Showing metabocard for 8,11,14-Eicosatrienoic acid (BMDB0002925)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
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Record Information
Version1.0
Creation Date2016-09-30 23:02:10 UTC
Update Date2020-06-04 20:33:32 UTC
MCDB ID BMDB0002925
Secondary Accession Numbers
  • BMDB02925
Metabolite Identification
Common Name8,11,14-Eicosatrienoic acid
Description8,11,14-Eicosatrienoic acid, also known as (Z,Z,Z)-8,11,14-icosatrienoate or dihomo-gamma-linolenic acid, 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. 8,11,14-Eicosatrienoic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. 8,11,14-Eicosatrienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 8,11,14-Eicosatrienoic acid participates in a number of enzymatic reactions, within cattle. In particular, 8,11,14-Eicosatrienoic acid can be biosynthesized from Gamma-linolenic acid through its interaction with the enzyme elongation OF very long chain fatty acids protein 5. In addition, 8,11,14-Eicosatrienoic acid can be converted into arachidonic acid; which is mediated by the enzyme fatty acid desaturase 1. In cattle, 8,11,14-eicosatrienoic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. 8,11,14-Eicosatrienoic acid has been found to be associated with the diseases known as colorectal cancer; also 8,11,14-eicosatrienoic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC20H34O2
Average Molecular Weight306.4828
Monoisotopic Molecular Weight306.255880332
IUPAC Name(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
Traditional Namedihomo-gamma-linolenic acid
CAS Registry Number1783-84-2
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
InChI KeyHOBAELRKJCKHQD-QNEBEIHSSA-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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.24ALOGPS
logP6.95ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.84 m³·mol⁻¹ChemAxon
Polarizability39.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Concentrations
StatusValueReferenceDetails
Detected and Quantified2577 +/- 619 uMTotal fatty acid
  • M. Ferrand et al....
 details
Detected and Quantified2447 +/- 522 uMTotal fatty acid
  • M. Ferrand et al....
 details
HMDB IDHMDB0002925
DrugBank IDDB00154
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023082
KNApSAcK IDNot Available
Chemspider ID4444199
KEGG Compound IDC03242
BioCyc IDNot Available
BiGG ID41475
Wikipedia LinkDihomo-γ-linolenic acid
METLIN ID259
PubChem Compound5280581
PDB IDNot Available
ChEBI ID53486
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
  2. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
  3. 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 ]
  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.