2.0 2015-09-08 19:54:48 -0600 2015-12-09 12:13:09 -0700 ECMDB24661 M2MDB006778 CDP-DG(14:0(3-OH)/12:0) CDP-DG(14:0(3-OH)/12:0) 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(3-OH)/12:0), in particular, consists of one 3-hydroxytetradecanoyl chain to C-1 atom, and one dodecanoyl 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) 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}({[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-(dodecanoyloxy)-3-[(3-hydroxytetradecanoyl)oxy]propoxy(hydroxy)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)CCCCCCCCCCC InChI=1S/C38H69N3O16P2/c1-3-5-7-9-11-13-15-17-19-21-29(42)25-34(44)52-26-30(55-33(43)22-20-18-16-14-12-10-8-6-4-2)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 IFFAXMBMFBBFFK-ASXHDNTPSA-N logp 3.63 ALOGPS logs -4.05 ALOGPS solubility 7.94e-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}({[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 885.923 ChemAxon mono_mass 885.41530715 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)CCCCCCCCCCC ChemAxon formula C38H69N3O16P2 ChemAxon inchi InChI=1S/C38H69N3O16P2/c1-3-5-7-9-11-13-15-17-19-21-29(42)25-34(44)52-26-30(55-33(43)22-20-18-16-14-12-10-8-6-4-2)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 IFFAXMBMFBBFFK-ASXHDNTPSA-N ChemAxon polar_surface_area 283.5 ChemAxon refractivity 214.12 ChemAxon polarizability 92.54 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(3-OH)/12:0/14:0(3-OH)/12:0)) 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. PW001935 Metabolic Specdb::EiMs 3209 Specdb::NmrOneD 246808 Specdb::NmrOneD 246809 Specdb::NmrOneD 246810 Specdb::NmrOneD 246811 Specdb::NmrOneD 246812 Specdb::NmrOneD 246813 Specdb::NmrOneD 246814 Specdb::NmrOneD 246815 Specdb::NmrOneD 246816 Specdb::NmrOneD 246817 Specdb::NmrOneD 246818 Specdb::NmrOneD 246819 Specdb::NmrOneD 246820 Specdb::NmrOneD 246821 Specdb::NmrOneD 246822 Specdb::NmrOneD 246823 Specdb::NmrOneD 246824 Specdb::NmrOneD 246825 Specdb::NmrOneD 246826 Specdb::NmrOneD 246827 Specdb::MsMs 1295602 Specdb::MsMs 1295603 Specdb::MsMs 1295604 Specdb::MsMs 1410259 Specdb::MsMs 1410260 Specdb::MsMs 1410261 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)/12:0/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(14:0(3-OH)/12:0) + Pyrophosphate PW_R005429 2 CDP-DG(14:0(3-OH)/12:0) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/12:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005430