2.0 2015-09-08 19:54:01 -0600 2015-09-14 11:20:11 -0600 ECMDB24653 M2MDB006770 CDP-DG(12:0(3-OH)/19:iso) CDP-DG(12:0(3-OH)/19:iso) 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(12:0(3-OH)/19:iso), in particular, consists of one 3-hydroxydodecanoyl chain to C-1 atom, and one 17-methylocatdecanoyl 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(12:0(3-OH)/19:iso) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C43H79N3O16P2 956.058 955.493557472 {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy]phosphoryl}oxy)phosphinic acid [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy)phosphoryl]oxy)phosphinic acid CCCCCCCCCC(O)CC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCCC(C)C InChI=1S/C43H79N3O16P2/c1-4-5-6-7-15-19-22-25-34(47)29-39(49)57-30-35(60-38(48)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-33(2)3)31-58-63(53,54)62-64(55,56)59-32-36-40(50)41(51)42(61-36)46-28-27-37(44)45-43(46)52/h27-28,33-36,40-42,47,50-51H,4-26,29-32H2,1-3H3,(H,53,54)(H,55,56)(H2,44,45,52)/t34?,35-,36-,40-,41-,42-/m1/s1 SSHMHANXDRKNQG-HQQMOLGISA-N logp 4.87 ALOGPS logs -4.78 ALOGPS solubility 1.58e-02 g/l ALOGPS logp 7.72 ChemAxon pka_strongest_acidic -0.032 ChemAxon pka_strongest_basic 3.27 ChemAxon iupac {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 956.058 ChemAxon mono_mass 955.493557472 ChemAxon smiles CCCCCCCCCC(O)CC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCCC(C)C ChemAxon formula C43H79N3O16P2 ChemAxon inchi InChI=1S/C43H79N3O16P2/c1-4-5-6-7-15-19-22-25-34(47)29-39(49)57-30-35(60-38(48)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-33(2)3)31-58-63(53,54)62-64(55,56)59-32-36-40(50)41(51)42(61-36)46-28-27-37(44)45-43(46)52/h27-28,33-36,40-42,47,50-51H,4-26,29-32H2,1-3H3,(H,53,54)(H,55,56)(H2,44,45,52)/t34?,35-,36-,40-,41-,42-/m1/s1 ChemAxon inchikey SSHMHANXDRKNQG-HQQMOLGISA-N ChemAxon polar_surface_area 283.5 ChemAxon refractivity 237.07 ChemAxon polarizability 102.88 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso)) 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. PW001926 Metabolic Specdb::EiMs 5214 Specdb::NmrOneD 274418 Specdb::NmrOneD 274419 Specdb::NmrOneD 274420 Specdb::NmrOneD 274421 Specdb::NmrOneD 274422 Specdb::NmrOneD 274423 Specdb::NmrOneD 274424 Specdb::NmrOneD 274425 Specdb::NmrOneD 274426 Specdb::NmrOneD 274427 Specdb::NmrOneD 274428 Specdb::NmrOneD 274429 Specdb::NmrOneD 274430 Specdb::NmrOneD 274431 Specdb::NmrOneD 274432 Specdb::NmrOneD 274433 Specdb::NmrOneD 274434 Specdb::NmrOneD 274435 Specdb::NmrOneD 274436 Specdb::NmrOneD 274437 Specdb::MsMs 41729 Specdb::MsMs 41730 Specdb::MsMs 41731 Specdb::MsMs 42437 Specdb::MsMs 42438 Specdb::MsMs 42439 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 CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase P0ABF8 PGSA_ECOLI pgsA http://ecmdb.ca/proteins/P0ABF8.xml Phosphatidate cytidylyltransferase P0ABG1 CDSA_ECOLI cdsA http://ecmdb.ca/proteins/P0ABG1.xml 2 DG(12:0(3-OH)/19:iso/0:0) + Cytidine triphosphate + Hydrogen ion >2 CDP-DG(12:0(3-OH)/19:iso) + Pyrophosphate PW_R005396 2 CDP-DG(12:0(3-OH)/19:iso) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005397