2.0 2015-09-08 19:32:30 -0600 2015-12-09 17:18:31 -0700 ECMDB24436 M2MDB006553 PGP(12:0(3-OH)/15:0cyclo) PGP(12:0(3-OH)/15:0cyclo) 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(12:0(3-OH)/15:0cyclo), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one cis-9,10-Methylenetetradecanoic acid 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. C33H64O14P2 746.809 746.377130737 [(2R)-3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)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)CCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCC InChI=1S/C33H64O14P2/c1-3-5-7-8-9-12-15-19-29(34)22-33(37)43-25-31(26-46-49(41,42)45-24-30(35)23-44-48(38,39)40)47-32(36)20-16-13-10-11-14-18-28-21-27(28)17-6-4-2/h27-31,34-35H,3-26H2,1-2H3,(H,41,42)(H2,38,39,40)/t27?,28?,29?,30-,31-/m1/s1 QNDQBDRULUOORK-FOMSTSDASA-N logp 4.18 ALOGPS logs -5.30 ALOGPS solubility 3.74e-03 g/l ALOGPS logp 6.58 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 746.809 ChemAxon mono_mass 746.377130737 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCC ChemAxon formula C33H64O14P2 ChemAxon inchi InChI=1S/C33H64O14P2/c1-3-5-7-8-9-12-15-19-29(34)22-33(37)43-25-31(26-46-49(41,42)45-24-30(35)23-44-48(38,39)40)47-32(36)20-16-13-10-11-14-18-28-21-27(28)17-6-4-2/h27-31,34-35H,3-26H2,1-2H3,(H,41,42)(H2,38,39,40)/t27?,28?,29?,30-,31-/m1/s1 ChemAxon inchikey QNDQBDRULUOORK-FOMSTSDASA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 182.79 ChemAxon polarizability 81.34 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0(3-OH)/15:0cyclo/12:0(3-OH)/15:0cyclo)) 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. PW001921 Metabolic Specdb::CMs 1087388 Specdb::EiMs 5552 Specdb::NmrOneD 252128 Specdb::NmrOneD 252129 Specdb::NmrOneD 252130 Specdb::NmrOneD 252131 Specdb::NmrOneD 252132 Specdb::NmrOneD 252133 Specdb::NmrOneD 252134 Specdb::NmrOneD 252135 Specdb::NmrOneD 252136 Specdb::NmrOneD 252137 Specdb::NmrOneD 252138 Specdb::NmrOneD 252139 Specdb::NmrOneD 252140 Specdb::NmrOneD 252141 Specdb::NmrOneD 252142 Specdb::NmrOneD 252143 Specdb::NmrOneD 252144 Specdb::NmrOneD 252145 Specdb::NmrOneD 252146 Specdb::NmrOneD 252147 Specdb::MsMs 1309234 Specdb::MsMs 1309235 Specdb::MsMs 1309236 Specdb::MsMs 1423732 Specdb::MsMs 1423733 Specdb::MsMs 1423734 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(12:0(3-OH)/15:0cyclo) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/15:0cyclo) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005375 2 PGP(12:0(3-OH)/15:0cyclo) + Water >2 PG(12:0(3-OH)/15:0cyclo) + Phosphate PW_R005376