2.0 2015-09-08 19:01:15 -0600 2015-12-09 17:04:07 -0700 ECMDB24311 M2MDB006428 PGP(18:1(11Z)/19:0) PGP(18:1(11Z)/19:0) 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(18:1(11Z)/19:0), in particular, consists of one 11Z-octadecenoyl chain to the C-1 atom, and one nonadecanoyl 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. C43H84O13P2 871.08 870.538716761 [(2R)-2-hydroxy-3-({hydroxy[(2R)-2-(nonadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid (2R)-2-hydroxy-3-{[hydroxy((2R)-2-(nonadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCC InChI=1S/C43H84O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-43(46)56-41(39-55-58(50,51)54-37-40(44)36-53-57(47,48)49)38-52-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,40-41,44H,3-13,15,17-39H2,1-2H3,(H,50,51)(H2,47,48,49)/b16-14-/t40-,41-/m1/s1 IYWRJLKOLCXYAV-RHYWPTEDSA-N logp 7.68 ALOGPS logs -6.25 ALOGPS solubility 4.87e-04 g/l ALOGPS logp 12.67 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-2-hydroxy-3-({hydroxy[(2R)-2-(nonadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid ChemAxon average_mass 871.08 ChemAxon mono_mass 870.538716761 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCC ChemAxon formula C43H84O13P2 ChemAxon inchi InChI=1S/C43H84O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-43(46)56-41(39-55-58(50,51)54-37-40(44)36-53-57(47,48)49)38-52-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16,40-41,44H,3-13,15,17-39H2,1-2H3,(H,50,51)(H2,47,48,49)/b16-14-/t40-,41-/m1/s1 ChemAxon inchikey IYWRJLKOLCXYAV-RHYWPTEDSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 230.3 ChemAxon polarizability 101.96 ChemAxon rotatable_bond_count 46 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(18:1(11Z)/19:0/18:1(11Z)/19:0)) 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. PW001980 Metabolic Specdb::NmrOneD 320811 Specdb::NmrOneD 320812 Specdb::NmrOneD 320813 Specdb::NmrOneD 320814 Specdb::NmrOneD 320815 Specdb::NmrOneD 320816 Specdb::NmrOneD 320817 Specdb::NmrOneD 320818 Specdb::NmrOneD 320819 Specdb::NmrOneD 320820 Specdb::NmrOneD 320821 Specdb::NmrOneD 320822 Specdb::NmrOneD 320823 Specdb::NmrOneD 320824 Specdb::NmrOneD 320825 Specdb::NmrOneD 320826 Specdb::NmrOneD 320827 Specdb::NmrOneD 320828 Specdb::NmrOneD 320829 Specdb::NmrOneD 320830 Specdb::MsMs 1283491 Specdb::MsMs 1283492 Specdb::MsMs 1283493 Specdb::MsMs 1398325 Specdb::MsMs 1398326 Specdb::MsMs 1398327 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 Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml 2 CDP-DG(18:1(11Z)/19:0) + Cytidine triphosphate + Hydrogen ion >2 PGP(18:1(11Z)/19:0) + Pyrophosphate PW_R005582 2 PGP(18:1(11Z)/19:0) + Water >2 PG(18:1(11Z)/19:0) + Phosphate PW_R005583