Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2015-07-20 21:49:46 UTC
Primary IDFDB002943
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGamolenic acid
DescriptionA minor component of many animal lipids Although GLA is an n?6 fatty acid, a type of acid which is generally pro-inflammatory, it has anti-inflammatory properties. (See discussion at Essential fatty acid interactions: The paradox of dietary GLA.); An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed) -- Pubchem; From GLA, the body forms dihomo-?-linolenic acid (DGLA). This is one of the body's three sources of eicosanoids (along with AA and EPA.) DGLA is the precursor of the prostaglandin PGH1, which in turn forms PGE1 and the thromboxane TXA1. PGE1 has a role in regulation of immune system function and is used as the medicine alprostadil. TXA1 modulates the pro-inflammatory properties of the thromboxane TXA2.; GLA is categorized as an n?6 (also called ??6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with n or ?) is the sixth bond. In physiological literature, GLA is designated as 18:3 (n?6). Chemically, GLA is a carboxylic acid with an 18-carbon chain and three cis double bonds. It is an isomer of ?-linolenic acid, which is the n?3 fatty acid found in flax seed.; The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by ?6-desaturase (D6D), an enzyme which allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states where there is excessive consumption of GLA metabolites.; ?-Linolenic acid (gamma-linolenic acid or GLA, sometimes called gamoleic acid) is a fatty acid found primarily in vegetable oils. It is sold as a dietary supplement for treating problems with inflammation and auto-immune diseases. The efficacy of such use is disputed.
CAS Number506-26-3
Structure
Thumb
Synonyms
SynonymSource
(6,9,12)-linolenatebiospider
(6,9,12)-linolenic acidbiospider
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acidbiospider
(6Z,9Z,12Z)-Octadecatrienoatebiospider
(6Z,9Z,12Z)-Octadecatrienoic acidbiospider
(Z,Z,Z)-6,9,12-Octadecatrienoatebiospider
(Z,Z,Z)-6,9,12-Octadecatrienoic acidbiospider
«gamma»-linolenic acidbiospider
18:3 (N-6)ChEBI
6-cis,9-cis,12-cis-OctadecatrienoateGenerator
6-cis,9-cis,12-cis-Octadecatrienoic acidbiospider
6,9,12-all-cis-Octadecatrienoatebiospider
6,9,12-all-cis-Octadecatrienoic acidbiospider
6,9,12-Octadecatrienoatebiospider
6,9,12-Octadecatrienoic acidbiospider
6,9,12-Octadecatrienoic acid, (6Z,9Z,12Z)-biospider
6,9,12-Octadecatrienoic acid, (Z,Z,Z)-biospider
6(Z),9(Z),12(Z)-Octadecatrienoatebiospider
6(Z),9(Z),12(Z)-Octadecatrienoic acidbiospider
6Z,9Z,12Z-octadecatrienoatebiospider
6Z,9Z,12Z-octadecatrienoic acidbiospider
Acido gamolenicobiospider
Acidum gamolenicumbiospider
all-cis-6,9,12-octadecatrienoatebiospider
all-cis-6,9,12-octadecatrienoic acidbiospider
C18:3 (N-6)ChEBI
C18:3, N-6,9,12 all-cisChEBI
cis-6, cis-9, cis-12-octadecatrienoic acidbiospider
cis-6,cis-9,cis-12-Octadecatrienoic acidbiospider
cis-Delta(6,9,12)-octadecatrienoatebiospider
cis-Delta(6,9,12)-octadecatrienoic acidbiospider
cis-δ(6,9,12)-octadecatrienoateGenerator
cis-δ(6,9,12)-octadecatrienoic acidGenerator
cis,cis,cis-6,9,12-Octadecatrienoic acidbiospider
Efamastbiospider
Efemastdb_source
Efomasedb_source
Epogamdb_source
g-LinolenateGenerator
g-Linolenic aciddb_source
g-LinolensaeureGenerator
Gamma-linolenatebiospider
Gamma-linolenic acidbiospider
gamma-LinolensaeureChEBI
Gamma-llnolenic acidbiospider
Gammalinolenic aciddb_source
Gammolindb_source
GamoleateGenerator
Gamoleic acidChEBI
GamolenateGenerator
Gamolenic acidbiospider
Gamolenic acid (inn)biospider
Gamolenic acid [inn:ban]biospider
Gamolenic acid, BAN, INNdb_source
GLAdb_source
Liglabiospider
Octadeca-6,9,12-triensaeureChEBI
Unigamdb_source
Viacutanbiospider
γ-linolenateGenerator
γ-linolenic acidGenerator
γ-linolensaeureGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.00025 g/LALOGPS
logP6.59ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability33.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H30O2
IUPAC name(6Z,9E,12Z)-octadeca-6,9,12-trienoic acid
InChI IdentifierInChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9+,13-12-
InChI KeyVZCCETWTMQHEPK-XQYVMNDBSA-N
Isomeric SMILESCCCCC\C=C/C\C=C\C\C=C/CCCCC(O)=O
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
Classification
DescriptionThis compound belongs to the class of chemical entities known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 77.65%; H 10.86%; O 11.49%DFC
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
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID4444436
ChEMBL IDCHEMBL464982
KEGG Compound IDC06426
Pubchem Compound ID5280933
Pubchem Substance IDNot Available
ChEBI ID28661
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03073
CRC / DFC (Dictionary of Food Compounds) IDCPL98-G:CPL99-H
EAFUS IDNot Available
Dr. Duke IDGAMMA-LINOLENIC-ACID
BIGG ID48234
KNApSAcK IDC00001226
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDgamma-Linolenic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
alpha-reductase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti aggregantDUKE
anti alcoholic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti asphycticDUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti eczemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hypercholesterolemicDUKE
anti menorrhagic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti monosodium-glutamateDUKE
anti obesity52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti premenstrual syndrome52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti prostatiticDUKE
anti Raynaud's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
hypocholesterolemicDUKE
hypotensiveDUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
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— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).