Molecule Identification Common Name PA(16:0/18:3(9Z,12Z,15Z)) Definition PA(16:0/18:3(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(16:0/18:3(9Z,12Z,15Z)), in particular, consists of one chain of palmitic 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)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C37H67O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,35H,3-4,6,8-10,12,14-16,19-34H2,1-2H3,(H2,40,41,42)/b7-5-,13-11-,18-17-/t35-/m1/s1 Synonyms Value Source 1-Palmitoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate HMDB 1-Palmitoyl-2-alpha-linolenoyl-sn-phosphatidic acid HMDB PA(16:0/18:3) HMDB PA(16:0/18:3N3) HMDB PA(16:0/18:3W3) HMDB PA(34:3) HMDB Phosphatidic acid(16:0/18:3(9Z,12Z,15Z)) HMDB Phosphatidic acid(16:0/18:3) HMDB Phosphatidic acid(16:0/18:3n3) HMDB Phosphatidic acid(16:0/18:3W3) HMDB Phosphatidic acid(34:3) HMDB Phosphatidate(16:0/18:3(9Z,12Z,15Z)) HMDB Phosphatidate(16:0/18:3) HMDB Phosphatidate(16:0/18:3N3) HMDB Phosphatidate(16:0/18:3W3) HMDB Phosphatidate(34:3) HMDB 1-palmitoyl-2-alpha-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-palmitoyl-2-alpha-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(16:0/18:3) SMPDB, HMDB PA(16:0/18:3n3) SMPDB, HMDB PA(16:0/18:3w3) SMPDB, HMDB PA(34:3) SMPDB, HMDB Phosphatidic acid(16:0/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidic acid(16:0/18:3) SMPDB, HMDB Phosphatidic acid(16:0/18:3n3) SMPDB, HMDB Phosphatidic acid(16:0/18:3w3) SMPDB, HMDB Phosphatidic acid(34:3) SMPDB, HMDB Phosphatidate(16:0/18:3(9Z,12Z,15Z)) SMPDB, HMDB Phosphatidate(16:0/18:3) SMPDB, HMDB Phosphatidate(16:0/18:3n3) SMPDB, HMDB Phosphatidate(16:0/18:3w3) SMPDB, HMDB PA(16:0/18:3(9Z,12Z,15Z)) SMPDB
Chemical Formula C37 H67 O8 P Average Molecular Weight 670.909 Monoisotopic Molecular Weight 670.457356115 IUPAC Name [(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphonic acid Traditional Name (2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphonic acid CAS Registry Number None SMILES [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier InChI=1S/C37H67O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,35H,3-4,6,8-10,12,14-16,19-34H2,1-2H3,(H2,40,41,42)/b7-5-,13-11-,18-17-/t35-/m1/s1
InChI Key IBNMUXZRFLNINV-RGDIWOFYSA-N Functional Ontology Physiological effect Not Available Disposition Process Naturally occurring process Biological process Biochemical pathway Metabolic pathway De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0065284 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0065291 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0065297 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:1(15Z)) (PathBank: SMP0065300 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) (PathBank: SMP0074036 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0074037 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0085816 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0089296 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0089298 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0089301 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0089302 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0089306 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/20:0) (PathBank: SMP0098602 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0098613 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0098617 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/22:0/22:1(13Z)) (PathBank: SMP0098621 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:0) (PathBank: SMP0065299 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0074040 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z)) (PathBank: SMP0074044 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0074045 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0083834 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0089311 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0098598 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0098601 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/20:1(11Z)) (PathBank: SMP0098603 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0098605 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0098608 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(11Z)/22:0) (PathBank: SMP0098611 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/22:0/22:0) (PathBank: SMP0098620 )Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0063824 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0065292 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0065296 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0098596 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0098599 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0098604 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/22:1(13Z)) (PathBank: SMP0098607 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0098612 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0098622 )Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0071726 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0098597 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0098600 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/22:0) (PathBank: SMP0098606 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0098614 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/16:0) (PathBank: SMP0018095 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:0) (PathBank: SMP0018096 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/14:1(9Z)) (PathBank: SMP0018100 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/16:1(9Z)) (PathBank: SMP0018101 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:1(11Z)) (PathBank: SMP0018102 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0018103 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) (PathBank: SMP0018108 )De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0018109 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081178 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/20:1(13Z)) (PathBank: SMP0081183 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081187 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081190 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(13Z)/22:0) (PathBank: SMP0081191 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081192 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0083836 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0083837 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0083840 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0083842 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0083843 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0083846 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0083847 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0083848 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0083849 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0083850 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0083851 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0083852 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0083853 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0083854 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0083855 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0083858 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0083860 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0083861 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0098609 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0098610 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0098615 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0098616 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0098618 )Cardiolipin Biosynthesis CL(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0098619 )Role Not Available 
