2.0 2015-09-08 19:54:40 -0600 2015-12-09 12:13:08 -0700 ECMDB24660 M2MDB006777 CDP-DG(14:0(3-OH)/12:0(3-OH)) CDP-DG(14:0(3-OH)/12:0(3-OH)) 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(3-OH)/12:0(3-OH)), in particular, consists of one 3-hydroxytetradecanoyl chain to C-1 atom, and one 3-hydroxydodecanoyl 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(3-OH)/12:0(3-OH)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C38H69N3O17P2 901.922 901.41022177 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CC(O)CCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CC(O)CCCCCCCCC InChI=1S/C38H69N3O17P2/c1-3-5-7-9-11-12-14-16-17-19-28(42)23-33(44)53-25-30(56-34(45)24-29(43)20-18-15-13-10-8-6-4-2)26-54-59(49,50)58-60(51,52)55-27-31-35(46)36(47)37(57-31)41-22-21-32(39)40-38(41)48/h21-22,28-31,35-37,42-43,46-47H,3-20,23-27H2,1-2H3,(H,49,50)(H,51,52)(H2,39,40,48)/t28?,29?,30-,31-,35+,36?,37-/m1/s1 CIHAQBMLUMEGPH-UZCGJLOUSA-N logp 2.86 ALOGPS logs -3.73 ALOGPS solubility 1.67e-01 g/l ALOGPS logp 4.43 ChemAxon pka_strongest_acidic -0.032 ChemAxon pka_strongest_basic 3.27 ChemAxon iupac {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 901.922 ChemAxon mono_mass 901.41022177 ChemAxon smiles [H][C@@](COC(=O)CC(O)CCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CC(O)CCCCCCCCC ChemAxon formula C38H69N3O17P2 ChemAxon inchi InChI=1S/C38H69N3O17P2/c1-3-5-7-9-11-12-14-16-17-19-28(42)23-33(44)53-25-30(56-34(45)24-29(43)20-18-15-13-10-8-6-4-2)26-54-59(49,50)58-60(51,52)55-27-31-35(46)36(47)37(57-31)41-22-21-32(39)40-38(41)48/h21-22,28-31,35-37,42-43,46-47H,3-20,23-27H2,1-2H3,(H,49,50)(H,51,52)(H2,39,40,48)/t28?,29?,30-,31-,35+,36?,37-/m1/s1 ChemAxon inchikey CIHAQBMLUMEGPH-UZCGJLOUSA-N ChemAxon polar_surface_area 303.73 ChemAxon refractivity 215.64 ChemAxon polarizability 94.13 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 14 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH))) 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. PW001934 Metabolic Specdb::EiMs 3175 Specdb::MsMs 1303519 Specdb::MsMs 1303520 Specdb::MsMs 1303521 Specdb::MsMs 1418080 Specdb::MsMs 1418081 Specdb::MsMs 1418082 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 Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. 22102590 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--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 2 DG(14:0(3-OH)/12:0(3-OH)/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(14:0(3-OH)/12:0(3-OH)) + Pyrophosphate PW_R005425 2 CDP-DG(14:0(3-OH)/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005426