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BRENDA support

Ligand oleic acid

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Basic Ligand Information

Molecular Structure
Picture of oleic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C18H34O2
oleic acid
ZQPPMHVWECSIRJ-KTKRTIGZSA-N
Synonyms:
(9Z)-octadec-9-enoate, (9Z)-octadec-9-enoic acid, (9Z)-octadecenoate, (9Z)-octadecenoic acid, cis-9-octadecenoate, cis-9-octadecenoic acid, cis-octadec-9-enoic acid, cis-oleic acid, heptadecyloleic acid, octadecenoate, oleate
Pathway Source
Pathways
BRENDA
arachidonate biosynthesis
KEGG
Biosynthesis of plant secondary metabolites, Biosynthesis of unsaturated fatty acids, Cutin, suberine and wax biosynthesis, Fatty acid biosynthesis, Longevity regulating pathway - worm
MetaCyc
10-methylstearate biosynthesis, cutin biosynthesis, linoleate biosynthesis II (animals), monoacylglycerol metabolism (yeast), oleate beta-oxidation more


Show all pahtways known for Show all BRENDA pathways known for oleic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (15 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
oleate + O2 = (9Z)-7,8-dihydroxyoctadeca-9-enoic acid
show the reaction diagram
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oleate + O2 = (8E,10S)-10-hydroperoxyoctadeca-8-enoate
show the reaction diagram
-
oleic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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ATP + oleic acid = ADP + oleyl phosphate
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (38 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
stearate + AH2 + O2 = oleate + A + 2 H2O
show the reaction diagram
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2-oleoylglycerol + H2O = oleic acid + glycerol
show the reaction diagram
1,2-dioleoyl-sn-glycero-3-phosphocholine + H2O = 1-oleoylglycerophosphocholine + oleic acid
show the reaction diagram
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oleoyl-CoA + H2O = CoA + oleate
show the reaction diagram
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oleoyl-CoA + H2O = oleate + CoA
show the reaction diagram
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(R)-10-Hydroxystearate = Oleate + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (89 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
oleate + O2 = (8E,10S)-10-hydroperoxyoctadeca-8-enoate
show the reaction diagram
-
oleic acid + ATP + CoA = oleoyl-CoA + AMP + diphosphate
show the reaction diagram
-
oleate + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxyoleate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
oleic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
oleic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxyoleic acid + [oxidized NADPH-hemoprotein reductase] + H2O
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
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oleic acid + ferrocytochrome b5 + O2 + H+ = ?
show the reaction diagram
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oleic acid + AH2 + O2 = ?
show the reaction diagram
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oleic acid + ferrocytochrome b5 + O2 + H+ = taxoleic acid + ferricytochrome b5 + H2O
show the reaction diagram
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(9Z)-octadecenoate + 2 ferrocytochrome b5 + O2 + 2 H+ = (9Z,12E)-octadeca-9,12-dienoate + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
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oleic acid + reduced acceptor + O2 = linoleic acid + acceptor + H2O
show the reaction diagram
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S-adenosyl-L-methionine + oleic acid = S-adenosyl-L-homocysteine + oleic acid methyl ester
show the reaction diagram
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glycerol + oleic acid = monoolein + H2O
show the reaction diagram
D-erythro-sphingosine + oleic acid = N-oleoyl-D-erythro-sphingosine + H2O
show the reaction diagram
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oleic acid + lyso-GM1a = ? + H2O
show the reaction diagram
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oleate + O2 = (9Z)-7,8-dihydroxyoctadeca-9-enoic acid
show the reaction diagram
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GTP + oleate + CoA = GDP + phosphate + oleoyl-CoA
show the reaction diagram
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ATP + oleate + CoA = AMP + diphosphate + oleoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (241 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
oleic acid hydroperoxide + NADPH + H+ = oleic acid + NADP+ + H2O
show the reaction diagram
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a [lipoyl-carrier protein]-N6-[(R)-dihydrolipoyl]-L-lysine + oleic acid hydroperoxide = a [lipoyl-carrier protein]-N6-lipoyl-L-lysine + H2O + oleic acid
show the reaction diagram
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stearic acid + NADH + ? = oleic acid + NAD+ + ?
show the reaction diagram
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oleoyldihydroxyacetone phosphate + hexadecanol = oleate + 1-O-hexadecyldihydroxyacetone phosphate
show the reaction diagram
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cholesteryl oleate + H2O = oleate + cholesterol
show the reaction diagram
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ethyl oleate + H2O = ethanol + oleate
show the reaction diagram
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oleoyl-CoA = oleate + CoA
show the reaction diagram
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Octadecenoyl-[acyl-carrier protein] + H2O = [Acyl-carrier protein] + octadecenoate
show the reaction diagram
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1-oleoyl-2-lysophosphatidate + H2O = oleic acid + sn-glycerol 3-phosphate
show the reaction diagram
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12-phosphonooxyoctadec-9Z-enoic acid + H2O = (9Z)-octadecenoic acid + phosphate
show the reaction diagram
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(R)-10-Hydroxystearate = Oleate + H2O
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (36 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
presence of oleate induces dephosphorylation of isoform Gat1p as well as an increment in its levels. In presence of oleate, Gat1p crescent structures are formed which are connected with the endoplasmic reticulum and are intimately associated with lipid particles
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stimulates below 0.015 mM
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EC50 value of 0.23 mM
-
approx. 4fold activiation
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activates only in presence of Triton X-100
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activates
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activates PDK2 and PDK4 nearly 2fold at 0.1 mM, not synergistic with palmitate, stimulation is completely inhibited by insulin at 0.001 mM
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activation, 0.2 mM
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induces enzyme expression in peroxisomes
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induces enzyme expression in peroxisomes
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1.9 fold stimulation at 0.5 mM
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approx. 40% stimulation at 0.8 mM, inhibition above
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Inhibitor in Enzyme-catalyzed Reactions (66 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
G6PDH-1 is more susceptible to oleic acid than G6PDH-2
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0.018 mM, complete inhibition, oxidation of estradiol
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the incubation of Jurkat cells with 0.2 mM oleic acid causes a significant decrease of catalase activity but not of protein or mRNA content
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3.6 mM, isoenzyme POX I, 62% inhibition of the activity with quercetin, 19% inhibition of the activity with o-dianisidine, isoenzyme POX I; 3.6 mM, isoenzyme POX II, 72% inhibition of the activity with quercetin, 41% inhibition of the activity with o-dianisidine, isoenzyme POX II
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at concentrations of oleate higher than 2.1 mM, the enzyme activity is inhibited by excess of substrate
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concentration above 10 microM
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weak inhibition
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irreversible enzyme inhibition
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noncompetitive inhibition, IC50: 0.0545 mM
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0.08 mM, 50% inhibition
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1-acyl lysolipids less inhibited than the 1-alkyl species
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0.3 mM, 58% inhibition
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IC50: 0.082 mM
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2 mM, 84% inhibition
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25-40% inhibition at 0.002-0.003 mM
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inhibits enzyme production, product inhibition
higher than 1.5 mM
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stimulation below 0.8 mM, approx. 10% inhibition at 3.2 mM
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IC50: 0.46 mM
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10 nM: 50% inhibition, 100 nM: 95% inhibition
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strong inhibition
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75% inhibition at 0.02 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (483 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (21 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
178
-
recombinant enzyme, pH and temperature not specified in the publication
0.02
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at pH 7.4 and 37°C
5.62
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recombinant enzyme, whole enzyme activity, pH 6.5, 40°C
0.016
-
pH 8.0

KM Value (52 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.071
-
pH 6.0, 40°C
0.085
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at pH 7.4 and 37°C
1.3
-
-
0.0333
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recombinant enzyme, whole enzyme activity, pH 6.5, 40°C
2.1
-
-

Ki Value (7 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0065
-
-
0.0267
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37°C, pH 7.0
0.009
-
-
0.000001
-
-
0.0018
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at pH 7.6 and 25°C

IC50 Value (7 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0545
-
noncompetitive inhibition, IC50: 0.0545 mM
0.082
-
IC50: 0.082 mM
0.007
-
pH 7.4, 37°C, recombinant CES1
0.46
-
IC50: 0.46 mM
0.115
-
enzym preparation from kidney

References & Links

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Links to other databases for oleic acid

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ChEBI
PubChem
ChEBI
PubChem