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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: oleate

Synonyms: oleic acid, (9Z)-octadec-9-enoate, (9Z)-octadecenoate, (9Z)-octadecenoic acid, (9Z)-octadec-9-enoic acid, (Z)-octadec-9-enoic acid, 18:1 n-9, 18:1Δ9cis, C18:1 n-9, cis-9-octadecenoic acid, cis-Δ9-octadecenoic acid, cis-oleic acid, octadec-9-enoic acid, octadecenoate (n-C18:1), 9-octadecenoic acid

Superclasses: an acid all carboxy acids a carboxylate a fatty acid a long-chain fatty acid
an acid all carboxy acids a carboxylate a fatty acid an unsaturated fatty acid a monounsaturated fatty acid

Summary:
Oleate is an unsaturated fatty acid found in plant and animal oils and fats; It is an important ingredient of olive oil, and is used for making soap, cosmetics and other products.

Chemical Formula: C18H33O2

Molecular Weight: 281.46 Daltons

Monoisotopic Molecular Weight: 282.2558803356 Daltons

SMILES: CCCCCCCCC=CCCCCCCCC([O-])=O

InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/p-1/b10-9-

InChIKey: InChIKey=ZQPPMHVWECSIRJ-KTKRTIGZSA-M

Unification Links: CAS:112-80-1 , ChEBI:30823 , ChemSpider:4573837 , HMDB:HMDB00207 , IAF1260:1451011 , KEGG:C00712 , MetaboLights:MTBLC30823 , PubChem:5460221

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 300.16492 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

cutin biosynthesis :
oleate + NADPH + oxygen + H+ → 18-hydroxyoleate + NADP+ + H2O
a lipid hydroperoxide + oleate → 9,10-epoxystearate + a lipid alcohol

cyclopropane and cyclopropene fatty acid biosynthesis :
oleate + S-adenosyl-L-methionine → dihydrosterculate + S-adenosyl-L-homocysteine + H+

dimorphecolate biosynthesis :
oleate → (9Z,12E)-octadecadienoate + 2 H+

linoleate biosynthesis I (plants) , linoleate biosynthesis II (animals) :
oleate + ATP + coenzyme A → oleoyl-CoA + AMP + diphosphate

ricinoleate biosynthesis :
oleate + NADH + oxygen + H+ → ricinoleate + NAD+ + H2O

stigma estolide biosynthesis :
3 oleate + OH- → estolide + CO2

suberin monomers biosynthesis :
oleate + NADPH + oxygen + H+ → 18-hydroxyoleate + NADP+ + H2O

Not in pathways:
oleate + hydrogen peroxide + H+ → 1,8-heptadecadiene + CO2 + 2 H2O
oleate + oxygen → (8E,10S)-10-hydroperoxyoctadec-8-enoate
oleate + ethanol + H+ → ethyl oleate + H2O
oleate + a reduced electron acceptor + oxygen → linoleate + an oxidized electron acceptor + 2 H2O

alkane biosynthesis I :
a long-chain fatty acid + a holo-[acyl-carrier protein] + ATP → a long-chain acyl-[acp] + AMP + diphosphate

alkane biosynthesis II , fatty acid activation , long chain fatty acid ester synthesis for microdiesel production , phosphatidylcholine acyl editing , wax esters biosynthesis II :
a long-chain fatty acid + ATP + coenzyme A → a long-chain acyl-CoA + AMP + diphosphate

terminal olefins biosynthesis I :
a long-chain fatty acid + hydrogen peroxide + H+ → a terminal olefin + CO2 + 2 H2O

alkane oxidation :
a fatty acid + NADPH + oxygen + H+ → an ω-hydroxy fatty acid + NADP+ + H2O

sophorolipid biosynthesis :
a fatty acid + NADPH + oxygen + H+ → an (ω-1)-hydroxy fatty acid + NADP+ + H2O
a fatty acid + NADPH + oxygen + H+ → an ω-hydroxy fatty acid + NADP+ + H2O

sporopollenin precursor biosynthesis :
a fatty acid + NADPH + oxygen + H+ → an in-chain hydroxy fatty acid + NADP+ + H2O
a fatty acid + NADPH + oxygen + H+ → an ω-hydroxy fatty acid + NADP+ + H2O


ATP + a holo-[acyl-carrier protein] + a fatty acid → AMP + a 2,3,4-saturated fatty acyl-[acp] + diphosphate
a fatty acid + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a fatty acid-methyl ester

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate


an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

monoacylglycerol metabolism (yeast) :
2-oleoylglycerol + H2O → glycerol + oleate + H+
1-oleoylglycerol + H2O → glycerol + oleate + H+

oleate biosynthesis I (plants) :
an oleoyl-[acp] + H2O → a holo-[acyl-carrier protein] + oleate + H+

oleate biosynthesis II (animals and fungi) , stigma estolide biosynthesis :
oleoyl-CoA + H2O → oleate + coenzyme A + H+

phospholipid remodeling (phosphatidate, yeast) :
1-18:1-2-18:1-phosphatidate + H2O → 1-oleyl-2-lyso-phosphatidate + oleate + H+

phospholipid remodeling (phosphatidylethanolamine, yeast) :
1-18:1-lysophosphatidylethanolamine + H2O → sn-glycero-3-phosphoethanolamine + oleate + H+
1-18:1-2-18:1-phosphatidylethanolamine + H2O → 1-18:1-lysophosphatidylethanolamine + oleate + H+

sterol:steryl ester interconversion (yeast) :
lanosteryl oleate + H2O → lanosterol + oleate + H+
ergosteryl oleate + H2O → ergosterol + oleate + H+

Not in pathways:
1-18:1-2-16:0-monogalactosyldiacylglycerol + H2O → sn-1-lyso-2-16:0-monogalactosyldiacylglycerol + oleate + H+

retinol biosynthesis :
an all-trans-retinyl ester + H2O → all-trans-retinol + a long-chain fatty acid + H+
a dietary all-trans-retinyl ester + H2O → all-trans-retinol + a long-chain fatty acid + H+


a long-chain-fatty-acyl ethyl ester + H2O → a long-chain fatty acid + ethanol + H+

acyl-ACP thioesterase pathway :
an acyl-[acyl-carrier protein] + H2O → a fatty acid + a holo-[acyl-carrier protein] + H+

alkane oxidation , fatty acid α-oxidation I :
a fatty aldehyde + NAD+ + H2O → a fatty acid + NADH + 2 H+

ceramide degradation :
a ceramide + H2O → a sphingoid base + a fatty acid

phosphatidylcholine acyl editing :
a phosphatidylcholine + H2O → a 2-lyso-phosphatidylcholine + a fatty acid + H+
a phosphatidylcholine + H2O → a 1-lysophosphatidylcholine + a fatty acid + H+

phospholipases :
a phosphatidylcholine + H2O → a 2-lyso-phosphatidylcholine + a fatty acid + H+
a phosphatidylcholine + H2O → a 1-lysophosphatidylcholine + a fatty acid + H+

sphingolipid biosynthesis (mammals) , sphingomyelin metabolism :
an N-acyl-sphingosylphosphorylcholine + H2O → a fatty acid + sphingosylphosphorylcholine

sphingosine and sphingosine-1-phosphate metabolism :
an N-acylsphingosine + H2O → sphingosine + a fatty acid

the visual cycle I (vertebrates) :
an all-trans-retinyl ester + H2O → 11-cis-retinol + a fatty acid

triacylglycerol degradation :
a 1-monoglyceride + H2O → a fatty acid + glycerol + H+
a triglyceride + H2O → a 1,2-diglyceride + a fatty acid + H+
a 1,2-diglyceride + H2O → a 2-monoglyceride + a fatty acid + H+


a 3-(acyloxy)acyl group of bacterial toxin + H2O → a 3-hydroxyacyl group of bacterial toxin + a fatty acid + H+
a steryl-ester + H2O → a fatty acid + a sterol + H+
an L-1-phosphatidyl-ethanolamine[periplasmic space] + H2O[periplasmic space] → a 1-lyso-2-acyl-sn-glycero-3-phosphoethanolamine[periplasmic space] + a fatty acid[periplasmic space] + H+[periplasmic space]
a 2-monoglyceride + H2O → glycerol + a fatty acid + H+
an L-1-phosphatidyl-ethanolamine[periplasmic space] + H2O[periplasmic space]a fatty acid[periplasmic space] + a 2-lyso-phosphatidyl-ethanolamine[periplasmic space] + H+[periplasmic space]
a 1,3-diglyceride + H2O → a monoglyceride + a fatty acid
an all-trans-retinyl ester + H2O → 13-cis-retinol + a fatty acid
an 11-cis-retinyl ester + H2O → 11-cis-retinol + a fatty acid
a 1,2-diacyl-sn-glycerol + H2O → a monoglyceride + a fatty acid
an O-acyl-L-carnitine + H2O → L-carnitine + a fatty acid

3,3'-thiodipropionate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropionate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+


an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
a 1-lysophosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

poly-hydroxy fatty acids biosynthesis :
oleate + 2 NADPH + oxygen = 9,10-epoxystearate + 2 NADP+ + H2O

Not in pathways:
(R)-10-Hydroxystearate = oleate + H2O
oleamide + H2O = oleate + ammonium
oleate = (11Z)-eicos-11-enoate


acetyl-CoA + n malonyl-CoA + 2n NADPH + 2n H+ = a long-chain fatty acid + n CO2 + (n+1) coenzyme A + 2n NADP+


a fatty acid + hydrogen peroxide = a 3- or 2-hydroxy fatty acid + H2O
a D-glucosyl-N-acylsphingosine + H2O = a fatty acid + D-glucosyl-sphingosine
a 1,2-diacyl-sn-glycerol + H2O = a 1-monoglyceride + a fatty acid + H+
a glycosphingolipid + H2O = a lyso-glycosphingolipid + a fatty acid


eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized electron acceptor + H2O = a carboxylate + a reduced electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

In Transport reactions:
a long-chain fatty acid[periplasmic space]a long-chain fatty acid[cytosol] ,
a long-chain fatty acid[extracellular space]a long-chain fatty acid[periplasmic space]

Enzymes activated by oleate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: acyl-CoA oxidase [Dmochowska90] , phospholipase D [Wang01a]

Enzymes inhibited by oleate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: (25R)-3α,7α,12α-trihydroxy-5β-cholestanoyl-CoA ligase [Falany02] , pyruvate dehydrogenase [Camp88]


References

Camp88: Camp, Pamela J, Miernyk, Jan A, Randall, Douglas D (1988). "Some kinetic and regulatory properties of the pea chloroplast pyruvate dehydrogenase complex." Biochimica et Biophysica Acta, 933:269-275.

Dmochowska90: Dmochowska A, Dignard D, Maleszka R, Thomas DY (1990). "Structure and transcriptional control of the Saccharomyces cerevisiae POX1 gene encoding acyl-coenzyme A oxidase." Gene 88(2);247-52. PMID: 2189786

Falany02: Falany CN, Xie X, Wheeler JB, Wang J, Smith M, He D, Barnes S (2002). "Molecular cloning and expression of rat liver bile acid CoA ligase." J Lipid Res 43(12);2062-71. PMID: 12454267

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Wang01a: Wang C, Wang X (2001). "A novel phospholipase D of Arabidopsis that is activated by oleic acid and associated with the plasma membrane." Plant Physiol 2001;127(3);1102-12. PMID: 11706190


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, biocyc13.