2.0 2015-09-08 19:57:04 -0600 2015-12-09 12:13:43 -0700 ECMDB24678 M2MDB006795 CDP-DG(15:0cyclo/14:0) CDP-DG(15:0cyclo/14:0) 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/14:0), in particular, consists of one cis-9,10-Methylenetetradecanoic acid chain to C-1 atom, and one tetradecanoyl 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/14:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C41H73N3O15P2 909.989 909.451692659 {[(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-(tetradecanoyloxy)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-(tetradecanoyloxy)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)CCCCCCCCCCCCC InChI=1S/C41H73N3O15P2/c1-3-5-7-8-9-10-11-12-13-16-20-24-37(46)57-33(28-54-36(45)23-19-17-14-15-18-22-32-27-31(32)21-6-4-2)29-55-60(50,51)59-61(52,53)56-30-34-38(47)39(48)40(58-34)44-26-25-35(42)43-41(44)49/h25-26,31-34,38-40,47-48H,3-24,27-30H2,1-2H3,(H,50,51)(H,52,53)(H2,42,43,49)/t31?,32?,33-,34-,38+,39?,40-/m1/s1 CZNAEFVPQZIGMR-NXJNZTMPSA-N logp 4.91 ALOGPS logs -4.70 ALOGPS solubility 1.81e-02 g/l ALOGPS logp 7.44 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-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 909.989 ChemAxon mono_mass 909.451692659 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)CCCCCCCCCCCCC ChemAxon formula C41H73N3O15P2 ChemAxon inchi InChI=1S/C41H73N3O15P2/c1-3-5-7-8-9-10-11-12-13-16-20-24-37(46)57-33(28-54-36(45)23-19-17-14-15-18-22-32-27-31(32)21-6-4-2)29-55-60(50,51)59-61(52,53)56-30-34-38(47)39(48)40(58-34)44-26-25-35(42)43-41(44)49/h25-26,31-34,38-40,47-48H,3-24,27-30H2,1-2H3,(H,50,51)(H,52,53)(H2,42,43,49)/t31?,32?,33-,34-,38+,39?,40-/m1/s1 ChemAxon inchikey CZNAEFVPQZIGMR-NXJNZTMPSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 224.5 ChemAxon polarizability 96.77 ChemAxon rotatable_bond_count 37 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/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." PW001221 Metabolic Specdb::EiMs 5162 Specdb::NmrOneD 266708 Specdb::NmrOneD 266709 Specdb::NmrOneD 266710 Specdb::NmrOneD 266711 Specdb::NmrOneD 266712 Specdb::NmrOneD 266713 Specdb::NmrOneD 266714 Specdb::NmrOneD 266715 Specdb::NmrOneD 266716 Specdb::NmrOneD 266717 Specdb::NmrOneD 266718 Specdb::NmrOneD 266719 Specdb::NmrOneD 266720 Specdb::NmrOneD 266721 Specdb::NmrOneD 266722 Specdb::NmrOneD 266723 Specdb::NmrOneD 266724 Specdb::NmrOneD 266725 Specdb::NmrOneD 266726 Specdb::NmrOneD 266727 Specdb::MsMs 1320511 Specdb::MsMs 1320512 Specdb::MsMs 1320513 Specdb::MsMs 1434940 Specdb::MsMs 1434941 Specdb::MsMs 1434942 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/14:0/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(15:0cyclo/14:0) + Pyrophosphate PW_R005680