2.0 2015-09-08 19:33:14 -0600 2015-12-09 17:05:35 -0700 ECMDB24452 M2MDB006569 PGP(14:0(3-OH)/14:0) PGP(14:0(3-OH)/14:0) 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(14:0(3-OH)/14:0), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one tetradecanoyl 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. C34H68O14P2 762.852 762.408430866 [(2R)-2-hydroxy-3-({hydroxy[(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid (2R)-2-hydroxy-3-{[hydroxy((2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-(tetradecanoyloxy)propoxy)phosphoryl]oxy}propoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC InChI=1S/C34H68O14P2/c1-3-5-7-9-11-13-14-16-18-20-22-24-33(37)48-32(29-47-50(42,43)46-27-31(36)26-45-49(39,40)41)28-44-34(38)25-30(35)23-21-19-17-15-12-10-8-6-4-2/h30-32,35-36H,3-29H2,1-2H3,(H,42,43)(H2,39,40,41)/t30?,31-,32-/m1/s1 YMGCHNGHPLMTRJ-YPHBKRNWSA-N logp 4.77 ALOGPS logs -5.26 ALOGPS solubility 4.21e-03 g/l ALOGPS logp 7.8 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-2-hydroxy-3-({hydroxy[(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid ChemAxon average_mass 762.852 ChemAxon mono_mass 762.408430866 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC ChemAxon formula C34H68O14P2 ChemAxon inchi InChI=1S/C34H68O14P2/c1-3-5-7-9-11-13-14-16-18-20-22-24-33(37)48-32(29-47-50(42,43)46-27-31(36)26-45-49(39,40)41)28-44-34(38)25-30(35)23-21-19-17-15-12-10-8-6-4-2/h30-32,35-36H,3-29H2,1-2H3,(H,42,43)(H2,39,40,41)/t30?,31-,32-/m1/s1 ChemAxon inchikey YMGCHNGHPLMTRJ-YPHBKRNWSA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 189.29 ChemAxon polarizability 84.63 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(16:1(9Z)/10:0/14:0/14:0)) 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. PW001954 Metabolic Specdb::CMs 1085000 Specdb::NmrOneD 283429 Specdb::NmrOneD 283430 Specdb::NmrOneD 283431 Specdb::NmrOneD 283432 Specdb::NmrOneD 283433 Specdb::NmrOneD 283434 Specdb::NmrOneD 283435 Specdb::NmrOneD 283436 Specdb::NmrOneD 283437 Specdb::NmrOneD 283438 Specdb::NmrOneD 283439 Specdb::NmrOneD 283440 Specdb::NmrOneD 283441 Specdb::NmrOneD 283442 Specdb::NmrOneD 283443 Specdb::NmrOneD 283444 Specdb::NmrOneD 283445 Specdb::NmrOneD 283446 Specdb::NmrOneD 283447 Specdb::NmrOneD 283448 Specdb::MsMs 1287625 Specdb::MsMs 1287626 Specdb::MsMs 1287627 Specdb::MsMs 1402402 Specdb::MsMs 1402403 Specdb::MsMs 1402404 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(14:0(3-OH)/14:0) + Water >2 PG(14:0(3-OH)/14:0) + Phosphate PW_R005712