You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 23:02:10 UTC
Update Date2020-06-04 20:33:32 UTC
BMDB IDBMDB0002925
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
Synonyms
ValueSource
(8Z,11Z,14Z)-Icosatrienoic acidChEBI
(Z,Z,Z)-8,11,14-Eicosatrienoic acidChEBI
(Z,Z,Z)-8,11,14-IcosatrienoateChEBI
(Z,Z,Z)-8,11,14-Icosatrienoic acidChEBI
20:3, N-6,9,12 all-cisChEBI
8,11,14-Eicosatrienoic acidChEBI
8C,11C,14C-Eicosatrienoic acidChEBI
8C,11C,14C-EicosatriensaeureChEBI
8Z,11Z,14Z-Eicosatrienoic acidChEBI
all-cis-8,11,14-Eicosatrienoic acidChEBI
all-cis-8,11,14-Icosatrienoic acidChEBI
all-cis-Eicosa-8,11,14-trienoic acidChEBI
all-cis-Eicosa-8,11,14-triensaeureChEBI
C20:3, N-6,9,12 all-cisChEBI
cis,cis,cis-8,11,14-Eicosatrienoic acidChEBI
DGLAChEBI
Eicosa-8Z,11Z,14Z-trienoic acidChEBI
gamma-Homolinolenic acidChEBI
Homo-gamma-linolenic acidChEBI
Homo-gamma-linolensaeureChEBI
(Z,Z,Z)-8,11,14-EicosatrienoateKegg
8,11,14-EicosatrienoateKegg
8,11,14-IcosatrienoateKegg
(8Z,11Z,14Z)-Icosa-8,11,14-trienoic acidKegg
(8Z,11Z,14Z)-IcosatrienoateGenerator
8C,11C,14C-EicosatrienoateGenerator
8Z,11Z,14Z-EicosatrienoateGenerator
all-cis-8,11,14-EicosatrienoateGenerator
all-cis-8,11,14-IcosatrienoateGenerator
all-cis-Eicosa-8,11,14-trienoateGenerator
cis,cis,cis-8,11,14-EicosatrienoateGenerator
Eicosa-8Z,11Z,14Z-trienoateGenerator
g-HomolinolenateGenerator
g-Homolinolenic acidGenerator
gamma-HomolinolenateGenerator
Γ-homolinolenateGenerator
Γ-homolinolenic acidGenerator
Homo-g-linolenateGenerator
Homo-g-linolenic acidGenerator
Homo-gamma-linolenateGenerator
Homo-γ-linolenateGenerator
Homo-γ-linolenic acidGenerator
Homo-g-linolensaeureGenerator
Homo-γ-linolensaeureGenerator
8,11,14-Icosatrienoic acidGenerator
(8Z,11Z,14Z)-Icosa-8,11,14-trienoateGenerator
Dihomo-g-linolenateGenerator
Dihomo-g-linolenic acidGenerator
Dihomo-gamma-linolenateGenerator
Dihomo-γ-linolenateGenerator
Dihomo-γ-linolenic acidGenerator
Dihomogammalinolenic acidHMDB
Dihomo gamma linolenic acidHMDB
Homo-gamma linolenic acidHMDB
Homo gamma linolenic acidHMDB
Linolenic acid, homo-gammaHMDB
8,11,14 Eicosatrienoic acidHMDB
(Z,Z,Z)-Icosatri-8,11,14-enoateHMDB
(Z,Z,Z)-Icosatri-8,11,14-enoic acidHMDB
8,11,14-all-cis-EicosatrienoateHMDB
8,11,14-all-cis-Eicosatrienoic acidHMDB
Bishomo-gamma-linolenateHMDB
Bishomo-gamma-linolenic acidHMDB
cis-8,11,14-EicosatrienoateHMDB
cis-8,11,14-Eicosatrienoic acidHMDB
cis-8,cis-11,cis-14-EicosatrienoateHMDB
cis-8,cis-11,cis-14-Eicosatrienoic acidHMDB
EicosatrienoateHMDB
Eicosatrienoic acidHMDB
Acid, dihomo-gamma-linolenicHMDB
DHLAHMDB
Acid, dihomogammalinolenicHMDB
Acid, homo-gamma linolenicHMDB
DihomolinolenateHMDB
Dihomolinolenic acidHMDB
FA(20:3(8Z,11Z,14Z))HMDB
Dihomo-linolenateHMDB
Dihomo-linolenic acidHMDB
FA(20:3n6)HMDB
dihomo-gamma-Linolenic acidChEBI
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9570000000-cd036d3430a12b16dfb6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-022i-9542000000-c2f35f73d1bcbb0128a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0019000000-38de24f5141b8fd24471View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066v-9700000000-ea3e83fc76a5e8bf96a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0k96-9200000000-2b1245d775cb6a9290a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0090000000-8151054828665541898dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-05e9-0491000000-a09d13fe83820b375121View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-052e-0692000000-aba537ad7f934032649fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0196000000-0cb348afdbc2bfa250adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5891000000-413e3aa407f0e1cb6465View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9760000000-b7aed55f7d8853fa6cf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-d1aef216444b744a8339View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1079000000-1eb636eb88d281beeffeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-c1354a863e0181f2b709View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Epidermis
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified2577.631 +/- 619.937 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified2447.118 +/- 522.0518 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002925
DrugBank IDDB00154
Phenol Explorer Compound IDNot Available
FooDB 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)Not Available
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.

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Acts as a fatty acyl-coenzyme A (CoA) desaturase that introduces a cis double bond at carbon 6 of the fatty acyl chain. Involved in biosynthesis of highly unsaturated fatty acids (HUFA) from the essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) and alpha-linolenic acid (ALA) (18:3n-3) precursors. Catalyzes the first and rate limiting step in this pathway which is the desaturation of LA (18:2n-6) and ALA (18:3n-3) into gamma-linoleate (GLA) (18:3n-6) and stearidonate (18:4n-3), respectively (By similarity). Subsequently, in the biosynthetic pathway of HUFA n-3 series, desaturates tetracosapentaenoate (24:5n-3) to tetracosahexaenoate (24:6n-3), which is then converted to docosahexaenoate (DHA)(22:6n-3), an important lipid for nervous system function (By similarity). Desaturates palmitate to produce the mono-unsaturated fatty acid sapienate, the most abundant fatty acid in sebum (By similarity). Also desaturates (11E)-octadecenoate (trans-vaccenoate)(18:1n-9), a metabolite in the biohydrogenation pathway of LA (18:2n-6) (By similarity).
Gene Name:
FADS2
Uniprot ID:
A4FV48
Molecular weight:
52533.0
Reactions
8,11,14-Eicosatrienoic acid → Arachidonic aciddetails
General function:
Not Available
Specific function:
Catalyzes the first and rate-limiting reaction of the four reactions that constitute the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process allows the addition of 2 carbons to the chain of long- and very long-chain fatty acids (VLCFAs) per cycle. Condensing enzyme that acts specifically toward polyunsaturated acyl-CoA with the higher activity toward C18:3(n-6) acyl-CoA. May participate in the production of monounsaturated and of polyunsaturated VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators (By similarity). In conditions where the essential linoleic and alpha linoleic fatty acids are lacking it is also involved in the synthesis of Mead acid from oleic acid (By similarity).
Gene Name:
ELOVL5
Uniprot ID:
Q2KJD9
Molecular weight:
35377.0
Reactions
Gamma-Linolenic acid → 8,11,14-Eicosatrienoic aciddetails