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Record Information
Version4.0
Creation Date2006-05-22 15:12:43 UTC
Update Date2017-09-25 17:29:52 UTC
HMDB IDHMDB0003231
Secondary Accession Numbers
  • HMDB03231
  • HMDB10377
StatusDetected and Quantified
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
(Z)-11-Octadecenoic acidChEBI
(Z)-Octadec-11-enoic acidChEBI
Asclepic acidChEBI
cis-11-Octadecenoic acidChEBI
cis-Octadec-11-enoic acidChEBI
trans-11-OctadecensaeureChEBI
(Z)-11-OctadecenoateGenerator
VaccenateGenerator
(Z)-Octadec-11-enoateGenerator
AsclepateGenerator
cis-11-OctadecenoateGenerator
cis-Octadec-11-enoateGenerator
(11Z)-OctadecenoateHMDB
(11Z)-Octadecenoic acidHMDB
11-OctadecenoateHMDB
11-Octadecenoic acidHMDB
11Z-OctadecenoateHMDB
11Z-Octadecenoic acidHMDB
trans-11-OctadecenoateHMDB
trans-11-Octadecenoic acidHMDB
Chemical FormulaC18H34O2
Average Molecular Weight282.4614
Monoisotopic Molecular Weight282.255880332
IUPAC Name(11Z)-octadec-11-enoic acid
Traditional Namecis-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-FPLPWBNLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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:
Source:
Subcellular:
Biofluid and excreta:
Process
Naturally occurring process:
Biological process:
Cellular process:
Role
Industrial application:
Pharmaceutical industry:
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 Solubility0.000123 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m3·mol-1ChemAxon
Polarizability37.1 Å3ChemAxon
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-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0090000000-dee621bf09f57d88e5edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9340000000-654e2ea72d5477e26606View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aou-9000000000-413d3363f22e7baf1df7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0apl-9200000000-f39f178414756ab6ad8aView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ID4445888
KEGG Compound IDC08367
BioCyc IDNot Available
BiGG ID2217962
Wikipedia LinkVaccenic acid
NuGOwiki LinkHMDB0003231
METLIN ID3407
PubChem Compound5282761
PDB IDVCA
ChEBI ID50464
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 ]