2.0 2015-09-08 19:58:37 -0600 2015-12-09 12:14:00 -0700 ECMDB24687 M2MDB006804 CDP-DG(16:0/19:0cycv8c) CDP-DG(16:0/19:0cycv8c) 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(16:0/19:0cycv8c), in particular, consists of one hexadecanoyl chain to C-1 atom, and one heptadec-11-12-cyclo-anoyl 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(16:0/19:0cycv8c) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C47H85N3O15P2 994.151 993.545593045 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-(hexadecanoyloxy)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-3-(hexadecanoyloxy)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCC1CC1CCCCCC InChI=1S/C47H85N3O15P2/c1-3-5-7-9-10-11-12-13-14-15-18-21-25-29-42(51)60-34-39(63-43(52)30-26-22-19-16-17-20-24-28-38-33-37(38)27-23-8-6-4-2)35-61-66(56,57)65-67(58,59)62-36-40-44(53)45(54)46(64-40)50-32-31-41(48)49-47(50)55/h31-32,37-40,44-46,53-54H,3-30,33-36H2,1-2H3,(H,56,57)(H,58,59)(H2,48,49,55)/t37?,38?,39-,40-,44+,45?,46-/m1/s1 PDSJTTHYYFORQS-DROLUKFBSA-N logp 6.52 ALOGPS logs -5.45 ALOGPS solubility 3.51e-03 g/l ALOGPS logp 10.11 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -0.032 ChemAxon iupac {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-(hexadecanoyloxy)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 994.151 ChemAxon mono_mass 993.545593045 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCC1CC1CCCCCC ChemAxon formula C47H85N3O15P2 ChemAxon inchi InChI=1S/C47H85N3O15P2/c1-3-5-7-9-10-11-12-13-14-15-18-21-25-29-42(51)60-34-39(63-43(52)30-26-22-19-16-17-20-24-28-38-33-37(38)27-23-8-6-4-2)35-61-66(56,57)65-67(58,59)62-36-40-44(53)45(54)46(64-40)50-32-31-41(48)49-47(50)55/h31-32,37-40,44-46,53-54H,3-30,33-36H2,1-2H3,(H,56,57)(H,58,59)(H2,48,49,55)/t37?,38?,39-,40-,44+,45?,46-/m1/s1 ChemAxon inchikey PDSJTTHYYFORQS-DROLUKFBSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 252.11 ChemAxon polarizability 109.49 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(16:0/16:0/16:0/19:0cycv8c) "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." PW001259 Metabolic Specdb::EiMs 5167 Specdb::NmrOneD 276918 Specdb::NmrOneD 276919 Specdb::NmrOneD 276920 Specdb::NmrOneD 276921 Specdb::NmrOneD 276922 Specdb::NmrOneD 276923 Specdb::NmrOneD 276924 Specdb::NmrOneD 276925 Specdb::NmrOneD 276926 Specdb::NmrOneD 276927 Specdb::NmrOneD 276928 Specdb::NmrOneD 276929 Specdb::NmrOneD 276930 Specdb::NmrOneD 276931 Specdb::NmrOneD 276932 Specdb::NmrOneD 276933 Specdb::NmrOneD 276934 Specdb::NmrOneD 276935 Specdb::NmrOneD 276936 Specdb::NmrOneD 276937 Specdb::MsMs 1270468 Specdb::MsMs 1270469 Specdb::MsMs 1270470 Specdb::MsMs 1385476 Specdb::MsMs 1385477 Specdb::MsMs 1385478 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 DG(16:0/19:0cycv8c/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(16:0/19:0cycv8c) + Pyrophosphate PW_R005691