DT-Web

DB00132 - Alpha-Linolenic Acid


Identification
Name Alpha-Linolenic Acid
Accession Number DB00132 (NUTR00034)
Type small molecule
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
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 278.4296
Groups approved
Monoisotopic Weight 278.224580204
Pharmacology
Indication For nutritional supplementation and for treating dietary shortage or imbalance.
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
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


BC269730_2
Name BC269730_2
Gene Name FADS1
Pharmacological action yes
Actions ligand
References
  • 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
  • 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
  • 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
  • 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
  • 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
DTHybrid score 1.058
Delta-6 fatty acid desaturase
Name Delta-6 fatty acid desaturase
Gene Name FADS2
Pharmacological action yes
Actions ligand
References
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
DTHybrid score 1.0588
Sodium/calcium exchanger 1
Name Sodium/calcium exchanger 1
Gene Name SLC8A1
Pharmacological action unknown
Actions Not Available
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • 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
  • 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
DTHybrid score 1.0507
Transient receptor potential cation channel subfamily V member 1
Name Transient receptor potential cation channel subfamily V member 1
Gene Name TRPV1
Pharmacological action unknown
Actions Not Available
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • 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
DTHybrid score 0.9942
Elongation of very long chain fatty acids protein 4
Name Elongation of very long chain fatty acids protein 4
Gene Name ELOVL4
Pharmacological action unknown
Actions Not Available
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • 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
DTHybrid score 1.0543

Carriers


Predictions


Id Partner name Gene Name Score
759 Free fatty acid receptor 1 FFAR1 0.2372
1818 Long-chain-fatty-acid--CoA ligase 3 ACSL3 0.2371
1457 Long-chain-fatty-acid--CoA ligase 4 ACSL4 0.1546
290 Prostaglandin G/H synthase 2 PTGS2 0.1217
1502 Peroxisome proliferator-activated receptor delta PPARD 0.1192
20 Prostaglandin G/H synthase 1 PTGS1 0.1131
438 Taste receptor type 1 member 2 TAS1R2 0.1066
238 Peroxisome proliferator-activated receptor gamma PPARG 0.0896
1024 Solute carrier family 22 member 11 SLC22A11 0.0434
2853 14 kDa fatty acid-binding protein Not Available 0.0391
6142 Solute carrier family 22 member 8 SLC22A8 0.0373
2211 Fatty acid-binding protein, heart FABP3 0.0358
1729 Solute carrier family 22 member 6 SLC22A6 0.0344
6677 Myelin P2 protein PMP2 0.0332
6501 Fatty acid-binding protein, liver FABP1 0.0316
3382 Glycolipid transfer protein GLTP 0.0293
1992 Vitamin D-binding protein GC 0.0289
2183 Fatty acid-binding protein, adipocyte FABP4 0.0254
587 Serum albumin ALB 0.0128
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