Showing metabocard for Oleic acid (BMDB0000207)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
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Record Information
Version1.0
Creation Date2016-09-30 22:26:42 UTC
Update Date2020-06-04 22:58:57 UTC
BMDB IDBMDB0000207
Secondary Accession Numbers
  • BMDB00207
Metabolite Identification
Common NameOleic acid
DescriptionOleic acid, also known as pamolyn or oleate, 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 exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oleic acid exists in all living species, ranging from bacteria to humans. Oleic acid is a potentially toxic compound. Oleic acid has been found to be associated with several diseases known as colorectal cancer, schizophrenia, gestational diabetes, and lung cancer; also oleic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Chemical FormulaC18H34O2
Average Molecular Weight282.4614
Monoisotopic Molecular Weight282.255880332
IUPAC Name(9Z)-octadec-9-enoic acid
Traditional Nameoleic acid
CAS Registry Number112-80-1
SMILES
CCCCCCCC\C=C/CCCCCCCC(O)=O
InChI Identifier
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)/b10-9-
InChI KeyZQPPMHVWECSIRJ-KTKRTIGZSA-N
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point13.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00vi-9500000000-cdb5366d3ece43c3e166View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-fc03835c9c8fddb27970View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9100000000-7618883a87bd14687fd5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00vi-9500000000-cdb5366d3ece43c3e166View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-fc03835c9c8fddb27970View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb401View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ls-4790000000-d753b2905852ca2a8cbdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aou-9000000000-64594906d693e8a08650View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00l2-4790000000-aefa66e9f83fcb24ead6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0apm-9100000000-a71c58b95cb65487eeedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aou-9000000000-5889cbe3dd606123df50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-001i-0090000000-89531b488fbe899c09e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-052f-9100000000-de078efada08e691dbb8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-92096c6b229762c5295fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-5fe8495a19b387bf702cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-5d40399b1c736b476445View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-45785aeb659bd8a09240View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0091000000-3946ac7663105c7c2700View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0090000000-ce1372cb3b5e84122349View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-92096c6b229762c5295fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-755e8d1537818580a2fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-4690000000-ca39c5846217fe093227View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9830000000-fcb2923d448d11c54559View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e809fd7222cf63431b77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-9c340e3d19cbe7013ccdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-6e517cda629fcd4df07dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b67View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Blood
  • Epidermis
  • Intestine
  • Liver
  • Mammary Gland
  • Milk
  • Muscle
  • Oocyte
  • Pancreas
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semen
  • Skeletal Muscle
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Heat stress		 details
HMDB IDHMDB0000207
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012858
KNApSAcK IDC00001232
Chemspider ID393217
KEGG Compound IDC00712
BioCyc IDOLEATE-CPD
BiGG IDNot Available
Wikipedia LinkOleic_acid
METLIN ID190
PubChem Compound445639
PDB IDNot Available
ChEBI ID16196
References
Synthesis ReferenceHu, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  2. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
  3. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  5. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
  6. Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.