2.0 2012-05-31 13:51:24 -0600 2015-10-02 02:25:49 -0600 ECMDB01388 M2MDB000365 alpha-Linolenic acid Alpha-linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism. Alpha linolenic acid and other omega 3 fatty acids may regulate gene expression by interacting with specific transcription factors. ALA is an intermediate in alpha-Linolenic acid metabolism and biosynthesis of unsaturated fatty acids pathway in E. coli (KEGG compound: C06427). (9,12,15)-linolenate (9,12,15)-linolenic acid (9E,12E,15E)-9,12,15-Octadecatrienoate (9E,12E,15E)-9,12,15-Octadecatrienoic acid (9Z,12Z,15Z)-Octadecatrienoate (9Z,12Z,15Z)-Octadecatrienoic acid (Z,Z,Z)-9,12,15-Octadecatrienoate (Z,Z,Z)-9,12,15-Octadecatrienoic acid 9,12,15-Octadecatrienoate 9,12,15-Octadecatrienoic acid 9-cis,12-cis,15-cis-Octadecatrienoate 9-cis,12-cis,15-cis-Octadecatrienoic acid 9Z,12Z,15Z-octadecatrienoate 9Z,12Z,15Z-octadecatrienoic acid A-Linolenate A-Linolenic acid All-cis-9,12,15-Octadecatrienoate All-cis-9,12,15-Octadecatrienoic acid alpha-Linolenate Alpha-Linolenic acid Cis,cis,cis-9,12,15-Octadecatrienoate Cis,cis,cis-9,12,15-Octadecatrienoic acid Cis-9,12,15-Octadecatrienoate Cis-9,12,15-Octadecatrienoic acid Industrene 120 Linolenate Linolenic acid α-Linolenate α-Linolenic acid C18H30O2 278.4296 278.224580204 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid α linolenic acid 463-40-1 CCC=CCC=CCC=CCCCCCCCC(O)=O 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) DTOSIQBPPRVQHS-UHFFFAOYSA-N Liquid Inner membrane Membrane Outer membrane logp 6.62 ALOGPS logs -6.02 ALOGPS solubility 2.66e-04 g/l ALOGPS melting_point -16.5 oC logp 6.06 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid ChemAxon average_mass 278.4296 ChemAxon mono_mass 278.224580204 ChemAxon smiles CCC=CCC=CCC=CCCCCCCCC(O)=O ChemAxon formula C18H30O2 ChemAxon 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) ChemAxon inchikey DTOSIQBPPRVQHS-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 89.64 ChemAxon polarizability 34.98 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon alpha-Linolenic acid metabolism ec00592 Biosynthesis of unsaturated fatty acids ec01040 Specdb::CMs 733 Specdb::CMs 734 Specdb::CMs 1876 Specdb::CMs 8404 Specdb::CMs 30215 Specdb::CMs 30902 Specdb::CMs 31318 Specdb::CMs 32104 Specdb::CMs 38049 Specdb::CMs 160280 Specdb::NmrOneD 1692 Specdb::NmrOneD 324392 Specdb::NmrOneD 324393 Specdb::NmrOneD 324394 Specdb::NmrOneD 324395 Specdb::NmrOneD 324396 Specdb::NmrOneD 324397 Specdb::NmrOneD 324398 Specdb::NmrOneD 324399 Specdb::NmrOneD 324400 Specdb::NmrOneD 324401 Specdb::NmrOneD 324402 Specdb::NmrOneD 324403 Specdb::NmrOneD 324404 Specdb::NmrOneD 324405 Specdb::NmrOneD 324406 Specdb::NmrOneD 324407 Specdb::NmrOneD 324408 Specdb::NmrOneD 324409 Specdb::NmrOneD 324410 Specdb::NmrOneD 324411 Specdb::MsMs 1544 Specdb::MsMs 1545 Specdb::MsMs 1546 Specdb::MsMs 259530 Specdb::MsMs 259531 Specdb::MsMs 259532 Specdb::MsMs 279468 Specdb::MsMs 279469 Specdb::MsMs 279470 Specdb::MsMs 373605 Specdb::MsMs 373606 Specdb::MsMs 373607 Specdb::MsMs 373608 Specdb::MsMs 373609 Specdb::MsMs 438667 Specdb::MsMs 440489 Specdb::MsMs 440490 Specdb::MsMs 440491 Specdb::MsMs 1470931 Specdb::MsMs 1470932 Specdb::MsMs 1470933 Specdb::MsMs 2226809 Specdb::MsMs 2227885 Specdb::MsMs 2236018 Specdb::MsMs 2238108 Specdb::NmrTwoD 1633 HMDB01388 860 4445949 C06427 27432 LINOLENIC_ACID Linolenic acid Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC. Li, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi. Preparation of a-linolenic acid from linseed oil. Zhengzhou Gongcheng Xueyuan Xuebao (2004), 25(3), 13-15. http://hmdb.ca/system/metabolites/msds/000/001/250/original/HMDB01388.pdf?1358462860 Phospholipase A1 P0A921 PA1_ECOLI pldA http://ecmdb.ca/proteins/P0A921.xml Phosphatidylcholine + Water <> 2-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic acid R07860 phosphatidylcholine(1+) > alpha-Linolenic acid + Alpha-Linolenic acid PW_R002445