Ligand linoleic acid

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Basic Ligand Information

Molecular Structure
Picture of linoleic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C18H32O2
linoleic acid
OYHQOLUKZRVURQ-HZJYTTRNSA-N
Synonyms:
(9Z,12Z)-octadec-9,12-dienoic acid, (9Z,12Z)-octadeca-9,12-dienoate, (9Z,12Z)-octadeca-9,12-dienoic acid, (9Z,12Z)-octadecadienoate, (9Z,12Z)-octadecadienoic acid, (Z,Z)-9,12-octadecadienoic acid, 9,12-octadecadienoic acid, 9-cis,12-cis-linoleic acid, 9-cis,12-cis-octadecadienoate, 9-cis,12-cis-octadecadienoic acid, all-cis-9,12-octadecadienoic acid, alpha-linoleate, cis,cis-9,12-octadecadienoic acid, cis-linoleic acid, linoic acid, linolate, linoleate, linolelaidic acid, linoleoate, linolic acid, octadeca-9c,12c-dienoic acid, omega-6 linoleic acid, trans-9,12-linoleic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (42 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
linoleic acid + O2 = (9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
show the reaction diagram
-
linoleate + O2 = (8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoate
show the reaction diagram
-
linoleic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxylinoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
linoleic acid + AH2 + O2 = gamma-linolenic acid + A + H2O
show the reaction diagram
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linoleic acid + reduced ferredoxin [iron-sulfur] cluster + O2 + H+ = gamma-linolenic acid + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
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linoleic acid = (Z)-3-nonenal + 9-oxononanoic acid
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
thioredoxin + linoleic acid hydroperoxide = thioredoxin disulfide + H2O + linoleic acid
show the reaction diagram
-
-
cis,cis-9,12-octadecadienal + NAD+ + H2O = cis,cis-9,12-octadecadienoic acid + NADH
show the reaction diagram
-
-
N-linoleoylethanolamide + H2O = linoleate + ethanolamine
show the reaction diagram
-
-
echinocandin A + H2O = cyclo-hexapeptide + linoleic acid
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (126 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
linoleic acid + O2 = ?
show the reaction diagram
-
linoleate + O2 = (8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoate
show the reaction diagram
-
linoleic acid + O2 = (10E,12E)-9,14-dihydroxy-10,12-octadecadienoic acid
show the reaction diagram
-
linoleic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxylinoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
omega-6 linoleic acid + 2 ferrocytochrome b5 + O2 + 2 H+ = linolenic acid + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
-
linoleic acid + ferrocytochrome b5 + O2 + H+ = pinolenic acid + ferricytochrome b5 + H2O
show the reaction diagram
-
linoleic acid + reduced ferredoxin [iron-sulfur] cluster + O2 + H+ = gamma-linolenic acid + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
-
linoleic acid + AH2 + O2 = 9-hydroxyoctadecadienoic acid + 13-hydroxyoctadecadienoic acid + ?
show the reaction diagram
linoleate + ethanol = ethyl linoleate + H2O
show the reaction diagram
-
D-erythro-sphingosine + linoleic acid = N-linoleoyl-D-erythro-sphingosine + H2O
show the reaction diagram
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linoleic acid = ?
show the reaction diagram
-
linoleate = (7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
show the reaction diagram
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ATP + linoleic acid + [acyl-carrier protein] = AMP + diphosphate + linoleoyl-[acyl-carrier protein]
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (57 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
thioredoxin + linoleic acid hydroperoxide = thioredoxin disulfide + H2O + linoleic acid
show the reaction diagram
-
-
oleate + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+ = linoleate + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O
show the reaction diagram
-
-
oleic acid + reduced acceptor + O2 = linoleic acid + acceptor + H2O
show the reaction diagram
-
-
cis,cis-9,12-octadecadienal + NAD+ + H2O = cis,cis-9,12-octadecadienoic acid + NADH
show the reaction diagram
-
1-linoleoyl-sn-glycero-3-phosphocholine + H2O = linoleic acid + glycerophosphorylcholine
show the reaction diagram
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-
dilinolein + H2O = monolineoylglycerol + linoleate
show the reaction diagram
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linoleoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + linoleate
show the reaction diagram
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-
linoleoylsphingosine + H2O = linoleic acid + sphingosine
show the reaction diagram
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-
N-linoleoylethanolamide + H2O = linoleate + ethanolamine
show the reaction diagram
-
-
(9Z,12Z)-octadeca-9,12-dienamide + H2O = (9Z,12Z)-octadeca-9,12-dienoate + NH3
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulates
-
EC50 value of 0.089 mM
-
approx. 4fold activiation
-
both conjugated and gamma-linoleic acid, increase activity
-
both conjugated and gamma-linoleic acid, increase activity
-
weak activation
-
approx. 20% stimulation at 0.8 mM, inhibition above
-
strong activation at 0.1 mM
-

Inhibitor in Enzyme-catalyzed Reactions (47 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.01 mM, 30% inhibition
-
0.018 mM, 58% inhibition, oxidation of estradiol
-
0.003 mM, 40% inhibition of chloroplastic form and 43% inhibition of cytosolic form
-
the incubation of Jurkat cells with 0.1 mM linoleic acid causes a significant decrease of catalase activity but not of protein or mRNA content
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3.6 mM, 76% inhibition of the activity with quercetin, 48% inhibition of the activity with o-dianisidine, isoenzyme POX II; 3.6 mM, no inhibition of the activity with quercetin, 32% inhibition of the activity with o-dianisidine, isoenzyme POX I
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16% inhibition at 0.02 mM
-
0.1 mM, partial inactivation, may indicate product inhibition
-
concentration above 10 microM
-
potent inhibitor
-
IC50: 0.048 mM
-
slight stimulation below 0.8 mM, approx. 45% inhibition at 3.2 mM
-
50% inhibition at 0.0438 mM
-
IC50: 0.375 mM
-
ACMSD mRNA levels in primary hepatocytes are decreased by the incubation with high concentrations of linoleic acid
-
strong inhibition
-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (41 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
138
-
-
5.12
-
recombinant enzyme, pH 8.5, 15°C
135
-
recombinant enzyme, pH and temperature not specified in the publication
29.3
-
CYP102A7, at pH 7.5

KM Value (89 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.078
-
pH 6.0, 40°C
0.05
-
pH and temperature not specified in the publication
0.0136
-
-
0.0551
-
CYP102A7, at pH 7.5
0.5
-
mutant enzyme R123N, at pH 7.5 and 25°C; wild type enzyme, at pH 7.5 and 25°C
1.4
-
-
0.023
-
pH 8.0, 30°C

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
TABLE ID
0.0125
-
-
5651
0.051
-
37°C, pH 7.0
25074

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.048
-
IC50: 0.048 mM
0.009
-
pH 7.4, 37°C, recombinant CES1
0.375
-
IC50: 0.375 mM

References & Links

Links to other databases for linoleic acid

ChEBI
PubChem
ChEBI
PubChem