Record Information
Version1.0
Creation date2010-04-08 22:10:14 UTC
Update date2020-09-17 15:41:30 UTC
Primary IDFDB012569
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGondoic acid
DescriptionEicosenoic acid C20:1, a monounsaturated fatty acid that exists in three different forms: 9-eicosenoic acid (gadoleic acid), an omega-11 fatty acid common in fish oils, 11-eicosenoic acid (gondoic acid), an omega-9 fatty acid characteristic of jojoba oil, and 13-eicosenoic acid (paullinic acid), an omega-7 fatty acid. Also, eicosenoic acid C20:1 is one of the fatty acids that have been identified in hemp (cannabis) seed oil (PMID: 28448475).
CAS Number26764-41-0
Structure
Thumb
Synonyms
SynonymSource
(11Z)-Eicosenoic acidChEBI
(11Z)-Icosenoic acidChEBI
(Z)-Eicos-11-enoic acidChEBI
(Z)-Icos-11-enoic acidChEBI
(Z)-Icosa-11-enoic acidChEBI
11-Eicosenoic acidChEBI
11-Icosenoic acidChEBI
20:1ChEBI
cis-11-Eicosenoic acidChEBI
cis-Delta(11)-Eicosenoic acidChEBI
cis-Gondoic acidChEBI
Eicosenoic acidChEBI
Gondoic acidChEBI
Z-Delta(11)-EicosensaeureChEBI
(11Z)-EicosenoateGenerator
(11Z)-IcosenoateGenerator
(Z)-Eicos-11-enoateGenerator
(Z)-Icos-11-enoateGenerator
(Z)-Icosa-11-enoateGenerator
11-EicosenoateGenerator
11-IcosenoateGenerator
cis-11-EicosenoateGenerator
cis-delta(11)-EicosenoateGenerator
cis-Δ(11)-eicosenoateGenerator
cis-Δ(11)-eicosenoic acidGenerator
cis-GondoateGenerator
EicosenoateGenerator
GondoateGenerator
Z-Δ(11)-eicosensaeureGenerator
11Z-EicosenoateGenerator
(11Z)-Icos-11-enoateHMDB
(11Z)-Icos-11-enoic acidHMDB
11(Z)-EicosenoateHMDB
11(Z)-Eicosenoic acidHMDB
11-cis-EicosenoateHMDB
11-cis-Eicosenoic acidHMDB
11Z-Eicosenoic acidHMDB
20:1(N-9)HMDB
20:1n9HMDB
cis-11-IcosenoateHMDB
cis-11-Icosenoic acidHMDB
FA(20:1(11Z))HMDB
FA(20:1n9)HMDB
(11Z)-11-Eicosenoic acidPhytoBank
(Z)-11-Eicosenoic acidPhytoBank
cis-delta11-Eicosenoic acidPhytoBank
cis-Δ11-Eicosenoic acidPhytoBank
(Z)-11-Eicosenic acidbiospider
20:1N9HMDB
cis-δ(11)-eicosenoateGenerator
cis-δ(11)-eicosenoic acidGenerator
Icosenoic acidmanual
Z-δ(11)-eicosensaeureGenerator
Predicted Properties
PropertyValueSource
Water Solubility4.9e-05 g/LALOGPS
logP8.4ALOGPS
logP7.67ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
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(11Z)-icos-11-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/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9-
InChI KeyBITHHVVYSMSWAG-KTKRTIGZSA-N
Isomeric SMILESCCCCCCCC\C=C/CCCCCCCCCC(O)=O
Average Molecular Weight310.5145
Monoisotopic Molecular Weight310.28718046
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 77.36%; H 12.33%; O 10.30%DFC
Melting PointMp 24-25°DFC
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
GC-MSGondoic acid, non-derivatized, GC-MS Spectrumsplash10-00mk-3900000000-c719ddc966597d00d2c5Spectrum
GC-MSGondoic acid, non-derivatized, GC-MS Spectrumsplash10-00mk-3900000000-c719ddc966597d00d2c5Spectrum
Predicted GC-MSGondoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9450000000-350fb3d4ba5a967ba8b5Spectrum
Predicted GC-MSGondoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g70-9551000000-c82b71c168fb5563f7d4Spectrum
Predicted GC-MSGondoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGondoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGondoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGondoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0006-0090000000-1756232c26bf8fc138c5Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0290000000-fa5d9f6e60781ae83e2eSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0006-5490000000-0cbb37e5b7ecad5adaaaSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-000y-9650000000-ba5e2b939e8a556b6d1fSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-00l2-9410000000-9496a07390108fe35cabSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-05nb-9300000000-b3b200aebba967262b9bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-067j-9200000000-91f2ccafad22a2bb8069Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-067j-9100000000-dbb0d513ad4f77e24d3cSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 26V, positivesplash10-067i-9000000000-1b21d5d4d80742618d4cSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-067i-9000000000-d00f7dd8a36d506bf1b5Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 39V, positivesplash10-0aor-9000000000-de7f5670d39d685918e0Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 47V, positivesplash10-0ar0-9000000000-509d8fad571b85568099Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-004i-2890000000-dcdc3d85495da91cc6dbSpectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-070e-1920000000-1c2aeaf08cc4ea4f0540Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0197000000-fa25affc2bb6f0cd695bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i03-4691000000-b79f41c0508982a46111Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9850000000-3d2cfec12ab1aec5686bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-c49b53bb3e3caf9cb042Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1079000000-9504027ae4d5b071c4a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-7e3a558d23fc622e0aa2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-0d96115f81e42756fc2fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1059000000-4c31464e6f8ead1139f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9020000000-90362612fe130589b56dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5397000000-d942974f980afe9a14c5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btc-9561000000-bf355ad19adfba5af8dfSpectrum
NMRNot Available
ChemSpider ID4445895
ChEMBL IDNot Available
KEGG Compound IDC16526
Pubchem Compound ID5282768
Pubchem Substance IDNot Available
ChEBI ID32425
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02231
CRC / DFC (Dictionary of Food Compounds) IDHJM00-P:HJB52-D
EAFUS IDNot Available
Dr. Duke IDEICOSENOIC-ACID
BIGG IDNot Available
KNApSAcK IDC00035628
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEicosenoic_acid
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).