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Namespace Prefixes

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Statements

Subject Item
n2:DB00132
rdf:type
n3:Drug
n3: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]
n3:generalReferences
# 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":http://www.ncbi.nlm.nih.gov/pubmed/12438303 # Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10617967 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15051847 # 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":http://www.ncbi.nlm.nih.gov/pubmed/11157315 # 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":http://www.ncbi.nlm.nih.gov/pubmed/10775263
n3:group
nutraceutical approved
n3:indication
For nutritional supplementation and for treating dietary shortage or imbalance.
owl:sameAs
n15:DB00132 n21:DB00132
dcterms:title
Alpha-Linolenic Acid
adms:identifier
n7:1049 n8:C06427 n9:DB00132 n10:1049 n11:27432 n12:4444437 n13:46507620 n16:LNL n17:5280934 n18:Alpha-linolenic_acid n19:PA449384
n3:mechanismOfAction
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.
n3:packager
n20:271B4904-363D-11E5-9242-09173F13E4C5 n20:271B4905-363D-11E5-9242-09173F13E4C5
n3:synonym
alpha-Linolenic acid 9,12,15-Octadecatrienoic acid cis-delta(9,12,15)-Octadecatrienoic acid α-linolenic acid (Z,Z,Z)-9,12,15-octadecatrienoic acid (9Z,12Z,15Z)-Octadecatrienoic acid all-cis-9,12,15-Octadecatrienoic acid Linolenic acid ALA 9-cis,12-cis,15-cis-octadecatrienoic acid cis,cis,cis-9,12,15-Octadecatrienoic acid (9,12,15)-linolenic acid
n3:synthesisReference
Jean-Pierre Masse, "Therapeutic composition containing alpha-linolenic acid and a compound capable of promoting the passage of the acid through the cell membrane, plant extract comprising the acid and the compound, and process for the preparation of the extract." U.S. Patent US5002767, issued February, 1986.
n23:hasConcept
n24:M0027126
n3:IUPAC-Name
n5:271B490C-363D-11E5-9242-09173F13E4C5
n3:InChI
n5:271B4912-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n5:271B4911-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n5:271B490E-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n5:271B490F-363D-11E5-9242-09173F13E4C5
n3:SMILES
n5:271B4910-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n5:271B490A-363D-11E5-9242-09173F13E4C5 n5:271B4921-363D-11E5-9242-09173F13E4C5
n3:logP
n5:271B4908-363D-11E5-9242-09173F13E4C5 n5:271B490B-363D-11E5-9242-09173F13E4C5 n5:271B4924-363D-11E5-9242-09173F13E4C5
n3:logS
n5:271B4909-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n5:271B4918-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n5:271B4919-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n5:271B4913-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n5:271B4914-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n5:271B4916-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n5:271B4915-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n5:271B4917-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
463-40-1
n3:category
n3:containedIn
n4:271B4906-363D-11E5-9242-09173F13E4C5 n4:271B4907-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n5:271B491D-363D-11E5-9242-09173F13E4C5
n3:Boiling-Point
n5:271B4923-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n5:271B491F-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n5:271B4920-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n5:271B4922-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n5:271B491C-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n5:271B491B-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n5:271B491E-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n5:271B490D-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n5:271B491A-363D-11E5-9242-09173F13E4C5