2.0 2015-09-08 19:34:17 -0600 2015-12-09 17:19:34 -0700 ECMDB24473 M2MDB006590 PGP(15:0cyclo/10:0(3-OH)) PGP(15:0cyclo/10:0(3-OH)) 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(15:0cyclo/10:0(3-OH)), in particular, consists of one cis-9,10-Methylenetetradecanoic acid chain to the C-1 atom, and one 3-hydroxydecanoyl 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. C31H60O14P2 718.755 718.345830608 [(2R)-3-({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCC InChI=1S/C31H60O14P2/c1-3-5-7-9-13-17-27(32)20-31(35)45-29(24-44-47(39,40)43-22-28(33)21-42-46(36,37)38)23-41-30(34)18-14-11-8-10-12-16-26-19-25(26)15-6-4-2/h25-29,32-33H,3-24H2,1-2H3,(H,39,40)(H2,36,37,38)/t25?,26?,27?,28-,29-/m1/s1 CHFARPUFXFULQH-BSRKSAPBSA-N logp 3.63 ALOGPS logs -5.03 ALOGPS solubility 6.76e-03 g/l ALOGPS logp 5.69 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 718.755 ChemAxon mono_mass 718.345830608 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCC ChemAxon formula C31H60O14P2 ChemAxon inchi InChI=1S/C31H60O14P2/c1-3-5-7-9-13-17-27(32)20-31(35)45-29(24-44-47(39,40)43-22-28(33)21-42-46(36,37)38)23-41-30(34)18-14-11-8-10-12-16-26-19-25(26)15-6-4-2/h25-29,32-33H,3-24H2,1-2H3,(H,39,40)(H2,36,37,38)/t25?,26?,27?,28-,29-/m1/s1 ChemAxon inchikey CHFARPUFXFULQH-BSRKSAPBSA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 173.58 ChemAxon polarizability 77.88 ChemAxon rotatable_bond_count 33 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(15:0cyclo/10:0(3-OH)/15:0cyclo/10:0(3-OH))) 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. PW001948 Metabolic Specdb::CMs 1087048 Specdb::EiMs 2243 Specdb::NmrOneD 262908 Specdb::NmrOneD 262909 Specdb::NmrOneD 262910 Specdb::NmrOneD 262911 Specdb::NmrOneD 262912 Specdb::NmrOneD 262913 Specdb::NmrOneD 262914 Specdb::NmrOneD 262915 Specdb::NmrOneD 262916 Specdb::NmrOneD 262917 Specdb::NmrOneD 262918 Specdb::NmrOneD 262919 Specdb::NmrOneD 262920 Specdb::NmrOneD 262921 Specdb::NmrOneD 262922 Specdb::NmrOneD 262923 Specdb::NmrOneD 262924 Specdb::NmrOneD 262925 Specdb::NmrOneD 262926 Specdb::NmrOneD 262927 Specdb::MsMs 1311262 Specdb::MsMs 1311263 Specdb::MsMs 1311264 Specdb::MsMs 1425742 Specdb::MsMs 1425743 Specdb::MsMs 1425744 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(15:0cyclo/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(15:0cyclo/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005480 2 PGP(15:0cyclo/10:0(3-OH)) + Water >2 PG(15:0cyclo/10:0(3-OH)) + Phosphate PW_R005481