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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 05:00:19 UTC
Update Date2018-05-19 22:23:31 UTC
HMDB IDHMDB0003797
Secondary Accession Numbers
  • HMDB03797
Metabolite Identification
Common NameBovinic acid
DescriptionBovinic acid is a conjugated linoleic acid, present in human adipose tissue; the amount of bovinic acid in humans is significantly related to milk fat intake. Conjugated linoleic acids (CLAs) are a group of naturally occurring fatty acids present mainly in fats from ruminants. Milk contains over 20 isomers of CLA but the predominant one is cis-9,trans-11-CLA (bovinic acid). Biomedical studies with animal models have shown that this isomer has anticarcinogenic and anti-atherogenic activities. Bovinic acid is produced as an intermediate in the rumen biohydrogenation of linoleic acid but not of linolenic acid. However, it is only a transient intermediate, and the major source of milk fat CLA is from endogenous synthesis. (PMID 10393134 , 15736916 ).
Structure
Thumb
Synonyms
ValueSource
(9Z,11E)-Octadecadienoic acidChEBI
(Z,e)-Octadeca-9,11-dienoic acidChEBI
9(Z),11(e)-Octadecadienoic acidChEBI
9,11-cis,trans-Octadecanoic acidChEBI
9-cis-11-trans-Linoleic acidChEBI
C18:2, N-7,9 trans,cisChEBI
cis-9,trans-11 Conjugated linoleic acidChEBI
cis-9,trans-11-CLAChEBI
Rumenic acidChEBI
(9Z,11E)-OctadecadienoateGenerator
BovinateGenerator
(Z,e)-Octadeca-9,11-dienoateGenerator
9(Z),11(e)-OctadecadienoateGenerator
9,11-cis,trans-OctadecanoateGenerator
9-cis-11-trans-LinoleateGenerator
cis-9,trans-11 Conjugated linoleateGenerator
RumenateGenerator
(9Z,11E)-Conjugated linoleic acidHMDB
(9Z,11E)-Octadeca-9,11-dienoateHMDB
(9Z,11E)-Octadeca-9,11-dienoic acidHMDB
9-cis,11-trans-OctadecadienoateHMDB
9-cis,11-trans-Octadecadienoic acidHMDB
9-cis,11-trans-Octadecadienoic acid solutionHMDB
9Z,11E-CLAHMDB
9Z,11E-OctadecadienoateHMDB
9Z,11E-Octadecadienoic acidHMDB
cis-9, trans-11-OctadecadienoateHMDB
cis-9, trans-11-Octadecadienoic acidHMDB
Conjugated (9Z,11E)-linoleic acid solutionHMDB
(9Z,11E)-9,11-Octadecadienoic acidMeSH
9,11-Linoleic acidMeSH
9,11-Linoleic acid, (Z,e)-isomerMeSH
9,11-Linoleic acid, (e,e)-isomerMeSH
9,11-Linoleic acid, (e,Z)-isomerMeSH
cis-9-trans-11-Octadecadienoic acidMeSH
9,11-Isolinoleic acidMeSH
9,11-Octadecadienoic acidMeSH
9-cis-11-trans-Octadecadienoic acidMeSH
Octadeca-9,11-dienoic acidMeSH
9,11-Linoleic acid, potassium saltMeSH
9,11-OctadecadienoateMeSH
c9t11 CLAMeSH
9,11-Linoleic acid, (Z,Z)-isomerMeSH
Chemical FormulaC18H32O2
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
IUPAC Name(9Z,11E)-octadeca-9,11-dienoic acid
Traditional Namecis-9,trans-11-CLA
CAS Registry Number2540-56-9
SMILES
CCCCCC\C=C\C=C/CCCCCCCC(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/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9-
InChI KeyJBYXPOFIGCOSSB-GOJKSUSPSA-N
Chemical Taxonomy
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.11ALOGPS
logP6.42ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m³·mol⁻¹ChemAxon
Polarizability36.55 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-052f-9550000000-f91f775c11691e572339View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9531000000-ff0f0a6283e777000b03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-e92f42e010cf8de7d842View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-b39dc5a43bb0b5730a2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-5eb9e4ae49ad1fb539cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0091010000-52cb4af6370469644ffaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-e92f42e010cf8de7d842View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-b39dc5a43bb0b5730a2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-5eb9e4ae49ad1fb539cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-f2c6c9de24118516f0dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022j-5690000000-f4c090f44fe34f660b19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9830000000-42ee75da80e6ee682b90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-b43315d97b9995f922a3View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.03 +/- 1.3 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021827
KNApSAcK IDNot Available
Chemspider ID4444245
KEGG Compound IDC04056
BioCyc IDCPD-7535
BiGG IDNot Available
Wikipedia LinkRumenic acid
METLIN IDNot Available
PubChem Compound5280644
PDB IDNot Available
ChEBI ID32798
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jiang J, Wolk A, Vessby B: Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue. Am J Clin Nutr. 1999 Jul;70(1):21-7. [PubMed:10393134 ]
  2. Lock AL, Bauman DE: Modifying milk fat composition of dairy cows to enhance fatty acids beneficial to human health. Lipids. 2004 Dec;39(12):1197-206. [PubMed:15736916 ]