1.0 2020-04-17 18:42:25 UTC 2020-12-07 19:11:05 UTC CDB004842 Xanthosine Xanthosine, also known as xanthine riboside, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Xanthosine is an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthosine exists in all living species, ranging from bacteria to humans. Within humans, xanthosine participates in a number of enzymatic reactions. In particular, xanthosine can be biosynthesized from xanthylic acid through the action of the enzyme cytosolic purine 5'-nucleotidase. In addition, xanthosine can be converted into xanthine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. A purine nucleoside in which xanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. In humans, xanthosine is involved in the metabolic disorder called the lesch-nyhan syndrome (lns) pathway. Xanthosine is expected to be in Cannabis as all living plants are known to produce and metabolize it. 9-beta-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione 9-beta-D-Ribofuranosylxanthine Xanthine 9-beta-D-ribofuranoside Xanthine riboside 9-b-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione 9-Β-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione 9-b-D-Ribofuranosylxanthine 9-Β-D-ribofuranosylxanthine Xanthine 9-b-D-ribofuranoside Xanthine 9-β-D-ribofuranoside 3,9-Dihydro-9-b-D-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 9-beta-delta-Ribofuranosylxanthine 9-D-Ribofuranosylxanthine 9-delta-Ribofuranosylxanthine 9 beta-D-Ribofuranosylxanthine C10H12N4O6 284.23 284.0757 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 belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Purine nucleosides Organic compounds Nucleosides, nucleotides, and analogues Purine nucleosides Aromatic heteropolycyclic compounds 6-oxopurines Alkaloids and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Lactams N-substituted imidazoles Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Pyrimidones Secondary alcohols Tetrahydrofurans Ureas Vinylogous amides Xanthines 6-oxopurine Alcohol Alkaloid or derivatives Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Lactam Monosaccharide N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Purine Purine nucleoside Purinone Pyrimidine Pyrimidone Secondary alcohol Tetrahydrofuran Urea Vinylogous amide Xanthine Purine alkaloids xanthosines logp -1.60 ALOGPS logs -1.01 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 284.23 ChemAxon mono_mass 284.0757 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 number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01762 FDB001604 58484 64959 18107 C00007222 Xanthosine XANTHOSINE 38352 3408