Showing metabocard for 10E,12Z-Octadecadienoic acid (BMDB0005048)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:02 UTC
Update Date2020-06-04 20:50:57 UTC
BMDB IDBMDB0005048
Secondary Accession Numbers
  • BMDB05048
Metabolite Identification
Common Name10E,12Z-Octadecadienoic acid
DescriptionBovinic acid, also known as rumenic acid or rumenate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Bovinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e,Z)-Octadeca-10,12-dienoic acidChEBI
10,12-trans,cis-Octadecanoic acidChEBI
10-trans-12-cis-CLAChEBI
10-trans-12-cis-Conjugated linoleic acidChEBI
10-trans-12-cis-Linoleic acidChEBI
10-trans-12-cis-Octadecadienoic acidChEBI
C18:2, N-6,8 cis,transChEBI
(e,Z)-Octadeca-10,12-dienoateGenerator
10,12-trans,cis-OctadecanoateGenerator
10-trans-12-cis-Conjugated linoleateGenerator
10-trans-12-cis-LinoleateGenerator
10-trans-12-cis-OctadecadienoateGenerator
(10E,12Z)-OctadecadienoateGenerator
10E,12Z-OctadecadienoateHMDB
(10E,12Z)-Octadeca-10,12-dienoateHMDB
trans-10,cis-12-Conjugated linoleic acidHMDB
trans-12,cis-10-Conjugated linoleic acidHMDB
10E12Z-CLAHMDB
trans10cis12-Conjugated linoleic acidHMDB
trans-10, trans-12 Conjugated linoleic acidHMDB
t10,C12 CLAHMDB
FA(18:2(10E,12Z))HMDB
Chemical FormulaC18H32O2
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
IUPAC Name(10E,12Z)-octadeca-10,12-dienoic acid
Traditional Name10E,12Z-octadecadienoic acid
CAS Registry Number2420-56-6
SMILES
CCCCC\C=C/C=C/CCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-9H,2-5,10-17H2,1H3,(H,19,20)/b7-6-,9-8+
InChI KeyGKJZMAHZJGSBKD-NMMTYZSQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • 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
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.1ALOGPS
logP6.42ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)5.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m³·mol⁻¹ChemAxon
Polarizability36.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9840000000-8de71f047c5cd3fb9e62View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-8c1cd1f8ffc64efeec3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-38586249179f8a1229fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-62a4185fa41d6545e722View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-62a4185fa41d6545e722View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-8c1cd1f8ffc64efeec3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-38586249179f8a1229fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0190000000-704dcc047e3570ab2deeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0080-5690000000-73c7802d63562d58060aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9830000000-bbd12ad9fd72f8383890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-4fed8cf7e37a5b8b0a9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1090000000-b69008c130db39eb7682View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-73d8a764573648d2a263View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-03fd7d53d39127d02766View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1090000000-96b6f2a16f2aa6a1afa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9310000000-5ea5d86bf1df8fbb1ca4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-4590000000-5805569743dbf711a9faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-9510000000-d66d9ade15210b5ad3c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apj-9000000000-acfe7e05ea26fee958c6View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueDetected and Quantified7.0495 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
 details
Adipose TissueDetected and Quantified3.91 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
 details
Adipose TissueDetected and Quantified135.028 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
 details
Adipose TissueDetected and Quantified97.68 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
 details
Adipose TissueDetected and Quantified63.16 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
 details
Adipose TissueDetected and Quantified87.62 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005048
DrugBank IDDB04746
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445927
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282800
PDB IDNot Available
ChEBI ID44526
References
Synthesis ReferenceAnikin, A. V.; Chupin, V. V.; Chudinov, M. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Synthesis of glycerophosphatidylcholines containing polymerizable fatty acids. Bioorganicheskaya Khimiya (1990), 16(2), 254-61.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53. [PubMed:11556330 ]