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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 05:00:19 UTC
Update Date2021-10-13 04:42:22 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
Data?1584651507
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
9-cis,11-trans-OctadecadienoateKegg
(9Z,11E)-OctadecadienoateGenerator
(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
9-cis,11-trans-Octadecadienoic acidGenerator
BovinateGenerator
(9Z,11E)-Conjugated linoleic acidHMDB
(9Z,11E)-Octadeca-9,11-dienoateHMDB
(9Z,11E)-Octadeca-9,11-dienoic 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 acidHMDB
9,11-Linoleic acidHMDB
9,11-Linoleic acid, (Z,e)-isomerHMDB
cis-9-trans-11-Octadecadienoic acidHMDB
9,11-Isolinoleic acidHMDB
9,11-Octadecadienoic acidHMDB
9-cis-11-trans-Octadecadienoic acidHMDB
Octadeca-9,11-dienoic acidHMDB
9,11-OctadecadienoateHMDB
c9t11 CLAHMDB
9-cis,11-trans-Linoleic acidHMDB
FA(18:2(9Z,11E))HMDB
cis-9,trans-11-Octadecadienoic acidHMDB
trans-11-cis-9-Octadecadienoic acidHMDB
Bovinic acidHMDB
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
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP10(7.11) g/LALOGPS
logP10(6.42) g/LChemAxon
logS10(-6.3) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.2931661259
DarkChem[M-H]-177.28331661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bovinic acid,1TMS,#1CCCCCC/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C2290.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Bovinic acid,1TBDMS,#1CCCCCC/C=C/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2526.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bovinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9550000000-f91f775c11691e5723392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bovinic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9531000000-ff0f0a6283e777000b032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bovinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bovinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0090000000-e92f42e010cf8de7d8422017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid ESI-TOF 30V, Negative-QTOFsplash10-004i-0090000000-b39dc5a43bb0b5730a2f2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid ESI-TOF 20V, Negative-QTOFsplash10-004i-0090000000-5eb9e4ae49ad1fb539cd2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid ESI-TOF , Negative-QTOFsplash10-004i-0091010000-52cb4af6370469644ffa2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-e92f42e010cf8de7d8422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-b39dc5a43bb0b5730a2f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid LC-ESI-TOF , negative-QTOFsplash10-004i-0090000000-5eb9e4ae49ad1fb539cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid 10V, Positive-QTOFsplash10-004i-0090000000-e92f42e010cf8de7d8422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid 20V, Positive-QTOFsplash10-004i-0090000000-5eb9e4ae49ad1fb539cd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bovinic acid 30V, Positive-QTOFsplash10-004i-0090000000-b39dc5a43bb0b5730a2f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 10V, Negative-QTOFsplash10-004i-0090000000-f1e9e4b543f7d4f48bf82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 20V, Negative-QTOFsplash10-01ti-0090000000-665523c6142ff4e39c962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-b43315d97b9995f922a32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 10V, Negative-QTOFsplash10-004i-0090000000-03fd7d53d39127d027662021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 20V, Negative-QTOFsplash10-01t9-1090000000-c03baa3d5c1c48e8c45c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 40V, Negative-QTOFsplash10-0006-9310000000-07f427d77d98dab09f402021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 10V, Positive-QTOFsplash10-03di-0090000000-f2c6c9de24118516f0db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 20V, Positive-QTOFsplash10-022j-5690000000-f4c090f44fe34f660b192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 40V, Positive-QTOFsplash10-006x-9830000000-42ee75da80e6ee682b902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 10V, Positive-QTOFsplash10-01qa-5590000000-6740409ad0ee9d0c387c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 20V, Positive-QTOFsplash10-05mk-9510000000-78bd3b0ecfca1dab2bac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovinic acid 40V, Positive-QTOFsplash10-0apm-9000000000-98f6af2debd76c0c3c6e2021-09-24Wishart LabView Spectrum
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
FooDB IDFDB093753
KNApSAcK IDC00052217
Chemspider ID4444245
KEGG Compound IDC04056
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRumenic acid
METLIN IDNot Available
PubChem Compound5280644
PDB IDNot Available
ChEBI ID32798
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1894541
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 ]