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Record Information
Version3.6
Creation Date2006-05-22 14:17:43 UTC
Update Date2016-02-11 01:05:28 UTC
HMDB IDHMDB02231
Secondary Accession NumbersNone
Metabolite Identification
Common NameEicosenoic acid
DescriptionEicosenoic acid is an monounsaturated omega-9 fatty acid found in a variety of plant oils. It is also found in the red cell membrane with increased concentrations in children with regressive autism (16581239).
Structure
Thumb
Synonyms
ValueSource
(11Z)-Eicosenoic acidChEBI
(11Z)-Icosenoic acidChEBI
(Z)-Eicos-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
Eicosenoic acidChEBI
Z-Delta(11)-EicosensaeureChEBI
(11Z)-EicosenoateGenerator
(Z)-Icos-11-enoateGenerator
(11Z)-IcosenoateGenerator
(Z)-Eicos-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
EicosenoateGenerator
Z-δ(11)-eicosensaeureGenerator
(11Z)-Icos-11-enoateHMDB
(11Z)-Icos-11-enoic acidHMDB
11(Z)-EicosenoateHMDB
11(Z)-Eicosenoic acidHMDB
11-cis-EicosenoateHMDB
11-cis-Eicosenoic acidHMDB
11Z-EicosenoateHMDB
11Z-Eicosenoic acidHMDB
20:1(N-9)HMDB
20:1n9HMDB
cis-11-IcosenoateHMDB
cis-11-Icosenoic acidHMDB
cis-GondoateHMDB
cis-Gondoic acidHMDB
GondoateHMDB
Gondoic acidHMDB
Chemical FormulaC20H38O2
Average Molecular Weight310.5145
Monoisotopic Molecular Weight310.28718046
IUPAC Name(11Z)-icos-11-enoic acid
Traditional Namecis-11-eicosenoic acid
CAS Registry Number26764-41-0
SMILES
CCCCCCCC\C=C/CCCCCCCCCC(O)=O
InChI Identifier
InChI=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 KeyInChIKey=BITHHVVYSMSWAG-KTKRTIGZSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.95e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity96.6 m3·mol-1ChemAxon
Polarizability41.32 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
Tissue Location
  • Red Blood Cell
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.663 +/- 0.59 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.498 +/- 1.213 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012569
KNApSAcK IDC00035628
Chemspider ID4445895
KEGG Compound IDC16526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02231
Metagene LinkHMDB02231
METLIN ID6563
PubChem Compound5282768
PDB IDNot Available
ChEBI ID32425
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bu B, Ashwood P, Harvey D, King IB, Water JV, Jin LW: Fatty acid compositions of red blood cell phospholipids in children with autism. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):215-21. [16581239 ]
  2. Deshimaru R, Ishitani K, Makita K, Horiguchi F, Nozawa S: Analysis of fatty acid composition in human bone marrow aspirates. Keio J Med. 2005 Sep;54(3):150-5. [16237277 ]