2.0 2012-05-31 10:21:42 -0600 2015-09-13 12:56:06 -0600 ECMDB00133 M2MDB000052 Guanosine Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate). (Wikipedia) 2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one 2-amino-1,9-dihydro-9-b-delta-Ribofuranosyl-6H-purin-6-one 2-amino-1,9-dihydro-9-b-δ-Ribofuranosyl-6H-purin-6-one 2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one 2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one 2-amino-1,9-dihydro-9-β-D-Ribofuranosyl-6H-purin-6-one 2-amino-1,9-dihydro-9-β-δ-Ribofuranosyl-6H-purin-6-one 2-Amino-Inosine 9-b-D-ribofuranosyl-Guanine 9-b-delta-Ribofuranosyl-guanine 9-b-δ-Ribofuranosyl-guanine 9-beta-D-Ribofuranosyl-Guanine 9-beta-delta-Ribofuranosyl-Guanine 9-β-D-Ribofuranosyl-guanine 9-β-δ-Ribofuranosyl-guanine B-D-Ribofuranoside guanine-9 b-delta-Ribofuranoside guanine-9 b-δ-Ribofuranoside guanine-9 Beta-D-Ribofuranoside guanine-9 Beta-delta-Ribofuranoside guanine-9 Guanosine Nucleoside Q Ribonucleoside Vernine β-D-Ribofuranoside guanine-9 β-δ-Ribofuranoside guanine-9 C10H13N5O5 283.2407 283.091668551 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one guanosine 118-00-3 NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1 InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1 NYHBQMYGNKIUIF-UUOKFMHZSA-N Solid Cytosol Extra-organism Periplasm logp -2.06 ALOGPS logs -1.27 ALOGPS solubility 1.53e+01 g/l ALOGPS melting_point 239 oC logp -2.7 ChemAxon pka_strongest_acidic 10.16 ChemAxon pka_strongest_basic 0.45 ChemAxon iupac 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one ChemAxon average_mass 283.2407 ChemAxon mono_mass 283.091668551 ChemAxon smiles NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1 ChemAxon formula C10H13N5O5 ChemAxon inchi InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1 ChemAxon inchikey NYHBQMYGNKIUIF-UUOKFMHZSA-N ChemAxon polar_surface_area 155.22 ChemAxon refractivity 64.62 ChemAxon polarizability 26.03 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 guanine and guanosine salvage Guanosine can be converted into guanine through a phosphate driven guanosine phosphorylase resulting in the release of an alpha-D-ribose 1 phosphate and a guanine. This compound in turn reacts with a PRPP through a guanine phosphoribosyltransferase resulting in the release of a pyrophosphate and a GMP. Guanosine can also react with and ATP driven guanosine kinase resulting in the release of an ADP, s hydrogen ion and a GMP PW002074 Metabolic purine ribonucleosides degradation Purine ribonucleoside degradation leads to the production of alpha-D-ribose-1-phosphate. Xanthosine is transported into the cytosol through a xapB. Once in the cytosol xanthosine interacts with phosphate through a xanthosine phosphorylase resulting in the release of a xanthine and a alpha-D-ribose-1-phosphate. Adenosine is transported through a nupC or a nupG transporter, once inside the cytosol it can either react with a phosphate through a adenosine phosphorylase resultin in the release of a adenine and an alpha-D-ribose-1-phosphate. Adenosine reacts with water and hydrogen ion through a adenosine deaminase resulting in the release of ammonium and inosine. Inosine reacts with phosphate through a inosine phosphorylase resulting in the release of a hypoxanthine and an alpha-D-ribose-1-phosphate. Guanosine reacts with a phosphate through a guanosine phosphorylase resulting in the release of a guanine and a alpha-D-ribose-1-phosphate. PW002076 Metabolic purine ribonucleosides degradation to ribose-1-phosphate PWY0-1296 guanosine nucleotides degradation III PWY-6608 guanine and guanosine salvage I PWY-6620 guanine and guanosine salvage III PWY-6618 Specdb::CMs 356 Specdb::CMs 357 Specdb::CMs 358 Specdb::CMs 359 Specdb::CMs 2710 Specdb::CMs 30191 Specdb::CMs 30564 Specdb::CMs 30873 Specdb::CMs 30874 Specdb::CMs 37313 Specdb::CMs 131331 Specdb::CMs 139065 Specdb::CMs 1051195 Specdb::CMs 1051196 Specdb::CMs 1051197 Specdb::CMs 1051199 Specdb::CMs 1051201 Specdb::CMs 1051203 Specdb::CMs 1051205 Specdb::CMs 1051207 Specdb::CMs 1051209 Specdb::CMs 1051211 Specdb::CMs 1051213 Specdb::CMs 1051215 Specdb::CMs 1051217 Specdb::EiMs 1973 Specdb::NmrOneD 1103 Specdb::NmrOneD 1161 Specdb::NmrOneD 142450 Specdb::NmrOneD 142451 Specdb::NmrOneD 142452 Specdb::NmrOneD 142453 Specdb::NmrOneD 142454 Specdb::NmrOneD 142455 Specdb::NmrOneD 142456 Specdb::NmrOneD 142457 Specdb::NmrOneD 142458 Specdb::NmrOneD 142459 Specdb::NmrOneD 142460 Specdb::NmrOneD 142461 Specdb::NmrOneD 142462 Specdb::NmrOneD 142463 Specdb::NmrOneD 142464 Specdb::NmrOneD 142465 Specdb::NmrOneD 142466 Specdb::NmrOneD 142467 Specdb::NmrOneD 142468 Specdb::NmrOneD 142469 Specdb::NmrOneD 166526 Specdb::NmrOneD 166605 Specdb::MsMs 203 Specdb::MsMs 204 Specdb::MsMs 205 Specdb::MsMs 3006 Specdb::MsMs 3007 Specdb::MsMs 3008 Specdb::MsMs 3009 Specdb::MsMs 3010 Specdb::MsMs 3011 Specdb::MsMs 3012 Specdb::MsMs 3013 Specdb::MsMs 3014 Specdb::MsMs 3015 Specdb::MsMs 3016 Specdb::MsMs 3017 Specdb::MsMs 3018 Specdb::MsMs 3019 Specdb::MsMs 3020 Specdb::MsMs 3021 Specdb::MsMs 3022 Specdb::MsMs 3023 Specdb::MsMs 3024 Specdb::MsMs 3025 Specdb::MsMs 3026 Specdb::MsMs 3027 Specdb::NmrTwoD 965 Specdb::NmrTwoD 1161 HMDB00133 6802 6544 C00387 16750 GUANOSINE GMP Guanosine Keseler, I. 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Gongye Weishengwu (1998), 28(4), 11-16. http://hmdb.ca/system/metabolites/msds/000/000/093/original/HMDB00133.pdf?1358894469 Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.xml 2',3'-cyclic-nucleotide 2'-phosphodiesterase/3'-nucleotidase P08331 CPDB_ECOLI cpdB http://ecmdb.ca/proteins/P08331.xml Multifunctional protein surE P0A840 SURE_ECOLI surE http://ecmdb.ca/proteins/P0A840.xml 5'-nucleotidase yjjG P0A8Y1 YJJG_ECOLI yjjG http://ecmdb.ca/proteins/P0A8Y1.xml Purine nucleoside phosphorylase deoD-type P0ABP8 DEOD_ECOLI deoD http://ecmdb.ca/proteins/P0ABP8.xml Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Inosine-guanosine kinase P0AEW6 INGK_ECOLI gsk http://ecmdb.ca/proteins/P0AEW6.xml Deoxyguanosinetriphosphate triphosphohydrolase P15723 DGTP_ECOLI dgt http://ecmdb.ca/proteins/P15723.xml Pyrimidine-specific ribonucleoside hydrolase rihB P33022 RIHB_ECOLI rihB http://ecmdb.ca/proteins/P33022.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.xml Xanthosine phosphorylase P45563 XAPA_ECOLI xapA http://ecmdb.ca/proteins/P45563.xml Nucleoside permease nupG P0AFF4 NUPG_ECOLI nupG http://ecmdb.ca/proteins/P0AFF4.xml Nucleoside permease nupX P33021 NUPX_ECOLI nupX http://ecmdb.ca/proteins/P33021.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Guanosine monophosphate + Water > Guanosine + Phosphate Guanosine + Phosphate <> Guanine + Ribose-1-phosphate RXN0-5199 Guanosine triphosphate + Water > Guanosine + Triphosphate Adenosine triphosphate + Guanosine > ADP + Guanosine monophosphate + Hydrogen ion R01228 GUANOSINEKIN-RXN Guanosine 3'-phosphate + Water > Guanosine + Phosphate Guanosine monophosphate + Water <> Guanosine + Phosphate R01227 Adenosine triphosphate + Guanosine <> ADP + Guanosine monophosphate R01228 Guanosine + Water <> Guanine + Ribose R01677 Guanosine + Phosphate <> Guanine + alpha-D-Ribose 1-phosphate R02147 Guanosine + Phosphate > Ribose-1-phosphate + Guanine PW_R006058 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 1.62 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 6480 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 25.3 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 101200 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776