenoic acid + 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
-
i.e. linoleoyl-lysoPC
major product
-
?
11,14,17-eicosatrienoic acid + O2
?
show the reaction diagram
11,14-eicosadienoic acid + O2
?
show the reaction diagram
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
show the reaction diagram
20-hydroxyeicosatetraenoic acid methyl ester + O2
8,20-dihydroxyeicosatetraenoic acid + 12,20-dihydroxyeicosatetraenoic acid + 9,20-dihydroxyeicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
14-hydroxy-4,7,10,12,16,19-docosahexaenoic acid
show the reaction diagram
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
14-hydroxy-4,7,10,13,16,19-docosahexaenoic acid
show the reaction diagram
-
-
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
?
show the reaction diagram
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
show the reaction diagram
5,15-(5S,15S)-dihydroperoxyarachidonic acid + O2
5S,14R,15S-trihydroperoxy-6,10,12-trans-8-cis-eicosatetraenoic acid
show the reaction diagram
-
-
the product is reduced to 5S,14R,15S,-8-cis-lipoxin B due to 14R-oxygenase activity of the enzyme
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
show the reaction diagram
5,8,11-eicosatrienoic acid + O2
12-hydroxy-5,8,10-eicosatrienoic acid
show the reaction diagram
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
-
?
6,9,12-octadecatrienoic acid + O2
13-hydroxy-6,9,12-octadecatrienoic acid
show the reaction diagram
-
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
show the reaction diagram
adrenic acid + O2
?
show the reaction diagram
-
-
-
-
?
alpha-linolenic acid + O2
13-hydroxy-(9Z,11E,15Z)-octadecatrienoic acid
show the reaction diagram
-
-
-
?
alpha-linolenic acid + O2
?
show the reaction diagram
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
show the reaction diagram
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
show the reaction diagram
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
show the reaction diagram
arachidonic acid + O2
(12S)-hydroperoxy-(5Z,8Z,11Z,13Z)-eicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
(12S)-hydroperoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
arachidonic acid + O2
12R-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
show the reaction diagram
-
-
the mutant enzyme G441A converts arachidonic acid to 8S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 12R-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid in a 1.4:1 ratio
-
?
arachidonic acid + O2
?
show the reaction diagram
arachidonic acid methyl ester + O2
12-hydroxyeicosatetraenoic acid methyl ester
show the reaction diagram
-
activity with (12R)-lipoxygenase and epidermal-type-(12S)-lipoxygenase, no activity with platelet-type (12S)-lipoxygenase
epidermal-type (12S)-lipoxygenase produces only 12-hydroxyeicosatetraenoic acid methyl ester, (12R)-lipoxygenase produces (12R)-hydroxyeicosatetraenoic acid methyl ester and (4R)-hydroxyeicosatetraenoic acid methyl ester
?
dihomo-gamma linolenic acid + O2
?
show the reaction diagram
-
-
-
-
?
docosahexaenoic acid + O2
14-hydroxydocosahexaenoic acid
show the reaction diagram
eicosapentaenoic acid + O2
12-hydroxyeicosapentaenoic acid
show the reaction diagram
gamma linolenic acid + O2
10-hydroxy-octadeca-(6Z,8E,12Z)-trienoic acid
show the reaction diagram
-
poor substrate
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-(6Z,8E,12Z)-trienoic acid
show the reaction diagram
-
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
show the reaction diagram
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
13(S)-hydroxy-(9Z,11E)-octadecadienoic acid
show the reaction diagram
-
-
-
?
linoleic acid + O2
13(S)-hydroxy-9Z,11E-octadecadienoic acid
show the reaction diagram
linoleic acid + O2
?
show the reaction diagram
linoleic acid methyl ester + O2
(9R)-hydroxyoctadecadienoic acid methyl ester
show the reaction diagram
-
-
-
-
?
linoleic acid methyl ester + O2
13(S)-hydro(pero)xyoctadecadienoic acid methyl ester
show the reaction diagram
-
activity with epidermal-type (12S)-lipoxygenase, no activity with platelet-type (12S)-lipoxygenase and (12R)-lipoxygenase
-
?
linolenic acid + O2
?
show the reaction diagram
-
poor substrate
-
-
?
methyl arachidonate + O2
(15S,5Z,8Z,11Z,13E)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester
show the reaction diagram
-
-
-
-
?
methyl arachidonate + O2
?
show the reaction diagram
-
-
-
-
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
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 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
show the reaction diagram
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
show the reaction diagram
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe3+
-
non-heme iron-containing enzyme
Mg2+
-
stimulates
Mn2+
-
stimulates
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
11-thialinoleic acid
-
is a competitive inhibitor of 12-lipoxygenase with arachidonate as substrate. Presence of inhibitor does not alter the product distribution for 12-lipoxygenase. It does not change the regioselectivity of 12-lipoxygenase
2,2'-dipyridyl
-
1 mM, 87% inactivation, no reactivation by addition of excess Fe2+ or Fe3+
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
-
IC50: 0.0007 mM
2,3,4,5-tetrabromo-6-(4,5-dibromo-2-hydroxyphenoxy)phenol
-
IC50: 0.0041 mM
2,3,5-tribromo-6-(4,5-dibromo-2-hydroxyphenoxy)phenol
-
IC50: 0.00041 mM
2,4-dibromo-6-(2,4-dibromo-6-methoxyphenoxy)phenol
-
IC50: 0.012 mM
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
-
IC50: 0.007 mM
2-alkyl benzopyran-4-ones
-
weak inhibition
2-alkyl-6-hydroxy-4-H-benzopyran-4-one
-
weak inhibition
3'-chloro-7,8-dihydroxyisoflavone
-
-
3,15-dihydroxy-8,11,13-eicosatrienoic acid
-
IC50: 0.0075 mM
3,4,6,8-tetrabromooxanthren-1-ol
-
IC50: 0.05 mM
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
-
IC50: 0.006 mM
3,4-dibromo-2-(5-bromo-2-hydroxyphenoxy)phenol
-
IC50: 0.047 mM
3,6,8-tribromooxanthren-1-ol
-
IC50: 0.03 mM
3-O-acetyl-11-keto-boswellic acid
-
0.03 mM
3-[3-bromo-5-(2,6-dibromo-4-{2-[2-(3-bromo-4-hydroxy-phenyl)-ethylcarbamoyl]-2-[(E)-hydroxyimino]-ethyl}-phenoxy)-4-methyl-phenyl]-N-[(E)-2-(3,5-dibromo-4-hydroxy-phenyl)-vinyl]-2-[(E)-hydroxyimino]-propionamide
-
IC50: 0.0004 mM
4',6,7-trihydroxyisoflavan
-
-
4',6,7-trihydroxyisoflavanone
-
-
4',6,7-trihydroxyisoflavone
-
-
4'-chloro-7,8-dihydroxyisoflavone
-
-
4,15-dihydroxy-5,8,11,13-eicosatetraenoic acid
-
IC50: 0.0081 mM
4,4'-propane-2,2-diylbis(2,6-dibromophenol)
-
IC50: 0.01 mM
4-(2-oxapentadeca-4-yne) phenylpropanoic acid
-
-
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
4-[5-(1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-12 by 5%
4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-12 by 3%
5,15-dihydroxy-5,8,11,13,17-eicosapentaenoic acid
-
IC50: 0.0008 mM
5,8,11,14-Eicosatetraynoic acid
5,8,11-eicosatriynoic acid
-
-
5-Hydroxydopamine
-
-
6,17-dihydroxy-4,7,10,13,15,19-eicosahexaenoic acid
-
IC50: 0.0004 mM
6,7-dihydroxy-3',4'-methylenedioxyisoflavan
-
-
6,7-dihydroxy-3',4'-methylenedioxyisoflavone
-
-
6,7-dihydroxy-3'-methylisoflavan
-
-
6,7-dihydroxy-3'-methylisoflavanone
-
-
6,7-dihydroxy-4'-methoxyisoflavan
-
-
6,7-dihydroxy-4'-methoxyisoflavanone
-
-
6,7-dihydroxy-4'-methoxyisoflavone
-
-
6,7-dihydroxy-4'-nitroisoflavone
-
-
6-Hydroxydopamine
-
-
7,8-dihydroxy-3',4'-dimethoxyisoflavan
-
-
7,8-dihydroxy-3'-methylisoflavone
-
-
7,8-dihydroxy-3'-trifluoromethylisoflavone
-
-
7,8-dihydroxy-4'-methoxyisoflavan
-
-
7,8-dihydroxy-4'-methylisoflavan
-
-
7,8-dihydroxy-4'-methylisoflavone
-
-
7,8-dihydroxyisoflavone
-
-
7-hydroxy-H-benzopyran-4-one derivatives
-
weak inhibition
8-hydroxyquinoline
-
1 mM, 35% inhibition
alpha-mangostin
-
NSC30552, a natural product, caspase-3 pathway inhibitor, performs selective inhibition of 12-LO
arachidonic acid
baicalein
benzoyl chloride
-
-
bestatin 7
-
IC50: 0.0023 mM
BW755C
BWA137C
-
-
caffeic acid
-
0.01 mM, 20-30% inhibition
celecoxib
-
0.01 mM inhibits LOX-12 by 7%
chloroglyoxylic acid ethyl ester
-
-
chlorpromazine
-
-
cinnamyl 3,4-dihydroxy-cyanocinnamate
-
CDC
cinnamyl-3,4-dihydroxy-alpha-cyanocinnamate
Cu2+
-
-
dysidenin
-
-
EDTA
-
1 mM, 40% inhibition
eicosatetraynoic acid
epinephrine
-
-
esculetin
esculetine
-
inhibits the enzyme and its binding to cytoplasmic muscle fibrills, overview
fluphenazine
-
-
gossypol acetic acid
-
non-competitive with respect to arachidonate
GT-E
-
100 mM, dried radix of Glycine tomentella freeze-dried to a powder, IC50: 0.00072 mg/ml
-
H-benzopyran-4-one derivatives
-
weak inhibition
iodoacetate
-
1 mM, 5% inhibition
isonicotinaldehyde
-
-
Lubrol
-
0.2%, 60% inhibition
-
methyl-4-pyridyl ketone
-
-
michellamine B
-
NSC661755, potent but non-selective inhibitor, a natural anti-viral agent
N-(4-chlorophenyl)-N-hydroxy-N'-(3-chlorophenyl)urea
-
-
N-([5-chloro-2-(dimethylamino)-8-hydroxyquinolin-7-yl](furan-2-yl)methyl)acetamide
-
-
N-([5-chloro-8-hydroxy-2-(piperidin-1-yl)quinolin-7-yl](furan-2-yl)methyl)acetamide
-
-
N-benzyl-N-hydroxy-5-phenylpentanamide
N-[(2,5-dichloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(4-chloro-1-hydroxynaphthalen-2-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(5-bromofuran-2-yl)(5-chloro-8-hydroxyquinolin-7-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxy-1,2,3,4,4a,8a-hexahydroquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-fluorophenyl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(5-methylthiophen-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(cyclopropyl)methyl]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(cyclopropyl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]-4-methylbenzamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]benzamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)methyl]acetamide
-
-
N-[(5-chloro-8-methoxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(8-hydroxy-5-nitroquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(R)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(R)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(S)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(S)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-methylpropyl]acetamide
-
-
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-methylpropyl]propanamide
-
-
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]acetamide
-
-
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]propanamide
-
-
N-[1-(5-fluoro-8-hydroxyquinolin-7-yl)ethyl]acetamide
-
-
N-[furan-2-yl(8-hydroxy-5-nitroquinolin-7-yl)methyl]propanamide
-
-
NCTT-956
-
12-LOX inhibition attenuates platelet aggregation
NEM
-
1 mM, 15% inhibition
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
nicotinoyl chloride
-
-
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
p-hydroxymercuribenzoate
-
1 mM, 75% inhibition
PD146176
picolinaldehyde
-
-
pyruvoyl chloride
-
-
quercetin
-
-
Renex
-
-
siRNA
-
inhibition of p12-LOX in JB6 P+ cells by siRNA transfection, causes a significant suppression of 12-O-tetradecanoylphorbol-13-acetate-induced neoplastic transformation by 61% compared with that in control cells
-
Trifluoperazine
-
-
Triton X-100
-
-
Tween 20
-
-
Zn2+
-
3.7 mM, complete inhibition
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
13-hydroperoxy-octadecadienoic acid
-
-
2-arachidonoylglycerol
-
activates 12(S)-HETE production in vivo
alpha-Naphthol
slight activation of enzyme activity at 0.25 mM, but not at 0.5 mM
ATP
-
2 mM ATP + 1 mM CaCl2 stimulate approximately 2fold
beta-boswellic acid
-
0.03 mM, in the absence of Ca2+
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0039
(Z,Z,Z,E)-5,8,11,13-eicosatetraenoic acid
-
-
0.0355
1-linoleoyl lysophosphatidic acid
-
pH 7.5, 25C
0.0151
1-linoleoyl lysophosphatidylcholine
-
pH 7.5, 25C
0.0045
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid
-
-
0.003 - 0.03
5,8,11,14,17-eicosapentaenoic acid
0.0035 - 0.079
8,11,14-eicosatrienoic acid
0.004 - 0.08
arachidonic acid
0.0125 - 0.0312
linoleic acid
0.0114 - 0.018
methyl arachidonate
0.0052 - 7
O2
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.5 - 46
arachidonate
1.4 - 20
arachidonic acid
14.7 - 65.2
linoleic acid
0.3 - 13.7
O2
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.4 - 1950
arachidonic acid
830 - 3060
linoleic acid
170 - 760
methyl arachidonate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0025
11-thialinoleic acid
-
-
0.002 - 0.07
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
0.017
neodysidenin
-
pH 8.0, recombinant enzyme
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0007
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
Homo sapiens
-
IC50: 0.0007 mM
0.0041
2,3,4,5-tetrabromo-6-(4,5-dibromo-2-hydroxyphenoxy)phenol
Homo sapiens
-
IC50: 0.0041 mM
0.00041
2,3,5-tribromo-6-(4,5-dibromo-2-hydroxyphenoxy)phenol
Homo sapiens
-
IC50: 0.00041 mM
0.012
2,4-dibromo-6-(2,4-dibromo-6-methoxyphenoxy)phenol
Homo sapiens
-
IC50: 0.012 mM
0.007
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
Homo sapiens
-
IC50: 0.007 mM
0.00078
3'-chloro-7,8-dihydroxyisoflavone
Homo sapiens
-
pH 7.5, 22C
0.0075
3,15-dihydroxy-8,11,13-eicosatrienoic acid
Homo sapiens
-
IC50: 0.0075 mM
0.05
3,4,6,8-tetrabromooxanthren-1-ol
Homo sapiens
-
IC50: 0.05 mM
0.006
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
Homo sapiens
-
IC50: 0.006 mM
0.047
3,4-dibromo-2-(5-bromo-2-hydroxyphenoxy)phenol
Homo sapiens
-
IC50: 0.047 mM
0.03
3,6,8-tribromooxanthren-1-ol
Homo sapiens
-
IC50: 0.03 mM
0.0004
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: 0.0004 mM
0.017
4',6,7-trihydroxyisoflavan
Homo sapiens
-
pH 7.5, 22C
0.0038
4',6,7-trihydroxyisoflavanone
Homo sapiens
-
pH 7.5, 22C
0.0087
4',6,7-trihydroxyisoflavone
Homo sapiens
-
pH 7.5, 22C
0.00048
4'-chloro-7,8-dihydroxyisoflavone
Homo sapiens
-
pH 7.5, 22C
0.0081
4,15-dihydroxy-5,8,11,13-eicosatetraenoic acid
Homo sapiens
-
IC50: 0.0081 mM
0.01
4,4'-propane-2,2-diylbis(2,6-dibromophenol)
Homo sapiens
-
IC50: 0.01 mM
0.0008
5,15-dihydroxy-5,8,11,13,17-eicosapentaenoic acid
Homo sapiens
-
IC50: 0.0008 mM
0.00006
5,8,11,14-Eicosatetraynoic acid
Sus scrofa
-
IC50: 0.00006 mM
0.0004
6,17-dihydroxy-4,7,10,13,15,19-eicosahexaenoic acid
Homo sapiens
-
IC50: 0.0004 mM
0.011
6,7-dihydroxy-3',4'-methylenedioxyisoflavan
Homo sapiens
-
pH 7.5, 22C
0.1
6,7-dihydroxy-3',4'-methylenedioxyisoflavone
Homo sapiens
-
above, pH 7.5, 22C
0.015
6,7-dihydroxy-3'-methylisoflavan
Homo sapiens
-
pH 7.5, 22C
0.014
6,7-dihydroxy-3'-methylisoflavanone
Homo sapiens
-
pH 7.5, 22C
0.0076
6,7-dihydroxy-4'-methoxyisoflavan
Homo sapiens
-
pH 7.5, 22C
0.0016
6,7-dihydroxy-4'-methoxyisoflavanone
Homo sapiens
-
pH 7.5, 22C
0.1
6,7-dihydroxy-4'-methoxyisoflavone
Homo sapiens
-
above, pH 7.5, 22C
0.0058
6,7-dihydroxy-4'-nitroisoflavone
Homo sapiens
-
pH 7.5, 22C
0.1
7,8-dihydroxy-3',4'-dimethoxyisoflavan
Homo sapiens
-
above, pH 7.5, 22C
0.0036
7,8-dihydroxy-3'-methylisoflavone
Homo sapiens
-
pH 7.5, 22C
0.00062
7,8-dihydroxy-3'-trifluoromethylisoflavone
Homo sapiens
-
pH 7.5, 22C
0.026
7,8-dihydroxy-4'-methoxyisoflavan
Homo sapiens
-
pH 7.5, 22C
0.07
7,8-dihydroxy-4'-methylisoflavan
Homo sapiens
-
pH 7.5, 22C
0.0016
7,8-dihydroxy-4'-methylisoflavone
Homo sapiens
-
pH 7.5, 22C
0.0064
7,8-dihydroxyisoflavone
Homo sapiens
-
pH 7.5, 22C
0.00058
alpha-mangostin
Homo sapiens
-
pH 8.0, recombinant enzyme
0.0023
bestatin 7
Homo sapiens
-
IC50: 0.0023 mM
0.009
dysidenin
Homo sapiens
-
above, pH 8.0, recombinant enzyme
0.0049
michellamine B
Homo sapiens
-
pH 8.0, recombinant enzyme
0.075
N-([5-chloro-2-(dimethylamino)-8-hydroxyquinolin-7-yl](furan-2-yl)methyl)acetamide
0.002
N-[(5-bromo-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
0.001
N-[(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23C
0.014
N-[(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.075
N-[(5-bromofuran-2-yl)(5-chloro-8-hydroxyquinolin-7-yl)methyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23C
0.003
N-[(5-chloro-8-hydroxy-1,2,3,4,4a,8a-hexahydroquinolin-7-yl)(furan-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.05
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-fluorophenyl)methyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23C
0.15
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23C
0.0035
N-[(5-chloro-8-hydroxyquinolin-7-yl)(5-methylthiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.003
N-[(5-chloro-8-hydroxyquinolin-7-yl)(cyclopropyl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23C
0.0016
N-[(5-chloro-8-hydroxyquinolin-7-yl)(cyclopropyl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.025
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]-4-methylbenzamide
Homo sapiens
-
value above, pH 8.0, 23C
0.003
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23C
0.025
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]benzamide
Homo sapiens
-
value above, pH 8.0, 23C
0.001
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
0.15
N-[(5-chloro-8-hydroxyquinolin-7-yl)methyl]acetamide
Homo sapiens
-
value above, pH 8.0, 23C
0.075
N-[(5-chloro-8-methoxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23C
0.005
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23C
0.002
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23C
0.0008
N-[(8-hydroxy-5-nitroquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.0034
N-[(8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.025
N-[(R)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
0.00043
N-[(S)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Homo sapiens
-
pH 8.0, 23C
0.00038
N-[(S)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.0026
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-methylpropyl]acetamide
Homo sapiens
-
pH 8.0, 23C
0.0012
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-methylpropyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.15
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]acetamide
Homo sapiens
-
value above, pH 8.0, 23C
0.05
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]propanamide
Homo sapiens
-
value above, pH 8.0, 23C
0.075
N-[1-(5-fluoro-8-hydroxyquinolin-7-yl)ethyl]acetamide
Homo sapiens
-
value above, pH 8.0, 23C
0.0012
N-[furan-2-yl(8-hydroxy-5-nitroquinolin-7-yl)methyl]propanamide
Homo sapiens
-
pH 8.0, 23C
0.1
neodysidenin
Homo sapiens
-
above, pH 8.0, recombinant enzyme
0.0022 - 0.0051
nordihydroguaiaretic acid
0.00021
NSC172033
Homo sapiens
-
pH 8.0, recombinant enzyme
0.00015
NSC292213
Homo sapiens
-
pH 8.0, recombinant enzyme
0.00019
NSC617570
Homo sapiens
-
pH 8.0, recombinant enzyme
0.00044
quercetin
Homo sapiens
-
pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0003
-
enzyme from platelet
0.0011
-
enzyme from leukocyte
0.0018
-
-
0.033
-
-
0.7
-
leukocyte enzyme
1.7
-
-
8
-
purified enzyme
51.8
-
commercial preparation
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 9
-
almost inactive at pH 6 and pH 9
6.5 - 7
-
activity with arachidonate and linoleate
7 - 8
-
-
7
-
broad
7.3 - 7.9
-
-
7.4 - 8
-
-
7.5 - 8.5
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.1 - 8.6
-
pH 6.1: 37% of maximal activity, pH 8.6: 44% of maximal activity
6.3 - 8.8
-
pH 6.3: about 70% of maximal activity, pH 8.8: about 40% of maximal activity
7.4 - 8.7
-
-
7.5 - 11
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10
-
cytosolic fraction
22
-
assay at
23
-
assay at
25 - 37
-
-
30
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
induced by a Ca2+ ionophore, from acute myeloid leukemic and acute lymphoid leukemic patients, upregulation of the enzyme, quantitative expression analysis
Manually annotated by BRENDA team
-
primary human aortic smooth muscle cells
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
12-LOX overexpression
Manually annotated by BRENDA team
-
expression of both platelet and leukocyte-type 12-lipoxygenase in distal convoluted tubule cell line. mDCT cells show an active 12-LOX metabolism that appears to be modulated by cAMP and vasopressin
Manually annotated by BRENDA team
-
primary cortical culture
Manually annotated by BRENDA team
-
expression is dependent on differentiation of the ovary
Manually annotated by BRENDA team
-
very high 12-lipoxygenase activity
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
vascular smooth muscle, the enzyme associates with alpha-actin fibers
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
umbilical artery, the enzyme associates with alpha-actin fibers
Manually annotated by BRENDA team
-
prostate stromal cells
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
primarily associated with cytoplasmic vascular smooth muscle cell muscle fibrils binding to alpha-actin, a component of the cytoplasmic myofilaments, not associated with 12-LO serine or tyrosine phosphorylation, overview, the binding is induced by angiotensin II
Manually annotated by BRENDA team
additional information
-
subcellular distribution analysis, overview
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
77000
-
SDS-PAGE
158000
-
about, recombinant His-tagged wild-type and mutant enzymes, gel filtration
675000
-
about, recombinant no-PLAT-mutant, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 74700, dynamic light scattering
oligomer
-
x * 62650, recombinant no-PLAT-mutant, SDS-PAGE
additional information
-
structural modeling, overview
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
low-resolution 16 A structure of enzyme in solution, dynamic light scattering and SAXS analysis of hp-12LOX shows that this enzyme as a whole is stable in the dimeric form, while mutants without PLAT domains associate into larger aggregates
-
crystals diffracting to high resolution (1.9 A) are obtained for a complex between the catalytic domain of leukocyte 12-lipoxygenase and the isoform-specific inhibitor, 4-(2-oxapentadeca-4-yne) phenylpropanoic acid (OPP)
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0
-
loses appreciable activity when left overnight in an ice bath
25
-
significant activity decrease above 25C
37
-
rapid inactivation by the product hydroperoxy fatty acid, at low concentrations, 10-100 nM
40
-
10 min, stable below
45
-
10 min, 60% loss of activity
65
-
3 min, enzyme solubilized with 1% deoxycholate, complete loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
15-25% loss of activity upon freezing and thawing
-
severe autoinactivation is observed at high substrate concentrations if the substrate is not HPLC-purified and stored at -80C
-
the enzyme shows higher activity in 50 mM CAPS buffer (pH 10-11) and glycine buffer (pH 8.5-10.5) than in 50 mM Tris-HCl (pH 7-9)
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, remains stable for 6 weeks
-
-70C, 1 month
-
-70C, 1 month, no appreciable loss of activity
-
-70C, 20% glycerol, 10 mM 2-mercaptoethanol, 0.3% Triton X-305, enzyme retains complete activity after 1 month
-
-80C, 10% glycerol
-80C, 10-20% glycerol
-
-80C, stable for at least 1 week
-
-80C, stable for at least 4 months
-
4C, half-life of leukocyte enzyme is 2 h, half-life of platelet enzyme is 70 h
-
4C, half-life: 24 h, markedly stabilized by 0.02 mM Fe2+
-
4C, half-life: less than 1 h
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by anion exchange chromatography
-
by one step Ni2+ affinity chromatography, more than 90% pure
-
on Ni column
partial
recombinant His-tagged enzyme
-
recombinant His-tagged isozyme 12-hLO by nickel affinity chromatography
recombinant His-tagged wild-type and mutant enzymes from Spodoptera frugiperda Sf9 cells by nickel affinity chromatography
-
to greater than 90% purity
-
using Ni-NTA chromatography