Molecule Identification Common Name PA(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) Definition PA(18:2(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(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of linoleic 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)CCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C39H67O8P/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/h6,8,11-14,17-20,37H,3-5,7,9-10,15-16,21-36H2,1-2H3,(H2,42,43,44)/b8-6-,13-11-,14-12-,19-17-,20-18-/t37-/m1/s1 Synonyms Value Source 1-Linoleoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate HMDB 1-Linoleoyl-2-alpha-linolenoyl-sn-phosphatidic acid HMDB PA(18:2/18:3) HMDB PA(18:2N6/18:3N3) HMDB PA(18:2W6/18:3W3) HMDB PA(36:5) HMDB Phosphatidic acid(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) HMDB Phosphatidic acid(18:2/18:3) HMDB Phosphatidic acid(18:2n6/18:3n3) HMDB Phosphatidic acid(18:2W6/18:3W3) HMDB Phosphatidic acid(36:5) HMDB Phosphatidate(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) HMDB Phosphatidate(18:2/18:3) HMDB Phosphatidate(18:2N6/18:3N3) HMDB Phosphatidate(18:2W6/18:3W3) HMDB Phosphatidate(36:5) HMDB 1-linoleoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-linoleoyl-2-alpha-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:2/18:3) SMPDB, HMDB PA(18:2n6/18:3n3) SMPDB, HMDB PA(18:2w6/18:3w3) SMPDB, HMDB PA(36:5) SMPDB, HMDB Phosphatidic acid(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidic acid(18:2/18:3) SMPDB, HMDB Phosphatidic acid(18:2n6/18:3n3) SMPDB, HMDB Phosphatidic acid(18:2w6/18:3w3) SMPDB, HMDB Phosphatidic acid(36:5) SMPDB, HMDB Phosphatidate(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidate(18:2/18:3) SMPDB, HMDB Phosphatidate(18:2n6/18:3n3) SMPDB, HMDB Phosphatidate(18:2w6/18:3w3) SMPDB, HMDB PA(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) SMPDB
Chemical Formula C39 H67 O8 P Average Molecular Weight 694.931 Monoisotopic Molecular Weight 694.457356115 IUPAC Name [(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acid CAS Registry Number None SMILES [H][C@@](COC(=O)CCCCCCC\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/C39H67O8P/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/h6,8,11-14,17-20,37H,3-5,7,9-10,15-16,21-36H2,1-2H3,(H2,42,43,44)/b8-6-,13-11-,14-12-,19-17-,20-18-/t37-/m1/s1
InChI Key AQTVREATJUABJU-IOXPMDAXSA-N Functional Ontology Physiological effect Not Available Disposition Process Naturally occurring process Biological process Biochemical pathway Metabolic pathway De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0066668 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z)) (PathBank: SMP0066679 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0075421 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0075423 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0075426 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0075429 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0075432 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0075436 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0085334 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086262 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0090695 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) (PathBank: SMP0090696 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0090698 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0090699 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z)) (PathBank: SMP0090710 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:0) (PathBank: SMP0099758 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:0) (PathBank: SMP0099767 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099770 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0/22:0) (PathBank: SMP0099776 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0066681 )Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071764 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0075434 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0090702 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0090708 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099754 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099755 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:1(11Z)) (PathBank: SMP0099759 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099760 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/22:0) (PathBank: SMP0099762 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/22:1(13Z)) (PathBank: SMP0099763 )Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0063862 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:0) (PathBank: SMP0075438 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0085333 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0099756 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099761 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0099768 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099773 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0099778 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0099753 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0099757 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0099764 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099769 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0/22:1(13Z)) (PathBank: SMP0099777 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) (PathBank: SMP0024352 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0024353 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081969 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:1(13Z)) (PathBank: SMP0081974 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081978 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081981 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:0) (PathBank: SMP0081982 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081983 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085335 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085336 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085339 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0085341 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0085342 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085345 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085346 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085347 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085348 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085349 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085350 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085351 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085352 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085353 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085354 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085357 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085359 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085360 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099765 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099766 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0099771 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0099772 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0099774 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0099775 )Role Not Available 
