2.0 2015-09-08 19:33:26 -0600 2015-12-09 17:18:52 -0700 ECMDB24456 M2MDB006573 PGP(14:0(3-OH)/16:1(9Z)) PGP(14:0(3-OH)/16:1(9Z)) 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)/16:1(9Z)), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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. C36H70O14P2 788.89 788.42408093 [(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxytetradecanoyl)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)CCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C36H70O14P2/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-35(39)50-34(31-49-52(44,45)48-29-33(38)28-47-51(41,42)43)30-46-36(40)27-32(37)25-23-21-19-17-12-10-8-6-4-2/h13-14,32-34,37-38H,3-12,15-31H2,1-2H3,(H,44,45)(H2,41,42,43)/b14-13-/t32?,33-,34-/m1/s1 IRXCXKQFMUNBGB-FNFUOXECSA-N logp 5.34 ALOGPS logs -5.41 ALOGPS solubility 3.09e-03 g/l ALOGPS logp 8.33 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 788.89 ChemAxon mono_mass 788.42408093 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC ChemAxon formula C36H70O14P2 ChemAxon inchi InChI=1S/C36H70O14P2/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-35(39)50-34(31-49-52(44,45)48-29-33(38)28-47-51(41,42)43)30-46-36(40)27-32(37)25-23-21-19-17-12-10-8-6-4-2/h13-14,32-34,37-38H,3-12,15-31H2,1-2H3,(H,44,45)(H2,41,42,43)/b14-13-/t32?,33-,34-/m1/s1 ChemAxon inchikey IRXCXKQFMUNBGB-FNFUOXECSA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 199.61 ChemAxon polarizability 87.91 ChemAxon rotatable_bond_count 39 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(14:0(3-OH)/16:1(9Z)/14:0(3-OH)/16:1(9Z))) 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. PW001939 Metabolic Specdb::CMs 1088886 Specdb::NmrOneD 282889 Specdb::NmrOneD 282890 Specdb::NmrOneD 282891 Specdb::NmrOneD 282892 Specdb::NmrOneD 282893 Specdb::NmrOneD 282894 Specdb::NmrOneD 282895 Specdb::NmrOneD 282896 Specdb::NmrOneD 282897 Specdb::NmrOneD 282898 Specdb::NmrOneD 282899 Specdb::NmrOneD 282900 Specdb::NmrOneD 282901 Specdb::NmrOneD 282902 Specdb::NmrOneD 282903 Specdb::NmrOneD 282904 Specdb::NmrOneD 282905 Specdb::NmrOneD 282906 Specdb::NmrOneD 282907 Specdb::NmrOneD 282908 Specdb::MsMs 1331227 Specdb::MsMs 1331228 Specdb::MsMs 1331229 Specdb::MsMs 1445497 Specdb::MsMs 1445498 Specdb::MsMs 1445499 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(14:0(3-OH)/16:1(9Z)) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/16:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005447 2 PGP(14:0(3-OH)/16:1(9Z)) + Water >2 PG(14:0(3-OH)/16:1(9Z)) + Phosphate PW_R005448