2.0 2012-10-11 06:39:44 -0600 2015-12-09 12:15:16 -0700 ECMDB23391 M2MDB003781 CDP-DG(19:1(9Z)/19:1(9Z)) CDP-DG(19:1(9Z)/19:1(9Z)) 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 positions. CDP-DG(19:1(9Z)/19:1(9Z)), in particular, consists of two 9Z-nonadecenoyl chain at positions C-1 and C2. 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(19:1(9Z)/19:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1,2-di(9Z-nonadecenoyl)-rac-glycero-3-CDP 1,2-di(9Z-nonadecenoyl)-rac-glycero-3-cytidine-5'-diphosphate 1,2-Di(9Z-nonadecenoyl)-rac-glycero-3-cytidine-5'-diphosphoric acid 1,2-di9Z-nonadecenoyl-rac-glycero-3-cytidine-5'-diphosphate 1,2-Di9Z-nonadecenoyl-rac-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(19:1/19:1) CDP-DG(38:2) CDP-Diacylglycerol(19:1/19:1) CDP-Diacylglycerol(38:2) C50H89N3O15P2 1034.216 1033.576893174 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis[(9Z)-nonadec-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)-2,3-bis[(9Z)-nonadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCCCCC InChI=1S/C50H89N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-45(54)63-39-42(66-46(55)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h19-22,37-38,42-43,47-49,56-57H,3-18,23-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b21-19-,22-20-/t42-,43-,47+,48?,49-/m1/s1 UNXTYQGQWKPJGK-YBVHGPAUSA-N Solid Membrane logp 7.28 ALOGPS logs -5.74 ALOGPS solubility 1.86e-03 g/l ALOGPS logp 11.5 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)-2,3-bis[(9Z)-nonadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1034.216 ChemAxon mono_mass 1033.576893174 ChemAxon smiles [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCCCCC ChemAxon formula C50H89N3O15P2 ChemAxon inchi InChI=1S/C50H89N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-45(54)63-39-42(66-46(55)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h19-22,37-38,42-43,47-49,56-57H,3-18,23-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b21-19-,22-20-/t42-,43-,47+,48?,49-/m1/s1 ChemAxon inchikey UNXTYQGQWKPJGK-YBVHGPAUSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 270.05 ChemAxon polarizability 113.4 ChemAxon rotatable_bond_count 46 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (CDP-DG(19:1(9Z)/19:1(9Z))) 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. PW001792 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::NmrOneD 305371 Specdb::NmrOneD 305372 Specdb::NmrOneD 305373 Specdb::NmrOneD 305374 Specdb::NmrOneD 305375 Specdb::NmrOneD 305376 Specdb::NmrOneD 305377 Specdb::NmrOneD 305378 Specdb::NmrOneD 305379 Specdb::NmrOneD 305380 Specdb::NmrOneD 305381 Specdb::NmrOneD 305382 Specdb::NmrOneD 305383 Specdb::NmrOneD 305384 Specdb::NmrOneD 305385 Specdb::NmrOneD 305386 Specdb::NmrOneD 305387 Specdb::NmrOneD 305388 Specdb::NmrOneD 305389 Specdb::NmrOneD 305390 Specdb::MsMs 1316785 Specdb::MsMs 1316786 Specdb::MsMs 1316787 Specdb::MsMs 1431241 Specdb::MsMs 1431242 Specdb::MsMs 1431243 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 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 Protein crcA P37001 CRCA_ECOLI crcA http://ecmdb.ca/proteins/P37001.xml CDP-diacylglycerol--serine O-phosphatidyltransferase P23830 PSS_ECOLI pssA http://ecmdb.ca/proteins/P23830.xml Probable phospholipid ABC transporter-binding protein mlaB P64602 MLAB_ECOLI mlaB http://ecmdb.ca/proteins/P64602.xml Probable phospholipid ABC transporter-binding protein mlaD P64604 MLAD_ECOLI mlaD http://ecmdb.ca/proteins/P64604.xml Probable phospholipid ABC transporter permease protein mlaE P64606 MLAE_ECOLI mlaE http://ecmdb.ca/proteins/P64606.xml DG(19:1(9Z)/19:1(9Z)/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(19:1(9Z)/19:1(9Z)) + Pyrophosphate PW_R004764