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Identification
YMDB IDYMDB00131
NameOleic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionOleic acid, also known as oleate or 18:1 N-9, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Oleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oleic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (9Z)-9-Octadecenoate
  • (9Z)-9-Octadecenoic acid
  • (9Z)-Octadecenoate
  • (9Z)-Octadecenoic acid
  • (Z)-9-Octadecanoate
  • (Z)-9-Octadecanoic acid
  • (Z)-9-octadecenoic acid, ion(1-)
  • (Z)-Octadec-9-enoate
  • (Z)-Octadec-9-enoic acid
  • 9-(Z)-octadecenoate
  • 9-(Z)-octadecenoic acid
  • 9-Octadecenoate
  • 9-Octadecenoic acid
  • 9,10-Octadecenoate
  • 9,10-Octadecenoic acid
  • Century cd fatty acid
  • cis-9-Octadecenoate
  • cis-9-Octadecenoic acid
  • cis-Octadec-9-enoate
  • cis-Octadec-9-enoic acid
  • cis-Oleate
  • cis-Oleic acid
  • Distoline
  • Elaate
  • Elaic acid
  • Elaidoate
  • Elaidoic acid
  • Ethyl linoleate (JAN)
  • L'acide oleique
  • Metaupon
  • Oelsauere
  • Oleat
  • Oleate
  • Oleic acid
  • oleic acid anion
  • oleic acid extra pure
  • Oleinate
  • Oleinic acid
  • Red oil
  • Z-9-Octadecenoate
  • Z-9-Octadecenoic acid
  • 18:1 N-9
  • 18:1DElta9cis
  • C18:1 N-9
  • cis-Delta(9)-Octadecenoic acid
  • FA 18:1
  • Octadec-9-enoic acid
  • Oelsaeure
  • cis-delta(9)-Octadecenoate
  • cis-Δ(9)-octadecenoate
  • cis-Δ(9)-octadecenoic acid
  • Octadec-9-enoate
  • Emersol 210
  • Emersol 211
  • Emersol 213
  • Emersol 220 white oleate
  • Emersol 220 white oleic acid
  • Emersol 221 low titer white oleate
  • Emersol 221 low titer white oleic acid
  • Emersol 233LL
  • Emersol 6321
  • Emersol 6333 NF
  • Emersol 7021
  • Glycon ro
  • Glycon wo
  • Groco 2
  • Groco 4
  • Groco 5l
  • Groco 6
  • Industrene 104
  • Industrene 105
  • Industrene 205
  • Industrene 206
  • Pamolyn
  • Pamolyn 100
  • Pamolyn 100 FG
  • Pamolyn 100 FGK
  • Pamolyn 125
  • Priolene 6900
  • Tego-oleic 130
  • Vopcolene 27
  • Wecoline oo
  • Acid, 9-octadecenoic
  • Acid, oleic
  • 9 Octadecenoic acid
  • Acid, cis-9-octadecenoic
  • cis 9 Octadecenoic acid
  • FA(18:1(9Z))
CAS number112-80-1
WeightAverage: 282.4614
Monoisotopic: 282.255880332
InChI KeyZQPPMHVWECSIRJ-KTKRTIGZSA-N
InChIInChI=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)/b10-9-
IUPAC Name(9Z)-octadec-9-enoic acid
Traditional IUPAC Nameoleic acid
Chemical FormulaC18H34O2
SMILESCCCCCCCC\C=C/CCCCCCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point13.4 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP7.68ALOGPS
logP6.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Organoleptic Properties
Flavour/OdourSource
FaintFDB002951
FatFDB002951
FattyFDB002951
FriedFDB002951
LardFDB002951
WaxyFDB002951
SMPDB Pathways
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
Fatty acid biosynthesisec00061 Map00061
SMPDB ReactionsNot Available
KEGG Reactions
hydron + malonyl-CoA + oxygen + NADPH + Palmitic acidNADP + Carbon dioxide + Coenzyme A + Oleic acid + water
Adenosine triphosphate + Coenzyme A + Oleic acidAdenosine monophosphate + Pyrophosphate + oleoyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • LIGHT, R. J., LENNARZ, W. J., BLOCH, K. (1962). "The metabolism of hydroxystearic acids in yeast." J Biol Chem 237:1793-1800.14465241
  • Schneiter, R., Tatzer, V., Gogg, G., Leitner, E., Kohlwein, S. D. (2000). "Elo1p-dependent carboxy-terminal elongation of C14:1Delta(9) to C16:1Delta(11) fatty acids in Saccharomyces cerevisiae." J Bacteriol 182:3655-3660.10850979
Synthesis Reference:Hu, Sheng; Yuan, Ji-rong; Zhu, Jin; Yin, Ying-sui. Preparation of high-purity oleic acid by selective reaction. Yingyong Huagong (2005), 34(12), 748-750, 753.
External Links:
ResourceLink
CHEBI ID16196
HMDB IDHMDB00207
Pubchem Compound ID965
Kegg IDC00712
ChemSpider ID393217
FOODB IDFDB002951
WikipediaOleic_acid
BioCyc IDOLEATE-CPD

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:
FAS1
Uniprot ID:
P07149
Molecular weight:
228689.0
Reactions
Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.