2.0 2015-09-08 19:33:09 -0600 2015-12-09 17:05:29 -0700 ECMDB24450 M2MDB006567 PGP(14:0(3-OH)/12:0) PGP(14:0(3-OH)/12:0) 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)/12:0), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one dodecanoyl 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. C32H64O14P2 734.798 734.377130737 [(2R)-3-({[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2-(dodecanoyloxy)-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)CCCCCCCCCCC InChI=1S/C32H64O14P2/c1-3-5-7-9-11-13-15-17-19-21-28(33)23-32(36)42-26-30(46-31(35)22-20-18-16-14-12-10-8-6-4-2)27-45-48(40,41)44-25-29(34)24-43-47(37,38)39/h28-30,33-34H,3-27H2,1-2H3,(H,40,41)(H2,37,38,39)/t28?,29-,30-/m1/s1 PVXXUFKJRCCSIV-GVKMRLRKSA-N logp 4.16 ALOGPS logs -4.95 ALOGPS solubility 8.32e-03 g/l ALOGPS logp 6.92 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-({[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 734.798 ChemAxon mono_mass 734.377130737 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC ChemAxon formula C32H64O14P2 ChemAxon inchi InChI=1S/C32H64O14P2/c1-3-5-7-9-11-13-15-17-19-21-28(33)23-32(36)42-26-30(46-31(35)22-20-18-16-14-12-10-8-6-4-2)27-45-48(40,41)44-25-29(34)24-43-47(37,38)39/h28-30,33-34H,3-27H2,1-2H3,(H,40,41)(H2,37,38,39)/t28?,29-,30-/m1/s1 ChemAxon inchikey PVXXUFKJRCCSIV-GVKMRLRKSA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 180.09 ChemAxon polarizability 81.01 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(14:0(3-OH)/12:0/14:0(3-OH)/12:0)) 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. PW001935 Metabolic Specdb::CMs 1086540 Specdb::NmrOneD 252148 Specdb::NmrOneD 252149 Specdb::NmrOneD 252150 Specdb::NmrOneD 252151 Specdb::NmrOneD 252152 Specdb::NmrOneD 252153 Specdb::NmrOneD 252154 Specdb::NmrOneD 252155 Specdb::NmrOneD 252156 Specdb::NmrOneD 252157 Specdb::NmrOneD 252158 Specdb::NmrOneD 252159 Specdb::NmrOneD 252160 Specdb::NmrOneD 252161 Specdb::NmrOneD 252162 Specdb::NmrOneD 252163 Specdb::NmrOneD 252164 Specdb::NmrOneD 252165 Specdb::NmrOneD 252166 Specdb::NmrOneD 252167 Specdb::MsMs 1280833 Specdb::MsMs 1280834 Specdb::MsMs 1280835 Specdb::MsMs 1395709 Specdb::MsMs 1395710 Specdb::MsMs 1395711 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)/12:0) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/12:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005430 2 PGP(14:0(3-OH)/12:0) + Water >2 PG(14:0(3-OH)/12:0) + Phosphate PW_R005431