Molecule Identification Common Name PA(18:1(9Z)/18:3(9Z,12Z,15Z)) Definition PA(18:1(9Z)/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(18:1(9Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of oleic 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/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C39H69O8P/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/h6,8,12,14,17-20,37H,3-5,7,9-11,13,15-16,21-36H2,1-2H3,(H2,42,43,44)/b8-6-,14-12-,19-17-,20-18-/t37-/m1/s1 Synonyms Value Source 1-Oleoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate HMDB 1-Oleoyl-2-alpha-linolenoyl-sn-phosphatidic acid HMDB PA(18:1/18:3) HMDB PA(18:1N9/18:3N3) HMDB PA(18:1W9/18:3W3) HMDB PA(36:4) HMDB Phosphatidic acid(18:1(9Z)/18:3(9Z,12Z,15Z)) HMDB Phosphatidic acid(18:1/18:3) HMDB Phosphatidic acid(18:1n9/18:3n3) HMDB Phosphatidic acid(18:1W9/18:3W3) HMDB Phosphatidic acid(36:4) HMDB Phosphatidate(18:1(9Z)/18:3(9Z,12Z,15Z)) HMDB Phosphatidate(18:1/18:3) HMDB Phosphatidate(18:1N9/18:3N3) HMDB Phosphatidate(18:1W9/18:3W3) HMDB Phosphatidate(36:4) HMDB 1-oleoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-oleoyl-2-alpha-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:1/18:3) SMPDB, HMDB PA(18:1n9/18:3n3) SMPDB, HMDB PA(18:1w9/18:3w3) SMPDB, HMDB PA(36:4) SMPDB, HMDB Phosphatidic acid(18:1(9Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidic acid(18:1/18:3) SMPDB, HMDB Phosphatidic acid(18:1n9/18:3n3) SMPDB, HMDB Phosphatidic acid(18:1w9/18:3w3) SMPDB, HMDB Phosphatidic acid(36:4) SMPDB, HMDB Phosphatidate(18:1(9Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidate(18:1/18:3) SMPDB, HMDB Phosphatidate(18:1n9/18:3n3) SMPDB, HMDB Phosphatidate(18:1w9/18:3w3) SMPDB, HMDB PA(18:1(9Z)/18:3(9Z,12Z,15Z)) SMPDB
Chemical Formula C39 H69 O8 P Average Molecular Weight 696.947 Monoisotopic Molecular Weight 696.47300618 IUPAC Name [(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphonic acid CAS Registry Number None SMILES [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier InChI=1S/C39H69O8P/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/h6,8,12,14,17-20,37H,3-5,7,9-11,13,15-16,21-36H2,1-2H3,(H2,42,43,44)/b8-6-,14-12-,19-17-,20-18-/t37-/m1/s1
InChI Key ISQZDMYWHAMARJ-GXCBCVOFSA-N Functional Ontology Physiological effect Not Available Disposition Process Naturally occurring process Biological process Biochemical pathway Metabolic pathway De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0066437 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0066439 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0066441 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z)) (PathBank: SMP0066448 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0066452 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0075192 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) (PathBank: SMP0075194 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/20:0) (PathBank: SMP0084955 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086162 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0090472 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z)) (PathBank: SMP0090479 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0099467 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/22:1(13Z)) (PathBank: SMP0099477 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/22:0/22:0) (PathBank: SMP0099490 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0066450 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0066451 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0075198 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0075203 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0086160 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0090471 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0099471 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/20:1(11Z)) (PathBank: SMP0099473 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:0) (PathBank: SMP0099481 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099484 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099487 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/22:0/22:1(13Z)) (PathBank: SMP0099491 )Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0063845 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0066436 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0066442 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:0) (PathBank: SMP0075207 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0084948 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0099470 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/22:0) (PathBank: SMP0099476 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099483 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0099492 )Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071747 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0084949 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099468 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099469 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099474 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099475 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0099478 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0099482 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0022464 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) (PathBank: SMP0022469 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0022470 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081684 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/20:1(13Z)) (PathBank: SMP0081689 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081693 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081696 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:0) (PathBank: SMP0081697 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081698 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084950 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084951 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084954 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0084956 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0084957 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084960 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084961 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084962 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084963 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084964 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084965 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084966 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084967 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084968 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084969 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084972 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084974 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084975 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099479 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099480 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0099485 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0099486 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0099488 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0099489 )Role Not Available 
