2.02012-05-31 14:12:36 -06002015-06-03 15:55:01 -0600ECMDB07859M2MDB000744PA(16:0/18:1(9Z))PA(16:0/18:1(9Z)) 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(16:0/18:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of oleic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases. 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. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs). Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776).1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidate1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidic acid1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphate1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoric acidA 1,2-diacylglycerol-3-phosphatea 1,2-Diacylglycerol-3-phosphoric acidA 3-<i>sn</i>-phosphatidatea 3-sn-Phosphatidatea 3-sn-Phosphatidic acidA diacyl-glycerol-3pA diacyl-glycerol-pA diacylglycerol-3-phosphatea Diacylglycerol-3-phosphoric acidA phosphatidateA phosphatidic acidA phosphatidylglycerolAn L-phosphatidateAn L-phosphatidic acidDGPDiacylglycerol phosphateDiacylglycerol phosphoric acidPA(16:0/18:1)PA(16:0/18:1n9)PA(16:0/18:1w9)PA(34:1)Phosphatidate(16:0/18:1)Phosphatidate(16:0/18:1n9)Phosphatidate(16:0/18:1w9)Phosphatidate(34:1)Phosphatidic acid(16:0/18:1)Phosphatidic acid(16:0/18:1n9)Phosphatidic acid(16:0/18:1w9)Phosphatidic acid(34:1)C37H71O8P674.9286674.48865576[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acidCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/CCCCCCCCInChI=1S/C37H71O8P/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/h17-18,35H,3-16,19-34H2,1-2H3,(H2,40,41,42)/b18-17-/t35-/m1/s1OPVZUEPSMJNLOM-QEJMHMKOSA-NSolidInner membraneMembraneOuter membranelogp8.91logs-6.94solubility7.74e-05 g/llogp12.41pka_strongest_acidic1.32pka_strongest_basic-6.7iupac[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acidaverage_mass674.9286mono_mass674.48865576smilesCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/CCCCCCCCformulaC37H71O8PinchiInChI=1S/C37H71O8P/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/h17-18,35H,3-16,19-34H2,1-2H3,(H2,40,41,42)/b18-17-/t35-/m1/s1inchikeyOPVZUEPSMJNLOM-QEJMHMKOSA-Npolar_surface_area119.36refractivity188.89polarizability82.83rotatable_bond_count37acceptor_count5donor_count2physiological_charge-2formal_charge0Glycerophospholipid metabolismec00564Glycerolipid metabolismec00561CDP-diacylglycerol biosynthesis IPWY-5667CDP-diacylglycerol biosynthesis IIPWY0-1319phospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs17034Specdb::NmrOneD337308Specdb::NmrOneD337309Specdb::NmrOneD337310Specdb::NmrOneD337311Specdb::NmrOneD337312Specdb::NmrOneD337313Specdb::NmrOneD337314Specdb::NmrOneD337315Specdb::NmrOneD337316Specdb::NmrOneD337317Specdb::NmrOneD337318Specdb::NmrOneD337319Specdb::NmrOneD337320Specdb::NmrOneD337321Specdb::NmrOneD337322Specdb::NmrOneD337323Specdb::NmrOneD337324Specdb::NmrOneD337325Specdb::NmrOneD337326Specdb::NmrOneD337327Specdb::MsMs28553Specdb::MsMs28554Specdb::MsMs28555Specdb::MsMs35111Specdb::MsMs35112Specdb::MsMs35113Specdb::MsMs2281027Specdb::MsMs2281028Specdb::MsMs2281029Specdb::MsMs2772260Specdb::MsMs2772261Specdb::MsMs2772262Specdb::MsMs2909249Specdb::MsMs2909250Specdb::MsMs2909251HMDB078594446637C00416L-PHOSPHATIDATELecithinKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Niedernberg, 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 15:435-446.12618218Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APark KA, Vasko MR: Lipid mediators of sensitivity in sensory neurons. Trends Pharmacol Sci. 2005 Nov;26(11):571-7. Epub 2005 Sep 26.161857761-acyl-sn-glycerol-3-phosphate acyltransferaseP26647PLSC_ECOLIplsChttp://ecmdb.ca/proteins/P26647.xmlProtein crcAP37001CRCA_ECOLIcrcAhttp://ecmdb.ca/proteins/P37001.xmlProbable phospholipid ABC transporter-binding protein mlaBP64602MLAB_ECOLImlaBhttp://ecmdb.ca/proteins/P64602.xmlProbable phospholipid ABC transporter-binding protein mlaDP64604MLAD_ECOLImlaDhttp://ecmdb.ca/proteins/P64604.xmlProbable phospholipid ABC transporter permease protein mlaEP64606MLAE_ECOLImlaEhttp://ecmdb.ca/proteins/P64606.xml