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1.13.11.12: linoleate 13S-lipoxygenase

This is an abbreviated version!
For detailed information about linoleate 13S-lipoxygenase, go to the full flat file.

Word Map on EC 1.13.11.12

Reaction

alpha-linolenate
+
O2
=
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate

Synonyms

(13S)-lipoxygenase, 13-lipoxygenase, 13-LOX, 13S-lipoxygenase, 15-lipoxygenase-1, 15-LOX-1, 9/13-LOX, acidic lipoxygenase, Alox15, arachidonic acid 15S-lipoxygenating enzyme, AtLOX-2, AtLOX-3, AtLOX-4, AtLOX-6, CmLOX10, CmLOX13, iron 13S-lipoxygenase, liipoxygenase, linoleate 13-lipoxygenase, linoleate 13S-lipoxygenase, linoleate oxygen oxidoreductase, linoleate: oxygen oxidoreductase, linoleate:oxygen oxidoreductase, lipoxygenase, lipoxygenase 2, lipoxygenase-1, lipoxygenase-2, lipoxygenase-3, lipoxygenase-4, lipoxygenase-6, LO-1, LOX, LOX-1, LOX-2, LOX1, LOX10, LOX11, LOX12, LOX2, LOX2:Hv:1, LOX2:Md:2b, LOX2b, LOX3, LOX4, LOX6, LOX7, LOX8, LOX9, LoxA, Lpx-A2, MSD2, Oep1LOX2, Oep2LOX2, omega-6 linoleate lipoxygenase, PA-LOX, RCI-1, SBLO-1, secreted lipoxygenase, SLO, soybean lipoxygenase-1, StLOX2, StLOX3, type-1 LOX, type-2 13-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
                1.13.11.12 linoleate 13S-lipoxygenase

Inhibitors

Inhibitors on EC 1.13.11.12 - linoleate 13S-lipoxygenase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-(4-methoxyphenyl)-2-butanone
-
-
1-(4-methoxyphenyl)acetone
-
-
1-methoxy-4-(2-ethylallyl)benzene
-
-
1-methoxy-4-(2-methylallyl)benzene
-
-
11-thialinoleic acid
-
is a competitive inhibitor with respect to linoleic acid and a noncompetitive inhibitor with respect to arachidonic acid
14-thialinoleic acid
-
is a competitive inhibitor with respect to linoleic acid
2',4,6-trimethoxy-aurone
-
-
2'-hydroxy-2,4',6'-trimethoxy-chalcone
-
exhibits 20% inhibition
2'-hydroxy-2-methoxy-chalcone
-
-
2'-hydroxy-3,4,4',6'-tetra(methoxymethoxy)-chalcone
-
exhibits 14.1% inhibition
2'-hydroxy-3,4-dimethoxy-chalcone
-
-
2'-hydroxy-3-methoxy-chalcone
-
exhibits 36.4% inhibition
2'-hydroxy-4-chloro-4', 6'-dimethoxy-chalcone
-
-
2'-hydroxy-4-chloro-chalcone
-
-
2'-hydroxy-4-methyl-4',6'-dimethoxy-chalcone
-
-
2'-hydroxy-4-methyl-chalcone
-
-
2'-methoxy-aurone
-
exhibits 39.9% inhibition
2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one
-
quercetin is slowly oxidized by hydroperoxides to a rather stable intermediate, 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one, which still inhibits the enzymatic oxidation, probably as a chelator
2-(3-(hydroxy(phenyl)methyl)phenyl)-N-phenethylpropanamide
-
-
2-(3-(hydroxy(phenyl)methyl)phenyl)propanoic acid
-
-
2-(3-benzoylphenyl)-N-(cyclohexylmethyl)propanamide
-
-
2-(3-benzoylphenyl)-N-cyclohexylpropanamide
-
-
2-(3-benzoylphenyl)-N-cyclopentylpropanamide
-
-
2-(3-benzoylphenyl)-N-phenethylpropanamide
-
-
2-(3-benzylphenyl)-N,N-bis(2-hydroxyethyl)propanamide
-
-
2-(3-benzylphenyl)-N-(2-hydroxyethyl)propanamide
-
-
2-(3-benzylphenyl)-N-(3-hydroxypropyl)propanamide
-
-
2-(3-benzylphenyl)-N-(cyclohexylemethyl)propanamide
-
-
2-(3-benzylphenyl)-N-cyclohexylpropanamide
-
-
2-(3-benzylphenyl)-N-cyclopentylpropanamide
-
-
2-(3-benzylphenyl)-N-ethoxypropanamide
-
-
2-(3-benzylphenyl)-N-methoxypropanamide
-
12% and 27.5% inhibition at 0.1 and 0.5 mM, respectively
2-(3-benzylphenyl)-N-phenethylpropanamide
-
-
2-(3-benzylphenyl)propanamide
-
-
2-(3-benzylphenyl)propanoic acid
-
-
2-dodecyl-6-hydroxybenzoic acid
-
C12:0, competitive inhibitor
2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid
-
C15:1, E-isomer, competitive inhibitor
3'-methoxy-aurone
-
exhibits 34.9% inhibition
4'-chloro-4, 6-dimethoxy-aurone
-
-
4'-chloro-aurone
-
exhibits 26.4% inhibition
4'-methoxy-aurone
-
-
4'-methyl-aurone
-
exhibits 32.4% inhibition
4,4',6-trimethoxy-aurone
-
best LOX inhibitory activity
4-(allyloxy)phenyl benzoate
-
-
4-allylphenyl benzoate
-
-
4-Methoxyphenylacetic acid
-
-
4-methyl-2-(4-methylpiperazinyl)pyrimido[4,5-b]benzothiazine
-
-
6-(2'-ethylheptyl)salicylic acid
-
-
6-(4',8'-dimethylnonyl) salicylic acid
-
-
6-pentadecanylsalicylic acid
-
competitive inhibitor, dose-dependent inhibitory effect
6-[2'-(2'',4'',5''-trihydroxyphenyl)etyl]salicylic acid
-
inhibits lipoxygenase-catalyzed oxidation of linoleic acid, but to a lesser extent compared to 6-pentadecanylsalicylic acid
6-[2'-(2'',4''-dihydroxyphenyl)ethyl]salicylic acid
-
inhibits lipoxygenase-catalyzed oxidation of linoleic acid, but to a lesser extent compared to 6-pentadecanylsalicylic acid
6-[2'-(2'',5''-dihydroxyphenyl)ethyl]salicylic acid
-
inhibits lipoxygenase-catalyzed oxidation of linoleic acid, but to a lesser extent compared to 6-pentadecanylsalicylic acid
6-[2'-(3'',4''-dihydroxyphenyl)ethyl]salicylic acid
-
inhibits lipoxygenase-catalyzed oxidation of linoleic acid, but to a lesser extent compared to 6-pentadecanylsalicylic acid
6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid
-
from Anacardium occidentale
6-[8(Z),11(Z)-pentadecadienyl]salicylic acid
-
from Anacardium occidentale
6-[8(Z)-pentadecenyl]salicylic acid
-
from Anacardium occidentale
adamantyl caffeate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.074 mM
-
alpha-tocopherol
-
competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
apigenin
-
uncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
beta-carotene
-
-
bornyl vanillate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.401 mM
-
butyl 2-(4-methoxyphenyl)acetate
-
-
caffeic acid
-
-
catechin
-
competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
Cd2+
complete inhibition at 1 mM; complete inhibition at 1 mM; complete inhibition at 1 mM
cis-(+)-12-oxophytodienoic acid
isoform LOX2 exhibits 64% residual activity at 2.8 mM; isoform LOX3 exhibits 60% residual activity at 2.8 mM; isoform LOX4 exhibits 21% residual activity at 2.8 mM; isoform LOX6 exhibits 50% residual activity at 2.8 mM
Co2+
-
inhibits at 1 mM
cyanidin
-
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-arabinoside
-
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-galactoside
-
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-glucoside
-
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyclohexyl 2-(4-methoxyphenyl)acetate
-
-
cyclopentyl 2-(4-methoxyphenyl)acetate
-
-
delphinidin
-
from Vaccinium myrtillus berries, inhibits in a concentration-dependent manner
delphinidin 3-O-arabinoside
-
from Vaccinium myrtillus berries, inhibits in a concentration-dependent manner
delphinidin 3-O-galactoside
-
from Vaccinium myrtillus berries, most effective inhibitor, uncompetitive type, inhibits in a concentration-dependent manner
delphinidin 3-O-glucoside
-
from Vaccinium myrtillus berries, most effective inhibitor, uncompetitive type, inhibits in a concentration-dependent manner
esteragol
-
-
estragol
-
-
ethyl 2-(4-methoxyphenyl)acetate
-
-
eugenol
-
-
eugenyl benzoate
-
-
Fe2+
-
inhibits at 1 mM
fenchyl caffeate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.089 mM
-
ferulic acid
-
noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
gallic acid
-
competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
glutathione
-
-
hexyl 2-(4-methoxyphenyl)acetate
-
-
isobutyl 2-(4-methoxyphenyl)acetate
-
-
isopropyl 2-(4-methoxyphenyl)acetate
-
-
K+
38% residual activity at 50 mM
kaempferol
-
-
Ketoprofen
-
-
L-ascorbic acid
-
noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
lauric acid
-
-
lauroylethanolamide
-
-
methyl jasmonate
isoform LOX2 exhibits 87% residual activity at 2.8 mM; isoform LOX3 exhibits 85% residual activity at 2.8 mM; isoform LOX4 exhibits 95% residual activity at 2.8 mM; isoform LOX6 exhibits 94% residual activity at 2.8 mM
methyleugenol
-
-
N-(cyclohexylmethyl)-2-{3-[hydroxy(phenyl)methyl]phenyl}propanamide
-
-
N-benzhydryl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
N-benzhydryl-2-(3-benzoylphenyl)propanamide
-
-
N-benzhydryl-2-(3-benzylphenyl)propanamide
-
-
N-benzyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
N-benzyl-2-(3-benzoylphenyl)propanamide
-
-
N-benzyl-2-(3-benzylphenyl)propanamide
-
-
N-benzyloxy-2-(3-benzylphenyl)propanamide
-
-
N-cyclohexyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
N-cyclopentyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
N-ethylmaleimide
isoform LOX2 exhibits 84% residual activity at 2.8 mM; isoform LOX3 exhibits 51% residual activity at 2.8 mM; isoform LOX4 exhibits 11% residual activity at 2.8 mM; isoform LOX6 exhibits 47% residual activity at 2.8 mM
N-hydroxy-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
n-propyl gallate
-
causes a strong inhibition of the LOX-catalyzed enzymatic reaction
N1-(4-(allyloxy) phenyl)-1-admantancarboxamide
-
best inhibitor
N1-(4-(allyloxy) phenyl)-1-cyclobutanecarboxamide
-
-
N1-(4-(allyloxy) phenyl)-1-cyclohexanecarboxamide
-
-
N1-(4-(allyloxy) phenyl)-1-cyclopantanecarboxamide
-
-
N1-(4-(allyloxy) phenyl)-1-cyclopropanecarboxamide
-
-
N1-(4-(allyloxy) phenyl)-2-methylpropanamide
-
-
N1-(4-(allyloxy) phenyl)-3-chlorobenzamide
-
-
N1-(4-(allyloxy) phenyl)-3-fluorobenzamide
-
-
N1-(4-(allyloxy) phenyl)-3-methoxybenzamide
-
-
N1-(4-(allyloxy) phenyl)-3-methylbenzamide
-
-
N1-(4-(allyloxy) phenyl)-4-chlorobenzamide
-
-
N1-(4-(allyloxy) phenyl)-4-fluorobenzamide
-
-
N1-(4-(allyloxy) phenyl)-4-methoxybenzamide
-
-
N1-(4-(allyloxy) phenyl)-4-methylbenzamide
-
-
N1-(4-(allyloxy) phenyl)benzamide
-
-
NDGA
-
-
Ni2+
-
inhibits at 1 mM
nordihydroguaiaretic acid
PD146176
-
-
pentyl 2-(4-methoxyphenyl)acetate
-
long chain and lipophile 4-methoxyphenylacetic acid ester, behaves as the best SLO inhibitor
peonidin
-
from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-arabinoside
-
from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-galactoside
-
from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-glucoside
-
from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
Phenidone
-
inhibits the LOX-dependent defence response of the plant, whereby this inhibition can influence the behaviour of members of the associated insect community. Plants treated with phenidone are less attractive to Cotesia glomerata parasitoids than controls. Herbivores Pieris rapae and Pieris brassicae are less sensitive to changes in plant metabolic profiles induced by caterpillar feeding and LOX inhibition respectively than their natural enemy Cotesia glomerata. Preference of Plutella xylostella for Pieris rapae-infested plants over uninfested plants is LOX dependent, since phenidone treatment of uninfested and infested plants eliminates the preference. The inhibitor reduces the accumulation of internal signalling compounds in the octadecanoid pathway of the plant downstream of the step catalysed by LOX, i.e. 12-oxo-phytodienoic acid and jasmonic acid
propyl 2-(4-methoxyphenyl)acetate
-
-
propyl gallate
quercetin
-
noncompetitive inhibition by initially reducing the ferric form of the enzyme to an inactive ferrous form
resveratrol
-
uncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
rutin
-
-
Salicylhydroxamic acid
70% inhibition in the presence of 1 mM salicylhydroxamic acid
salicylic acid
isoform LOX2 exhibits 96% residual activity at 2.8 mM
sec-butyl 2-(4-methoxyphenyl)acetate
-
-
stylosin
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.101 mM
-
tert-butyl 2-(4-methoxyphenyl)acetate
-
-
traumatic acid
isoform LOX2 exhibits 95% residual activity at 2.8 mM
-
Trolox
-
noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction. At physiological pH 7.0 the LOX/4-nitroso-N,N-dimethylaniline assay is more sensitive to trolox inhibition
additional information
-