2.0 2012-10-11 06:39:38 -0600 2015-12-09 12:13:41 -0700 ECMDB23355 M2MDB003745 CDP-DG(15:0/19:1(9Z)) CDP-DG(15:0/19:1(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 atoms. CDP-DG(15:0/19:1(9Z)), in particular, consists of one pentadecanoyl chain to C-1 atom, and one 9Z-nonadecenoyl 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(15:0/19:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-pentadecanoyl-2-(9Z-nonadecenoyl)-sn-glycero-3-CDP 1-pentadecanoyl-2-(9Z-nonadecenoyl)-sn-glycero-3-cytidine-5'-diphosphate 1-Pentadecanoyl-2-(9Z-nonadecenoyl)-sn-glycero-3-cytidine-5'-diphosphoric acid 1-pentadecanoyl-2-9Z-nonadecenoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Pentadecanoyl-2-9Z-nonadecenoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(15:0/19:1) CDP-DG(34:1) CDP-Diacylglycerol(15:0/19:1) CDP-Diacylglycerol(34:1) C46H83N3O15P2 980.124 979.529942981 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCCCCCC)(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/C46H83N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-42(51)62-38(35-59-41(50)31-29-27-25-23-21-16-14-12-10-8-6-4-2)36-60-65(55,56)64-66(57,58)61-37-39-43(52)44(53)45(63-39)49-34-33-40(47)48-46(49)54/h18-19,33-34,38-39,43-45,52-53H,3-17,20-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/b19-18-/t38-,39-,43+,44?,45-/m1/s1 BNHYYJPYYGIOOV-PJQGUHQXSA-N Solid Membrane logp 6.51 ALOGPS logs -5.36 ALOGPS solubility 4.31e-03 g/l ALOGPS logp 10.08 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}({hydroxy[(2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 980.124 ChemAxon mono_mass 979.529942981 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCC)(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 C46H83N3O15P2 ChemAxon inchi InChI=1S/C46H83N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-42(51)62-38(35-59-41(50)31-29-27-25-23-21-16-14-12-10-8-6-4-2)36-60-65(55,56)64-66(57,58)61-37-39-43(52)44(53)45(63-39)49-34-33-40(47)48-46(49)54/h18-19,33-34,38-39,43-45,52-53H,3-17,20-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/b19-18-/t38-,39-,43+,44?,45-/m1/s1 ChemAxon inchikey BNHYYJPYYGIOOV-PJQGUHQXSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 250.53 ChemAxon polarizability 106.9 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CDP-DG(15:0/19:1(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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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. PW001813 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::EiMs 2605 Specdb::NmrOneD 315241 Specdb::NmrOneD 315242 Specdb::NmrOneD 315243 Specdb::NmrOneD 315244 Specdb::NmrOneD 315245 Specdb::NmrOneD 315246 Specdb::NmrOneD 315247 Specdb::NmrOneD 315248 Specdb::NmrOneD 315249 Specdb::NmrOneD 315250 Specdb::NmrOneD 315251 Specdb::NmrOneD 315252 Specdb::NmrOneD 315253 Specdb::NmrOneD 315254 Specdb::NmrOneD 315255 Specdb::NmrOneD 315256 Specdb::NmrOneD 315257 Specdb::NmrOneD 315258 Specdb::NmrOneD 315259 Specdb::NmrOneD 315260 Specdb::MsMs 1246633 Specdb::MsMs 1246634 Specdb::MsMs 1246635 Specdb::MsMs 1361974 Specdb::MsMs 1361975 Specdb::MsMs 1361976 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(15:0/19:1(9Z)/0:0) + Hydrogen ion + Cytidine triphosphate > CDP-DG(15:0/19:1(9Z)) + Pyrophosphate PW_R004801