2.0 2012-10-11 06:39:33 -0600 2015-12-09 12:12:44 -0700 ECMDB23328 M2MDB003718 CDP-DG(10:0/18:0) CDP-DG(10:0/18:0) 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(10:0/18:0), in particular, consists of one decanoyl chain to C-1 atom, and one octadecanoyl 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(10:0/18:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-decanoyl-2-octadecanoyl-sn-glycero-3-CDP 1-decanoyl-2-octadecanoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Decanoyl-2-octadecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid 1-decanoyl-2-stearoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Decanoyl-2-stearoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(28:0) CDP-Diacylglycerol(10:0/18:0) CDP-Diacylglycerol(28:0) C40H73N3O15P2 897.978 897.451692659 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-(decanoyloxy)-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-3-(decanoyloxy)-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)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)CCCCCCCCCCCCCCCCC InChI=1S/C40H73N3O15P2/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-36(45)56-32(29-53-35(44)25-23-21-19-10-8-6-4-2)30-54-59(49,50)58-60(51,52)55-31-33-37(46)38(47)39(57-33)43-28-27-34(41)42-40(43)48/h27-28,32-33,37-39,46-47H,3-26,29-31H2,1-2H3,(H,49,50)(H,51,52)(H2,41,42,48)/t32-,33-,37+,38?,39-/m1/s1 KFYXOQRBHXFBFT-IBIGLQDYSA-N Solid Membrane logp 4.90 ALOGPS logs -4.72 ALOGPS solubility 1.70e-02 g/l ALOGPS logp 7.78 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-(decanoyloxy)-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 897.978 ChemAxon mono_mass 897.451692659 ChemAxon smiles [H][C@@](COC(=O)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)CCCCCCCCCCCCCCCCC ChemAxon formula C40H73N3O15P2 ChemAxon inchi InChI=1S/C40H73N3O15P2/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-36(45)56-32(29-53-35(44)25-23-21-19-10-8-6-4-2)30-54-59(49,50)58-60(51,52)55-31-33-37(46)38(47)39(57-33)43-28-27-34(41)42-40(43)48/h27-28,32-33,37-39,46-47H,3-26,29-31H2,1-2H3,(H,49,50)(H,51,52)(H2,41,42,48)/t32-,33-,37+,38?,39-/m1/s1 ChemAxon inchikey KFYXOQRBHXFBFT-IBIGLQDYSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 221.81 ChemAxon polarizability 97.35 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CDP-DG(10:0/18:0) 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 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. PW001754 Metabolic phospholipid biosynthesis CDP-DG(10:0/18:0) III 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. PW001833 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::EiMs 5572 Specdb::NmrOneD 315421 Specdb::NmrOneD 315422 Specdb::NmrOneD 315423 Specdb::NmrOneD 315424 Specdb::NmrOneD 315425 Specdb::NmrOneD 315426 Specdb::NmrOneD 315427 Specdb::NmrOneD 315428 Specdb::NmrOneD 315429 Specdb::NmrOneD 315430 Specdb::NmrOneD 315431 Specdb::NmrOneD 315432 Specdb::NmrOneD 315433 Specdb::NmrOneD 315434 Specdb::NmrOneD 315435 Specdb::NmrOneD 315436 Specdb::NmrOneD 315437 Specdb::NmrOneD 315438 Specdb::NmrOneD 315439 Specdb::NmrOneD 315440 Specdb::MsMs 1311982 Specdb::MsMs 1311983 Specdb::MsMs 1311984 Specdb::MsMs 1426453 Specdb::MsMs 1426454 Specdb::MsMs 1426455 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(10:0/18:0/0:0) + Hydrogen ion + Cytidine triphosphate > CDP-DG(10:0/18:0) + Pyrophosphate PW_R004704 CDP-DG(10:0/18:0) + L-Serine + L-Serine > PS(10:0(3-OH)/18:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R004851