Molecule Identification Common Name PA(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) Definition PA(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) 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)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of gamma-linolenic acid at the C-1 position and one chain of alpha-linolenic 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)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C39H65O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-20,23,25,37H,3-5,7,9-10,15-16,21-22,24,26-36H2,1-2H3,(H2,42,43,44)/b8-6-,13-11-,14-12-,19-17-,20-18-,25-23-/t37-/m1/s1 Synonyms Value Source 1-gamma-Linolenoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate HMDB 1-gamma-Linolenoyl-2-alpha-linolenoyl-sn-phosphatidic acid HMDB PA(18:3/18:3) HMDB PA(18:3N6/18:3N3) HMDB PA(18:3W6/18:3W3) HMDB PA(36:6) HMDB Phosphatidic acid(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) HMDB Phosphatidic acid(18:3/18:3) HMDB Phosphatidic acid(18:3n6/18:3n3) HMDB Phosphatidic acid(18:3W6/18:3W3) HMDB Phosphatidic acid(36:6) HMDB Phosphatidate(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) HMDB Phosphatidate(18:3/18:3) HMDB Phosphatidate(18:3N6/18:3N3) HMDB Phosphatidate(18:3W6/18:3W3) HMDB Phosphatidate(36:6) HMDB 1-gamma-linolenoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-gamma-linolenoyl-2-alpha-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:3/18:3) SMPDB, HMDB PA(18:3n6/18:3n3) SMPDB, HMDB PA(18:3w6/18:3w3) SMPDB, HMDB PA(36:6) SMPDB, HMDB Phosphatidic acid(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidic acid(18:3/18:3) SMPDB, HMDB Phosphatidic acid(18:3n6/18:3n3) SMPDB, HMDB Phosphatidic acid(18:3w6/18:3w3) SMPDB, HMDB Phosphatidic acid(36:6) SMPDB, HMDB Phosphatidate(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidate(18:3/18:3) SMPDB, HMDB Phosphatidate(18:3n6/18:3n3) SMPDB, HMDB Phosphatidate(18:3w6/18:3w3) SMPDB, HMDB PA(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) SMPDB
Chemical Formula C39 H65 O8 P Average Molecular Weight 692.915 Monoisotopic Molecular Weight 692.441706051 IUPAC Name [(2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-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)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier InChI=1S/C39H65O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-20,23,25,37H,3-5,7,9-10,15-16,21-22,24,26-36H2,1-2H3,(H2,42,43,44)/b8-6-,13-11-,14-12-,19-17-,20-18-,25-23-/t37-/m1/s1
InChI Key TWGHPDKJWDJGNI-UEJJDHNXSA-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)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) (PathBank: SMP0066883 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0066893 )Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071771 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0075637 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0075640 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0086297 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0090905 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0090906 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0090911 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z)) (PathBank: SMP0090916 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0066892 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0075631 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0075641 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0075642 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0086294 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0090919 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0066895 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:0) (PathBank: SMP0075648 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z)) (PathBank: SMP0075649 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0086424 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:0) (PathBank: SMP0086430 )Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0063869 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0075634 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0086423 )De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0024655 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0082052 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0082053 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0082054 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0082055 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:1(11Z)) (PathBank: SMP0082057 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:1(13Z)) (PathBank: SMP0082058 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/22:0) (PathBank: SMP0082059 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/22:1(13Z)) (PathBank: SMP0082060 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0082061 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0082062 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:0) (PathBank: SMP0082063 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0082064 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0082065 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:0) (PathBank: SMP0082066 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0082067 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0/22:0) (PathBank: SMP0082068 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0/22:1(13Z)) (PathBank: SMP0082069 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0082070 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0086425 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0086426 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0086427 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0086428 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086429 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0086431 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0086432 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0086433 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0086434 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086435 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0086436 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0086437 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0086439 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0086440 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086441 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0086442 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0086443 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0086444 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086445 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0086446 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0086447 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086448 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0086449 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086450 )Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086451 )Role Not Available 
