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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2019-03-14 18:02:29 UTC
HMDB IDHMDB0002231
Secondary Accession Numbers
  • HMDB02231
Metabolite Identification
Common Name11Z-Eicosenoic acid
Description11Z-Eicosenoic acid, also known as gondoic acid, 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. 11Z-Eicosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). More specifically, 11Z-Eicosenoic acid is a monounsaturated omega-9 fatty acid found in a variety of nuts and plant oils. It is not produced by humans and comes from the diet. It has been found in the red blood cell membrane with increased concentrations in children with regressive autism (PMID: 16581239 ).
Structure
Data?1550095304
Synonyms
ValueSource
(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
20:1(N-9)HMDB
20:1n9HMDB
cis-11-IcosenoateHMDB
cis-11-Icosenoic acidHMDB
FA(20:1(11Z))HMDB
11Z-Eicosenoic 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 Number5561-99-9
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 KeyBITHHVVYSMSWAG-KTKRTIGZSA-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 effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility5.0e-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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-c719ddc966597d00d2c5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-c719ddc966597d00d2c5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9450000000-350fb3d4ba5a967ba8b5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g70-9551000000-c82b71c168fb5563f7d4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0197000000-fa25affc2bb6f0cd695bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i03-4691000000-b79f41c0508982a46111JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9850000000-3d2cfec12ab1aec5686bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-c49b53bb3e3caf9cb042JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1079000000-9504027ae4d5b071c4a0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-7e3a558d23fc622e0aa2JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue Locations
  • Red Blood Cell
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.663 +/- 0.59 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.498 +/- 1.213 uMAdult (>18 years old)BothNormal details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected and Quantified11.722 +/- 5.378 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012569
KNApSAcK IDC00035628
Chemspider ID4445895
KEGG Compound IDC16526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEicosenoic acid
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. [PubMed: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. [PubMed:16237277 ]