2.0 2012-05-31 13:00:13 -0600 2015-09-13 12:56:08 -0600 ECMDB00674 M2MDB000169 PA(16:0/16:0) PA(16:0/16:0) 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(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphate 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid 1,2-Dihexadecanoyl-rac-phosphatidate 1,2-Dihexadecanoyl-rac-phosphatidic acid 1,2-Dipalmitoyl-3-sn-phosphatidate 1,2-Dipalmitoyl-3-sn-phosphatidic acid 1,2-Dipalmitoyl-sn-glycerol 3-phosphate 1,2-Dipalmitoyl-sn-glycerol 3-phosphoric acid 1,2-Dipalmitoyl-sn-glycerol-3-phosphate 1,2-Dipalmitoyl-sn-glycerol-3-phosphorate 1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid A 1,2-diacylglycerol-3-phosphate a 1,2-Diacylglycerol-3-phosphoric acid A 3-<i>sn</i>-phosphatidate a 3-sn-Phosphatidate a 3-sn-Phosphatidic acid A diacyl-glycerol-3p A diacyl-glycerol-p A diacylglycerol-3-phosphate a Diacylglycerol-3-phosphoric acid A phosphatidate A phosphatidic acid A phosphatidylglycerol An L-phosphatidate An L-phosphatidic acid DGP Diacylglycerol phosphate Diacylglycerol phosphoric acid Dipalmitoyl phosphatidate Dipalmitoyl-L-a-phosphatidate Dipalmitoyl-L-a-phosphatidic acid Dipalmitoyl-L-alpha-phosphatidate Dipalmitoyl-L-alpha-phosphatidic acid Dipalmitoyl-L-α-phosphatidate Dipalmitoyl-L-α-phosphatidic acid Dipalmitoylphosphatidate Dipalmitoylphosphatidic acid L-a-Dipalmitoyl-phosphatidate L-a-Dipalmitoyl-phosphatidic acid L-a-Dipalmitoylphosphatidate L-a-Dipalmitoylphosphatidic acid L-alpha-Dipalmitoyl-phosphatidate L-alpha-Dipalmitoyl-phosphatidic acid L-alpha-Dipalmitoylphosphatidate L-alpha-Dipalmitoylphosphatidic acid L-α-Dipalmitoyl-phosphatidate L-α-Dipalmitoyl-phosphatidic acid L-α-Dipalmitoylphosphatidate L-α-Dipalmitoylphosphatidic acid PA(32:0) Phosphatidate(16:0/16:0) Phosphatidate(32:0) Phosphatidic acid(16:0/16:0) Phosphatidic acid(32:0) C35H69O8P 648.8913 648.473005696 [(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid dipalmitoyl 7091-44-3 CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1 PORPENFLTBBHSG-MGBGTMOVSA-N Solid Inner membrane Membrane Outer membrane logp 8.66 ALOGPS logs -6.74 ALOGPS solubility 1.18e-04 g/l ALOGPS melting_point 161-165 oC logp 11.88 ChemAxon pka_strongest_acidic 1.32 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac [(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid ChemAxon average_mass 648.8913 ChemAxon mono_mass 648.473005696 ChemAxon smiles CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C35H69O8P ChemAxon inchi InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1 ChemAxon inchikey PORPENFLTBBHSG-MGBGTMOVSA-N ChemAxon polar_surface_area 119.36 ChemAxon refractivity 178.57 ChemAxon polarizability 80.08 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 Glycerolipid metabolism ec00561 Metabolic pathways eco01100 CDP-diacylglycerol biosynthesis I PWY-5667 CDP-diacylglycerol biosynthesis II PWY0-1319 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 11917 Specdb::NmrOneD 1472 Specdb::NmrOneD 335698 Specdb::NmrOneD 335699 Specdb::NmrOneD 335700 Specdb::NmrOneD 335701 Specdb::NmrOneD 335702 Specdb::NmrOneD 335703 Specdb::NmrOneD 335704 Specdb::NmrOneD 335705 Specdb::NmrOneD 335706 Specdb::NmrOneD 335707 Specdb::NmrOneD 335708 Specdb::NmrOneD 335709 Specdb::NmrOneD 335710 Specdb::NmrOneD 335711 Specdb::NmrOneD 335712 Specdb::NmrOneD 335713 Specdb::NmrOneD 335714 Specdb::NmrOneD 335715 Specdb::NmrOneD 335716 Specdb::NmrOneD 335717 Specdb::MsMs 933 Specdb::MsMs 934 Specdb::MsMs 935 Specdb::MsMs 183743 Specdb::MsMs 332392 Specdb::MsMs 332393 Specdb::MsMs 332394 Specdb::MsMs 2240553 Specdb::MsMs 2360144 Specdb::MsMs 2360145 Specdb::MsMs 2360146 Specdb::MsMs 2683593 Specdb::MsMs 2683594 Specdb::MsMs 2683595 Specdb::MsMs 3021783 Specdb::MsMs 3021784 Specdb::MsMs 3021785 Specdb::NmrTwoD 1417 HMDB00674 446066 393518 C00416 L-PHOSPHATIDATE PX6 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Niedernberg, A., Tunaru, S., Blaukat, A., Ardati, A., Kostenis, E. (2003). "Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63." Cell Signal 15:435-446. 12618218 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Park KA, Vasko MR: Lipid mediators of sensitivity in sensory neurons. Trends Pharmacol Sci. 2005 Nov;26(11):571-7. Epub 2005 Sep 26. 16185776 Ando, Yoshihiro; Oda, Hiroshi; Matsuyoshi, Shigeru; Maekawa, Naoya. Manufacture of phosphatidic acid alkali metal or ammonium salts using phospholipase D. Jpn. Kokai Tokkyo Koho (2001), 8 pp. http://hmdb.ca/system/metabolites/msds/000/000/593/original/HMDB00674.pdf?1358463451 CDP-diacylglycerol pyrophosphatase P06282 CDH_ECOLI cdh http://ecmdb.ca/proteins/P06282.xml Phospholipase A1 P0A921 PA1_ECOLI pldA http://ecmdb.ca/proteins/P0A921.xml Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml Diacylglycerol kinase P0ABN1 KDGL_ECOLI dgkA http://ecmdb.ca/proteins/P0ABN1.xml 1-acyl-sn-glycerol-3-phosphate acyltransferase P26647 PLSC_ECOLI plsC http://ecmdb.ca/proteins/P26647.xml Uncharacterized protein ynbB P76091 YNBB_ECOLI ynbB http://ecmdb.ca/proteins/P76091.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-didodecanoylglycerol + Pyrophosphate Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dihexadec-9-enoylglycerol + Pyrophosphate Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dihexadecanoylglycerol + Pyrophosphate Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dioctadec-11-enoylglycerol + Pyrophosphate Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-Dioctadecanoylglycerol + Pyrophosphate Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-ditetradec-7-enoylglycerol + Pyrophosphate Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-ditetradecanoylglycerol + Pyrophosphate Adenosine triphosphate + Water + PA(16:0/16:0) > ADP + Hydrogen ion + Phosphate + PA(16:0/16:0) Adenosine triphosphate + Water + PA(16:0/16:0) > ADP + Hydrogen ion + Phosphate + PA(16:0/16:0) Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + Phosphate Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphate Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadecanoyl, n-C16:0) + Phosphate Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Phosphate Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dioctadecanoyl, n-C18:0) + Phosphate Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (ditetradec-7-enoyl, n-C14:1) + Phosphate Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Phosphate 1-Dodecanoyl-sn-glycerol 3-phosphate + Dodecanoyl-ACP (n-C12:0ACP) > acyl carrier protein + PA(16:0/16:0) 1-Hexadec-9-enoyl-sn-glycerol 3-phosphate + cis-hexadec-9-enoyl-[acyl-carrier protein] (n-C16:1) > acyl carrier protein + PA(16:0/16:0) 1-hexadecanoyl-sn-glycerol 3-phosphate + Palmitoyl-ACP (n-C16:0ACP) > acyl carrier protein + PA(16:0/16:0) 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1) > acyl carrier protein + PA(16:0/16:0) 1-Octadecanoyl-sn-glycerol 3-phosphate + Octadecanoyl-ACP (n-C18:0ACP) > acyl carrier protein + PA(16:0/16:0) 1-Tetradec-7-enoyl-sn-glycerol 3-phosphate + cis-tetradec-7-enoyl-[acyl-carrier protein] (n-C14:1) > acyl carrier protein + PA(16:0/16:0) 1-Tetradecanoyl-sn-glycerol 3-phosphate + Myristoyl-ACP (n-C14:0ACP) > acyl carrier protein + PA(16:0/16:0) Water + PA(16:0/16:0) > 1-Dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0) + Hydrogen ion Water + PA(16:0/16:0) > 1-Hexadec-9-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Hexadecenoate (n-C16:1) Water + PA(16:0/16:0) > 1-hexadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Palmitic acid Water + PA(16:0/16:0) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecenoate (N-C18:1) Water + PA(16:0/16:0) > 1-Octadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecanoate (N-C18:0) Water + PA(16:0/16:0) > 1-Tetradec-7-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Tetradecenoate (N-C14:1) Water + PA(16:0/16:0) > 1-Tetradecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + tetradecanoate (n-C14:0) Water + PA(16:0/16:0) > 2-dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0) Water + PA(16:0/16:0) > 2-hexadec-9-enoyl-sn-glycerol 3-phosphate + Hexadecenoate (n-C16:1) Water + PA(16:0/16:0) > 2-hexadecanoyl-sn-glycerol 3-phosphate + Palmitic acid Water + PA(16:0/16:0) > 2-octadec-11-enoyl-sn-glycerol 3-phosphate + Octadecenoate (N-C18:1) Water + PA(16:0/16:0) > 2-octadecanoyl-sn-glycerol 3-phosphate + Octadecanoate (N-C18:0) Water + PA(16:0/16:0) > 2-tetradec-7-enoyl-sn-glycerol 3-phosphate + Tetradecenoate (N-C14:1) Water + PA(16:0/16:0) > 2-tetradecanoyl-sn-glycerol 3-phosphate + tetradecanoate (n-C14:0) CDP-1,2-didodecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) CDP-1,2-dihexadec-9-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) CDP-1,2-dihexadecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) CDP-1,2-dioctadec-11-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) CDP-1,2-Dioctadecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) CDP-1,2-ditetradec-7-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) CDP-1,2-ditetradecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (dihexadecanoyl, n-C16:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (dioctadecanoyl, n-C18:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (ditetradec-7-enoyl, n-C14:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0) CDP-diacylglycerol + Water <> Cytidine monophosphate + PA(16:0/16:0) R01797 Cytidine triphosphate + PA(16:0/16:0) <> Pyrophosphate + CDP-diacylglycerol R01799 Adenosine triphosphate + 1,2-Diacyl-sn-glycerol + 1,2-Diacyl-sn-glycerol <> ADP + PA(16:0/16:0) R02240 PA(16:0/16:0) + Coenzyme A + Acyl-CoA + 1-Acyl-sn-glycerol 3-phosphate <> 1-Acyl-sn-glycerol 3-phosphate + Acyl-CoA R02241 Acyl-[acyl-carrier protein] + 1-Acyl-sn-glycerol 3-phosphate <> Acyl-carrier protein + PA(16:0/16:0) R09381 a 1,2-diacyl-<i>sn</i>-glycerol 3-diphosphate + Water PA(16:0/16:0) + Phosphate + Hydrogen ion RXN0-4461 a CDP-diacylglycerol + Water <> PA(16:0/16:0) + Cytidine monophosphate + Hydrogen ion CDPDIGLYPYPHOSPHA-RXN Cytidine triphosphate + PA(16:0/16:0) + Hydrogen ion > Pyrophosphate + a CDP-diacylglycerol CDPDIGLYSYN-RXN Adenosine triphosphate + a 1,2-diacylglycerol <> Hydrogen ion + PA(16:0/16:0) + ADP DIACYLGLYKIN-RXN a 1-acyl-<i>sn</i>-glycerol-3-phosphate + a long-chain acyl-CoA > Coenzyme A + PA(16:0/16:0) RXN-1623 Adenosine triphosphate + 1,2-Diacyl-sn-glycerol <> ADP + PA(16:0/16:0) Cytidine triphosphate + PA(16:0/16:0) <> Pyrophosphate + CDP-diacylglycerol Adenosine triphosphate + 1,2-Diacyl-sn-glycerol <> ADP + PA(16:0/16:0)