2.0 2012-05-31 14:10:55 -0600 2015-09-17 15:41:24 -0600 ECMDB06977 M2MDB000717 CDP-DG(18:0/16:0) CDP-DG(18:0/16:0) 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(18:0/16:0), in particular, consists of one octadecanoyl chain to C-1 atom, and one hexadecanoyl 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(18:0/16:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-CDP 1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid 1-Stearoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Stearoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(18:0/16:0) CDP-DG(34:0) CDP-Diacylglycerol(18:0/16:0) CDP-Diacylglycerol(34:0) C46H85N3O15P2 982.1257 981.545592089 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C46H85N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)59-35-38(62-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)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/h33-34,38-39,43-45,52-53H,3-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/t38-,39-,43+,44?,45-/m1/s1 IYHZDHRWSOSUSF-IOYUWRPMSA-N Solid Inner membrane Membrane Outer membrane logp 6.43 ALOGPS logs -5.37 ALOGPS solubility 4.18e-03 g/l ALOGPS logp 10.45 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-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 982.1257 ChemAxon mono_mass 981.545592089 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCC ChemAxon formula C46H85N3O15P2 ChemAxon inchi InChI=1S/C46H85N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)59-35-38(62-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)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/h33-34,38-39,43-45,52-53H,3-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/t38-,39-,43+,44?,45-/m1/s1 ChemAxon inchikey IYHZDHRWSOSUSF-IOYUWRPMSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 249.41 ChemAxon polarizability 108.79 ChemAxon rotatable_bond_count 44 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis (PE(18:0/16:0)) 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. PW001767 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::NmrOneD 336978 Specdb::NmrOneD 336979 Specdb::NmrOneD 336980 Specdb::NmrOneD 336981 Specdb::NmrOneD 336982 Specdb::NmrOneD 336983 Specdb::NmrOneD 336984 Specdb::NmrOneD 336985 Specdb::NmrOneD 336986 Specdb::NmrOneD 336987 Specdb::NmrOneD 336988 Specdb::NmrOneD 336989 Specdb::NmrOneD 336990 Specdb::NmrOneD 336991 Specdb::NmrOneD 336992 Specdb::NmrOneD 336993 Specdb::NmrOneD 336994 Specdb::NmrOneD 336995 Specdb::NmrOneD 336996 Specdb::NmrOneD 336997 Specdb::MsMs 312532 Specdb::MsMs 312533 Specdb::MsMs 312534 Specdb::MsMs 357814 Specdb::MsMs 357815 Specdb::MsMs 357816 Specdb::MsMs 2406662 Specdb::MsMs 2406663 Specdb::MsMs 2406664 Specdb::MsMs 2531691 Specdb::MsMs 2531692 Specdb::MsMs 2531693 HMDB06977 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 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(18:0/16:0/0:0) + Cytidine triphosphate + Hydrogen ion + DG(18:0/16:0/0:0) > CDP-DG(18:0/16:0) + Pyrophosphate + CDP-DG(18:0/16:0) PW_R004724 CDP-DG(18:0/16:0) + L-Serine + CDP-DG(18:0/16:0) + L-Serine > PS(18:0/16:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R004726