Molecule Identification Common Name PA(18:1(11Z)/18:3(6Z,9Z,12Z)) Definition PA(18:1(11Z)/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(18:1(11Z)/18:3(6Z,9Z,12Z)), in particular, consists of one chain of cis-vaccenic 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)CCCCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC 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/h12-15,18,20,24,26,37H,3-11,16-17,19,21-23,25,27-36H2,1-2H3,(H2,42,43,44)/b14-12-,15-13-,20-18-,26-24-/t37-/m1/s1 Synonyms Value Source 1-cis-Vaccenoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate HMDB 1-cis-Vaccenoyl-2-gamma-linolenoyl-sn-phosphatidic acid HMDB PA(18:1/18:3) HMDB PA(18:1N7/18:3N6) HMDB PA(18:1W7/18:3W6) HMDB PA(36:4) HMDB Phosphatidic acid(18:1(11Z)/18:3(6Z,9Z,12Z)) HMDB Phosphatidic acid(18:1/18:3) HMDB Phosphatidic acid(18:1n7/18:3n6) HMDB Phosphatidic acid(18:1W7/18:3W6) HMDB Phosphatidic acid(36:4) HMDB Phosphatidate(18:1(11Z)/18:3(6Z,9Z,12Z)) HMDB Phosphatidate(18:1/18:3) HMDB Phosphatidate(18:1N7/18:3N6) HMDB Phosphatidate(18:1W7/18:3W6) HMDB Phosphatidate(36:4) HMDB [(2R)-3-[(11Z)-Octadec-11-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonate HMDB 1-cis-vaccenoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-cis-vaccenoyl-2-gamma-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:1/18:3) SMPDB, HMDB PA(18:1n7/18:3n6) SMPDB, HMDB PA(18:1w7/18:3w6) SMPDB, HMDB PA(36:4) SMPDB, HMDB Phosphatidic acid(18:1(11Z)/18:3(6Z,9Z,12Z)) SMPDB, HMDB Phosphatidic acid(18:1/18:3) SMPDB, HMDB Phosphatidic acid(18:1n7/18:3n6) SMPDB, HMDB Phosphatidic acid(18:1w7/18:3w6) SMPDB, HMDB Phosphatidic acid(36:4) SMPDB, HMDB Phosphatidate(18:1(11Z)/18:3(6Z,9Z,12Z)) SMPDB, HMDB Phosphatidate(18:1/18:3) SMPDB, HMDB Phosphatidate(18:1n7/18:3n6) SMPDB, HMDB Phosphatidate(18:1w7/18:3w6) SMPDB, HMDB PA(18:1(11Z)/18:3(6Z,9Z,12Z)) 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-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxyphosphonic acid CAS Registry Number None SMILES [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC
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/h12-15,18,20,24,26,37H,3-11,16-17,19,21-23,25,27-36H2,1-2H3,(H2,42,43,44)/b14-12-,15-13-,20-18-,26-24-/t37-/m1/s1
InChI Key UDUKISYCYVTRKP-VIUOHOEASA-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(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0066170 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0066173 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0066178 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0066180 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z)) (PathBank: SMP0074928 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0074931 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:0) (PathBank: SMP0074933 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0085134 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/20:0) (PathBank: SMP0085147 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0086204 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0090184 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0090186 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0090192 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0090195 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0090196 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0090198 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0085133 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0085140 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0086206 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0090187 )Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0063853 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0066167 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0066172 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:1(15Z)) (PathBank: SMP0074934 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0085141 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) (PathBank: SMP0090189 )Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0071755 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0085132 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0021939 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0021940 )De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0021945 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0081821 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0081822 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0081823 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0081824 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0081827 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081828 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0081829 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0081830 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/20:1(11Z)) (PathBank: SMP0081832 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/20:1(13Z)) (PathBank: SMP0081833 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/22:0) (PathBank: SMP0081834 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/22:1(13Z)) (PathBank: SMP0081835 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0081836 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081837 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/22:0) (PathBank: SMP0081838 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0081839 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081840 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/22:0) (PathBank: SMP0081841 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081842 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/22:0/22:0) (PathBank: SMP0081843 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/22:0/22:1(13Z)) (PathBank: SMP0081844 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0081845 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085135 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085136 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085137 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085138 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085139 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085142 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085143 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085144 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085145 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085146 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0085148 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0085149 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085150 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085151 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085152 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085153 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085154 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085155 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085156 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085157 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085158 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085159 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085160 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085161 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085162 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085163 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085164 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085165 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085166 )Cardiolipin Biosynthesis CL(18:1(11Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085167 )Role Not Available 
