Molecule Identification Common Name PA(18:0/18:3(6Z,9Z,12Z)) Definition PA(18:0/18:3(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(18:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of stearic 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)CCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C39H71O8P/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/h12,14,18,20,24,26,37H,3-11,13,15-17,19,21-23,25,27-36H2,1-2H3,(H2,42,43,44)/b14-12-,20-18-,26-24-/t37-/m1/s1 Synonyms Value Source 1-Stearoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate HMDB 1-Stearoyl-2-gamma-linolenoyl-sn-phosphatidic acid HMDB PA(18:0/18:3) HMDB PA(18:0/18:3N6) HMDB PA(18:0/18:3W6) HMDB PA(36:3) HMDB Phosphatidic acid(18:0/18:3(6Z,9Z,12Z)) HMDB Phosphatidic acid(18:0/18:3) HMDB Phosphatidic acid(18:0/18:3n6) HMDB Phosphatidic acid(18:0/18:3W6) HMDB Phosphatidic acid(36:3) HMDB Phosphatidate(18:0/18:3(6Z,9Z,12Z)) HMDB Phosphatidate(18:0/18:3) HMDB Phosphatidate(18:0/18:3N6) HMDB Phosphatidate(18:0/18:3W6) HMDB Phosphatidate(36:3) HMDB 1-stearoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate SMPDB, HMDB 1-stearoyl-2-gamma-linolenoyl-sn-phosphatidic acid SMPDB, HMDB PA(18:0/18:3) SMPDB, HMDB PA(18:0/18:3n6) SMPDB, HMDB PA(18:0/18:3w6) SMPDB, HMDB PA(36:3) SMPDB, HMDB Phosphatidic acid(18:0/18:3(6Z,9Z,12Z)) SMPDB, HMDB Phosphatidic acid(18:0/18:3) SMPDB, HMDB Phosphatidic acid(18:0/18:3n6) SMPDB, HMDB Phosphatidic acid(18:0/18:3w6) SMPDB, HMDB Phosphatidic acid(36:3) SMPDB, HMDB Phosphatidate(18:0/18:3(6Z,9Z,12Z)) SMPDB, HMDB Phosphatidate(18:0/18:3) SMPDB, HMDB Phosphatidate(18:0/18:3n6) SMPDB, HMDB Phosphatidate(18:0/18:3w6) SMPDB, HMDB PA(18:0/18:3(6Z,9Z,12Z)) SMPDB
Chemical Formula C39 H71 O8 P Average Molecular Weight 698.963 Monoisotopic Molecular Weight 698.488656244 IUPAC Name [(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid Traditional Name (2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid CAS Registry Number None SMILES [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier InChI=1S/C39H71O8P/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/h12,14,18,20,24,26,37H,3-11,13,15-17,19,21-23,25,27-36H2,1-2H3,(H2,42,43,44)/b14-12-,20-18-,26-24-/t37-/m1/s1
InChI Key SUSLYXMZVULDQY-NSXWPADESA-N Functional Ontology Physiological effect Not Available Disposition Process Naturally occurring process Biological process Biochemical pathway Metabolic pathway Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0063834 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0065896 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0065897 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0065899 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0074637 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0074638 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0074640 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0074641 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0074643 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0074644 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z)) (PathBank: SMP0074650 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0074653 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0084622 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0084623 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0089916 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:0) (PathBank: SMP0089923 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:1(15Z)) (PathBank: SMP0089924 )Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0071736 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0074651 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0084629 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0084630 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0089922 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0065889 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0084621 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z)) (PathBank: SMP0089910 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0065895 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0065902 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/20:0) (PathBank: SMP0084637 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0018600 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/14:1(9Z)) (PathBank: SMP0018604 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/16:1(9Z)) (PathBank: SMP0018605 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0018606 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0018607 )De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0018612 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0081436 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0081437 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0081438 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0081439 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0081442 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0081443 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0081444 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0081445 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/20:1(11Z)) (PathBank: SMP0081447 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/20:1(13Z)) (PathBank: SMP0081448 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/22:0) (PathBank: SMP0081449 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/22:1(13Z)) (PathBank: SMP0081450 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0081451 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081452 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:1(11Z)/22:0) (PathBank: SMP0081453 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0081454 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081455 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:1(13Z)/22:0) (PathBank: SMP0081456 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081457 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/22:0/22:0) (PathBank: SMP0081458 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/22:0/22:1(13Z)) (PathBank: SMP0081459 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0081460 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084624 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084625 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084626 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084627 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084628 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084631 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084632 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084633 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084635 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084636 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0084638 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0084639 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084640 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084641 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084642 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0084643 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084644 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084645 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084646 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084647 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0084648 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084649 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084650 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084651 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0084652 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084653 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084654 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0084655 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084657 )Cardiolipin Biosynthesis CL(18:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0084658 )Role Not Available 
