Molecule Identification Common Name PA(18:1(9Z)/18:3(6Z,9Z,12Z)) Definition PA(18:1(9Z)/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(9Z)/18:3(6Z,9Z,12Z)), in particular, consists of one chain of oleic 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/CCCCCCCC)(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/h12,14,17-20,24,26,37H,3-11,13,15-16,21-23,25,27-36H2,1-2H3,(H2,42,43,44)/b14-12-,19-17-,20-18-,26-24-/t37-/m1/s1 Synonyms Value Source 1-Oleoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate HMDB 1-Oleoyl-2-gamma-linolenoyl-sn-phosphatidic acid HMDB PA(18:1/18:3) HMDB PA(18:1N9/18:3N6) HMDB PA(18:1W9/18:3W6) HMDB PA(36:4) HMDB Phosphatidic acid(18:1(9Z)/18:3(6Z,9Z,12Z)) HMDB Phosphatidic acid(18:1/18:3) HMDB Phosphatidic acid(18:1n9/18:3n6) HMDB Phosphatidic acid(18:1W9/18:3W6) HMDB Phosphatidic acid(36:4) HMDB Phosphatidate(18:1(9Z)/18:3(6Z,9Z,12Z)) HMDB Phosphatidate(18:1/18:3) HMDB Phosphatidate(18:1N9/18:3N6) HMDB Phosphatidate(18:1W9/18:3W6) HMDB Phosphatidate(36:4) HMDB 1-oleoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-oleoyl-2-gamma-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:1/18:3) SMPDB, HMDB PA(18:1n9/18:3n6) SMPDB, HMDB PA(18:1w9/18:3w6) SMPDB, HMDB PA(36:4) SMPDB, HMDB Phosphatidic acid(18:1(9Z)/18:3(6Z,9Z,12Z)) SMPDB, HMDB Phosphatidic acid(18:1/18:3) SMPDB, HMDB Phosphatidic acid(18:1n9/18:3n6) SMPDB, HMDB Phosphatidic acid(18:1w9/18:3w6) SMPDB, HMDB Phosphatidic acid(36:4) SMPDB, HMDB Phosphatidate(18:1(9Z)/18:3(6Z,9Z,12Z)) SMPDB, HMDB Phosphatidate(18:1/18:3) SMPDB, HMDB Phosphatidate(18:1n9/18:3n6) SMPDB, HMDB Phosphatidate(18:1w9/18:3w6) SMPDB, HMDB PA(18:1(9Z)/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-[(9Z)-octadec-9-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxyphosphonic acid CAS Registry Number None SMILES [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(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/h12,14,17-20,24,26,37H,3-11,13,15-16,21-23,25,27-36H2,1-2H3,(H2,42,43,44)/b14-12-,19-17-,20-18-,26-24-/t37-/m1/s1
InChI Key KHNGPLHSMOZXOH-XVQVCCCCSA-N Functional Ontology Physiological effect Not Available Disposition Process Naturally occurring process Biological process Biochemical pathway Metabolic pathway Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0063844 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0066416 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0066420 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z)) (PathBank: SMP0066429 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0066432 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0075170 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0075171 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) (PathBank: SMP0075174 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0075183 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0075184 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0084912 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0086150 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0086153 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0086154 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0090447 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0090448 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0090451 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z)) (PathBank: SMP0090460 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:0) (PathBank: SMP0075188 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0066428 )Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0071746 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0075187 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0084913 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0084914 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0075180 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0084920 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:0) (PathBank: SMP0084927 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0084921 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0022380 )De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0022385 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0081656 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0081657 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0081658 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0081659 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0081662 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081663 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0081664 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0081665 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:1(11Z)) (PathBank: SMP0081667 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:1(13Z)) (PathBank: SMP0081668 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/22:0) (PathBank: SMP0081669 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/22:1(13Z)) (PathBank: SMP0081670 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0081671 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081672 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/22:0) (PathBank: SMP0081673 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0081674 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081675 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/22:0) (PathBank: SMP0081676 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081677 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0/22:0) (PathBank: SMP0081678 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0/22:1(13Z)) (PathBank: SMP0081679 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0081680 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084915 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084916 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084917 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084918 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084919 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084922 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084923 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084924 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084925 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084926 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0084928 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0084929 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084930 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084931 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084932 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084933 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084934 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084935 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084936 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084937 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084938 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084939 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084940 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084941 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084942 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084943 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084944 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084945 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084946 )Cardiolipin Biosynthesis CL(18:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084947 )Role Not Available 
