2.0 2015-09-08 19:38:30 -0600 2016-09-13 16:36:09 -0600 ECMDB24532 M2MDB006649 PGP(19:iso/10:0(3-OH)) PGP(19:iso/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(19:iso/10:0(3-OH)), in particular, consists of one 17-methylocatdecanoyl 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. C35H70O14P2 776.879 776.42408093 [(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid (2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CC(O)CCCCCCC InChI=1S/C35H70O14P2/c1-4-5-6-16-20-23-31(36)25-35(39)49-33(29-48-51(43,44)47-27-32(37)26-46-50(40,41)42)28-45-34(38)24-21-18-15-13-11-9-7-8-10-12-14-17-19-22-30(2)3/h30-33,36-37H,4-29H2,1-3H3,(H,43,44)(H2,40,41,42)/t31?,32-,33+/m0/s1 TYYGITZUMMNIGV-ADIDXWPESA-N logp 4.88 ALOGPS logs -5.43 ALOGPS solubility 2.90e-03 g/l ALOGPS logp 8.09 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid ChemAxon average_mass 776.879 ChemAxon mono_mass 776.42408093 ChemAxon smiles [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CC(O)CCCCCCC ChemAxon formula C35H70O14P2 ChemAxon inchi InChI=1S/C35H70O14P2/c1-4-5-6-16-20-23-31(36)25-35(39)49-33(29-48-51(43,44)47-27-32(37)26-46-50(40,41)42)28-45-34(38)24-21-18-15-13-11-9-7-8-10-12-14-17-19-22-30(2)3/h30-33,36-37H,4-29H2,1-3H3,(H,43,44)(H2,40,41,42)/t31?,32-,33+/m0/s1 ChemAxon inchikey TYYGITZUMMNIGV-ADIDXWPESA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 193.84 ChemAxon polarizability 87.48 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(19:iso/10:0(3-OH)/10:0/10:0)) 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. PW001996 Metabolic phospholipid biosynthesis (CL(19:iso/10:0(3-OH)/19:iso/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. PW001997 Metabolic Specdb::CMs 1085386 Specdb::NmrOneD 334898 Specdb::NmrOneD 334899 Specdb::NmrOneD 334900 Specdb::NmrOneD 334901 Specdb::NmrOneD 334902 Specdb::NmrOneD 334903 Specdb::NmrOneD 334904 Specdb::NmrOneD 334905 Specdb::NmrOneD 334906 Specdb::NmrOneD 334907 Specdb::NmrOneD 334908 Specdb::NmrOneD 334909 Specdb::NmrOneD 334910 Specdb::NmrOneD 334911 Specdb::NmrOneD 334912 Specdb::NmrOneD 334913 Specdb::NmrOneD 334914 Specdb::NmrOneD 334915 Specdb::NmrOneD 334916 Specdb::NmrOneD 334917 Specdb::MsMs 24947 Specdb::MsMs 24948 Specdb::MsMs 24949 Specdb::MsMs 31505 Specdb::MsMs 31506 Specdb::MsMs 31507 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/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(19:iso/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005621 2 PGP(19:iso/10:0(3-OH)) + Water >2 PG(19:iso/10:0(3-OH)) + Phosphate PW_R005622