2.0 2012-07-30 14:54:48 -0600 2015-06-03 17:20:51 -0600 ECMDB21193 M2MDB001602 CDP-1,2-ditetradecanoylglycerol Cdp-1,2-ditetradecanoylglycerol belongs to the class of CDP-Diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. (inferred from compound structure) C40H73N3O15P2 897.9662 897.451691705 [({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(2R)-2,3-bis(tetradecanoyloxy)propoxy]phosphinic acid {[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2R)-2,3-bis(tetradecanoyloxy)propoxyphosphinic acid CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCC InChI=1S/C40H73N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-35(44)53-29-32(56-36(45)26-24-22-20-18-16-14-12-10-8-6-4-2)30-54-59(49,50)58-60(51,52)55-31-33-37(46)38(47)39(57-33)43-28-27-34(41)42-40(43)48/h27-28,32-33,37-39,46-47H,3-26,29-31H2,1-2H3,(H,49,50)(H,51,52)(H2,41,42,48)/t32-,33-,37-,38-,39-/m1/s1 ICFWXMWHAMIZGF-WNAWUNHNSA-N Membrane logp 4.87 ALOGPS logs -4.70 ALOGPS solubility 1.80e-02 g/l ALOGPS logp 7.5 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -0.52 ChemAxon iupac [({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(2R)-2,3-bis(tetradecanoyloxy)propoxy]phosphinic acid ChemAxon average_mass 897.9662 ChemAxon mono_mass 897.451691705 ChemAxon smiles CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCC ChemAxon formula C40H73N3O15P2 ChemAxon inchi InChI=1S/C40H73N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-35(44)53-29-32(56-36(45)26-24-22-20-18-16-14-12-10-8-6-4-2)30-54-59(49,50)58-60(51,52)55-31-33-37(46)38(47)39(57-33)43-28-27-34(41)42-40(43)48/h27-28,32-33,37-39,46-47H,3-26,29-31H2,1-2H3,(H,49,50)(H,51,52)(H2,41,42,48)/t32-,33-,37-,38-,39-/m1/s1 ChemAxon inchikey ICFWXMWHAMIZGF-WNAWUNHNSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 221.81 ChemAxon polarizability 95.51 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(10:0(3-OH)/17:0cycw7c/14:0/14:0)) 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. PW001907 Metabolic phospholipid biosynthesis (CL(10:0/17:0cycw7c/14:0/14:0)) 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. PW001912 Metabolic phospholipid biosynthesis (CL(14:0(3-OH)/17:0cycw7c/14:0/14:0)) 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. PW001942 Metabolic Specdb::NmrOneD 323672 Specdb::NmrOneD 323673 Specdb::NmrOneD 323674 Specdb::NmrOneD 323675 Specdb::NmrOneD 323676 Specdb::NmrOneD 323677 Specdb::NmrOneD 323678 Specdb::NmrOneD 323679 Specdb::NmrOneD 323680 Specdb::NmrOneD 323681 Specdb::NmrOneD 323682 Specdb::NmrOneD 323683 Specdb::NmrOneD 323684 Specdb::NmrOneD 323685 Specdb::NmrOneD 323686 Specdb::NmrOneD 323687 Specdb::NmrOneD 323688 Specdb::NmrOneD 323689 Specdb::NmrOneD 323690 Specdb::NmrOneD 323691 Specdb::MsMs 36950 Specdb::MsMs 36951 Specdb::MsMs 36952 Specdb::MsMs 39398 Specdb::MsMs 39399 Specdb::MsMs 39400 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 CDP-diacylglycerol pyrophosphatase P06282 CDH_ECOLI cdh http://ecmdb.ca/proteins/P06282.xml CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase P0ABF8 PGSA_ECOLI pgsA http://ecmdb.ca/proteins/P0ABF8.xml Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml CDP-diacylglycerol--serine O-phosphatidyltransferase P23830 PSS_ECOLI pssA http://ecmdb.ca/proteins/P23830.xml Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-ditetradecanoylglycerol + Pyrophosphate CDP-1,2-ditetradecanoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(14:0/14:0) CDP-1,2-ditetradecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0) CDP-1,2-ditetradecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0) 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Cytidine triphosphate + Hydrogen ion > CDP-1,2-ditetradecanoylglycerol + Pyrophosphate PW_R005311 2 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-1,2-ditetradecanoylglycerol + Pyrophosphate PW_R005334 CDP-1,2-ditetradecanoylglycerol + L-Serine + L-Serine > PS(14:0/14:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005312 2 CDP-1,2-ditetradecanoylglycerol + Glycerol 3-phosphate >2 PGP(14:0/14:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005335