2.0 2015-09-08 19:54:34 -0600 2015-09-14 11:20:12 -0600 ECMDB24659 M2MDB006776 CDP-DG(12:0/19:iso) CDP-DG(12:0/19:iso) 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(12:0/19:iso), in particular, consists of one dodecanoyl chain to C-1 atom, and one 17-methylocatdecanoyl 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(12:0/19:iso) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C43H79N3O15P2 940.059 939.498642852 {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-(dodecanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-3-(dodecanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid CCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCCC(C)C InChI=1S/C43H79N3O15P2/c1-4-5-6-7-8-14-18-21-24-27-38(47)56-31-35(59-39(48)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-34(2)3)32-57-62(52,53)61-63(54,55)58-33-36-40(49)41(50)42(60-36)46-30-29-37(44)45-43(46)51/h29-30,34-36,40-42,49-50H,4-28,31-33H2,1-3H3,(H,52,53)(H,54,55)(H2,44,45,51)/t35-,36-,40-,41-,42-/m1/s1 XLKDVENKGINCQC-FLNZYWDJSA-N logp 5.57 ALOGPS logs -5.06 ALOGPS solubility 8.16e-03 g/l ALOGPS logp 8.95 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -0.032 ChemAxon iupac {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-(dodecanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 940.059 ChemAxon mono_mass 939.498642852 ChemAxon smiles CCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCCC(C)C ChemAxon formula C43H79N3O15P2 ChemAxon inchi InChI=1S/C43H79N3O15P2/c1-4-5-6-7-8-14-18-21-24-27-38(47)56-31-35(59-39(48)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-34(2)3)32-57-62(52,53)61-63(54,55)58-33-36-40(49)41(50)42(60-36)46-30-29-37(44)45-43(46)51/h29-30,34-36,40-42,49-50H,4-28,31-33H2,1-3H3,(H,52,53)(H,54,55)(H2,44,45,51)/t35-,36-,40-,41-,42-/m1/s1 ChemAxon inchikey XLKDVENKGINCQC-FLNZYWDJSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 235.56 ChemAxon polarizability 101.84 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0/19:iso/12:0/19:iso)) 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. PW001933 Metabolic Specdb::NmrOneD 287335 Specdb::NmrOneD 287336 Specdb::NmrOneD 287337 Specdb::NmrOneD 287338 Specdb::NmrOneD 287339 Specdb::NmrOneD 287340 Specdb::NmrOneD 287341 Specdb::NmrOneD 287342 Specdb::NmrOneD 287343 Specdb::NmrOneD 287344 Specdb::NmrOneD 287345 Specdb::NmrOneD 287346 Specdb::NmrOneD 287347 Specdb::NmrOneD 287348 Specdb::NmrOneD 287349 Specdb::NmrOneD 287350 Specdb::NmrOneD 287351 Specdb::NmrOneD 287352 Specdb::NmrOneD 287353 Specdb::NmrOneD 287354 Specdb::MsMs 41336 Specdb::MsMs 41337 Specdb::MsMs 41338 Specdb::MsMs 42044 Specdb::MsMs 42045 Specdb::MsMs 42046 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(12:0/19:iso/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(12:0/19:iso) + Pyrophosphate PW_R005421 2 CDP-DG(12:0/19:iso) + Glycerol 3-phosphate >2 PGP(12:0/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005422