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Identification
Name Alpha-Linolenic Acid
Accession Number DB00132 (NUTR00034)
Type small molecule
Groups approved, nutraceutical
Description

Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(9Z,12Z,15Z)-Octadecatrienoic acid
9,12,15-Octadecatrienoic acid
ALA
alpha-Linolenate
linolenate
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Dietary supplement
  • Micronutrient
CAS number 463-40-1
Weight Average: 278.4296
Monoisotopic: 278.224580204
Chemical Formula C18H30O2
InChI Key InChIKey=DTOSIQBPPRVQHS-PDBXOOCHSA-N
InChI
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
Plain Text
IUPAC Name
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O
Plain Text
Mass Spec show (10.9 KB)
Taxonomy
Kingdom Organic
Classes
  • Fatty Acids
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Carboxylic Acids and Derivatives
  • Fatty Acids
Pharmacology
Indication For nutritional supplementation and for treating dietary shortage or imbalance.
Pharmacodynamics Alpha Linolenic Acid (ALA) is an 18-carbon polyunsaturated fatty acid with three double bonds. It is also called an omega-3 fatty acid, and is essential for all mammals. Alpha-linolenic acid (or omega 3 fatty acid) intake can decrease the risk of cardiovascular diseases by 1) preventing arrhythmias that can lead to sudden cardiac death, 2) decreasing the risk of thrombosis (blood clot formation) that can lead to heart attack or stroke, 3) decreasing serum triglyceride levels, 4) slowing the growth of atherosclerotic plaque, 5) improving vascular endothelial function, 6) lowering blood pressure slightly, and 7) decreasing inflammation. ALA deficiencies can lead to visual problems and sensory neuropathy. Scaly and hemorrhagic skin or scalp inflammations may also develop.
Mechanism of action Alpha Linolenic Acid or ALA is considered an essential fatty acid because it is required for human health, but cannot be synthesized by humans. It is in fact a plant-derived fatty acid. Humans can synthesize other omega-3 fatty acids from ALA, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes. These eicosanoids have anti-inflammatory and anti-atherogenic properties. ALA metabolites may also inhibit the production of the pro-inflammatory eicosanoids, prostaglandin E2 (PGE2) and leukotriene B4 (LTB4), as well as the pro-inflammatory cytokines, tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta). Omega-3 fatty acids like ALA and its byproducts can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. They regulate gene expression through their effects on the activity of transcription factors including NF-kappa B and members of the peroxisome proliferator-activated receptor (PPAR) family. Incorporation of ALA and its metabolites in cell membranes can affect membrane fluidity and may play a role in anti-inflammatory activity, inhibition of platelet aggregation and possibly in anti-proliferative actions of ALA. ALA is first metabolized by delta6 desaturease into steridonic acid.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Alpha lipoic acid 200 mg tablet 0.22 USD tablet
Alpha-lipoic acid 50 mg caplet 0.12 USD caplet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point -16.5 °C PhysProp
boiling point 231 °C at 1.70E+01 mm Hg PhysProp
water solubility 0.000124 mg/mL at 25 °C MEYLAN,WM et al. (1996)
logP 6.46 SANGSTER (1993)
Predicted Properties
Property Value Source
water solubility 2.66e-04 g/l ALOGPS
logP 6.62 ALOGPS
logP 6.06 ChemAxon
logS -6 ALOGPS
pKa (strongest acidic) 4.99 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 37.3 ChemAxon
rotatable bond count 13 ChemAxon
refractivity 89.64 ChemAxon
polarizability 34.98 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. Pubmed
  2. Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. Pubmed
  3. Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. Pubmed
  4. Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. Pubmed
  5. Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. Pubmed
External Links
Resource Link
KEGG Compound C06427 Link_out
PubChem Compound 5280934 Link_out
PubChem Substance 46507620 Link_out
ChemSpider 4444437 Link_out
ChEBI 27432 Link_out
ChEMBL 27432 Link_out
PharmGKB PA449384 Link_out
IUPHAR 1049 Link_out
Guide to Pharmacology 1049 Link_out
HET LNL Link_out
Wikipedia http://en.wikipedia.org/wiki/Alpha-linolenic_acid Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (19 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. BC269730_2

Pharmacological action: yes
Actions: ligand
Organism class: human
UniProt ID: O60427 Link_out
Gene: DKFZp762M2311 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Xiang M, Rahman MA, Ai H, Li X, Harbige LS: Diet and gene expression: delta-5 and delta-6 desaturases in healthy Chinese and European subjects. Ann Nutr Metab. 2006;50(6):492-8. Epub 2006 Sep 19. Pubmed
  2. Descomps B, Rodriguez A: [Essential fatty acids and prematurity: a triple experimental approach] C R Seances Soc Biol Fil. 1995;189(5):781-96. Pubmed
  3. Hoffman DR, DeMar JC, Heird WC, Birch DG, Anderson RE: Impaired synthesis of DHA in patients with X-linked retinitis pigmentosa. J Lipid Res. 2001 Sep;42(9):1395-401. Pubmed
  4. Maniongui C, Blond JP, Ulmann L, Durand G, Poisson JP, Bezard J: Age-related changes in delta 6 and delta 5 desaturase activities in rat liver microsomes. Lipids. 1993 Apr;28(4):291-7. Pubmed
  5. Mohan IK, Das UN: Effect of L-arginine-nitric oxide system on the metabolism of essential fatty acids in chemical-induced diabetes mellitus. Prostaglandins Leukot Essent Fatty Acids. 2000 Jan;62(1):35-46. Pubmed

2. Delta-6 fatty acid desaturase

Pharmacological action: yes
Actions: ligand
Organism class: human
UniProt ID: O95864 Link_out
Gene: FADS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Portolesi R, Powell BC, Gibson RA: Competition between 24:5n-3 and ALA for Delta 6 desaturase may limit the accumulation of DHA in HepG2 cell membranes. J Lipid Res. 2007 Jul;48(7):1592-8. Epub 2007 Apr 4. Pubmed
  2. Xiang M, Rahman MA, Ai H, Li X, Harbige LS: Diet and gene expression: delta-5 and delta-6 desaturases in healthy Chinese and European subjects. Ann Nutr Metab. 2006;50(6):492-8. Epub 2006 Sep 19. Pubmed
  3. Baylin A, Ruiz-Narvaez E, Kraft P, Campos H: alpha-Linolenic acid, Delta6-desaturase gene polymorphism, and the risk of nonfatal myocardial infarction. Am J Clin Nutr. 2007 Feb;85(2):554-60. Pubmed
  4. Li MC, Bu YP, Wang GK, Hu GW, Xing LJ: [Heteologous expression of Mortierella isabellina delta6 -fatty acid desaturase gene in soybean] Yi Chuan Xue Bao. 2004 Aug;31(8):858-63. Pubmed
  5. Ge L, Gordon JS, Hsuan C, Stenn K, Prouty SM: Identification of the delta-6 desaturase of human sebaceous glands: expression and enzyme activity. J Invest Dermatol. 2003 May;120(5):707-14. Pubmed
  6. Tan L, Meesapyodsuk D, Qiu X: Molecular analysis of 6 desaturase and 6 elongase from Conidiobolus obscurus in the biosynthesis of eicosatetraenoic acid, a omega3 fatty acid with nutraceutical potentials. Appl Microbiol Biotechnol. 2011 Jan 6. Pubmed

3. Sodium/calcium exchanger 1

Pharmacological action: unknown

Rapidly transports Ca(2+) during excitation-contraction coupling. Ca(2+) is extruded from the cell during relaxation so as to prevent overloading of intracellular stores

Organism class: human
UniProt ID: P32418 Link_out
Gene: SLC8A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Ander BP, Hurtado C, Raposo CS, Maddaford TG, Deniset JF, Hryshko LV, Pierce GN, Lukas A: Differential sensitivities of the NCX1.1 and NCX1.3 isoforms of the Na+-Ca2+ exchanger to alpha-linolenic acid. Cardiovasc Res. 2007 Jan 15;73(2):395-403. Epub 2006 Sep 23. Pubmed

4. Transient receptor potential cation channel subfamily V member 1

Pharmacological action: unknown

Receptor-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. May be involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL

Organism class: human
UniProt ID: Q8NER1 Link_out
Gene: TRPV1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

5. Elongation of very long chain fatty acids protein 4

Pharmacological action: unknown

Involved in the biosynthesis of very long chain fatty acids. Seems to represent a photoreceptor-specific component of the fatty acid elongation system residing on the endoplasmic reticulum. May be implicated in docosahexaenoic acid (DHA) biosynthesis, which requires dietary consumption of the essential alpha-linolenic acid and a subsequent series of three elongation steps. May be involved in one of these three elongation steps

Organism class: human
UniProt ID: Q9GZR5 Link_out
Gene: ELOVL4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Carriers

1. Fatty acid-binding protein, brain

B-FABP could be involved in the transport of a so far unknown hydrophobic ligand with potential morphogenic activity during CNS development. It is required for the establishment of the radial glial fiber system in developing brain, a system that is necessary for the migration of immature neurons to establish cortical layers

UniProt ID: O15540 Link_out
Gene: FABP7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Balendiran GK, Schnutgen F, Scapin G, Borchers T, Xhong N, Lim K, Godbout R, Spener F, Sacchettini JC: Crystal structure and thermodynamic analysis of human brain fatty acid-binding protein. J Biol Chem. 2000 Sep 1;275(35):27045-54. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19