2.0 2012-05-31 10:25:59 -0600 2015-09-13 12:56:07 -0600 ECMDB00299 M2MDB000125 Xanthosine Xanthosine 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-dione 3,9-dihydro-9-b-delta-Ribofuranosyl-1H-purine-2,6-dione 3,9-dihydro-9-b-δ-Ribofuranosyl-1H-purine-2,6-dione 3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione 3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dione 3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione 3,9-dihydro-9-β-δ-Ribofuranosyl-1H-purine-2,6-dione 3,9-dihydro-9-δ-Ribofuranosyl-1H-purine-2,6-dione 9 &beta;-D-ribofuranosylxanthine 9 b-D-Ribofuranosylxanthine 9 beta-D-Ribofuranosylxanthine 9 β-D-Ribofuranosylxanthine 9-b-D-Ribofuranosylxanthine 9-b-delta-Ribofuranosylxanthine 9-b-δ-Ribofuranosylxanthine 9-beta-delta-Ribofuranosylxanthine 9-D-Ribofuranosylxanthine 9-delta-Ribofuranosylxanthine 9-β-δ-Ribofuranosylxanthine 9-δ-Ribofuranosylxanthine Xanthosine C10H12N4O6 284.2255 284.075684136 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol 146-80-5 OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O InChI=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/s1 UBORTCNDUKBEOP-UUOKFMHZSA-N Solid Cytosol Extra-organism Periplasm logp -1.60 ALOGPS logs -1.01 ALOGPS solubility 2.78e+01 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 11.33 ChemAxon pka_strongest_basic 0.078 ChemAxon iupac 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol ChemAxon average_mass 284.2255 ChemAxon mono_mass 284.075684136 ChemAxon smiles OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O ChemAxon formula C10H12N4O6 ChemAxon inchi InChI=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/s1 ChemAxon inchikey UBORTCNDUKBEOP-UUOKFMHZSA-N ChemAxon polar_surface_area 153.98 ChemAxon refractivity 62.4 ChemAxon polarizability 25.55 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 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 xanthine and xanthosine salvage SALVPURINE2-PWY Specdb::CMs 528 Specdb::CMs 11174 Specdb::CMs 30713 Specdb::CMs 37410 Specdb::CMs 149033 Specdb::CMs 1057380 Specdb::CMs 1057382 Specdb::CMs 1057384 Specdb::CMs 1057386 Specdb::CMs 1057388 Specdb::CMs 1057390 Specdb::CMs 1057391 Specdb::CMs 1057393 Specdb::CMs 1057395 Specdb::CMs 1057396 Specdb::CMs 1057398 Specdb::CMs 1057400 Specdb::CMs 1057402 Specdb::CMs 1057404 Specdb::CMs 1057406 Specdb::CMs 1057408 Specdb::CMs 1057410 Specdb::CMs 1057411 Specdb::CMs 1057413 Specdb::CMs 1057415 Specdb::NmrOneD 1320 Specdb::NmrOneD 4907 Specdb::NmrOneD 6502 Specdb::NmrOneD 6503 Specdb::NmrOneD 6504 Specdb::NmrOneD 6505 Specdb::NmrOneD 6506 Specdb::NmrOneD 6507 Specdb::NmrOneD 6508 Specdb::NmrOneD 6509 Specdb::NmrOneD 6510 Specdb::NmrOneD 6511 Specdb::NmrOneD 6512 Specdb::NmrOneD 6513 Specdb::NmrOneD 6514 Specdb::NmrOneD 6515 Specdb::NmrOneD 6516 Specdb::NmrOneD 6517 Specdb::NmrOneD 6518 Specdb::NmrOneD 6519 Specdb::NmrOneD 6520 Specdb::NmrOneD 6521 Specdb::MsMs 507 Specdb::MsMs 508 Specdb::MsMs 509 Specdb::MsMs 3962 Specdb::MsMs 3963 Specdb::MsMs 180069 Specdb::MsMs 180070 Specdb::MsMs 180071 Specdb::MsMs 182403 Specdb::MsMs 182404 Specdb::MsMs 182405 Specdb::MsMs 439175 Specdb::MsMs 439238 Specdb::MsMs 2226758 Specdb::MsMs 2227950 Specdb::MsMs 2229191 Specdb::MsMs 2230284 Specdb::MsMs 2231625 Specdb::MsMs 2232553 Specdb::MsMs 2233992 Specdb::MsMs 2234957 Specdb::MsMs 2235732 Specdb::MsMs 2237626 Specdb::MsMs 2237825 Specdb::MsMs 2239768 Specdb::NmrTwoD 1016 Specdb::NmrTwoD 1262 HMDB00299 64959 58484 C01762 18107 XANTHOSINE Keseler, I. 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Kokai Tokkyo Koho (1975), 3 pp. http://hmdb.ca/system/metabolites/msds/000/000/218/original/HMDB00299.pdf?1358462070 Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.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 Non-specific ribonucleoside hydrolase rihC P22564 RIHC_ECOLI rihC http://ecmdb.ca/proteins/P22564.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 Xanthosine permease P45562 XAPB_ECOLI xapB http://ecmdb.ca/proteins/P45562.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 Water + Xanthylic acid > Phosphate + Xanthosine Water + Xanthosine > Ribose + Xanthine Phosphate + Xanthosine <> Ribose-1-phosphate + Xanthine XANTHOSINEPHOSPHORY-RXN Xanthosine + Phosphate <> Xanthine + alpha-D-Ribose 1-phosphate R02297 Xanthylic acid + Water <> Xanthosine + Phosphate R02719 Xanthosine + Water > D-ribose + Xanthine RXN0-363 Xanthosine + Phosphate > Ribose-1-phosphate + Xanthine XANTHOSINEPHOSPHORY-RXN