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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-11-20 21:43:09 UTC
Update Date2021-09-07 17:05:39 UTC
HMDB IDHMDB0240219
Secondary Accession NumbersNone
Metabolite Identification
Common Namecis-Vaccenic acid
Descriptioncis-11-Octadecenoic acid, also known as (Z)-octadec-11-enoic acid or asclepic 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. cis-11-Octadecenoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1563892731
Synonyms
ValueSource
(Z)-11-Octadecenoic acidChEBI
(Z)-Octadec-11-enoic acidChEBI
Asclepic acidChEBI
cis-Octadec-11-enoic acidChEBI
VACCENIC ACIDChEBI
(Z)-11-OctadecenoateGenerator
(Z)-Octadec-11-enoateGenerator
AsclepateGenerator
cis-Octadec-11-enoateGenerator
VACCENateGenerator
cis-11-OctadecenoateGenerator
cis-11-Octadecenoic acidChEBI
(11Z)-OctadecenoateHMDB
(11Z)-Octadecenoic acidHMDB
11-OctadecenoateHMDB
11-Octadecenoic acidHMDB
11Z-OctadecenoateHMDB
11Z-Octadecenoic acidHMDB
cis-VaccenateGenerator
Chemical FormulaC18H34O2
Average Molecular Weight282.4614
Monoisotopic Molecular Weight282.255880332
IUPAC Name(11Z)-octadec-11-enoic acid
Traditional Namecis-vaccenic acid
CAS Registry Number506-17-2
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
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 effectNot Available
Disposition
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available174.946http://allccs.zhulab.cn/database/detail?ID=AllCCS00000268
Predicted Molecular Properties
PropertyValueSource
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
Polarizability37.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.10631661259
DarkChem[M-H]-178.52331661259
DeepCCS[M+H]+177.82330932474
DeepCCS[M-H]-173.80430932474
DeepCCS[M-2H]-210.9930932474
DeepCCS[M+Na]+186.88730932474
AllCCS[M+H]+179.632859911
AllCCS[M+H-H2O]+176.632859911
AllCCS[M+NH4]+182.332859911
AllCCS[M+Na]+183.132859911
AllCCS[M-H]-179.432859911
AllCCS[M+Na-2H]-181.032859911
AllCCS[M+HCOO]-182.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-Vaccenic acidCCCCCC\C=C/CCCCCCCCCC(O)=O3141.9Standard polar33892256
cis-Vaccenic acidCCCCCC\C=C/CCCCCCCCCC(O)=O2093.7Standard non polar33892256
cis-Vaccenic acidCCCCCC\C=C/CCCCCCCCCC(O)=O2152.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis-Vaccenic acid,1TMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C2218.9Semi standard non polar33892256
cis-Vaccenic acid,1TBDMS,isomer #1CCCCCC/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2477.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cis-Vaccenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9740000000-12d0456cbe2e20785a592017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Vaccenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9541000000-161e2d96dfa3731866552017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Vaccenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Vaccenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0apl-9200000000-f39f178414756ab6ad8a2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Vaccenic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0090000000-dee621bf09f57d88e5ed2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Vaccenic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9340000000-654e2ea72d5477e266062012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Vaccenic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0aou-9000000000-413d3363f22e7baf1df72012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Vaccenic acid LC-ESI-QFT , negative-QTOFsplash10-001i-0090000000-58579e8fd3d4191bcfad2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Vaccenic acid LC-ESI-QTOF 35V, negative-QTOFsplash10-001i-0090000000-c103acdc552ec63933b32020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Vaccenic acid n/a 19V, negative-QTOFsplash10-03di-0090000000-65d62db890dca1a5d6872020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - cis-Vaccenic acid 35V, Negative-QTOFsplash10-001i-0090000000-da9002214663921b23ee2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 10V, Positive-QTOFsplash10-00lr-0090000000-1f781254725896ac3b8d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 20V, Positive-QTOFsplash10-0079-5590000000-f37f297862ce49aba5692017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 40V, Positive-QTOFsplash10-006x-9830000000-9d6de2e63255b7b0f4352017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 10V, Negative-QTOFsplash10-001i-0090000000-431aee5e7f472babb97b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 20V, Negative-QTOFsplash10-001r-1090000000-0721ddce5ca61545b4dd2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-504045e17f7775e10a622017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 10V, Negative-QTOFsplash10-001i-0090000000-8b8562cadde7e7a8ba4f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 20V, Negative-QTOFsplash10-01q9-1090000000-827ccf4b0fb321cd543d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 40V, Negative-QTOFsplash10-0006-9220000000-9024da2ccb79132d937a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 10V, Positive-QTOFsplash10-00lr-4290000000-ef21daa5591bbeb17f872021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 20V, Positive-QTOFsplash10-067j-9310000000-8cc733ca58b618258ca02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenic acid 40V, Positive-QTOFsplash10-0aou-9000000000-60e1d3c5c8de0e9f209c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04801
Phenol Explorer Compound IDNot Available
FooDB IDFDB002952
KNApSAcK IDC00000347
Chemspider ID4445888
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282761
PDB IDNot Available
ChEBI ID50464
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available