Showing Compound Gamolenic acid (FDB002943)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:35 UTC

Update date

2019-11-26 02:58:12 UTC

Primary ID

FDB002943

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Gamolenic acid

Description

A 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 Number

506-26-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Gamolenate	Generator
(6,9,12)-linolenate	biospider
(6,9,12)-linolenic acid	biospider
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid	biospider
(6Z,9Z,12Z)-Octadecatrienoate	biospider
(6Z,9Z,12Z)-Octadecatrienoic acid	biospider
(Z,Z,Z)-6,9,12-Octadecatrienoate	biospider
(Z,Z,Z)-6,9,12-Octadecatrienoic acid	biospider
«gamma»-linolenic acid	biospider
18:3 (N-6)	ChEBI
6-cis,9-cis,12-cis-Octadecatrienoate	Generator
6-cis,9-cis,12-cis-Octadecatrienoic acid	biospider
6,9,12-all-cis-Octadecatrienoate	biospider
6,9,12-all-cis-Octadecatrienoic acid	biospider
6,9,12-Octadecatrienoate	biospider
6,9,12-Octadecatrienoic acid	biospider
6,9,12-Octadecatrienoic acid, (6Z,9Z,12Z)-	biospider
6,9,12-Octadecatrienoic acid, (Z,Z,Z)-	biospider
6(Z),9(Z),12(Z)-Octadecatrienoate	biospider
6(Z),9(Z),12(Z)-Octadecatrienoic acid	biospider
6Z,9Z,12Z-octadecatrienoate	biospider
6Z,9Z,12Z-octadecatrienoic acid	biospider
Acido gamolenico	biospider
Acidum gamolenicum	biospider
all-cis-6,9,12-octadecatrienoate	biospider
all-cis-6,9,12-octadecatrienoic acid	biospider
C18:3 (N-6)	ChEBI
C18:3, N-6,9,12 all-cis	ChEBI
cis-6, cis-9, cis-12-octadecatrienoic acid	biospider
cis-6,cis-9,cis-12-Octadecatrienoic acid	biospider
cis-Delta(6,9,12)-octadecatrienoate	biospider
cis-Delta(6,9,12)-octadecatrienoic acid	biospider
cis-δ(6,9,12)-octadecatrienoate	Generator
cis-δ(6,9,12)-octadecatrienoic acid	Generator
cis,cis,cis-6,9,12-Octadecatrienoic acid	biospider
Efamast	biospider
Efemast	db_source
Efomase	db_source
Epogam	db_source
g-Linolenate	Generator
g-Linolenic acid	db_source
g-Linolensaeure	Generator
Gamma-linolenate	biospider
Gamma-linolenic acid	biospider
gamma-Linolensaeure	ChEBI
Gamma-llnolenic acid	biospider
Gammalinolenic acid	db_source
Gammolin	db_source
Gamoleate	Generator
Gamoleic acid	ChEBI
Gamolenic acid	biospider
Gamolenic acid (inn)	biospider
Gamolenic acid [inn:ban]	biospider
Gamolenic acid, BAN, INN	db_source
GLA	db_source
Ligla	biospider
Octadeca-6,9,12-triensaeure	ChEBI
Unigam	db_source
Viacutan	biospider
γ-linolenate	Generator
γ-linolenic acid	Generator
γ-linolensaeure	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.00025 g/L	ALOGPS
logP	6.59	ALOGPS
logP	6.06	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	33.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H30O2

IUPAC name

(6Z,9E,12Z)-octadeca-6,9,12-trienoic acid

InChI Identifier

InChI=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 Key

VZCCETWTMQHEPK-XQYVMNDBSA-N

Isomeric SMILES

CCCCC\C=C/C\C=C\C\C=C/CCCCC(O)=O

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

Classification

Description

Belongs to the class of organic compounds 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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 77.65%; H 10.86%; O 11.49%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28661

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03073

CRC / DFC (Dictionary of Food Compounds) ID

CPL98-G:CPL99-H

EAFUS ID

Not Available

Dr. Duke ID

GAMMA-LINOLENIC-ACID

BIGG ID

48234

KNApSAcK ID

C00001226

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

gamma-Linolenic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Alpha-reductase inhibitor	23924	An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats conditions like benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing sebum production and slowing hair loss.	DUKE
Anti-acne	50177	An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin.	DUKE
Anti-aggregant		An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.	DUKE
Anti-alcoholic	52217	An agent that reduces alcohol cravings and withdrawal symptoms, commonly used in managing alcohol dependence and addiction, aiding in the treatment of alcohol use disorder by blocking the rewarding aspects of alcohol consumption.	DUKE
Anti-arthritic	52217	An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.	DUKE
Anti asphyctic		An agent that enhances the blood's ability to carry oxygen, playing a crucial role in preventing hypoxia. Therapeutically, it is used to treat conditions where oxygen delivery is compromised, such as high-altitude sickness, anemia, and respiratory disorders, improving oxygenation and reducing symptoms of asphyxiation.	DUKE
Anti-atherosclerotic	38070	An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.	DUKE
Anti eczemic	52217	An agent that reduces inflammation and itching, commonly used to manage eczema symptoms, atopic dermatitis, and other skin allergies, providing relief and preventing flare-ups.	DUKE
Anti hypercholesterolemic		An agent that prevents or controls an increase of cholesterol in the blood, playing a crucial role in reducing cardiovascular risk. Therapeutically, it helps manage hypercholesterolemia, preventing plaque buildup and lowering the risk of heart disease, making it a key treatment for conditions like atherosclerosis and coronary artery disease.	DUKE
Anti-menorrhagic	52217	An agent that reduces heavy menstrual bleeding, playing a biological role in regulating menstrual flow. Therapeutically, it is used to treat menorrhagia, with key medical applications including managing excessive uterine bleeding, dysmenorrhea, and menstrual disorders.	DUKE
Anti monosodium-glutamate		An antidote for MSG poisoning, neutralizing excessive glutamate effects. Biologically, it regulates glutamate levels, mitigating neurotoxicity. Therapeutically, it's used to treat MSG-induced adverse reactions, such as headaches and nausea, and may have applications in managing conditions like migraines and neuropathic pain.	DUKE
Anti-obesity	52217	An agent that reduces body weight, commonly used in managing obesity and related disorders, by regulating appetite, metabolism, and fat storage, with therapeutic applications in preventing chronic diseases such as diabetes and cardiovascular disease.	DUKE
Anti premenstrual syndrome	52217	An agent that alleviates symptoms of premenstrual syndrome (PMS), reducing physical and emotional discomfort. Its biological role involves regulating hormonal fluctuations, and its therapeutic applications include managing mood swings, bloating, and breast tenderness. Key medical uses include treating PMS, premenstrual dysphoric disorder (PMDD), and other menstrual-related disorders.	DUKE
Anti-prostatitic		An agent that relieves prostatitis, reducing inflammation of the prostate gland, and is used to treat benign prostatic hyperplasia (BPH) and chronic pelvic pain syndrome.	DUKE
Anti Raynaud's	52217	An agent that improves blood flow to extremities, reducing vasospasm and relieving symptoms of Raynaud's disease, commonly used to manage cold-induced digital ulcers, pain, and discoloration in fingers and toes.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Hypocholesterolemic		An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.	DUKE
Hypotensive		An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.	DUKE
Immunomodulator	50846	An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.	DUKE
Vasodilator	35620	An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2