Molecule Identification Common Name PA(18:1(11Z)/18:3(9Z,12Z,15Z)) Definition PA(18:1(11Z)/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(11Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of cis-vaccenic 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)CCCCCCCCC\C=C/CCCCCC)(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/h6,8,12-15,18,20,37H,3-5,7,9-11,16-17,19,21-36H2,1-2H3,(H2,42,43,44)/b8-6-,14-12-,15-13-,20-18-/t37-/m1/s1 Synonyms Value Source 1-cis-Vaccenoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate HMDB 1-cis-Vaccenoyl-2-alpha-linolenoyl-sn-phosphatidic acid HMDB PA(18:1/18:3) HMDB PA(18:1N7/18:3N3) HMDB PA(18:1W7/18:3W3) HMDB PA(36:4) HMDB Phosphatidic acid(18:1(11Z)/18:3(9Z,12Z,15Z)) HMDB Phosphatidic acid(18:1/18:3) HMDB Phosphatidic acid(18:1n7/18:3n3) HMDB Phosphatidic acid(18:1W7/18:3W3) HMDB Phosphatidic acid(36:4) HMDB Phosphatidate(18:1(11Z)/18:3(9Z,12Z,15Z)) HMDB Phosphatidate(18:1/18:3) HMDB Phosphatidate(18:1N7/18:3N3) HMDB Phosphatidate(18:1W7/18:3W3) HMDB Phosphatidate(36:4) HMDB [(2R)-3-[(11Z)-Octadec-11-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphonate HMDB 1-cis-vaccenoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-cis-vaccenoyl-2-alpha-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:1/18:3) SMPDB, HMDB PA(18:1n7/18:3n3) SMPDB, HMDB PA(18:1w7/18:3w3) SMPDB, HMDB PA(36:4) SMPDB, HMDB Phosphatidic acid(18:1(11Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidic acid(18:1/18:3) SMPDB, HMDB Phosphatidic acid(18:1n7/18:3n3) SMPDB, HMDB Phosphatidic acid(18:1w7/18:3w3) SMPDB, HMDB Phosphatidic acid(36:4) SMPDB, HMDB Phosphatidate(18:1(11Z)/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidate(18:1/18:3) SMPDB, HMDB Phosphatidate(18:1n7/18:3n3) SMPDB, HMDB Phosphatidate(18:1w7/18:3w3) SMPDB, HMDB PA(18:1(11Z)/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-[(11Z)-octadec-11-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphonic acid CAS Registry Number None SMILES [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(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/h6,8,12-15,18,20,37H,3-5,7,9-11,16-17,19,21-36H2,1-2H3,(H2,42,43,44)/b8-6-,14-12-,15-13-,20-18-/t37-/m1/s1
InChI Key VKPOVKZLBQJHML-AOVZEUAOSA-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(11Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0066184 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) (PathBank: SMP0066187 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0066198 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0074941 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z)) (PathBank: SMP0074947 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:0) (PathBank: SMP0074952 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0090211 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:0) (PathBank: SMP0099638 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0099644 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:0) (PathBank: SMP0099647 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0099648 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0/22:1(13Z)) (PathBank: SMP0099657 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0066183 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0066188 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0066191 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0066192 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0066194 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0066197 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:1(15Z)) (PathBank: SMP0066201 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0074938 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0074945 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0090206 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0090220 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0099636 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099640 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099641 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0099658 )Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0063854 )Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071756 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0074948 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0085168 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0099637 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:1(11Z)) (PathBank: SMP0099639 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0/22:0) (PathBank: SMP0099656 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0085169 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0099633 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099634 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099635 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/22:0) (PathBank: SMP0099642 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/22:1(13Z)) (PathBank: SMP0099643 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099649 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099650 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099653 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:1(11Z)) (PathBank: SMP0022029 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0022030 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) (PathBank: SMP0022035 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0022036 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081849 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:1(13Z)) (PathBank: SMP0081854 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081858 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081861 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:0) (PathBank: SMP0081862 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081863 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085170 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085171 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085174 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0085176 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0085177 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085180 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085181 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085182 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085183 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085184 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085185 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085186 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085187 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085188 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085189 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085192 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085194 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085195 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099645 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099646 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0099651 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0099652 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0099654 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0099655 )Role Not Available 
