2.0 2015-09-08 19:57:35 -0600 2015-12-09 12:13:46 -0700 ECMDB24681 M2MDB006798 CDP-DG(15:0cyclo/17:0cycw7c) CDP-DG(15:0cyclo/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(15:0cyclo/17:0cycw7c), in particular, consists of one cis-9,10-Methylenetetradecanoic acid 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(15:0cyclo/17:0cycw7c) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C44H77N3O15P2 950.054 949.482992787 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[8-(2-hexylcyclopropyl)octanoyl]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-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCC1CC1CCCC)(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/C44H77N3O15P2/c1-3-5-7-14-20-34-28-35(34)22-16-11-9-13-18-24-40(49)60-36(29-57-39(48)23-17-12-8-10-15-21-33-27-32(33)19-6-4-2)30-58-63(53,54)62-64(55,56)59-31-37-41(50)42(51)43(61-37)47-26-25-38(45)46-44(47)52/h25-26,32-37,41-43,50-51H,3-24,27-31H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/t32?,33?,34?,35?,36-,37-,41+,42?,43-/m1/s1 MKFASCNKVSHIFK-MBFDINJASA-N logp 5.34 ALOGPS logs -4.98 ALOGPS solubility 9.94e-03 g/l ALOGPS logp 8 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-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 950.054 ChemAxon mono_mass 949.482992787 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCC1CC1CCCC)(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 C44H77N3O15P2 ChemAxon inchi InChI=1S/C44H77N3O15P2/c1-3-5-7-14-20-34-28-35(34)22-16-11-9-13-18-24-40(49)60-36(29-57-39(48)23-17-12-8-10-15-21-33-27-32(33)19-6-4-2)30-58-63(53,54)62-64(55,56)59-31-37-41(50)42(51)43(61-37)47-26-25-38(45)46-44(47)52/h25-26,32-37,41-43,50-51H,3-24,27-31H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/t32?,33?,34?,35?,36-,37-,41+,42?,43-/m1/s1 ChemAxon inchikey MKFASCNKVSHIFK-MBFDINJASA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 236.4 ChemAxon polarizability 101.74 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/16:0/16:0) "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." PW001145 Metabolic Specdb::MsMs 1249132 Specdb::MsMs 1249133 Specdb::MsMs 1249134 Specdb::MsMs 1364446 Specdb::MsMs 1364447 Specdb::MsMs 1364448 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(15:0cyclo/17:0cycw7c/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(15:0cyclo/17:0cycw7c) + Pyrophosphate PW_R005683