Showing Compound Card for Cis-Vaccenic acid (CDB000377)

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Record Information
Version1.0
Created at2020-03-19 00:33:50 UTC
Updated at2020-11-18 16:35:07 UTC
CannabisDB IDCDB000377
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCis-Vaccenic acid
DescriptionCis-Vaccenic acid, (11Z)-11-octadecenoic acid, 18:1 cis-11, also known as vaccenate or asclepic acid, is an isomer of vaccenic acid. It 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-Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cis-Vaccenic acid, an omega-7 fatty acid, is a naturally occurring trans fatty acid found in Sea Buckthorn (Hippophae rhamnoides) oil. Vaccenic acid was first discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid. In a study of chemically induced mammary carcinogenesis in rats, vaccenic acid, when converted to cis-9, trans-11 conjugated linoleic acid (CLA) by delta 9-desaturase, had anticarcinogenic properties (PMID: 15465769 ). Cis-Vaccenic acid is one of several unsaturated fatty acid that are found in the essential oil of cannabis seed (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight282.46
Monoisotopic Molecular Weight282.2559
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
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted 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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0apl-9200000000-f39f178414756ab6ad8a2015-03-01View Spectrum
Predicted GC-MSCis-Vaccenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9740000000-12d0456cbe2e20785a59Spectrum
Predicted GC-MSCis-Vaccenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00g0-9541000000-161e2d96dfa373186655Spectrum
Predicted GC-MSCis-Vaccenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCis-Vaccenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0090000000-dee621bf09f57d88e5ed2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9340000000-654e2ea72d5477e266062012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aou-9000000000-413d3363f22e7baf1df72012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0090000000-58579e8fd3d4191bcfad2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-001i-0090000000-c103acdc552ec63933b32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, negativesplash10-03di-0090000000-65d62db890dca1a5d6872020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0090000000-da9002214663921b23ee2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-1f781254725896ac3b8d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-5590000000-f37f297862ce49aba5692017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9830000000-9d6de2e63255b7b0f4352017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-431aee5e7f472babb97b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-0721ddce5ca61545b4dd2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-504045e17f7775e10a622017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-8b8562cadde7e7a8ba4f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1090000000-827ccf4b0fb321cd543d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-9024da2ccb79132d937a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-4290000000-ef21daa5591bbeb17f872021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067j-9310000000-8cc733ca58b618258ca02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9000000000-60e1d3c5c8de0e9f209c2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0240219
DrugBank IDDB04801
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C: The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats. J Nutr. 2004 Oct;134(10):2698-704. doi: 10.1093/jn/134.10.2698. [PubMed:15465769 ]