2.0 2015-09-08 19:31:53 -0600 2015-12-09 17:04:49 -0700 ECMDB24423 M2MDB006540 PGP(10:0(3-OH)/19:0cycv8c) PGP(10:0(3-OH)/19:0cycv8c) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(10:0(3-OH)/19:0cycv8c), in particular, consists of one 3-hydroxydecanoyl chain to the C-1 atom, and one heptadec-11-12-cyclo-anoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase. C35H68O14P2 774.863 774.408430866 [(2R)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(3-hydroxydecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC InChI=1S/C35H68O14P2/c1-3-5-7-12-17-21-31(36)24-35(39)45-27-33(28-48-51(43,44)47-26-32(37)25-46-50(40,41)42)49-34(38)22-18-14-11-9-10-13-16-20-30-23-29(30)19-15-8-6-4-2/h29-33,36-37H,3-28H2,1-2H3,(H,43,44)(H2,40,41,42)/t29?,30?,31?,32-,33-/m1/s1 KAHVTGIHPZPBLD-CDWAUKDPSA-N logp 4.77 ALOGPS logs -5.44 ALOGPS solubility 2.82e-03 g/l ALOGPS logp 7.47 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 774.863 ChemAxon mono_mass 774.408430866 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC ChemAxon formula C35H68O14P2 ChemAxon inchi InChI=1S/C35H68O14P2/c1-3-5-7-12-17-21-31(36)24-35(39)45-27-33(28-48-51(43,44)47-26-32(37)25-46-50(40,41)42)49-34(38)22-18-14-11-9-10-13-16-20-30-23-29(30)19-15-8-6-4-2/h29-33,36-37H,3-28H2,1-2H3,(H,43,44)(H2,40,41,42)/t29?,30?,31?,32-,33-/m1/s1 ChemAxon inchikey KAHVTGIHPZPBLD-CDWAUKDPSA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 191.99 ChemAxon polarizability 85.19 ChemAxon rotatable_bond_count 37 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(10:0(3-OH)/19:0cycv8c/10:0(3-OH)/19:0cycv8c)) 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. PW001908 Metabolic Specdb::CMs 1088228 Specdb::EiMs 5253 Specdb::MsMs 1296274 Specdb::MsMs 1296275 Specdb::MsMs 1296276 Specdb::MsMs 1410919 Specdb::MsMs 1410920 Specdb::MsMs 1410921 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 CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase P0ABF8 PGSA_ECOLI pgsA http://ecmdb.ca/proteins/P0ABF8.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml 2 CDP-DG(10:0(3-OH)/19:0cycv8c) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/19:0cycv8c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005316 2 PGP(10:0(3-OH)/19:0cycv8c) + Water >2 PG(10:0(3-OH)/19:0cycv8c) + Phosphate PW_R005317