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Record Information
Version1.0
Creation date2011-09-21 00:24:24 UTC
Update date2019-11-26 03:21:07 UTC
Primary IDFDB023082
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8,11,14-Eicosatrienoic acid
Description8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids [HMDB]
CAS Number1783-84-2
Structure
Thumb
Synonyms
SynonymSource
8,11,14-EicosatrienoateGenerator
(8Z,11Z,14Z)-Icosatrienoatehmdb
(8Z,11Z,14Z)-Icosatrienoic acidhmdb
(Z,Z,Z)-8,11,14-Eicosatrienoatehmdb
(Z,Z,Z)-8,11,14-Eicosatrienoic acidhmdb
(Z,Z,Z)-8,11,14-Icosatrienoatehmdb
(Z,Z,Z)-8,11,14-Icosatrienoic acidhmdb
(Z,Z,Z)-icosatri-8,11,14-enoatehmdb
(Z,Z,Z)-icosatri-8,11,14-enoic acidhmdb
20:3, N-6,9,12 all-cisChEBI
8,11,14-all-cis-Eicosatrienoatehmdb
8,11,14-all-cis-Eicosatrienoic acidhmdb
8,11,14-Eicosatrienoic acidhmdb
8,11,14-Icosatrienoatehmdb
8,11,14-Icosatrienoic acidhmdb
8c,11c,14c-EicosatrienoateGenerator
8c,11c,14c-Eicosatrienoic acidChEBI
8c,11c,14c-EicosatriensaeureChEBI
8Z,11Z,14Z-eicosatrienoatehmdb
8Z,11Z,14Z-eicosatrienoic acidhmdb
all-cis-8,11,14-Eicosatrienoatehmdb
all-cis-8,11,14-Eicosatrienoic acidhmdb
all-cis-8,11,14-IcosatrienoateGenerator
all-cis-8,11,14-Icosatrienoic acidChEBI
all-cis-Eicosa-8,11,14-trienoateGenerator
all-cis-Eicosa-8,11,14-trienoic acidChEBI
all-cis-Eicosa-8,11,14-triensaeureChEBI
Bishomo-gamma-linolenatehmdb
Bishomo-gamma-linolenic acidhmdb
C20:3, N-6,9,12 all-cisChEBI
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
cis,cis,cis-8,11,14-Eicosatrienoatehmdb
cis,cis,cis-8,11,14-Eicosatrienoic acidhmdb
DGLAhmdb
Dihomo-g-linolenateGenerator
Dihomo-g-linolenic acidGenerator
Dihomo-gamma-linolenatehmdb
Dihomo-gamma-linolenic acidhmdb
Dihomo-γ-linolenateGenerator
Dihomo-γ-linolenic acidGenerator
Eicosa-8Z,11Z,14Z-trienoateGenerator
Eicosa-8Z,11Z,14Z-trienoic acidChEBI
Eicosatrienoatehmdb
Eicosatrienoic acidhmdb
g-HomolinolenateGenerator
g-Homolinolenic acidGenerator
gamma-Homolinolenatehmdb
gamma-Homolinolenic acidhmdb
Homo-g-linolenateGenerator
Homo-g-linolenic acidGenerator
Homo-g-linolensaeureGenerator
Homo-gamma-linolenatehmdb
Homo-gamma-linolenic acidChEBI
Homo-gamma-linolensaeureChEBI
Homo-γ-linolenateGenerator
Homo-γ-linolenic acidGenerator
Homo-γ-linolensaeureGenerator
γ-homolinolenateGenerator
γ-homolinolenic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility7.7e-05 g/LALOGPS
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
Polarizability38.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H34O2
IUPAC nameicosa-8,11,14-trienoic acid
InChI IdentifierInChI=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)
InChI KeyHOBAELRKJCKHQD-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=CCC=CCC=CCCCCCCC(O)=O
Average Molecular Weight306.4828
Monoisotopic Molecular Weight306.255880332
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4444199
ChEMBL IDCHEMBL465183
KEGG Compound IDC03242
Pubchem Compound ID5280581
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00154
HMDB IDHMDB02925
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID41475
KNApSAcK IDNot Available
HET IDLAX
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDGLA
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018 map00592
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference