2.0 2015-09-08 19:34:34 -0600 2015-12-09 17:19:51 -0700 ECMDB24479 M2MDB006596 PGP(15:0cyclo/17:0cycw7c) PGP(15:0cyclo/17:0cycw7c) 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/17:0cycw7c), in particular, consists of one cis-9,10-Methylenetetradecanoic acid chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl 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. C38H72O13P2 798.929 798.444816374 [(2R)-3-({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[8-(2-hexylcyclopropyl)octanoyl]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)CCCCCCCC1CC1CCCCCC InChI=1S/C38H72O13P2/c1-3-5-7-14-20-33-26-34(33)22-16-11-9-13-18-24-38(41)51-36(30-50-53(45,46)49-28-35(39)27-48-52(42,43)44)29-47-37(40)23-17-12-8-10-15-21-32-25-31(32)19-6-4-2/h31-36,39H,3-30H2,1-2H3,(H,45,46)(H2,42,43,44)/t31?,32?,33?,34?,35-,36-/m1/s1 PZEOLUITSWNUHI-YAHPJHIGSA-N logp 6.02 ALOGPS logs -5.90 ALOGPS solubility 9.98e-04 g/l ALOGPS logp 9.26 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-3-({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 798.929 ChemAxon mono_mass 798.444816374 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCC1CC1CCCCCC ChemAxon formula C38H72O13P2 ChemAxon inchi InChI=1S/C38H72O13P2/c1-3-5-7-14-20-33-26-34(33)22-16-11-9-13-18-24-38(41)51-36(30-50-53(45,46)49-28-35(39)27-48-52(42,43)44)29-47-37(40)23-17-12-8-10-15-21-32-25-31(32)19-6-4-2/h31-36,39H,3-30H2,1-2H3,(H,45,46)(H2,42,43,44)/t31?,32?,33?,34?,35-,36-/m1/s1 ChemAxon inchikey PZEOLUITSWNUHI-YAHPJHIGSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 202.37 ChemAxon polarizability 90.1 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/17:0cycw7c/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." PW001193 Metabolic Specdb::CMs 1086758 Specdb::EiMs 5155 Specdb::NmrOneD 252448 Specdb::NmrOneD 252449 Specdb::NmrOneD 252450 Specdb::NmrOneD 252451 Specdb::NmrOneD 252452 Specdb::NmrOneD 252453 Specdb::NmrOneD 252454 Specdb::NmrOneD 252455 Specdb::NmrOneD 252456 Specdb::NmrOneD 252457 Specdb::NmrOneD 252458 Specdb::NmrOneD 252459 Specdb::NmrOneD 252460 Specdb::NmrOneD 252461 Specdb::NmrOneD 252462 Specdb::NmrOneD 252463 Specdb::NmrOneD 252464 Specdb::NmrOneD 252465 Specdb::NmrOneD 252466 Specdb::NmrOneD 252467 Specdb::MsMs 1305937 Specdb::MsMs 1305938 Specdb::MsMs 1305939 Specdb::MsMs 1420456 Specdb::MsMs 1420457 Specdb::MsMs 1420458 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 Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml 2 PGP(15:0cyclo/17:0cycw7c) + Water >2 PG(15:0cyclo/17:0cycw7c) + Phosphate PW_R005778