2.0 2012-05-31 14:12:43 -0600 2015-06-03 15:55:02 -0600 ECMDB07861 M2MDB000746 PA(18:0/18:2(9Z,12Z)) PA(18:0/18:2(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(18:0/18:2(9Z,12Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of linoleic 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-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-phosphatidate 1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-phosphatidic acid 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphate 1-Stearoyl-2-linoleoyl-sn-glycero-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 PA(18:0/18:2) PA(18:0/18:2n6) PA(18:0/18:2w6) PA(36:2) Phosphatidate(18:0/18:2) Phosphatidate(18:0/18:2n6) Phosphatidate(18:0/18:2w6) Phosphatidate(36:2) Phosphatidic acid(18:0/18:2) Phosphatidic acid(18:0/18:2n6) Phosphatidic acid(18:0/18:2w6) Phosphatidic acid(36:2) C39H73O8P 700.9659 700.504305824 [(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid (2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C39H73O8P/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/h12,14,18,20,37H,3-11,13,15-17,19,21-36H2,1-2H3,(H2,42,43,44)/b14-12-,20-18-/t37-/m1/s1 QYYWMYCDFOLKKH-DAKWMOBOSA-N Solid Inner membrane Membrane Outer membrane logp 9.14 ALOGPS logs -7.02 ALOGPS solubility 6.77e-05 g/l ALOGPS logp 12.93 ChemAxon pka_strongest_acidic 1.32 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac [(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid ChemAxon average_mass 700.9659 ChemAxon mono_mass 700.504305824 ChemAxon smiles CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C39H73O8P ChemAxon inchi InChI=1S/C39H73O8P/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/h12,14,18,20,37H,3-11,13,15-17,19,21-36H2,1-2H3,(H2,42,43,44)/b14-12-,20-18-/t37-/m1/s1 ChemAxon inchikey QYYWMYCDFOLKKH-DAKWMOBOSA-N ChemAxon polar_surface_area 119.36 ChemAxon refractivity 199.21 ChemAxon polarizability 85.11 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 Glycerolipid metabolism ec00561 CDP-diacylglycerol biosynthesis I PWY-5667 CDP-diacylglycerol biosynthesis II PWY0-1319 phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::CMs 1086475 Specdb::NmrOneD 303851 Specdb::NmrOneD 303852 Specdb::NmrOneD 303853 Specdb::NmrOneD 303854 Specdb::NmrOneD 303855 Specdb::NmrOneD 303856 Specdb::NmrOneD 303857 Specdb::NmrOneD 303858 Specdb::NmrOneD 303859 Specdb::NmrOneD 303860 Specdb::NmrOneD 303861 Specdb::NmrOneD 303862 Specdb::NmrOneD 303863 Specdb::NmrOneD 303864 Specdb::NmrOneD 303865 Specdb::NmrOneD 303866 Specdb::NmrOneD 303867 Specdb::NmrOneD 303868 Specdb::NmrOneD 303869 Specdb::NmrOneD 303870 Specdb::MsMs 24068 Specdb::MsMs 24069 Specdb::MsMs 24070 Specdb::MsMs 30866 Specdb::MsMs 30867 Specdb::MsMs 30868 Specdb::MsMs 2590777 Specdb::MsMs 2590778 Specdb::MsMs 2590779 Specdb::MsMs 2674096 Specdb::MsMs 2674097 Specdb::MsMs 2674098 Specdb::MsMs 3034232 Specdb::MsMs 3034233 Specdb::MsMs 3034234 HMDB07861 24766515 C00416 L-PHOSPHATIDATE Lecithin 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 1-acyl-sn-glycerol-3-phosphate acyltransferase P26647 PLSC_ECOLI plsC http://ecmdb.ca/proteins/P26647.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 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