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Record Information
Version1.0
Created at2006-05-22 15:12:20 UTC
Updated at2021-08-19 23:58:50 UTC
NP-MRD IDNP0001142
Secondary Accession NumbersNone
Natural Product 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
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 Mass306.4828 Da
Monoisotopic Mass306.25588 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ailuropoda melanoleucaLOTUS Database
Eurhynchium striatumLOTUS Database
Homo sapiensLOTUS Database
Myuroclada maximowicziiLOTUS Database
Sargassum pallidumLOTUS Database
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 Solubility0.0024 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
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
Polarizability39.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002925
DrugBank IDDB00154
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112210
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
Good Scents IDrw1230471
References
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:2550526 ]