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1.13.11.31: arachidonate 12-lipoxygenase

This is an abbreviated version!
For detailed information about arachidonate 12-lipoxygenase, go to the full flat file.

Word Map on EC 1.13.11.31

Reaction

arachidonate
+
O2
=
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate

Synonyms

(12R)-lipoxygenase, (12R)-LOX, 11R-lipoxygenase, 11R-LOX, 12(R)-lipoxygenase, 12(S)-lipoxygenase, 12-hLO, 12-lipoxygenase, 12-LO, 12-LOX, 12/15 lipoxygenase, 12/15 Lox, 12/15-lipoxygenase, 12/15-lipoxygenases, 12/15-LO, 12/15-LOX, 12/15LO, 12DELTA-lipoxygenase, 12LO, 12R-lipoxygenase, 12R-LOX, 12R-LOX-2, 12S-lipoxygenase, 15-lipoxygenase, 15-LO, 15-LOX-1, 2-lipoxygenase, 2/15-lipoxygenase, ALOX 12, ALOX 12/15, ALOX12, Alox12b, Alox12e, Alox15, ALOX15B, ALOX5, arachidonate 12/15-lipoxygenase, C-12 lipoxygenase, cardiac 12/15-LOX, DELTA 12-lipoxygenase, epidermal-type lipoxygenase, hp-12LOX, human platelet 12-lipoxygenase, leukocyte-type 12-lipoxygenase, leukocyte-type 12-LOX, leukocyte-type 12/15-lipoxygenase, leukocyte-type lipoxygenase, leukotriene A4 synthase M, lipoxygenase 12, LOX, LOX-12, LOX1, LTA4 synthase, oxylipin-producing enzyme, oygenase, arachidonate 12-lip-, P-12LOX, p12-LO, p12-LOX, platelet 12-lipoxygenase, platelet-type 12(S)-lipoxygenase, platelet-type 12-human lipoxygenase, platelet-type 12-lipoxygenase, platelet-type 12-LOX, platelet-type 12LO, Platelet-type lipoxygenase 12, WP_046712474, zf12-LOX

ECTree

     1 Oxidoreductases
         1.13 Acting on single donors with incorporation of molecular oxygen (oxygenases)
             1.13.11 With incorporation of two atoms of oxygen
                1.13.11.31 arachidonate 12-lipoxygenase

Inhibitors

Inhibitors on EC 1.13.11.31 - arachidonate 12-lipoxygenase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octa-dienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-cis-p-coumaroyl)-beta-D-glucopyranoside
liguroside B, NMR spectral analysis
(2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octadienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-trans-p-coumaroyl)-beta-D-glucopyranoside
liguroside A, NMR spectral analysis
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
4,5-dichloro-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
4-(2-oxapentadeca-4-yne) phenylpropanoic acid
-
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
4-methyl-2-(4-methylpiperazinyl)pyrimido[4,5-b]benzothiazine
-
-
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-(methylamino)-2-(naphthalen-1-yl)-4,5-dihydro-1,3-oxazole-4-carbonitrile
-
-
5-chloro-N-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxamide
-
-
5-Hydroxydopamine
-
-
6,17-dihydroxy-4,7,10,13,15,19-eicosahexaenoic acid
-
IC50: 0.0004 mM
6,6a,11,11a-tetrahydro[1]benzothiopyrano[4,3-b]indole
-
-
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
AA861
adamantyl caffeate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.074 mM
-
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
bornyl vanillate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.401 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
cinnamyl-3,4-dihydroxy-cyanocinnamate
-
Cu2+
-
-
dysidenin
-
EDTA
-
1 mM, 40% inhibition
eicosatetraynoic acid
epigallocatechin gallate
-
epinephrine
-
-
esculetin
esculetine
-
inhibits the enzyme and its binding to cytoplasmic muscle fibrills, overview
ethyl 6-chloro-3-[(3S)-3-hydroxy-7-methyloctanoyl]-2,3-dihydro-1H-indole-2-carboxylate
-
-
fenchyl caffeate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.089 mM
-
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
-
-
kudingoside B
NMR spectral analysis
Lubrol
-
0.2%, 60% inhibition
-
methyl-4-pyridyl ketone
-
-
michellamine B
NSC661755, potent but non-selective inhibitor, a natural anti-viral agent
ML355
N-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxamide
-
N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
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
-
stylosin
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.101 mM
-
Trifluoperazine
-
-
Triton X-100
-
-
Tween 20
-
-
Zn2+
-
3.7 mM, complete inhibition
additional information
-