2.0 2015-09-08 20:06:40 -0600 2015-09-14 11:20:13 -0600 ECMDB24736 M2MDB006853 CDP-DG(19:iso/19:0cycv8c) CDP-DG(19:iso/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(19:iso/19:0cycv8c), in particular, consists of one 17-methylocatdecanoyl 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(19:iso/19:0cycv8c) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C50H91N3O15P2 1036.232 1035.592543238 [(1R,9R,24S,25S,27R)-27-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-23-hexyl-4,6,24,25-tetrahydroxy-4,6,11-trioxo-3,5,7,10,26-pentaoxa-4λ⁵,6λ⁵-diphosphabicyclo[19.4.2]heptacosan-9-yl]methyl 17-methyloctadecanoate [(1R,9R,24S,25S,27R)-27-(4-amino-2-oxopyrimidin-1-yl)-23-hexyl-4,6,24,25-tetrahydroxy-4,6,11-trioxo-3,5,7,10,26-pentaoxa-4λ⁵,6λ⁵-diphosphabicyclo[19.4.2]heptacosan-9-yl]methyl 17-methyloctadecanoate CCCCCCC1CC2CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OP(O)(=O)OC[C@@H](O[C@H]2N2C=CC(N)=NC2=O)[C@@H](O)[C@H]1O InChI=1S/C50H91N3O15P2/c1-4-5-6-24-29-40-35-41-30-25-20-16-14-18-22-27-32-46(55)66-42(36-63-45(54)31-26-21-17-13-11-9-7-8-10-12-15-19-23-28-39(2)3)37-64-69(59,60)68-70(61,62)65-38-43(48(57)47(40)56)67-49(41)53-34-33-44(51)52-50(53)58/h33-34,39-43,47-49,56-57H,4-32,35-38H2,1-3H3,(H,59,60)(H,61,62)(H2,51,52,58)/t40?,41?,42-,43-,47+,48-,49-/m1/s1 KZDVTXQPRNWSAQ-QQXYXHBCSA-N logp 5.75 ALOGPS logs -5.09 ALOGPS solubility 8.45e-03 g/l ALOGPS logp 10.83 ChemAxon pka_strongest_acidic 1.88 ChemAxon pka_strongest_basic 0.54 ChemAxon iupac [(1R,9R,24S,25S,27R)-27-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-23-hexyl-4,6,24,25-tetrahydroxy-4,6,11-trioxo-3,5,7,10,26-pentaoxa-4λ⁵,6λ⁵-diphosphabicyclo[19.4.2]heptacosan-9-yl]methyl 17-methyloctadecanoate ChemAxon average_mass 1036.232 ChemAxon mono_mass 1035.592543238 ChemAxon smiles CCCCCCC1CC2CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OP(O)(=O)OC[C@@H](O[C@H]2N2C=CC(N)=NC2=O)[C@@H](O)[C@H]1O ChemAxon formula C50H91N3O15P2 ChemAxon inchi InChI=1S/C50H91N3O15P2/c1-4-5-6-24-29-40-35-41-30-25-20-16-14-18-22-27-32-46(55)66-42(36-63-45(54)31-26-21-17-13-11-9-7-8-10-12-15-19-23-28-39(2)3)37-64-69(59,60)68-70(61,62)65-38-43(48(57)47(40)56)67-49(41)53-34-33-44(51)52-50(53)58/h33-34,39-43,47-49,56-57H,4-32,35-38H2,1-3H3,(H,59,60)(H,61,62)(H2,51,52,58)/t40?,41?,42-,43-,47+,48-,49-/m1/s1 ChemAxon inchikey KZDVTXQPRNWSAQ-QQXYXHBCSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 266.07 ChemAxon polarizability 115.88 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(19:iso/19:0cycv8c/19:0/19:0)) 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. PW002008 Metabolic Specdb::EiMs 3872 Specdb::NmrOneD 291635 Specdb::NmrOneD 291636 Specdb::NmrOneD 291637 Specdb::NmrOneD 291638 Specdb::NmrOneD 291639 Specdb::NmrOneD 291640 Specdb::NmrOneD 291641 Specdb::NmrOneD 291642 Specdb::NmrOneD 291643 Specdb::NmrOneD 291644 Specdb::NmrOneD 291645 Specdb::NmrOneD 291646 Specdb::NmrOneD 291647 Specdb::NmrOneD 291648 Specdb::NmrOneD 291649 Specdb::NmrOneD 291650 Specdb::NmrOneD 291651 Specdb::NmrOneD 291652 Specdb::NmrOneD 291653 Specdb::NmrOneD 291654 Specdb::MsMs 41426 Specdb::MsMs 41427 Specdb::MsMs 41428 Specdb::MsMs 42134 Specdb::MsMs 42135 Specdb::MsMs 42136 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:iso/19:0cycv8c/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(19:iso/19:0cycv8c) + Pyrophosphate PW_R005657 2 CDP-DG(19:iso/19:0cycv8c) + Glycerol 3-phosphate >2 PGP(19:iso/19:0cycv8c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005658