2.0 2015-09-08 19:52:55 -0600 2015-12-09 12:12:49 -0700 ECMDB24644 M2MDB006761 CDP-DG(12:0(3-OH)/12:0(3-OH)) CDP-DG(12:0(3-OH)/12:0(3-OH)) 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 positions. CDP-DG(12:0(3-OH)/12:0(3-OH)), in particular, consists of two 3-hydroxydodecanoyl chain at positions C-1 and C2. 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)/12:0(3-OH)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway. C36H65N3O17P2 873.868 873.378921641 {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2,3-bis[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CC(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)CC(O)CCCCCCCCC InChI=1S/C36H65N3O17P2/c1-3-5-7-9-11-13-15-17-26(40)21-31(42)51-23-28(54-32(43)22-27(41)18-16-14-12-10-8-6-4-2)24-52-57(47,48)56-58(49,50)53-25-29-33(44)34(45)35(55-29)39-20-19-30(37)38-36(39)46/h19-20,26-29,33-35,40-41,44-45H,3-18,21-25H2,1-2H3,(H,47,48)(H,49,50)(H2,37,38,46)/t26?,27?,28-,29-,33+,34?,35-/m1/s1 BJRQFQWDPVIYFO-RLBVJZQSSA-N logp 2.27 ALOGPS logs -3.45 ALOGPS solubility 3.10e-01 g/l ALOGPS logp 3.54 ChemAxon pka_strongest_acidic -0.032 ChemAxon pka_strongest_basic 3.27 ChemAxon iupac {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 873.868 ChemAxon mono_mass 873.378921641 ChemAxon smiles [H][C@@](COC(=O)CC(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)CC(O)CCCCCCCCC ChemAxon formula C36H65N3O17P2 ChemAxon inchi InChI=1S/C36H65N3O17P2/c1-3-5-7-9-11-13-15-17-26(40)21-31(42)51-23-28(54-32(43)22-27(41)18-16-14-12-10-8-6-4-2)24-52-57(47,48)56-58(49,50)53-25-29-33(44)34(45)35(55-29)39-20-19-30(37)38-36(39)46/h19-20,26-29,33-35,40-41,44-45H,3-18,21-25H2,1-2H3,(H,47,48)(H,49,50)(H2,37,38,46)/t26?,27?,28-,29-,33+,34?,35-/m1/s1 ChemAxon inchikey BJRQFQWDPVIYFO-RLBVJZQSSA-N ChemAxon polar_surface_area 303.73 ChemAxon refractivity 206.43 ChemAxon polarizability 90.82 ChemAxon rotatable_bond_count 34 ChemAxon acceptor_count 14 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0)) 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. PW001915 Metabolic Specdb::EiMs 3959 Specdb::NmrOneD 286515 Specdb::NmrOneD 286516 Specdb::NmrOneD 286517 Specdb::NmrOneD 286518 Specdb::NmrOneD 286519 Specdb::NmrOneD 286520 Specdb::NmrOneD 286521 Specdb::NmrOneD 286522 Specdb::NmrOneD 286523 Specdb::NmrOneD 286524 Specdb::NmrOneD 286525 Specdb::NmrOneD 286526 Specdb::NmrOneD 286527 Specdb::NmrOneD 286528 Specdb::NmrOneD 286529 Specdb::NmrOneD 286530 Specdb::NmrOneD 286531 Specdb::NmrOneD 286532 Specdb::NmrOneD 286533 Specdb::NmrOneD 286534 Specdb::MsMs 1314307 Specdb::MsMs 1314308 Specdb::MsMs 1314309 Specdb::MsMs 1428793 Specdb::MsMs 1428794 Specdb::MsMs 1428795 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 CDP-diacylglycerol--serine O-phosphatidyltransferase P23830 PSS_ECOLI pssA http://ecmdb.ca/proteins/P23830.xml DG(12:0(3-OH)/12:0(3-OH)/0:0) + Cytidine triphosphate + Hydrogen ion > CDP-DG(12:0(3-OH)/12:0(3-OH)) + Pyrophosphate PW_R005347 CDP-DG(12:0(3-OH)/12:0(3-OH)) + L-Serine + L-Serine > PS(12:0(3-OH)/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005348