2.0 2012-10-11 06:39:36 -0600 2015-12-09 12:13:19 -0700 ECMDB23341 M2MDB003731 CDP-DG(14:0/15:0) CDP-DG(14:0/15:0) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. CDP-DG(14:0/15:0), in particular, consists of one tetradecanoyl chain to C-1 atom, and one pentadecanoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, The biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(14:0/15:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-myristoyl-2-pentadecanoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Myristoyl-2-pentadecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid 1-tetradecanoyl-2-pentadecanoyl-sn-glycero-3-CDP 1-tetradecanoyl-2-pentadecanoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Tetradecanoyl-2-pentadecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(29:0) CDP-Diacylglycerol(14:0/15:0) CDP-Diacylglycerol(29:0) C41H75N3O15P2 912.005 911.467342723 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-(pentadecanoyloxy)-3-(tetradecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-2-(pentadecanoyloxy)-3-(tetradecanoyloxy)propoxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCC InChI=1S/C41H75N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-37(46)57-33(30-54-36(45)26-24-22-20-18-16-14-12-10-8-6-4-2)31-55-60(50,51)59-61(52,53)56-32-34-38(47)39(48)40(58-34)44-29-28-35(42)43-41(44)49/h28-29,33-34,38-40,47-48H,3-27,30-32H2,1-2H3,(H,50,51)(H,52,53)(H2,42,43,49)/t33-,34-,38+,39?,40-/m1/s1 BOVUZWHURDMJAD-BGBHGZNASA-N Solid Membrane logp 5.18 ALOGPS logs -4.83 ALOGPS solubility 1.34e-02 g/l ALOGPS logp 8.22 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -0.032 ChemAxon iupac {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-(pentadecanoyloxy)-3-(tetradecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 912.005 ChemAxon mono_mass 911.467342723 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCC ChemAxon formula C41H75N3O15P2 ChemAxon inchi InChI=1S/C41H75N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-37(46)57-33(30-54-36(45)26-24-22-20-18-16-14-12-10-8-6-4-2)31-55-60(50,51)59-61(52,53)56-32-34-38(47)39(48)40(58-34)44-29-28-35(42)43-41(44)49/h28-29,33-34,38-40,47-48H,3-27,30-32H2,1-2H3,(H,50,51)(H,52,53)(H2,42,43,49)/t33-,34-,38+,39?,40-/m1/s1 ChemAxon inchikey BOVUZWHURDMJAD-BGBHGZNASA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 226.41 ChemAxon polarizability 98.17 ChemAxon rotatable_bond_count 39 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CDP-DG(14:0/15:0) 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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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. PW001795 Metabolic phospholipid biosynthesis CDP-DG(14:0/15:0) II 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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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. PW001857 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::EiMs 4011 Specdb::NmrOneD 315221 Specdb::NmrOneD 315222 Specdb::NmrOneD 315223 Specdb::NmrOneD 315224 Specdb::NmrOneD 315225 Specdb::NmrOneD 315226 Specdb::NmrOneD 315227 Specdb::NmrOneD 315228 Specdb::NmrOneD 315229 Specdb::NmrOneD 315230 Specdb::NmrOneD 315231 Specdb::NmrOneD 315232 Specdb::NmrOneD 315233 Specdb::NmrOneD 315234 Specdb::NmrOneD 315235 Specdb::NmrOneD 315236 Specdb::NmrOneD 315237 Specdb::NmrOneD 315238 Specdb::NmrOneD 315239 Specdb::NmrOneD 315240 Specdb::MsMs 1307188 Specdb::MsMs 1307189 Specdb::MsMs 1307190 Specdb::MsMs 1421701 Specdb::MsMs 1421702 Specdb::MsMs 1421703 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 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 Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml CDP-diacylglycerol--serine O-phosphatidyltransferase P23830 PSS_ECOLI pssA http://ecmdb.ca/proteins/P23830.xml Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml DG(14:0/15:0/0:0) + Hydrogen ion + Cytidine triphosphate + DG(14:0/15:0/0:0) > CDP-DG(14:0/15:0) + Pyrophosphate PW_R004768 CDP-DG(14:0/15:0) + L-Serine + L-Serine > PS(14:0(3-OH)/15:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R004944 CDP-DG(14:0/15:0) + L-Serine + L-Serine > PS(14:0(3-OH)/15:0cyclo) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R004948