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Record Information
Version3.6
Creation Date2006-05-22 15:12:20 UTC
Update Date2016-02-11 01:05:53 UTC
HMDB IDHMDB02925
Secondary Accession Numbers
  • HMDB06735
Metabolite Identification
Common 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.
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
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
dihomo-gamma-Linolenic acidChEBI
Eicosa-8Z,11Z,14Z-trienoic acidChEBI
gamma-Homolinolenic acidChEBI
homo-gamma-Linolenic acidChEBI
homo-gamma-LinolensaeureChEBI
(8Z,11Z,14Z)-IcosatrienoateGenerator
8,11,14-EicosatrienoateGenerator
(Z,Z,Z)-8,11,14-EicosatrienoateGenerator
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
dihomo-g-LinolenateGenerator
dihomo-g-Linolenic acidGenerator
dihomo-gamma-LinolenateGenerator
dihomo-γ-linolenateGenerator
dihomo-γ-linolenic acidGenerator
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
(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
8,11,14-IcosatrienoateHMDB
8,11,14-Icosatrienoic 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
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 KeyInChIKey=HOBAELRKJCKHQD-QNEBEIHSSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
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 Solubility7.71e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.84 m3·mol-1ChemAxon
Polarizability39.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Epidermis
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.542 +/- 0.005 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.61 +/- 2.1 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.420 +/- 0.207 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.005 +/- 16.600 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023082
KNApSAcK IDNot Available
Chemspider ID4444199
KEGG Compound IDC03242
BioCyc IDCPD-7196
BiGG ID41475
Wikipedia LinkDGLA
NuGOwiki LinkHMDB02925
Metagene LinkHMDB02925
METLIN ID259
PubChem Compound5280581
PDB IDLAX
ChEBI ID53486
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Abraham RD, Riemersma RA, Elton RA, Macintyre C, Oliver MF: Effects of safflower oil and evening primrose oil in men with a low dihomo-gamma-linolenic level. Atherosclerosis. 1990 Apr;81(3):199-208. [2112389 ]
  2. Du L, Yermalitsky V, Hachey DL, Jagadeesh SG, Falck JR, Keeney DS: A biosynthetic pathway generating 12-hydroxy-5,8,14-eicosatrienoic acid from arachidonic acid is active in mouse skin microsomes. J Pharmacol Exp Ther. 2006 Jan;316(1):371-9. Epub 2005 Sep 16. [16169934 ]
  3. Hamilton RM, Gillespie CT, Cook HW: Relationships between levels of essential fatty acids and zinc in plasma of cystic fibrosis patients. Lipids. 1981 May;16(5):374-6. [6789026 ]
  4. Thijs C, Houwelingen A, Poorterman I, Mordant A, van den Brandt P: Essential fatty acids in breast milk of atopic mothers: comparison with non-atopic mothers, and effect of borage oil supplementation. Eur J Clin Nutr. 2000 Mar;54(3):234-8. [10713746 ]
  5. Emken EA, Adlof RO, Duval SM, Nelson GJ: Influence of dietary arachidonic acid on metabolism in vivo of 8cis,11cis,14-eicosatrienoic acid in humans. Lipids. 1997 Apr;32(4):441-8. [9113634 ]
  6. Melnik BC, Plewig G: Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? J Am Acad Dermatol. 1989 Sep;21(3 Pt 1):557-63. [2550526 ]

Enzymes

General function:
Involved in thiolester hydrolase activity
Specific function:
Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:
BAAT
Uniprot ID:
Q14032
Molecular weight:
46298.865
General function:
Lipid transport and metabolism
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:
ACOT7
Uniprot ID:
O00154
Molecular weight:
40454.945
Reactions
Dihomo-gamma-linolenyl coenzyme A + Water → Coenzyme A + 8,11,14-Eicosatrienoic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:
ACOT2
Uniprot ID:
P49753
Molecular weight:
53218.02
Reactions
Dihomo-gamma-linolenyl coenzyme A + Water → Coenzyme A + 8,11,14-Eicosatrienoic aciddetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Molecular weight:
46326.09
Reactions
Dihomo-gamma-linolenyl coenzyme A + Water → Coenzyme A + 8,11,14-Eicosatrienoic aciddetails
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:
ACOT8
Uniprot ID:
O14734
Molecular weight:
35914.02
General function:
Involved in thiolester hydrolase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:
ACOT1
Uniprot ID:
Q86TX2
Molecular weight:
46276.96
Reactions
Dihomo-gamma-linolenyl coenzyme A + Water → Coenzyme A + 8,11,14-Eicosatrienoic aciddetails