2.0 2015-09-08 20:04:28 -0600 2015-12-09 12:15:00 -0700 ECMDB24722 M2MDB006839 CDP-DG(19:0cycv8c/15:0cyclo) CDP-DG(19:0cycv8c/15:0cyclo) 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(19:0cycv8c/15:0cyclo), in particular, consists of one heptadec-11-12-cyclo-anoyl chain to C-1 atom, and one cis-9,10-Methylenetetradecanoic acid 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(19:0cycv8c/15:0cyclo) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C46H81N3O15P2 978.108 977.514292916 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[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)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCC1CC1CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC1CC1CCCC InChI=1S/C46H81N3O15P2/c1-3-5-7-16-22-36-30-37(36)24-17-12-9-8-10-14-19-25-41(50)59-31-38(62-42(51)26-20-15-11-13-18-23-35-29-34(35)21-6-4-2)32-60-65(55,56)64-66(57,58)61-33-39-43(52)44(53)45(63-39)49-28-27-40(47)48-46(49)54/h27-28,34-39,43-45,52-53H,3-26,29-33H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/t34?,35?,36?,37?,38-,39-,43+,44?,45-/m1/s1 XIKXECDDMUIMQZ-RGFCLLEESA-N logp 5.89 ALOGPS logs -5.27 ALOGPS solubility 5.30e-03 g/l ALOGPS logp 8.89 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-butylcyclopropyl)octanoyl]oxy}-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 978.108 ChemAxon mono_mass 977.514292916 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCC1CC1CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC1CC1CCCC ChemAxon formula C46H81N3O15P2 ChemAxon inchi InChI=1S/C46H81N3O15P2/c1-3-5-7-16-22-36-30-37(36)24-17-12-9-8-10-14-19-25-41(50)59-31-38(62-42(51)26-20-15-11-13-18-23-35-29-34(35)21-6-4-2)32-60-65(55,56)64-66(57,58)61-33-39-43(52)44(53)45(63-39)49-28-27-40(47)48-46(49)54/h27-28,34-39,43-45,52-53H,3-26,29-33H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/t34?,35?,36?,37?,38-,39-,43+,44?,45-/m1/s1 ChemAxon inchikey XIKXECDDMUIMQZ-RGFCLLEESA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 245.6 ChemAxon polarizability 105.92 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(19:0cycv8c/15:0cyclo/17:0cycw7c/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. PW001302 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/14:0)) 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. PW001309 Metabolic phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/16:0)) 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. PW001316 Metabolic Specdb::EiMs 5549 Specdb::NmrOneD 291795 Specdb::NmrOneD 291796 Specdb::NmrOneD 291797 Specdb::NmrOneD 291798 Specdb::NmrOneD 291799 Specdb::NmrOneD 291800 Specdb::NmrOneD 291801 Specdb::NmrOneD 291802 Specdb::NmrOneD 291803 Specdb::NmrOneD 291804 Specdb::NmrOneD 291805 Specdb::NmrOneD 291806 Specdb::NmrOneD 291807 Specdb::NmrOneD 291808 Specdb::NmrOneD 291809 Specdb::NmrOneD 291810 Specdb::NmrOneD 291811 Specdb::NmrOneD 291812 Specdb::NmrOneD 291813 Specdb::NmrOneD 291814 Specdb::MsMs 1313260 Specdb::MsMs 1313261 Specdb::MsMs 1313262 Specdb::MsMs 1427728 Specdb::MsMs 1427729 Specdb::MsMs 1427730 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(19:0cycv8c/15:0cyclo/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(19:0cycv8c/15:0cyclo) + Pyrophosphate PW_R005220 2 CDP-DG(19:0cycv8c/15:0cyclo) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/15:0cyclo) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005219