2.0 2015-09-08 19:33:53 -0600 2015-12-09 17:19:14 -0700 ECMDB24465 M2MDB006582 PGP(14:0/17:0cycw7c) PGP(14:0/17:0cycw7c) 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(14:0/17:0cycw7c), in particular, consists of one tetradecanoyl 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. C37H72O13P2 786.918 786.444816374 [(2R)-3-({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCCCC InChI=1S/C37H72O13P2/c1-3-5-7-9-10-11-12-13-14-17-21-25-36(39)46-30-35(31-49-52(44,45)48-29-34(38)28-47-51(41,42)43)50-37(40)26-22-18-15-16-20-24-33-27-32(33)23-19-8-6-4-2/h32-35,38H,3-31H2,1-2H3,(H,44,45)(H2,41,42,43)/t32?,33?,34-,35-/m1/s1 ODDDJYDQTIQYJL-RWHWJHECSA-N logp 6.15 ALOGPS logs -5.84 ALOGPS solubility 1.14e-03 g/l ALOGPS logp 9.59 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-3-({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 786.918 ChemAxon mono_mass 786.444816374 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCCCC ChemAxon formula C37H72O13P2 ChemAxon inchi InChI=1S/C37H72O13P2/c1-3-5-7-9-10-11-12-13-14-17-21-25-36(39)46-30-35(31-49-52(44,45)48-29-34(38)28-47-51(41,42)43)50-37(40)26-22-18-15-16-20-24-33-27-32(33)23-19-8-6-4-2/h32-35,38H,3-31H2,1-2H3,(H,44,45)(H2,41,42,43)/t32?,33?,34-,35-/m1/s1 ChemAxon inchikey ODDDJYDQTIQYJL-RWHWJHECSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 199.67 ChemAxon polarizability 89.33 ChemAxon rotatable_bond_count 39 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(18:1(9Z)/14:0/17:0cycw7c/14:0)) 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. PW001498 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/17:0cycw7c/14:0/17:0cycw7c)) 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. PW001403 Metabolic Specdb::CMs 1085019 Specdb::EiMs 5190 Specdb::NmrOneD 252428 Specdb::NmrOneD 252429 Specdb::NmrOneD 252430 Specdb::NmrOneD 252431 Specdb::NmrOneD 252432 Specdb::NmrOneD 252433 Specdb::NmrOneD 252434 Specdb::NmrOneD 252435 Specdb::NmrOneD 252436 Specdb::NmrOneD 252437 Specdb::NmrOneD 252438 Specdb::NmrOneD 252439 Specdb::NmrOneD 252440 Specdb::NmrOneD 252441 Specdb::NmrOneD 252442 Specdb::NmrOneD 252443 Specdb::NmrOneD 252444 Specdb::NmrOneD 252445 Specdb::NmrOneD 252446 Specdb::NmrOneD 252447 Specdb::MsMs 1279588 Specdb::MsMs 1279589 Specdb::MsMs 1279590 Specdb::MsMs 1394479 Specdb::MsMs 1394480 Specdb::MsMs 1394481 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(14:0/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(14:0/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005257 PGP(14:0/17:0cycw7c) + Water > PG(14:0/17:0cycw7c) + Phosphate PW_R005256