2.0 2015-09-08 19:58:51 -0600 2015-12-09 12:14:01 -0700 ECMDB24688 M2MDB006805 CDP-DG(16:0/19:0cycw8c) CDP-DG(16:0/19:0cycw8c) 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(16:0/19:0cycw8c), in particular, consists of one hexadecanoyl chain to C-1 atom, and one 9-(2-heptylcyclopropyl)nonanoyl 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(16:0/19:0cycw8c) 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)-2-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}-3-(hexadecanoyloxy)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)CCCCCCCCC1CC1CCCCCCC InChI=1S/C47H85N3O15P2/c1-3-5-7-9-10-11-12-13-14-15-16-21-25-29-42(51)60-34-39(63-43(52)30-26-22-18-17-20-24-28-38-33-37(38)27-23-19-8-6-4-2)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 YGJSLCRITUKIJT-DROLUKFBSA-N logp 6.51 ALOGPS logs -5.45 ALOGPS solubility 3.52e-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)-2-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}-3-(hexadecanoyloxy)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)CCCCCCCCC1CC1CCCCCCC ChemAxon formula C47H85N3O15P2 ChemAxon inchi InChI=1S/C47H85N3O15P2/c1-3-5-7-9-10-11-12-13-14-15-16-21-25-29-42(51)60-34-39(63-43(52)30-26-22-18-17-20-24-28-38-33-37(38)27-23-19-8-6-4-2)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 YGJSLCRITUKIJT-DROLUKFBSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 252.11 ChemAxon polarizability 108.5 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(16:0/18:1(9Z)/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." PW001361 Metabolic Specdb::NmrOneD 272398 Specdb::NmrOneD 272399 Specdb::NmrOneD 272400 Specdb::NmrOneD 272401 Specdb::NmrOneD 272402 Specdb::NmrOneD 272403 Specdb::NmrOneD 272404 Specdb::NmrOneD 272405 Specdb::NmrOneD 272406 Specdb::NmrOneD 272407 Specdb::NmrOneD 272408 Specdb::NmrOneD 272409 Specdb::NmrOneD 272410 Specdb::NmrOneD 272411 Specdb::NmrOneD 272412 Specdb::NmrOneD 272413 Specdb::NmrOneD 272414 Specdb::NmrOneD 272415 Specdb::NmrOneD 272416 Specdb::NmrOneD 272417 Specdb::MsMs 1270213 Specdb::MsMs 1270214 Specdb::MsMs 1270215 Specdb::MsMs 1385224 Specdb::MsMs 1385225 Specdb::MsMs 1385226 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(16:0/19:0cycw8c/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(16:0/19:0cycw8c) + Pyrophosphate PW_R005692