2.0 2012-10-11 06:39:33 -0600 2015-12-09 12:12:41 -0700 ECMDB23326 M2MDB003716 CDP-DG(10:0/16:0) CDP-DG(10:0/16:0) 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(10:0/16:0), in particular, consists of one decanoyl 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(10:0/16:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. 1-decanoyl-2-hexadecanoyl-sn-glycero-3-CDP 1-decanoyl-2-hexadecanoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Decanoyl-2-hexadecanoyl-sn-glycero-3-cytidine-5'-diphosphoric acid 1-decanoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Decanoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphoric acid CDP-DG(26:0) CDP-Diacylglycerol(10:0/16:0) CDP-Diacylglycerol(26:0) C38H69N3O15P2 869.924 869.42039253 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-(decanoyloxy)-2-(hexadecanoyloxy)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-(hexadecanoyloxy)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)CCCCCCCCCCCCCCC InChI=1S/C38H69N3O15P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-34(43)54-30(27-51-33(42)23-21-19-17-10-8-6-4-2)28-52-57(47,48)56-58(49,50)53-29-31-35(44)36(45)37(55-31)41-26-25-32(39)40-38(41)46/h25-26,30-31,35-37,44-45H,3-24,27-29H2,1-2H3,(H,47,48)(H,49,50)(H2,39,40,46)/t30-,31-,35+,36?,37-/m1/s1 FMCHGYHCSKACEL-RBBNTGEOSA-N Solid Membrane logp 4.33 ALOGPS logs -4.46 ALOGPS solubility 3.04e-02 g/l ALOGPS logp 6.89 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-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 869.924 ChemAxon mono_mass 869.42039253 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)CCCCCCCCCCCCCCC ChemAxon formula C38H69N3O15P2 ChemAxon inchi InChI=1S/C38H69N3O15P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-34(43)54-30(27-51-33(42)23-21-19-17-10-8-6-4-2)28-52-57(47,48)56-58(49,50)53-29-31-35(44)36(45)37(55-31)41-26-25-32(39)40-38(41)46/h25-26,30-31,35-37,44-45H,3-24,27-29H2,1-2H3,(H,47,48)(H,49,50)(H2,39,40,46)/t30-,31-,35+,36?,37-/m1/s1 ChemAxon inchikey FMCHGYHCSKACEL-RBBNTGEOSA-N ChemAxon polar_surface_area 263.27 ChemAxon refractivity 212.6 ChemAxon polarizability 93.09 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 12 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerophospholipid metabolism ec00564 phospholipid biosynthesis CDP-DG(10:0/16:0) 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 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. PW001750 Metabolic phospholipid biosynthesis CDP-DG(10:0/16:0) II 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. PW001827 Metabolic phospholipid biosynthesis I PHOSLIPSYN-PWY Specdb::EiMs 3696 Specdb::NmrOneD 323632 Specdb::NmrOneD 323633 Specdb::NmrOneD 323634 Specdb::NmrOneD 323635 Specdb::NmrOneD 323636 Specdb::NmrOneD 323637 Specdb::NmrOneD 323638 Specdb::NmrOneD 323639 Specdb::NmrOneD 323640 Specdb::NmrOneD 323641 Specdb::NmrOneD 323642 Specdb::NmrOneD 323643 Specdb::NmrOneD 323644 Specdb::NmrOneD 323645 Specdb::NmrOneD 323646 Specdb::NmrOneD 323647 Specdb::NmrOneD 323648 Specdb::NmrOneD 323649 Specdb::NmrOneD 323650 Specdb::NmrOneD 323651 Specdb::MsMs 1250638 Specdb::MsMs 1250639 Specdb::MsMs 1250640 Specdb::MsMs 1365934 Specdb::MsMs 1365935 Specdb::MsMs 1365936 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(10:0/16:0/0:0) + Hydrogen ion + Cytidine triphosphate > CDP-DG(10:0/16:0) + Pyrophosphate PW_R004697 CDP-DG(10:0/16:0) + L-Serine + L-Serine > PS(10:0(3-OH)/16:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R004842