2.0 2015-09-08 19:35:57 -0600 2016-09-13 16:36:07 -0600 ECMDB24505 M2MDB006622 PGP(17:0cycw7c/19:iso) PGP(17:0cycw7c/19:iso) 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(17:0cycw7c/19:iso), in particular, consists of one heptadec-9-10-cyclo-anoyl chain to the C-1 atom, and one 17-methylocatdecanoyl 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. C42H82O13P2 857.053 856.523066696 [(2S)-3-({[(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2S)-3-{[(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCCCCCCCC(C)C InChI=1S/C42H82O13P2/c1-4-5-6-22-27-37-31-38(37)28-23-18-16-20-24-29-41(44)51-34-40(35-54-57(49,50)53-33-39(43)32-52-56(46,47)48)55-42(45)30-25-19-15-13-11-9-7-8-10-12-14-17-21-26-36(2)3/h36-40,43H,4-35H2,1-3H3,(H,49,50)(H2,46,47,48)/t37?,38?,39-,40+/m0/s1 OQLGDGYTSXEVAG-UXYHKRDYSA-N logp 7.04 ALOGPS logs -6.26 ALOGPS solubility 4.76e-04 g/l ALOGPS logp 11.66 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2S)-3-({[(2R)-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-2-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 857.053 ChemAxon mono_mass 856.523066696 ChemAxon smiles [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCCCCCCCC(C)C ChemAxon formula C42H82O13P2 ChemAxon inchi InChI=1S/C42H82O13P2/c1-4-5-6-22-27-37-31-38(37)28-23-18-16-20-24-29-41(44)51-34-40(35-54-57(49,50)53-33-39(43)32-52-56(46,47)48)55-42(45)30-25-19-15-13-11-9-7-8-10-12-14-17-21-26-36(2)3/h36-40,43H,4-35H2,1-3H3,(H,49,50)(H2,46,47,48)/t37?,38?,39-,40+/m0/s1 ChemAxon inchikey OQLGDGYTSXEVAG-UXYHKRDYSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 222.63 ChemAxon polarizability 99.97 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(17:0cycw7c/19:iso/17:0cycw7c/19:iso)) 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. PW001973 Metabolic Specdb::EiMs 3929 Specdb::NmrOneD 258808 Specdb::NmrOneD 258809 Specdb::NmrOneD 258810 Specdb::NmrOneD 258811 Specdb::NmrOneD 258812 Specdb::NmrOneD 258813 Specdb::NmrOneD 258814 Specdb::NmrOneD 258815 Specdb::NmrOneD 258816 Specdb::NmrOneD 258817 Specdb::NmrOneD 258818 Specdb::NmrOneD 258819 Specdb::NmrOneD 258820 Specdb::NmrOneD 258821 Specdb::NmrOneD 258822 Specdb::NmrOneD 258823 Specdb::NmrOneD 258824 Specdb::NmrOneD 258825 Specdb::NmrOneD 258826 Specdb::NmrOneD 258827 Specdb::MsMs 29180 Specdb::MsMs 29181 Specdb::MsMs 29182 Specdb::MsMs 35738 Specdb::MsMs 35739 Specdb::MsMs 35740 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(17:0cycw7c/19:iso) + Glycerol 3-phosphate >2 PGP(17:0cycw7c/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005553 2 PGP(17:0cycw7c/19:iso) + Water >2 PG(17:0cycw7c/19:iso) + Phosphate PW_R005554