2.0 2015-09-08 19:01:25 -0600 2015-12-09 17:04:12 -0700 ECMDB24315 M2MDB006432 PGP(19:0/14:0) PGP(19:0/14:0) 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(19:0/14:0), in particular, consists of one nonadecanoyl 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. C39H78O13P2 816.988 816.491766568 [(2R)-2-hydroxy-3-({hydroxy[(2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid (2R)-2-hydroxy-3-{[hydroxy((2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxy)phosphoryl]oxy}propoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC InChI=1S/C39H78O13P2/c1-3-5-7-9-11-13-15-16-17-18-19-21-22-24-26-28-30-38(41)48-34-37(35-51-54(46,47)50-33-36(40)32-49-53(43,44)45)52-39(42)31-29-27-25-23-20-14-12-10-8-6-4-2/h36-37,40H,3-35H2,1-2H3,(H,46,47)(H2,43,44,45)/t36-,37-/m1/s1 WLDCWECGXYOYIO-FZNHDDJXSA-N logp 6.82 ALOGPS logs -6.04 ALOGPS solubility 7.38e-04 g/l ALOGPS logp 11.26 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-2-hydroxy-3-({hydroxy[(2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid ChemAxon average_mass 816.988 ChemAxon mono_mass 816.491766568 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC ChemAxon formula C39H78O13P2 ChemAxon inchi InChI=1S/C39H78O13P2/c1-3-5-7-9-11-13-15-16-17-18-19-21-22-24-26-28-30-38(41)48-34-37(35-51-54(46,47)50-33-36(40)32-49-53(43,44)45)52-39(42)31-29-27-25-23-20-14-12-10-8-6-4-2/h36-37,40H,3-35H2,1-2H3,(H,46,47)(H2,43,44,45)/t36-,37-/m1/s1 ChemAxon inchikey WLDCWECGXYOYIO-FZNHDDJXSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 210.78 ChemAxon polarizability 95.5 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(19:0/16:1(9Z)/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. PW001983 Metabolic Specdb::CMs 1088057 Specdb::NmrOneD 254968 Specdb::NmrOneD 254969 Specdb::NmrOneD 254970 Specdb::NmrOneD 254971 Specdb::NmrOneD 254972 Specdb::NmrOneD 254973 Specdb::NmrOneD 254974 Specdb::NmrOneD 254975 Specdb::NmrOneD 254976 Specdb::NmrOneD 254977 Specdb::NmrOneD 254978 Specdb::NmrOneD 254979 Specdb::NmrOneD 254980 Specdb::NmrOneD 254981 Specdb::NmrOneD 254982 Specdb::NmrOneD 254983 Specdb::NmrOneD 254984 Specdb::NmrOneD 254985 Specdb::NmrOneD 254986 Specdb::NmrOneD 254987 Specdb::MsMs 1244824 Specdb::MsMs 1244825 Specdb::MsMs 1244826 Specdb::MsMs 1360192 Specdb::MsMs 1360193 Specdb::MsMs 1360194 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(19:0/14:0) + Water >2 PG(19:0/14:0) + Phosphate PW_R005771