Molecule Identification Common Name PA(18:3(6Z,9Z,12Z)/22:1(13Z)) Definition PA(18:3(6Z,9Z,12Z)/22:1(13Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(18:3(6Z,9Z,12Z)/22:1(13Z)), in particular, consists of one chain of gamma-linolenic acid at the C-1 position and one chain of erucic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Structure [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC InChI=1S/C43H77O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h12,14,17-19,23,27,29,41H,3-11,13,15-16,20-22,24-26,28,30-40H2,1-2H3,(H2,46,47,48)/b14-12-,19-17-,23-18-,29-27-/t41-/m1/s1 Synonyms Value Source 1-gamma-Linolenoyl-2-erucoyl-sn-glycero-3-phosphate HMDB 1-gamma-Linolenoyl-2-erucoyl-sn-phosphatidic acid HMDB PA(18:3/22:1) HMDB PA(18:3N6/22:1N9) HMDB PA(18:3W6/22:1W9) HMDB PA(40:4) HMDB Phosphatidic acid(18:3(6Z,9Z,12Z)/22:1(13Z)) HMDB Phosphatidic acid(18:3/22:1) HMDB Phosphatidic acid(18:3n6/22:1n9) HMDB Phosphatidic acid(18:3W6/22:1W9) HMDB Phosphatidic acid(40:4) HMDB Phosphatidate(18:3(6Z,9Z,12Z)/22:1(13Z)) HMDB Phosphatidate(18:3/22:1) HMDB Phosphatidate(18:3N6/22:1N9) HMDB Phosphatidate(18:3W6/22:1W9) HMDB Phosphatidate(40:4) HMDB [(2R)-2-[(13Z)-Docos-13-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonate HMDB 1-gamma-linolenoyl-2-erucoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-gamma-linolenoyl-2-erucoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:3/22:1) SMPDB, HMDB PA(18:3n6/22:1n9) SMPDB, HMDB PA(18:3w6/22:1w9) SMPDB, HMDB PA(40:4) SMPDB, HMDB Phosphatidic acid(18:3(6Z,9Z,12Z)/22:1(13Z)) SMPDB, HMDB Phosphatidic acid(18:3/22:1) SMPDB, HMDB Phosphatidic acid(18:3n6/22:1n9) SMPDB, HMDB Phosphatidic acid(18:3w6/22:1w9) SMPDB, HMDB Phosphatidic acid(40:4) SMPDB, HMDB Phosphatidate(18:3(6Z,9Z,12Z)/22:1(13Z)) SMPDB, HMDB Phosphatidate(18:3/22:1) SMPDB, HMDB Phosphatidate(18:3n6/22:1n9) SMPDB, HMDB Phosphatidate(18:3w6/22:1w9) SMPDB, HMDB PA(18:3(6Z,9Z,12Z)/22:1(13Z)) SMPDB
Chemical Formula C43 H77 O8 P Average Molecular Weight 753.055 Monoisotopic Molecular Weight 752.535606437 IUPAC Name [(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxyphosphonic acid CAS Registry Number None SMILES [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier InChI=1S/C43H77O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h12,14,17-19,23,27,29,41H,3-11,13,15-16,20-22,24-26,28,30-40H2,1-2H3,(H2,46,47,48)/b14-12-,19-17-,23-18-,29-27-/t41-/m1/s1
InChI Key NYOMTDGMSMPGNM-ZBWUBBSDSA-N Functional Ontology Physiological effect Not Available Disposition Process Naturally occurring process Biological process Biochemical pathway Metabolic pathway De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0067038 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0067040 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:2(13Z,16Z)) (PathBank: SMP0075786 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0075789 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0091058 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0091060 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:1(15Z)) (PathBank: SMP0091065 )Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0063874 )Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0071776 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:0) (PathBank: SMP0075791 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0024567 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0024568 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0024572 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0024573 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0024574 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0024575 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:2(11Z,14Z)) (PathBank: SMP0033363 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0033364 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0082106 )Role Not Available 
