2.0 2015-09-08 20:03:10 -0600 2015-12-09 12:14:51 -0700 ECMDB24714 M2MDB006831 CDP-DG(18:1(9Z)/17:0cycw7c) CDP-DG(18:1(9Z)/17:0cycw7c) 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(18:1(9Z)/17:0cycw7c), in particular, consists of one 9Z-octadecenoyl chain to C-1 atom, and one heptadec-9-10-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(18:1(9Z)/17:0cycw7c) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C47H83N3O15P2 992.135 991.529942981 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(9Z)-octadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC1CC1CCCCCC InChI=1S/C47H83N3O15P2/c1-3-5-7-9-10-11-12-13-14-15-16-17-18-21-25-29-42(51)60-34-39(63-43(52)30-26-22-19-20-24-28-38-33-37(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/h13-14,31-32,37-40,44-46,53-54H,3-12,15-30,33-36H2,1-2H3,(H,56,57)(H,58,59)(H2,48,49,55)/b14-13-/t37?,38?,39-,40-,44+,45?,46-/m1/s1 WHVAUJBXHRPPER-QSPAHEJSSA-N logp 6.52 ALOGPS logs -5.38 ALOGPS solubility 4.10e-03 g/l ALOGPS logp 9.75 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-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 992.135 ChemAxon mono_mass 991.529942981 ChemAxon smiles [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC1CC1CCCCCC ChemAxon formula C47H83N3O15P2 ChemAxon inchi InChI=1S/C47H83N3O15P2/c1-3-5-7-9-10-11-12-13-14-15-16-17-18-21-25-29-42(51)60-34-39(63-43(52)30-26-22-19-20-24-28-38-33-37(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/h13-14,31-32,37-40,44-46,53-54H,3-12,15-30,33-36H2,1-2H3,(H,56,57)(H,58,59)(H2,48,49,55)/b14-13-/t37?,38?,39-,40-,44+,45?,46-/m1/s1 ChemAxon inchikey WHVAUJBXHRPPER-QSPAHEJSSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 253.22 ChemAxon polarizability 107.97 ChemAxon rotatable_bond_count 42 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/17:0cycw7c)) 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. PW002014 Metabolic Specdb::NmrOneD 250108 Specdb::NmrOneD 250109 Specdb::NmrOneD 250110 Specdb::NmrOneD 250111 Specdb::NmrOneD 250112 Specdb::NmrOneD 250113 Specdb::NmrOneD 250114 Specdb::NmrOneD 250115 Specdb::NmrOneD 250116 Specdb::NmrOneD 250117 Specdb::NmrOneD 250118 Specdb::NmrOneD 250119 Specdb::NmrOneD 250120 Specdb::NmrOneD 250121 Specdb::NmrOneD 250122 Specdb::NmrOneD 250123 Specdb::NmrOneD 250124 Specdb::NmrOneD 250125 Specdb::NmrOneD 250126 Specdb::NmrOneD 250127 Specdb::MsMs 1300198 Specdb::MsMs 1300199 Specdb::MsMs 1300200 Specdb::MsMs 1414783 Specdb::MsMs 1414784 Specdb::MsMs 1414785 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(18:1(9Z)/17:0cycw7c/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(18:1(9Z)/17:0cycw7c) + Pyrophosphate PW_R005675