Molecule Identification Common Name PA(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) Definition PA(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) 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(6Z,9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of gamma-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)CCCC\C=C/C\C=C/C\C=C/CCCCC 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/h11-14,17-20,24,26,37H,3-10,15-16,21-23,25,27-36H2,1-2H3,(H2,42,43,44)/b13-11-,14-12-,19-17-,20-18-,26-24-/t37-/m1/s1 Synonyms Value Source 1-Linoleoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate HMDB 1-Linoleoyl-2-gamma-linolenoyl-sn-phosphatidic acid HMDB PA(18:2/18:3) HMDB PA(18:2N6/18:3N6) HMDB PA(18:2W6/18:3W6) HMDB PA(36:5) HMDB Phosphatidic acid(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) HMDB Phosphatidic acid(18:2/18:3) HMDB Phosphatidic acid(18:2n6/18:3n6) HMDB Phosphatidic acid(18:2W6/18:3W6) HMDB Phosphatidic acid(36:5) HMDB Phosphatidate(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) HMDB Phosphatidate(18:2/18:3) HMDB Phosphatidate(18:2N6/18:3N6) HMDB Phosphatidate(18:2W6/18:3W6) HMDB Phosphatidate(36:5) HMDB 1-linoleoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-linoleoyl-2-gamma-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:2/18:3) SMPDB, HMDB PA(18:2n6/18:3n6) SMPDB, HMDB PA(18:2w6/18:3w6) SMPDB, HMDB PA(36:5) SMPDB, HMDB Phosphatidic acid(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) SMPDB, HMDB Phosphatidic acid(18:2/18:3) SMPDB, HMDB Phosphatidic acid(18:2n6/18:3n6) SMPDB, HMDB Phosphatidic acid(18:2w6/18:3w6) SMPDB, HMDB Phosphatidic acid(36:5) SMPDB, HMDB Phosphatidate(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) SMPDB, HMDB Phosphatidate(18:2/18:3) SMPDB, HMDB Phosphatidate(18:2n6/18:3n6) SMPDB, HMDB Phosphatidate(18:2w6/18:3w6) SMPDB, HMDB PA(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) SMPDB
Chemical Formula C39 H67 O8 P Average Molecular Weight 694.931 Monoisotopic Molecular Weight 694.457356115 IUPAC Name [(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-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)CCCC\C=C/C\C=C/C\C=C/CCCCC
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/h11-14,17-20,24,26,37H,3-10,15-16,21-23,25,27-36H2,1-2H3,(H2,42,43,44)/b13-11-,14-12-,19-17-,20-18-,26-24-/t37-/m1/s1
InChI Key VKNJXYLLZUGTCV-ZVMKNGRMSA-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(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0066648 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0066655 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0066656 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0066657 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0066662 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) (PathBank: SMP0075406 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0075408 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0075412 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0075417 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:0) (PathBank: SMP0075419 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/20:0) (PathBank: SMP0085312 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0086250 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z)) (PathBank: SMP0090685 )Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0063861 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0075401 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0075415 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0085298 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0085305 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0085306 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0086251 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0090674 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0090676 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0090684 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0090689 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0085297 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0085299 )Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0071763 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z)) (PathBank: SMP0075420 )De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0024293 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0081941 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0081942 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0081943 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0081944 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0081947 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081948 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0081949 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0081950 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/20:1(11Z)) (PathBank: SMP0081952 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/20:1(13Z)) (PathBank: SMP0081953 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/22:0) (PathBank: SMP0081954 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/22:1(13Z)) (PathBank: SMP0081955 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0081956 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081957 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/22:0) (PathBank: SMP0081958 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0081959 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081960 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/22:0) (PathBank: SMP0081961 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081962 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:0/22:0) (PathBank: SMP0081963 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:0/22:1(13Z)) (PathBank: SMP0081964 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0081965 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085300 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085301 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085302 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085303 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085304 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085307 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085308 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085309 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085310 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085311 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0085313 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0085314 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085315 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085316 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085317 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085318 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085319 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085320 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085321 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085322 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085323 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085324 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085325 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085326 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085327 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085328 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085329 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085330 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085331 )Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085332 )Role Not Available 
