2.0 2015-09-08 19:38:50 -0600 2016-09-13 16:36:09 -0600 ECMDB24535 M2MDB006652 PGP(19:iso/12:0) PGP(19:iso/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(19:iso/12:0), in particular, consists of one 17-methylocatdecanoyl 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. C37H74O13P2 788.934 788.460466439 [(2S)-3-({[(2R)-2-(dodecanoyloxy)-3-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2S)-3-{[(2R)-2-(dodecanoyloxy)-3-[(17-methyloctadecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCCC InChI=1S/C37H74O13P2/c1-4-5-6-7-8-14-19-22-25-28-37(40)50-35(32-49-52(44,45)48-30-34(38)29-47-51(41,42)43)31-46-36(39)27-24-21-18-16-13-11-9-10-12-15-17-20-23-26-33(2)3/h33-35,38H,4-32H2,1-3H3,(H,44,45)(H2,41,42,43)/t34-,35+/m0/s1 UMRPWNXTBMMWES-OIDHKYIRSA-N logp 6.04 ALOGPS logs -5.86 ALOGPS solubility 1.09e-03 g/l ALOGPS logp 10.21 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2S)-3-({[(2R)-2-(dodecanoyloxy)-3-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 788.934 ChemAxon mono_mass 788.460466439 ChemAxon smiles [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCCC ChemAxon formula C37H74O13P2 ChemAxon inchi InChI=1S/C37H74O13P2/c1-4-5-6-7-8-14-19-22-25-28-37(40)50-35(32-49-52(44,45)48-30-34(38)29-47-51(41,42)43)31-46-36(39)27-24-21-18-16-13-11-9-10-12-15-17-20-23-26-33(2)3/h33-35,38H,4-32H2,1-3H3,(H,44,45)(H2,41,42,43)/t34-,35+/m0/s1 ChemAxon inchikey UMRPWNXTBMMWES-OIDHKYIRSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 201.53 ChemAxon polarizability 90.9 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(19:iso/12:0/19:iso/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. PW002001 Metabolic Specdb::CMs 1088113 Specdb::NmrOneD 329862 Specdb::NmrOneD 329863 Specdb::NmrOneD 329864 Specdb::NmrOneD 329865 Specdb::NmrOneD 329866 Specdb::NmrOneD 329867 Specdb::NmrOneD 329868 Specdb::NmrOneD 329869 Specdb::NmrOneD 329870 Specdb::NmrOneD 329871 Specdb::NmrOneD 329872 Specdb::NmrOneD 329873 Specdb::NmrOneD 329874 Specdb::NmrOneD 329875 Specdb::NmrOneD 329876 Specdb::NmrOneD 329877 Specdb::NmrOneD 329878 Specdb::NmrOneD 329879 Specdb::NmrOneD 329880 Specdb::NmrOneD 329881 Specdb::MsMs 26141 Specdb::MsMs 26142 Specdb::MsMs 26143 Specdb::MsMs 32699 Specdb::MsMs 32700 Specdb::MsMs 32701 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(19:iso/12:0) + Glycerol 3-phosphate >2 PGP(19:iso/12:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005635 2 PGP(19:iso/12:0) + Water >2 PG(19:iso/12:0) + Phosphate PW_R005636