2.0 2012-05-31 14:02:47 -0600 2015-06-03 15:54:38 -0600 ECMDB04033 M2MDB000569 CDPglucose CDPglucose is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. GDP-D-glucose is involved in Ebosin biosynthesis. The CDP-D glucose synthase encoded by ste17 gene is involved in the formation of nucleotide sugar (CDP-D-glucose) as glucose precursor in Ebosin biosynthesis. (PMID 19330326) CDP-D-Glucose CDP-GLC CDP-Glucose C15H23N3O16P2 563.3011 563.055354727 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-olate 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[({hydroxy[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl phosphonato}oxy)methyl]oxolan-2-yl]-4-iminopyrimidin-2-olate [H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(=N)N=C2[O-])[C@]([H])(O)[C@]1([H])O InChI=1S/C15H25N3O16P2/c16-7-1-2-18(15(25)17-7)13-11(23)9(21)6(31-13)4-30-35(26,27)34-36(28,29)33-14-12(24)10(22)8(20)5(3-19)32-14/h1-2,5-6,8-14,19-24H,3-4H2,(H,26,27)(H,28,29)(H2,16,17,25)/p-2/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1 CGPHZDRCVSLMCF-JZMIEXBBSA-L Cytoplasm Periplasm logp -1.80 ALOGPS logs -1.28 ALOGPS solubility 3.16e+01 g/l ALOGPS logp -6 ChemAxon pka_strongest_acidic 1.67 ChemAxon pka_strongest_basic 3.26 ChemAxon iupac 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-olate ChemAxon average_mass 563.3011 ChemAxon mono_mass 563.055354727 ChemAxon smiles [H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(=N)N=C2[O-])[C@]([H])(O)[C@]1([H])O ChemAxon formula C15H23N3O16P2 ChemAxon inchi InChI=1S/C15H25N3O16P2/c16-7-1-2-18(15(25)17-7)13-11(23)9(21)6(31-13)4-30-35(26,27)34-36(28,29)33-14-12(24)10(22)8(20)5(3-19)32-14/h1-2,5-6,8-14,19-24H,3-4H2,(H,26,27)(H,28,29)(H2,16,17,25)/p-2/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1 ChemAxon inchikey CGPHZDRCVSLMCF-JZMIEXBBSA-L ChemAxon polar_surface_area 307.47 ChemAxon refractivity 129.28 ChemAxon polarizability 46.15 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 16 ChemAxon donor_count 8 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Starch and sucrose metabolism The metabolism of starch and sucrose begins with D-fructose interacting with a D-glucose in a reversible reaction through a maltodextrin glucosidase resulting in a water molecule and a sucrose. D-fructose is phosphorylated through an ATP driven fructokinase resulting in the release of an ADP, a hydrogen ion and a Beta-D-fructofuranose 6-phosphate. This compound can also be introduced into the cytoplasm through either a mannose PTS permease or a hexose-6-phosphate:phosphate antiporter. The Beta-D-fructofuranose 6-phosphate is isomerized through a phosphoglucose isomerase resulting in a Beta-D-glucose 6-phosphate. This compound can also be incorporated by glucose PTS permease or a hexose-6-phosphate:phosphate antiporter. The beta-D-glucose 6 phosphate can also be produced by a D-glucose being phosphorylated by an ATP-driven glucokinase resulting in a ADP, a hydrogen ion and a Beta-D-glucose 6 phosphate. The beta-D-glucose can produce alpha-D-glucose-1-phosphate by two methods: 1.-Beta-D-glucose is isomerized into an alpha-D-Glucose 6-phosphate and then interacts in a reversible reaction through a phosphoglucomutase-1 resulting in a alpha-D-glucose-1-phosphate. 2.-Beta-D-glucose interacts with a putative beta-phosphoglucomutase resulting in a Beta-D-glucose 1-phosphate. Beta-D-glucose 1-phosphate can be incorporated into the cytoplasm through a glucose PTS permease. This compound is then isomerized into a Alpha-D-glucose-1-phosphate The beta-D-glucose can cycle back into a D-fructose by first interacting with D-fructose in a reversible reaction through a Polypeptide: predicted glucosyltransferase resulting in the release of a phosphate and a sucrose. The sucrose then interacts in a reversible reaction with a water molecule through a maltodextrin glucosidase resulting in a D-glucose and a D-fructose. Alpha-D-glucose-1-phosphate can produce glycogen in by two different sets of reactions: 1.-Alpha-D-glucose-1-phosphate interacts with a hydrogen ion and an ATP through a glucose-1-phosphate adenylyltransferase resulting in a pyrophosphate and an ADP-glucose. The ADP-glucose then interacts with an amylose through a glycogen synthase resulting in the release of an ADP and an Amylose. The amylose then interacts with 1,4-α-glucan branching enzyme resulting in glycogen 2.- Alpha-D-glucose-1-phosphate interacts with amylose through a maltodextrin phosphorylase resulting in a phosphate and a glycogen. Alpha-D-glucose-1-phosphate can also interacts with UDP-galactose through a galactose-1-phosphate uridylyltransferase resulting in a galactose 1-phosphate and a Uridine diphosphate glucose. The UDP-glucose then interacts with an alpha-D-glucose 6-phosphate through a trehalose-6-phosphate synthase resulting in a uridine 5'-diphosphate, a hydrogen ion and a Trehalose 6- phosphate. The latter compound can also be incorporated into the cytoplasm through a trehalose PTS permease. Trehalose interacts with a water molecule through a trehalose-6-phosphate phosphatase resulting in the release of a phosphate and an alpha,alpha-trehalose.The alpha,alpha-trehalose can also be obtained from glycogen being metabolized through a glycogen debranching enzyme resulting in a the alpha, alpha-trehalose. This compound ca then be hydrated through a cytoplasmic trehalase resulting in the release of an alpha-D-glucose and a beta-d-glucose. Glycogen is then metabolized by reacting with a phosphate through a glycogen phosphorylase resulting in a alpha-D-glucose-1-phosphate and a dextrin. The dextrin is then hydrated through a glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase resulting in the release of a debranched limit dextrin and a maltotetraose. This compound can also be incorporated into the cytoplasm through a maltose ABC transporter. The maltotetraose interacts with a phosphate through a maltodextrin phosphorylase releasing a alpha-D-glucose-1-phosphate and a maltotriose. The maltotriose can also be incorporated through a maltose ABC transporter. The maltotriose can then interact with water through a maltodextrin glucosidase resulting in a D-glucose and a D-maltose. D-maltose can also be incorporated through a maltose ABC transporter The D-maltose can then interact with a maltotriose through a amylomaltase resulting in a maltotetraose and a D-glucose. The D-glucose is then phosphorylated through an ATP driven glucokinase resulting in a hydrogen ion, an ADP and a Beta-D-glucose 6-phosphate PW000941 ec00500 Metabolic Amino sugar and nucleotide sugar metabolism ec00520 Specdb::NmrOneD 251588 Specdb::NmrOneD 251589 Specdb::NmrOneD 251590 Specdb::NmrOneD 251591 Specdb::NmrOneD 251592 Specdb::NmrOneD 251593 Specdb::NmrOneD 251594 Specdb::NmrOneD 251595 Specdb::NmrOneD 251596 Specdb::NmrOneD 251597 Specdb::NmrOneD 251598 Specdb::NmrOneD 251599 Specdb::NmrOneD 251600 Specdb::NmrOneD 251601 Specdb::NmrOneD 251602 Specdb::NmrOneD 251603 Specdb::NmrOneD 251604 Specdb::NmrOneD 251605 Specdb::NmrOneD 251606 Specdb::NmrOneD 251607 Specdb::MsMs 28907 Specdb::MsMs 28908 Specdb::MsMs 28909 Specdb::MsMs 35465 Specdb::MsMs 35466 Specdb::MsMs 35467 HMDB03369 25245528 C00501 CDP-D-GLUCOSE 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Qi, X. Q., Sun, Q. L., Bai, L. P., Shan, J. J., Zhang, Y., Zhang, R., Li, Y. (2009). "Identification of alpha-D-glucose-1-phosphate cytidylyltransferase involved in Ebosin biosynthesis of Streptomyces sp. 139." Appl Microbiol Biotechnol 83:361-368. 19330326