Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:43 UTC
Update Date2021-09-07 16:45:34 UTC
HMDB IDHMDB0003231
Secondary Accession Numbers
  • HMDB0010377
  • HMDB03231
  • HMDB10377
Metabolite Identification
Common NameVaccenic acid
DescriptionVaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food. Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow). Vaccenic acid 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. Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1582752267
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
(11E)-OctadecenoateGenerator
(e)-11-OctadecenoateGenerator
11(e)-VaccenateGenerator
Octadec-11(e)-enoateGenerator
trans-11-OctadecenoateGenerator
trans-Octadec-11-enoateGenerator
VaccenateGenerator
(e)-Octadec-11-enoateHMDB
11-Octadecenoic acid, (e)-isomerHMDB
11-Octadecenoic acidHMDB
trans-Vaccenic acidHMDB
FA(18:1(11Z))HMDB
FA(18:1n7)HMDB
Vaccenic acidChEBI
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
Description 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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point44 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP10(7.67) g/LALOGPS
logP10(6.78) g/LChemAxon
logS10(-6.4) g/LALOGPS
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
Polarizability37.62 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vaccenic acid,1TMS,#1CCCCCC/C=C/CCCCCCCCCC(=O)O[Si](C)(C)C2218.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Vaccenic acid,1TBDMS,#1CCCCCC/C=C/CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2477.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vaccenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0apl-9200000000-f39f178414756ab6ad8a2018-05-25Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vaccenic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0090000000-dee621bf09f57d88e5ed2018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vaccenic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9340000000-654e2ea72d5477e266062018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vaccenic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0aou-9000000000-413d3363f22e7baf1df72018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vaccenic acid 30V, Positive-QTOFsplash10-001i-0090000000-2a569bab7642a2f754012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOFsplash10-001i-0090000000-dd6c9ec9fb483004fb562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOFsplash10-001i-0090000000-6d641aebf861b449bc932021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOFsplash10-014i-0090000000-36b21b13adac790098f82019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOFsplash10-00rj-4490000000-16982dc88f830f9024c22019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 40V, Positive-QTOFsplash10-0096-9830000000-7359fa780da86e1ebab32019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 10V, Negative-QTOFsplash10-001i-0090000000-1b80c5a75129c09b94ae2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 20V, Negative-QTOFsplash10-01qi-0090000000-6bb63cb21fc095c3aa5c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-c86275a736982cfe31392019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOFsplash10-00lr-4290000000-ef21daa5591bbeb17f872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOFsplash10-067j-9310000000-8cc733ca58b618258ca02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 40V, Positive-QTOFsplash10-0aou-9000000000-60e1d3c5c8de0e9f209c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 10V, Negative-QTOFsplash10-001i-0090000000-8b8562cadde7e7a8ba4f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 20V, Negative-QTOFsplash10-01q9-1090000000-827ccf4b0fb321cd543d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenic acid 40V, Negative-QTOFsplash10-0006-9220000000-9024da2ccb79132d937a2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2018-05-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.7 +/- 5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified186.5 +/- 45.8 uMAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.390 +/- 4.279 uMAdult (>18 years old)Both
11-beta-hydroxylase deficiency
details
BloodDetected and Quantified115.3 +/- 25.6 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedobese details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 ]
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Obesity
  1. Haro C, Montes-Borrego M, Rangel-Zuniga OA, Alcala-Diaz JF, Gomez-Delgado F, Perez-Martinez P, Delgado-Lista J, Quintana-Navarro GM, Tinahones FJ, Landa BB, Lopez-Miranda J, Camargo A, Perez-Jimenez F: Two Healthy Diets Modulate Gut Microbial Community Improving Insulin Sensitivity in a Human Obese Population. J Clin Endocrinol Metab. 2016 Jan;101(1):233-42. doi: 10.1210/jc.2015-3351. Epub 2015 Oct 27. [PubMed:26505825 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002952
KNApSAcK IDC00052543
Chemspider ID4444571
KEGG Compound IDC08367
BioCyc IDNot Available
BiGG ID2217962
Wikipedia LinkVaccenic acid
METLIN ID3407
PubChem Compound5281127
PDB IDNot Available
ChEBI ID28727
Food Biomarker OntologyNot Available
VMH IDVACC
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]