2.0 2015-09-08 19:40:05 -0600 2016-09-13 16:36:11 -0600 ECMDB24544 M2MDB006661 PGP(19:iso/19:0cycv8c) PGP(19:iso/19:0cycv8c) 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/19:0cycv8c), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one heptadec-11-12-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. C44H86O13P2 885.107 884.554366825 [(2S)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2S)-3-{[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(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)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC1CC1CCCCCC InChI=1S/C44H86O13P2/c1-4-5-6-24-29-39-33-40(39)30-25-20-16-14-18-22-27-32-44(47)57-42(37-56-59(51,52)55-35-41(45)34-54-58(48,49)50)36-53-43(46)31-26-21-17-13-11-9-7-8-10-12-15-19-23-28-38(2)3/h38-42,45H,4-37H2,1-3H3,(H,51,52)(H2,48,49,50)/t39?,40?,41-,42+/m0/s1 GAQFRIUOLARGJR-IXDDWDRSSA-N logp 7.44 ALOGPS logs -6.35 ALOGPS solubility 3.97e-04 g/l ALOGPS logp 12.54 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2S)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 885.107 ChemAxon mono_mass 884.554366825 ChemAxon smiles [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC1CC1CCCCCC ChemAxon formula C44H86O13P2 ChemAxon inchi InChI=1S/C44H86O13P2/c1-4-5-6-24-29-39-33-40(39)30-25-20-16-14-18-22-27-32-44(47)57-42(37-56-59(51,52)55-35-41(45)34-54-58(48,49)50)36-53-43(46)31-26-21-17-13-11-9-7-8-10-12-15-19-23-28-38(2)3/h38-42,45H,4-37H2,1-3H3,(H,51,52)(H2,48,49,50)/t39?,40?,41-,42+/m0/s1 ChemAxon inchikey GAQFRIUOLARGJR-IXDDWDRSSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 231.83 ChemAxon polarizability 103.93 ChemAxon rotatable_bond_count 45 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(19:iso/19:0cycv8c/19:0/19:0)) 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. PW002008 Metabolic Specdb::NmrOneD 316161 Specdb::NmrOneD 316162 Specdb::NmrOneD 316163 Specdb::NmrOneD 316164 Specdb::NmrOneD 316165 Specdb::NmrOneD 316166 Specdb::NmrOneD 316167 Specdb::NmrOneD 316168 Specdb::NmrOneD 316169 Specdb::NmrOneD 316170 Specdb::NmrOneD 316171 Specdb::NmrOneD 316172 Specdb::NmrOneD 316173 Specdb::NmrOneD 316174 Specdb::NmrOneD 316175 Specdb::NmrOneD 316176 Specdb::NmrOneD 316177 Specdb::NmrOneD 316178 Specdb::NmrOneD 316179 Specdb::NmrOneD 316180 Specdb::MsMs 25439 Specdb::MsMs 25440 Specdb::MsMs 25441 Specdb::MsMs 31997 Specdb::MsMs 31998 Specdb::MsMs 31999 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/19:0cycv8c) + Glycerol 3-phosphate >2 PGP(19:iso/19:0cycv8c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005658 2 PGP(19:iso/19:0cycv8c) + Water >2 PG(19:iso/19:0cycv8c) + Phosphate PW_R005659