2.0 2015-09-08 18:59:48 -0600 2015-12-09 12:08:11 -0700 ECMDB24276 M2MDB006393 PG(18:1(9Z)/12:0) PG(18:1(9Z)/12:0) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(18:1(9Z)/12:0), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one dodecanoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes. C36H69O10P 692.912 692.46283542 [(2S)-2,3-dihydroxypropoxy][(2R)-3-(dodecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid (2S)-2,3-dihydroxypropoxy((2R)-3-(dodecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C36H69O10P/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-36(40)46-34(32-45-47(41,42)44-30-33(38)29-37)31-43-35(39)27-25-23-21-19-12-10-8-6-4-2/h15-16,33-34,37-38H,3-14,17-32H2,1-2H3,(H,41,42)/b16-15-/t33-,34+/m0/s1 QNXFSDDYPGKBOX-WYRVCTHCSA-N logp 7.25 ALOGPS logs -6.53 ALOGPS solubility 2.04e-04 g/l ALOGPS logp 9.69 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac [(2S)-2,3-dihydroxypropoxy][(2R)-3-(dodecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid ChemAxon average_mass 692.912 ChemAxon mono_mass 692.46283542 ChemAxon smiles [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C36H69O10P ChemAxon inchi InChI=1S/C36H69O10P/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-36(40)46-34(32-45-47(41,42)44-30-33(38)29-37)31-43-35(39)27-25-23-21-19-12-10-8-6-4-2/h15-16,33-34,37-38H,3-14,17-32H2,1-2H3,(H,41,42)/b16-15-/t33-,34+/m0/s1 ChemAxon inchikey QNXFSDDYPGKBOX-WYRVCTHCSA-N ChemAxon polar_surface_area 148.82 ChemAxon refractivity 187.22 ChemAxon polarizability 81.87 ChemAxon rotatable_bond_count 37 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(18:1(9Z)/12:0(3-OH)/18:1(9Z)/12:0(3-OH))) Phospholipids are membrane components in E. coli. The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase. Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin. PW001982 Metabolic Specdb::CMs 1088338 Specdb::NmrOneD 253808 Specdb::NmrOneD 253809 Specdb::NmrOneD 253810 Specdb::NmrOneD 253811 Specdb::NmrOneD 253812 Specdb::NmrOneD 253813 Specdb::NmrOneD 253814 Specdb::NmrOneD 253815 Specdb::NmrOneD 253816 Specdb::NmrOneD 253817 Specdb::NmrOneD 253818 Specdb::NmrOneD 253819 Specdb::NmrOneD 253820 Specdb::NmrOneD 253821 Specdb::NmrOneD 253822 Specdb::NmrOneD 253823 Specdb::NmrOneD 253824 Specdb::NmrOneD 253825 Specdb::NmrOneD 253826 Specdb::NmrOneD 253827 Specdb::MsMs 189499 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 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 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 Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml 2 PGP(18:1(9Z)/12:0) + Water >2 PG(18:1(9Z)/12:0) + Phosphate PW_R005798