Record Information
Version1.0
Creation date2010-04-08 22:05:57 UTC
Update date2019-11-26 02:59:34 UTC
Primary IDFDB003771
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGadoleic acid
DescriptionCis-gadoleic acid, also known as (Z)-eicos-9-enoic acid or 9c-eicosensaeure, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, cis-gadoleic acid is considered to be a fatty acid lipid molecule. Cis-gadoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-gadoleic acid can be found in a number of food items such as breakfast cereal, allium (onion), carrot, and sugar substitute, which makes cis-gadoleic acid a potential biomarker for the consumption of these food products. Cis-gadoleic acid can be found primarily in blood and feces.
CAS Number29204-02-2
Structure
Thumb
Synonyms
SynonymSource
(Z)-Eicos-9-enoic acidChEBI
9C-EicosensaeureChEBI
C20:1CChEBI
cis-9-Eicosenoic acidChEBI
cis-Delta(9)-Eicosenoic acidChEBI
Eicos-9C-enoic acidChEBI
Eicos-9C-ensaeureChEBI
(Z)-Eicos-9-enoateGenerator
cis-9-EicosenoateGenerator
cis-delta(9)-EicosenoateGenerator
cis-Δ(9)-eicosenoateGenerator
cis-Δ(9)-eicosenoic acidGenerator
Eicos-9C-enoateGenerator
9Z-EicosenoateGenerator
GadoleateHMDB
Gadoleic acidHMDB
FA(20:1(9Z))HMDB
cis-GadoleateHMDB
Predicted Properties
PropertyValueSource
Water Solubility4.9e-05 g/LALOGPS
logP8.41ALOGPS
logP7.67ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity96.6 m³·mol⁻¹ChemAxon
Polarizability41.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H38O2
IUPAC name(9Z)-icos-9-enoic acid
InChI IdentifierInChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-
InChI KeyLQJBNNIYVWPHFW-QXMHVHEDSA-N
Isomeric SMILES[H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(O)=O
Average Molecular Weight310.522
Monoisotopic Molecular Weight310.287180464
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGadoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-9770000000-8bafce752dcc0e83c211Spectrum
Predicted GC-MSGadoleic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00vi-9561000000-84617bccb2d2f0e64718Spectrum
Predicted GC-MSGadoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGadoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0197000000-f6093bc2d61dbe668e18Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxu-3591000000-835bb134b9d517428e95Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-8960000000-fa7ac5e35243596e982cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-053d5a3b1d592fd190c2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1079000000-323c653227521538a43cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-33c06ae5cc68dad15291Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-4297000000-a679e8ed0942db48f672Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-9572000000-31bd41e72217aeb75998Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9100000000-e4e0ee937a9dc02d22a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-0d96115f81e42756fc2fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1069000000-e54a7d130deccefa86bbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9020000000-c097ab1d18e1ea28f2f1Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGADOLEIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).