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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 an 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].

Oleate has also been reported from a few bacteria, including the obligate anaerobic bacterium Clostridium beijerinckii and the saprophytic bacterium Aerococcus viridans. Bacterial biosynthesis of oleate does not require oxygen and involves elongation of (7Z)-hexadec-7-enoate [Scheuerbrandt61, Goldfine71, Johnston83, Biebl02, Bi13].

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

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

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

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

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

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

saframycin A biosynthesis :
a fatty acid + a holo-[SfmA peptidyl-carrier-protein] + H+ → an acyl-[SfmA peptidyl-carrier-protein] + H2O

Not in pathways:
a fatty acid + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a fatty acid-methyl ester
a fatty acid + a holo-[acyl-carrier protein] + ATP → a 2,3,4-saturated fatty acyl-[acp] + AMP + diphosphate

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:

cutin biosynthesis , oleate biosynthesis II (animals and fungi) , sporopollenin precursors biosynthesis , suberin monomers biosynthesis :
oleoyl-CoA + H2O → oleate + coenzyme A + H+

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+

phospholipid remodeling (phosphatidate, yeast) :
dioleoyl 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:

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

Not in pathways:
a long-chain acyl-CoA + H2O = a long-chain fatty acid + coenzyme A + H+
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 fatty acid + L-alanine + glycine + a holo-[SfmB peptidyl-carrier-protein] + H+ = an acyl-L-alanyl-glycyl-[SfmB peptidyl-carrier-protein] + 3 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 oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown 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 [Wang01c]

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 , long-chain acyl-CoA synthetase , alkane ω-hydroxylase

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


References

Bi13: Bi H, Wang H, Cronan JE (2013). "FabQ, a dual-function dehydratase/isomerase, circumvents the last step of the classical fatty acid synthesis cycle." Chem Biol 20(9);1157-67. PMID: 23972938

Biebl02: Biebl H, Sproer C (2002). "Taxonomy of the glycerol fermenting clostridia and description of Clostridium diolis sp. nov." Syst Appl Microbiol 25(4);491-7. PMID: 12583708

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

Goldfine71: Goldfine H, Panos C (1971). "Phospholipids of Clostridium butyricum. IV. Analysis of the positional isomers of monounsaturated and cyclopropane fatty acids and alk-1'-enyl ethers by capillary column chromatography." J Lipid Res 12(2);214-20. PMID: 5554109

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

Johnston83: Johnston NC, Goldfine H (1983). "Lipid composition in the classification of the butyric acid-producing clostridia." J Gen Microbiol 129(4);1075-81. PMID: 6886674

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

Scheuerbrandt61: Scheuerbrandt G, Goldfine H, Baronowsky PE, Bloch K (1961). "A novel mechanism for the biosynthesis of unsaturated fatty acids." J Biol Chem 236;PC70-PC71. PMID: 14498314

Wang01c: 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 19.0 on Mon Aug 31, 2015, BIOCYC14B.