2.0 2015-09-08 19:53:00 -0600 2015-12-09 12:12:50 -0700 ECMDB24645 M2MDB006762 CDP-DG(12:0(3-OH)/12:0) CDP-DG(12:0(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(12:0(3-OH)/12:0), in particular, consists of one 3-hydroxydodecanoyl 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(12:0(3-OH)/12:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C36H65N3O16P2 857.869 857.384007021 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxydodecanoyl)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-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CC(O)CCCCCCCCC)(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/C36H65N3O16P2/c1-3-5-7-9-11-12-14-16-18-20-31(41)53-28(24-50-32(42)23-27(40)19-17-15-13-10-8-6-4-2)25-51-56(46,47)55-57(48,49)52-26-29-33(43)34(44)35(54-29)39-22-21-30(37)38-36(39)45/h21-22,27-29,33-35,40,43-44H,3-20,23-26H2,1-2H3,(H,46,47)(H,48,49)(H2,37,38,45)/t27?,28-,29-,33+,34?,35-/m1/s1 NXUDFZKAZZEHSL-BRZZSJEDSA-N logp 3.05 ALOGPS logs -3.68 ALOGPS solubility 1.81e-01 g/l ALOGPS logp 4.77 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-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 857.869 ChemAxon mono_mass 857.384007021 ChemAxon smiles [H][C@@](COC(=O)CC(O)CCCCCCCCC)(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 C36H65N3O16P2 ChemAxon inchi InChI=1S/C36H65N3O16P2/c1-3-5-7-9-11-12-14-16-18-20-31(41)53-28(24-50-32(42)23-27(40)19-17-15-13-10-8-6-4-2)25-51-56(46,47)55-57(48,49)52-26-29-33(43)34(44)35(54-29)39-22-21-30(37)38-36(39)45/h21-22,27-29,33-35,40,43-44H,3-20,23-26H2,1-2H3,(H,46,47)(H,48,49)(H2,37,38,45)/t27?,28-,29-,33+,34?,35-/m1/s1 ChemAxon inchikey NXUDFZKAZZEHSL-BRZZSJEDSA-N ChemAxon polar_surface_area 283.5 ChemAxon refractivity 204.92 ChemAxon polarizability 89.75 ChemAxon rotatable_bond_count 34 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0(3-OH)/12:0/12:0/12:0)) 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. PW001917 Metabolic Specdb::EiMs 4379 Specdb::NmrOneD 287315 Specdb::NmrOneD 287316 Specdb::NmrOneD 287317 Specdb::NmrOneD 287318 Specdb::NmrOneD 287319 Specdb::NmrOneD 287320 Specdb::NmrOneD 287321 Specdb::NmrOneD 287322 Specdb::NmrOneD 287323 Specdb::NmrOneD 287324 Specdb::NmrOneD 287325 Specdb::NmrOneD 287326 Specdb::NmrOneD 287327 Specdb::NmrOneD 287328 Specdb::NmrOneD 287329 Specdb::NmrOneD 287330 Specdb::NmrOneD 287331 Specdb::NmrOneD 287332 Specdb::NmrOneD 287333 Specdb::NmrOneD 287334 Specdb::MsMs 1321549 Specdb::MsMs 1321550 Specdb::MsMs 1321551 Specdb::MsMs 1435951 Specdb::MsMs 1435952 Specdb::MsMs 1435953 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(12:0(3-OH)/12:0/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(12:0(3-OH)/12:0) + Pyrophosphate PW_R005356 CDP-DG(12:0(3-OH)/12:0) + L-Serine + L-Serine > PS(12:0(3-OH)/12:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005358