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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:43 UTC
Update Date2017-11-20 21:46:02 UTC
HMDB IDHMDB0003231
Secondary Accession Numbers
  • HMDB03231
  • HMDB10377
Metabolite Identification
Common NameVaccenic acid
DescriptionVaccenic acid is present in all tissues. Present in virtually all lipid classes at a low concentration, 18:1n7 is present at about 25% of the concentration of 18:1n9 in most phospholipids. A notable exception is the phospholipid cardiolipin, which often contains as much 18:1n7 as 18:1n9. --www.lipomics.com.
Structure
Thumb
Synonyms
ValueSource
(11E)-Octadecenoic acidChEBI
(e)-11-Octadecenoic acidChEBI
11(e)-Vaccenic acidChEBI
18:1 trans-11ChEBI
C18:1 trans-11ChEBI
Octadec-11(e)-enoic acidChEBI
trans-11-Octadecenoic acidChEBI
trans-11-OctadecensaeureChEBI
trans-Octadec-11-enoic acidChEBI
TVAChEBI
Vaccenic acidChEBI
(11E)-OctadecenoateGenerator
(e)-Octadec-11-enoateGenerator
(e)-11-OctadecenoateGenerator
11(e)-VaccenateGenerator
Octadec-11(e)-enoateGenerator
trans-11-OctadecenoateGenerator
trans-Octadec-11-enoateGenerator
VaccenateGenerator
11-Octadecenoic acid, (e)-isomerMeSH
11-Octadecenoic acidMeSH
trans-Vaccenic acidMeSH
Chemical FormulaC18H34O2
Average Molecular Weight282.468
Monoisotopic Molecular Weight282.255880335
IUPAC Name(11E)-octadec-11-enoic acid
Traditional Nametrans-vaccenic acid
CAS Registry Number693-72-1
SMILES
CCCCCC\C=C\CCCCCCCCCC(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/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+
InChI KeyUWHZIFQPPBDJPM-BQYQJAHWSA-N
Chemical Taxonomy
DescriptionThis compound 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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point44 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP7.67ALOGPS
logP6.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.67 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.7 +/- 5 uMAdult (>18 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.390 +/- 4.279 uMAdult (>18 years old)Both
11-beta-hydroxylase deficiency
details
FecesDetected but not Quantified Adult (>18 years old)Not Specifiedobese details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
11-beta-hydroxylase deficiency
  1. Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. doi: 10.1371/journal.pone.0016957. [PubMed:21359215 ]
  2. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Associated OMIM IDs
  • 202010 (11-beta-hydroxylase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002952
KNApSAcK IDC00001240
Chemspider ID4444571
KEGG Compound IDC08367
BioCyc IDNot Available
BiGG ID2217962
Wikipedia LinkVaccenic acid
METLIN ID3407
PubChem Compound5281127
PDB IDVCA
ChEBI ID28727
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schatowitz B, Gercken G: Simultaneous determination of C2-C22 non-esterified fatty acids and other metabolically relevant carboxylic acids in biological material by gas chromatography of their benzyl esters. J Chromatogr. 1988 Mar 18;425(2):257-68. [PubMed:3372640 ]