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Human Metabolome Database Version 3.5

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Showing metabocard for Vaccenic acid (HMDB03231)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:43 -0600
Update Date 2013-02-08 17:12:22 -0700
HMDB ID HMDB03231
Secondary Accession Numbers
  • HMDB10377
Metabolite Identification
Common Name Vaccenic acid
Description Vaccenic 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (11Z)-Octadecenoate
  2. (11Z)-Octadecenoic acid
  3. (Z)-Octadec-11-enoate
  4. (Z)-Octadec-11-enoic acid
  5. 11-Octadecenoate
  6. 11-Octadecenoic acid
  7. 11Z-Octadecenoate
  8. 11Z-Octadecenoic acid
  9. trans-11-Octadecenoate
  10. trans-11-Octadecenoic acid
  11. Vaccenate
Chemical Formula C18H34O2
Average Molecular Weight 282.4614
Monoisotopic Molecular Weight 282.255880332
IUPAC Name (11Z)-octadec-11-enoic acid
Traditional IUPAC Name cis-vaccenic acid
CAS Registry Number 693-72-1
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 Key UWHZIFQPPBDJPM-FPLPWBNLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated fatty acids(Lipidmaps)
  • vaccenic acid(ChEBI)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct Parent Unsaturated Fatty Acids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 44 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.230E-04 g/L ALOGPS
LogP 7.67 ALOGPS
LogP 6.78 ChemAxon
LogS -6.36 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 15 ChemAxon
Refractivity 87.4 ChemAxon
Polarizability 37.12 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
10.7 +/- 5 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
6.390 +/- 4.279 uM Adult (>18 years old) Both Normal Quantified by Lipomics Technologies, Inc.
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References
11-beta-hydroxylase deficiency
  • 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. Pubmed: 21359215 Link_out
  • 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. 2008 Oct 25. Pubmed: 18953024 Link_out
    Associated OMIM IDs
    • 202010 Link_out (11-beta-hydroxylase deficiency)
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB002952
    KNApSAcK ID C00001240 Link_out
    Chemspider ID 4445888 Link_out
    KEGG Compound ID C08367 Link_out
    BioCyc ID Not Available
    BiGG ID 2217962 Link_out
    Wikipedia Link Vaccenic acid Link_out
    NuGOwiki Link HMDB03231 Link_out
    Metagene Link HMDB03231 Link_out
    METLIN ID 3407 Link_out
    PubChem Compound 5282761 Link_out
    PDB ID VCA Link_out
    ChEBI ID 50464 Link_out
    References
    Synthesis Reference Not 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 Link_out