2.0 2015-09-08 19:55:37 -0600 2015-12-09 12:13:17 -0700 ECMDB24668 M2MDB006785 CDP-DG(14:0/14:0(3-OH)) CDP-DG(14:0/14:0(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(14:0/14:0(3-OH)), in particular, consists of one tetradecanoyl chain to C-1 atom, and one 3-hydroxytetradecanoyl 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(14:0/14:0(3-OH)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C40H73N3O16P2 913.977 913.446607279 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(3-hydroxytetradecanoyl)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-hydroxytetradecanoyl)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)CCCCCCCCCCC InChI=1S/C40H73N3O16P2/c1-3-5-7-9-11-13-14-16-18-20-22-24-35(45)54-28-32(57-36(46)27-31(44)23-21-19-17-15-12-10-8-6-4-2)29-55-60(50,51)59-61(52,53)56-30-33-37(47)38(48)39(58-33)43-26-25-34(41)42-40(43)49/h25-26,31-33,37-39,44,47-48H,3-24,27-30H2,1-2H3,(H,50,51)(H,52,53)(H2,41,42,49)/t31?,32-,33-,37+,38?,39-/m1/s1 JIJIXCAZIUTYLA-FOFBOHEMSA-N logp 4.19 ALOGPS logs -4.40 ALOGPS solubility 3.64e-02 g/l ALOGPS logp 6.55 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-hydroxytetradecanoyl)oxy]-3-(tetradecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 913.977 ChemAxon mono_mass 913.446607279 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)CCCCCCCCCCC ChemAxon formula C40H73N3O16P2 ChemAxon inchi InChI=1S/C40H73N3O16P2/c1-3-5-7-9-11-13-14-16-18-20-22-24-35(45)54-28-32(57-36(46)27-31(44)23-21-19-17-15-12-10-8-6-4-2)29-55-60(50,51)59-61(52,53)56-30-33-37(47)38(48)39(58-33)43-26-25-34(41)42-40(43)49/h25-26,31-33,37-39,44,47-48H,3-24,27-30H2,1-2H3,(H,50,51)(H,52,53)(H2,41,42,49)/t31?,32-,33-,37+,38?,39-/m1/s1 ChemAxon inchikey JIJIXCAZIUTYLA-FOFBOHEMSA-N ChemAxon polar_surface_area 283.5 ChemAxon refractivity 223.32 ChemAxon polarizability 97.62 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(14:0/14:0(3-OH)/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. PW001944 Metabolic Specdb::EiMs 5283 Specdb::NmrOneD 247148 Specdb::NmrOneD 247149 Specdb::NmrOneD 247150 Specdb::NmrOneD 247151 Specdb::NmrOneD 247152 Specdb::NmrOneD 247153 Specdb::NmrOneD 247154 Specdb::NmrOneD 247155 Specdb::NmrOneD 247156 Specdb::NmrOneD 247157 Specdb::NmrOneD 247158 Specdb::NmrOneD 247159 Specdb::NmrOneD 247160 Specdb::NmrOneD 247161 Specdb::NmrOneD 247162 Specdb::NmrOneD 247163 Specdb::NmrOneD 247164 Specdb::NmrOneD 247165 Specdb::NmrOneD 247166 Specdb::NmrOneD 247167 Specdb::MsMs 1317451 Specdb::MsMs 1317452 Specdb::MsMs 1317453 Specdb::MsMs 1431907 Specdb::MsMs 1431908 Specdb::MsMs 1431909 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 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 DG(14:0/14:0(3-OH)/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(14:0/14:0(3-OH)) + Pyrophosphate PW_R005463 CDP-DG(14:0/14:0(3-OH)) + L-Serine + L-Serine > PS(14:0/14:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005464