2.02012-05-31 10:25:59 -06002015-09-13 12:56:07 -0600ECMDB00299M2MDB000125XanthosineXanthosine is a nucleoside derived from xanthine and ribose. It is a deamination product of guanosine. Xanthosine monophosphate is an intermediate in purine metabolism, formed from IMP, and forming GMP.(Wikipedia)3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dione3,9-dihydro-9-b-delta-Ribofuranosyl-1H-purine-2,6-dione3,9-dihydro-9-b-δ-Ribofuranosyl-1H-purine-2,6-dione3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dione3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione3,9-dihydro-9-β-δ-Ribofuranosyl-1H-purine-2,6-dione3,9-dihydro-9-δ-Ribofuranosyl-1H-purine-2,6-dione9 β-D-ribofuranosylxanthine9 b-D-Ribofuranosylxanthine9 beta-D-Ribofuranosylxanthine9 β-D-Ribofuranosylxanthine9-b-D-Ribofuranosylxanthine9-b-delta-Ribofuranosylxanthine9-b-δ-Ribofuranosylxanthine9-beta-delta-Ribofuranosylxanthine9-D-Ribofuranosylxanthine9-delta-Ribofuranosylxanthine9-β-δ-Ribofuranosylxanthine9-δ-RibofuranosylxanthineXanthosineC10H12N4O6284.2255284.0756841369-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol146-80-5OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2OInChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1UBORTCNDUKBEOP-UUOKFMHZSA-NSolidCytosolExtra-organismPeriplasmlogp-1.60logs-1.01solubility2.78e+01 g/llogp-1.2pka_strongest_acidic11.33pka_strongest_basic0.078iupac9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diolaverage_mass284.2255mono_mass284.075684136smilesOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2OformulaC10H12N4O6inchiInChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1inchikeyUBORTCNDUKBEOP-UUOKFMHZSA-Npolar_surface_area153.98refractivity62.4polarizability25.55rotatable_bond_count2acceptor_count9donor_count5physiological_charge0formal_charge0Purine metabolismec00230purine ribonucleosides degradationPurine 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.PW002076Metabolicpurine ribonucleosides degradation to ribose-1-phosphatePWY0-1296xanthine and xanthosine salvageSALVPURINE2-PWYSpecdb::CMs528Specdb::CMs11174Specdb::CMs30713Specdb::CMs37410Specdb::CMs149033Specdb::CMs1057380Specdb::CMs1057382Specdb::CMs1057384Specdb::CMs1057386Specdb::CMs1057388Specdb::CMs1057390Specdb::CMs1057391Specdb::CMs1057393Specdb::CMs1057395Specdb::CMs1057396Specdb::CMs1057398Specdb::CMs1057400Specdb::CMs1057402Specdb::CMs1057404Specdb::CMs1057406Specdb::CMs1057408Specdb::CMs1057410Specdb::CMs1057411Specdb::CMs1057413Specdb::CMs1057415Specdb::NmrOneD1320Specdb::NmrOneD4907Specdb::NmrOneD6502Specdb::NmrOneD6503Specdb::NmrOneD6504Specdb::NmrOneD6505Specdb::NmrOneD6506Specdb::NmrOneD6507Specdb::NmrOneD6508Specdb::NmrOneD6509Specdb::NmrOneD6510Specdb::NmrOneD6511Specdb::NmrOneD6512Specdb::NmrOneD6513Specdb::NmrOneD6514Specdb::NmrOneD6515Specdb::NmrOneD6516Specdb::NmrOneD6517Specdb::NmrOneD6518Specdb::NmrOneD6519Specdb::NmrOneD6520Specdb::NmrOneD6521Specdb::MsMs507Specdb::MsMs508Specdb::MsMs509Specdb::MsMs3962Specdb::MsMs3963Specdb::MsMs180069Specdb::MsMs180070Specdb::MsMs180071Specdb::MsMs182403Specdb::MsMs182404Specdb::MsMs182405Specdb::MsMs439175Specdb::MsMs439238Specdb::MsMs2226758Specdb::MsMs2227950Specdb::MsMs2229191Specdb::MsMs2230284Specdb::MsMs2231625Specdb::MsMs2232553Specdb::MsMs2233992Specdb::MsMs2234957Specdb::MsMs2235732Specdb::MsMs2237626Specdb::MsMs2237825Specdb::MsMs2239768Specdb::NmrTwoD1016Specdb::NmrTwoD1262HMDB002996495958484C0176218107XANTHOSINEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Marti R, Nishigaki Y, Hirano M: Elevated plasma deoxyuridine in patients with thymidine phosphorylase deficiency. Biochem Biophys Res Commun. 2003 Mar 28;303(1):14-8.12646159Dudley E, Lemiere F, Van Dongen W, Tuytten R, El-Sharkawi S, Brenton AG, Esmans EL, Newton RP: Analysis of urinary nucleosides. IV. Identification of urinary purine nucleosides by liquid chromatography/electrospray mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(22):2730-8.15499664Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7.9129323Khalil PN, Erb N, Khalil MN, Escherich G, Janka-Schaub GE: Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):1-7. Epub 2006 May 24.16725387Enei, Hitoshi; Sato, Katsuaki; Hirose, Yoshio. Xanthosine production by fermentation. Jpn. Kokai Tokkyo Koho (1975), 3 pp. http://hmdb.ca/system/metabolites/msds/000/000/218/original/HMDB00299.pdf?1358462070Protein ushAP07024USHA_ECOLIushAhttp://ecmdb.ca/proteins/P07024.xmlMultifunctional protein surEP0A840SURE_ECOLIsurEhttp://ecmdb.ca/proteins/P0A840.xml5'-nucleotidase yjjGP0A8Y1YJJG_ECOLIyjjGhttp://ecmdb.ca/proteins/P0A8Y1.xmlPurine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlClass B acid phosphataseP0AE22APHA_ECOLIaphAhttp://ecmdb.ca/proteins/P0AE22.xmlNon-specific ribonucleoside hydrolase rihCP22564RIHC_ECOLIrihChttp://ecmdb.ca/proteins/P22564.xml5'-nucleotidase yfbRP76491YFBR_ECOLIyfbRhttp://ecmdb.ca/proteins/P76491.xmlXanthosine phosphorylaseP45563XAPA_ECOLIxapAhttp://ecmdb.ca/proteins/P45563.xmlXanthosine permeaseP45562XAPB_ECOLIxapBhttp://ecmdb.ca/proteins/P45562.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlWater + Xanthylic acid > Phosphate + XanthosineWater + Xanthosine > Ribose + XanthinePhosphate + Xanthosine <> Ribose-1-phosphate + XanthineXANTHOSINEPHOSPHORY-RXNXanthosine + Phosphate <> Xanthine + alpha-D-Ribose 1-phosphateR02297Xanthylic acid + Water <> Xanthosine + PhosphateR02719Xanthosine + Water > D-ribose + XanthineRXN0-363Xanthosine + Phosphate > Ribose-1-phosphate + XanthineXANTHOSINEPHOSPHORY-RXN