2.0 2015-09-08 19:55:29 -0600 2015-12-09 12:13:16 -0700 ECMDB24667 M2MDB006784 CDP-DG(14:0/12:0(3-OH)) CDP-DG(14:0/12:0(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(14:0/12:0(3-OH)), in particular, consists of one tetradecanoyl 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(14:0/12:0(3-OH)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C38H69N3O16P2 885.923 885.41530715 {[(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-(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-[(3-hydroxydodecanoyl)oxy]-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)CC(O)CCCCCCCCC InChI=1S/C38H69N3O16P2/c1-3-5-7-9-11-12-13-14-16-18-20-22-33(43)52-26-30(55-34(44)25-29(42)21-19-17-15-10-8-6-4-2)27-53-58(48,49)57-59(50,51)54-28-31-35(45)36(46)37(56-31)41-24-23-32(39)40-38(41)47/h23-24,29-31,35-37,42,45-46H,3-22,25-28H2,1-2H3,(H,48,49)(H,50,51)(H2,39,40,47)/t29?,30-,31-,35+,36?,37-/m1/s1 NEDHOKGDBQLXFK-ASXHDNTPSA-N logp 3.62 ALOGPS logs -4.05 ALOGPS solubility 7.92e-02 g/l ALOGPS logp 5.66 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-(tetradecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 885.923 ChemAxon mono_mass 885.41530715 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)CC(O)CCCCCCCCC ChemAxon formula C38H69N3O16P2 ChemAxon inchi InChI=1S/C38H69N3O16P2/c1-3-5-7-9-11-12-13-14-16-18-20-22-33(43)52-26-30(55-34(44)25-29(42)21-19-17-15-10-8-6-4-2)27-53-58(48,49)57-59(50,51)54-28-31-35(45)36(46)37(56-31)41-24-23-32(39)40-38(41)47/h23-24,29-31,35-37,42,45-46H,3-22,25-28H2,1-2H3,(H,48,49)(H,50,51)(H2,39,40,47)/t29?,30-,31-,35+,36?,37-/m1/s1 ChemAxon inchikey NEDHOKGDBQLXFK-ASXHDNTPSA-N ChemAxon polar_surface_area 283.5 ChemAxon refractivity 214.12 ChemAxon polarizability 91.65 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(14:0/12:0(3-OH)/14:0/12:0(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. PW001943 Metabolic Specdb::EiMs 4825 Specdb::NmrOneD 255328 Specdb::NmrOneD 255329 Specdb::NmrOneD 255330 Specdb::NmrOneD 255331 Specdb::NmrOneD 255332 Specdb::NmrOneD 255333 Specdb::NmrOneD 255334 Specdb::NmrOneD 255335 Specdb::NmrOneD 255336 Specdb::NmrOneD 255337 Specdb::NmrOneD 255338 Specdb::NmrOneD 255339 Specdb::NmrOneD 255340 Specdb::NmrOneD 255341 Specdb::NmrOneD 255342 Specdb::NmrOneD 255343 Specdb::NmrOneD 255344 Specdb::NmrOneD 255345 Specdb::NmrOneD 255346 Specdb::NmrOneD 255347 Specdb::MsMs 1312330 Specdb::MsMs 1312331 Specdb::MsMs 1312332 Specdb::MsMs 1426795 Specdb::MsMs 1426796 Specdb::MsMs 1426797 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(14:0/12:0(3-OH)/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(14:0/12:0(3-OH)) + Pyrophosphate PW_R005459 2 CDP-DG(14:0/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(14:0/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005460