Showing metabocard for Eicosadienoic acid (BMDB0005060)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:08 UTC
Update Date2020-06-04 20:33:30 UTC
BMDB IDBMDB0005060
Secondary Accession Numbers
  • BMDB05060
Metabolite Identification
Common NameEicosadienoic acid
DescriptionEicosadienoic acid, also known as 11,14-eicosadienoate or delta11,14-20:2, 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. Eicosadienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Eicosadienoic acid has been found to be associated with the diseases known as colorectal cancer; also eicosadienoic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(11Z,14Z)-Eicosa-11,14-dienoic acidChEBI
(11Z,14Z)-Eicosadienoic acidChEBI
(11Z,14Z)-Icosa-11,14-dienoic acidChEBI
11,14-Eicosadienoic acidChEBI
11,14-Icosadienoic acidChEBI
(11Z,14Z)-Eicosa-11,14-dienoateGenerator
(11Z,14Z)-EicosadienoateGenerator
(11Z,14Z)-Icosa-11,14-dienoateGenerator
11,14-EicosadienoateGenerator
11,14-IcosadienoateGenerator
EicosadienoateGenerator
11, 14-IcosadienoateHMDB
11, 14-Icosadienoic acidHMDB
11,14-trans-Eicosadienoic acidHMDB
delta11,14-20:2HMDB
Eicosa-11,14-dienoic acidHMDB
Eicosa-11,14-dienoic acid, (Z,Z)-isomerHMDB
N-6 Eicosadienoic acidHMDB
DihomolinoleateHMDB
(11Z,14Z)-IcosadienoateHMDB
(11Z,14Z)-11,14-EicosadienateHMDB
(11Z,14Z)-11,14-Eicosadienic acidHMDB
(11Z,14Z)-11,14-EicosadienoateHMDB
(11Z,14Z)-11,14-Eicosadienoic acidHMDB
11,14-all-cis-EicosadienoateHMDB
11,14-all-cis-Eicosadienoic acidHMDB
11-cis,14-cis-EicosadienoateHMDB
11-cis,14-cis-Eicosadienoic acidHMDB
BishomolinoleateHMDB
Bishomolinoleic acidHMDB
Dihomo-linoleate (20:2n6)HMDB
Dihomo-linoleic acid (20:2n6)HMDB
FA(20:2(11Z,14Z))HMDB
Homo-gamma-linoleateHMDB
Homo-gamma-linoleic acidHMDB
Homo-γ-linoleateHMDB
Homo-γ-linoleic acidHMDB
all-cis-11,14-EicosadienoateHMDB
all-cis-11,14-Eicosadienoic acidHMDB
cis,cis-Eicosa-11,14-dienoateHMDB
cis,cis-Eicosa-11,14-dienoic acidHMDB
cis,cis-delta11,14-EicosadienoateHMDB
cis,cis-delta11,14-Eicosadienoic acidHMDB
cis,cis-Δ11,14-eicosadienoateHMDB
cis,cis-Δ11,14-eicosadienoic acidHMDB
cis-11,cis-14-EicosadienoateHMDB
cis-11,cis-14-Eicosadienoic acidHMDB
delta11,14-EicosadienoateHMDB
delta11,14-Eicosadienoic acidHMDB
Δ11,14-eicosadienoateHMDB
Δ11,14-eicosadienoic acidHMDB
FA(20:2n6)HMDB
Eicosadienoic acidChEBI
Chemical FormulaC20H36O2
Average Molecular Weight308.4986
Monoisotopic Molecular Weight308.271530396
IUPAC Name(11Z,14Z)-icosa-11,14-dienoic acid
Traditional Nameeicosadienoic acid
CAS Registry Number2091-39-6
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9-
InChI KeyXSXIVVZCUAHUJO-HZJYTTRNSA-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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.251Not Available
Predicted Properties
PropertyValueSource
logP7.83ALOGPS
logP7.31ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity97.72 m³·mol⁻¹ChemAxon
Polarizability39.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Milk
  • Oocyte
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected and Quantified2560.786 +/- 615.885 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
 details
MilkDetected and Quantified2431.126 +/- 518.640 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
 details
OocyteDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005060
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012619
KNApSAcK IDNot Available
Chemspider ID4944228
KEGG Compound IDC16525
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6439848
PDB IDNot Available
ChEBI ID73731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  2. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  4. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.