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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
an acid all carboxy acids a carboxylate a fatty acid an unsaturated fatty acid a omega-9 fatty acid

Summary:
Oleate (oleic acid) is the first unsaturated fatty acid that is generated from the saturated fatty acids produced by the fatty acid synthase. It's name is derived from the olive tree, since it makes up 55-80% of olive oil.

Oleate synthesis occurs with membrane-bound systems. The desaturase enzymes that produce oleate have been isolated from fungi, yeast, and mammalian liver and found to be specific for stearoyl-CoA. In plants, on the other hand, oleate is produced via a stearoyl-[acp], an acyl-carrier-protein bound intermediate [Jaworski74].

Like other fatty acids, oleate is rarely found in its free form. It is usually found as either oleoyl-[acp], oleoyl-CoA, or incorporated into a lipid.

Chemical Formula: C18H33O2

Molecular Weight: 281.46 Daltons

Monoisotopic Molecular Weight: 282.2558803356 Daltons

oleate compound structure

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 :
a hydroperoxy fatty acid in a glycerolipid + oleate → 9,10-epoxystearate + a hydroxy fatty acid in a glycerolipid
oleate + NADPH + oxygen + H+ → 18-hydroxyoleate + NADP+ + H2O

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

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

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

Not in pathways:
oleate + hydrogen peroxide + H+ → 1E,8Z-heptadecadiene + CO2 + 2 H2O
oleate + oxygen → (8E,10S)-10-hydroperoxyoctadec-8-enoate
oleate + ethanol + H+ → ethyl oleate + 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

rhizobactin 1021 biosynthesis :
rhizobactin 1021 core + a fatty acid → rhizobactin 1021

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

Not in pathways:
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

Not in pathways:
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-oleoyl-sn-glycerol + 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) :
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+

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

phospholipases :
a phosphatidylcholine + H2O → a 1-acyl 2-lyso-phosphatidylcholine + a long-chain fatty acid + H+
a phosphatidylcholine + H2O → a 2-acyl 1-lyso-phosphatidylcholine + a long-chain fatty acid + 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+

Not in pathways:
a wax ester + H2O → a long-chain alcohol + 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

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

sphingosine and sphingosine-1-phosphate metabolism :
a (4E)-sphing-4-enine ceramide + H2O → sphingosine + a fatty acid

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

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

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 + NADPH + oxygen + H+ = 9,10-epoxystearate + NADP+ + H2O

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

Not in pathways:
an acylglycerone phosphate + a long-chain alcohol = a 1-alkyl-glycerone 3-phosphate + a long-chain fatty acid + H+
a long-chain alcohol + 2 NAD+ + H2O = a long-chain fatty acid + 2 NADH + 3 H+
a long-chain aldehyde + NAD+ + H2O = a long-chain fatty acid + NADH + 2 H+
an N-long-chain-fatty-acyl-L-glutamate + H2O = L-glutamate + a long-chain fatty acid
an N-(long-chain-acyl)ethanolamine + H2O = a long-chain fatty acid + ethanolamine
acetyl-CoA + n malonyl-CoA + 2n NADPH + 2n H+ = a long-chain fatty acid + n CO2 + (n+1) coenzyme A + 2n NADP+

Not in pathways:
a fatty acid + hydrogen peroxide = a 3- or 2-hydroxy fatty acid + H2O
a D-glucosyl-N-acylsphingosine + H2O = a fatty acid + O-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

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
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 unknown oxidized electron acceptor + H2O = a carboxylate + an unknown reduced electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid

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 [Wang01b]

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]

This compound has been characterized as an alternative substrate of the following enzymes: fatty acid (ω-1)-hydroxylase , alkane ω-hydroxylase , long-chain acyl-CoA synthetase

Credits:
Revised 01-Dec-2014 by Caspi R , SRI International


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

Jaworski74: Jaworski JG, Stumpf PK (1974). "Fat metabolism in higher plants. Properties of a soluble stearyl-acyl carrier protein desaturase from maturing Carthamus tinctorius." Arch Biochem Biophys 162(1);158-65. PMID: 4831331

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

Wang01b: 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


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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 19.0 on Tue Mar 31, 2015, biocyc12.