2.0 2015-09-08 19:55:06 -0600 2015-12-09 12:13:12 -0700 ECMDB24664 M2MDB006781 CDP-DG(14:0(3-OH)/16:0) CDP-DG(14:0(3-OH)/16:0) 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)/16:0), in particular, consists of one 3-hydroxytetradecanoyl chain to C-1 atom, and one hexadecanoyl 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)/16:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C42H77N3O16P2 942.031 941.477907407 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-(hexadecanoyloxy)-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-(hexadecanoyloxy)-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)CCCCCCCCCCCCCCC InChI=1S/C42H77N3O16P2/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-37(47)59-34(30-56-38(48)29-33(46)25-23-21-19-17-12-10-8-6-4-2)31-57-62(52,53)61-63(54,55)58-32-35-39(49)40(50)41(60-35)45-28-27-36(43)44-42(45)51/h27-28,33-35,39-41,46,49-50H,3-26,29-32H2,1-2H3,(H,52,53)(H,54,55)(H2,43,44,51)/t33?,34-,35-,39+,40?,41-/m1/s1 ZHRKYQIKCCIFHH-SRCBNSNESA-N logp 4.71 ALOGPS logs -4.67 ALOGPS solubility 2.02e-02 g/l ALOGPS logp 7.44 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-(hexadecanoyloxy)-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 942.031 ChemAxon mono_mass 941.477907407 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)CCCCCCCCCCCCCCC ChemAxon formula C42H77N3O16P2 ChemAxon inchi InChI=1S/C42H77N3O16P2/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-37(47)59-34(30-56-38(48)29-33(46)25-23-21-19-17-12-10-8-6-4-2)31-57-62(52,53)61-63(54,55)58-32-35-39(49)40(50)41(60-35)45-28-27-36(43)44-42(45)51/h27-28,33-35,39-41,46,49-50H,3-26,29-32H2,1-2H3,(H,52,53)(H,54,55)(H2,43,44,51)/t33?,34-,35-,39+,40?,41-/m1/s1 ChemAxon inchikey ZHRKYQIKCCIFHH-SRCBNSNESA-N ChemAxon polar_surface_area 283.5 ChemAxon refractivity 232.52 ChemAxon polarizability 101.35 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(14:0(3-OH)/16:0/16:0/16:0)) 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. PW001938 Metabolic Specdb::EiMs 5366 Specdb::NmrOneD 266348 Specdb::NmrOneD 266349 Specdb::NmrOneD 266350 Specdb::NmrOneD 266351 Specdb::NmrOneD 266352 Specdb::NmrOneD 266353 Specdb::NmrOneD 266354 Specdb::NmrOneD 266355 Specdb::NmrOneD 266356 Specdb::NmrOneD 266357 Specdb::NmrOneD 266358 Specdb::NmrOneD 266359 Specdb::NmrOneD 266360 Specdb::NmrOneD 266361 Specdb::NmrOneD 266362 Specdb::NmrOneD 266363 Specdb::NmrOneD 266364 Specdb::NmrOneD 266365 Specdb::NmrOneD 266366 Specdb::NmrOneD 266367 Specdb::MsMs 1287520 Specdb::MsMs 1287521 Specdb::MsMs 1287522 Specdb::MsMs 1402300 Specdb::MsMs 1402301 Specdb::MsMs 1402302 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(3-OH)/16:0/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(14:0(3-OH)/16:0) + Pyrophosphate PW_R005442 CDP-DG(14:0(3-OH)/16:0) + L-Serine + L-Serine > PS(14:0(3-OH)/16:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005443