2.0 2012-07-30 14:55:10 -0600 2015-12-09 17:01:33 -0700 ECMDB21274 M2MDB001681 PGP(18:1(11Z)/18:1(11Z)) PGP(18:1(11Z)/18:1(11Z)) 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(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl chains at positions C-1 and C-2. 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. 1,2-di(11Z-octadecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) 1,2-Di(11Z-octadecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid) 1,2-divaccenoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) 1,2-Divaccenoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid) 3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphate 3-Sn-phosphatidyl-1'-sn-glycerol 3'-phosphorate 3-Sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid PGP(18:1/18:1) PGP(18:1n7/18:1n7) PGP(18:1w7/18:1w7) PGP(36:2) C42H80O13P2 855.037 854.507416632 [(2R)-3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC InChI=1S/C42H80O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,39-40,43H,3-12,17-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b15-13-,16-14-/t39-,40-/m1/s1 JUWFWNRVCXDDFB-ZAQZKMIBSA-N Solid Membrane logp 7.47 ALOGPS logs -6.15 ALOGPS solubility 6.04e-04 g/l ALOGPS logp 11.87 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 855.037 ChemAxon mono_mass 854.507416632 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC ChemAxon formula C42H80O13P2 ChemAxon inchi InChI=1S/C42H80O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,39-40,43H,3-12,17-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b15-13-,16-14-/t39-,40-/m1/s1 ChemAxon inchikey JUWFWNRVCXDDFB-ZAQZKMIBSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 226.82 ChemAxon polarizability 98.22 ChemAxon rotatable_bond_count 44 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(18:1(11Z)/19:0/18:1(11Z)/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. PW001980 Metabolic phospholipid biosynthesis (CL(19:0/18:1(11Z)/19:0/18:1(11Z))) 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. PW001987 Metabolic Specdb::NmrOneD 341688 Specdb::NmrOneD 341689 Specdb::NmrOneD 341690 Specdb::NmrOneD 341691 Specdb::NmrOneD 341692 Specdb::NmrOneD 341693 Specdb::NmrOneD 341694 Specdb::NmrOneD 341695 Specdb::NmrOneD 341696 Specdb::NmrOneD 341697 Specdb::NmrOneD 341698 Specdb::NmrOneD 341699 Specdb::NmrOneD 341700 Specdb::NmrOneD 341701 Specdb::NmrOneD 341702 Specdb::NmrOneD 341703 Specdb::NmrOneD 341704 Specdb::NmrOneD 341705 Specdb::NmrOneD 341706 Specdb::NmrOneD 341707 Specdb::MsMs 1233316 Specdb::MsMs 1233317 Specdb::MsMs 1233318 Specdb::MsMs 1348825 Specdb::MsMs 1348826 Specdb::MsMs 1348827 HMDB13520 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 Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Lipid A export ATP-binding/permease protein msbA P60752 MSBA_ECOLI msbA http://ecmdb.ca/proteins/P60752.xml Water + PGP(18:1(11Z)/18:1(11Z)) > PG(18:1(11Z)/18:1(11Z)) + Phosphate Adenosine triphosphate + Water + PGP(18:1(11Z)/18:1(11Z)) > ADP + Hydrogen ion + Phosphate + PGP(18:1(11Z)/18:1(11Z)) Adenosine triphosphate + Water + PGP(18:1(11Z)/18:1(11Z)) > ADP + Hydrogen ion + Phosphate + PGP(18:1(11Z)/18:1(11Z)) CDP-1,2-dioctadec-11-enoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(18:1(11Z)/18:1(11Z)) 2 CDP-DG(18:1(9Z)/18:1(11Z)) + Glycerol 3-phosphate >2 PGP(18:1(11Z)/18:1(11Z)) + Cytidine monophosphate + Hydrogen ion PW_R005864 2 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(11Z)/18:1(11Z)) + Phosphate PW_R005856 2 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(11Z)/18:1(9Z)) + Phosphate PW_R005857 2 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(9Z)/18:1(11Z)) + Phosphate PW_R005860