di-homo-γ-linolenate (PAMDB120015)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120015
Identification
Name: di-homo-γ-linolenate
Description:An unsaturated fatty acid anion that is the conjugate base of all-cis-icosa-8,11,14-trienoic acid arising from deprotonation of the carboxy group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (8Z,11Z,14Z)-eicosa-8,11,14-trienoate
  • (8Z,11Z,14Z)-eicosatrienoate
  • (8Z,11Z,14Z)-eicosatrienoate
  • (8Z,11Z,14Z)-icosatrienoate
  • (Z,Z,Z)-eicosa-8,11,14-trienoate
  • (Z,Z,Z)-icosa-8,11,14-trienoate
  • all-cis-8,11,14-eicosatrienoate
  • all-cis-8,11,14-icosatrienoate
  • dihomo-γ-linolenate
Chemical Formula: C20H33O2
Average Molecular Weight: 305.479
Monoisotopic Molecular Weight: 306.2559
InChI Key: HOBAELRKJCKHQD-QNEBEIHSSA-M
InChI: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)/p-1/b7-6-,10-9-,13-12-
CAS number: 1783-84-2
IUPAC Name:(8Z,11Z,14Z)-icosa-8,11,14-trienoate
Traditional IUPAC Name: dihomo-gamma-linolenic acid
SMILES:CCCCCC=CCC=CCC=CCCCCCCC(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent Long-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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
dihomo γ-linolenoyl-CoA + Water → di-homo-γ-linolenate + coenzyme A + Hydrogen ion
Pathways:
  • Alpha Linolenic Acid and Linoleic Acid Metabolism pae00592
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
References
References:
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
HMDBHMDB02925
CHEBI71589
CHEMSPIDER20117973
PUBCHEM21158448
LIGAND-CPDC03242