1.0 2011-09-21 00:07:54 UTC 2015-07-21 06:56:57 UTC FDB022067 Allopurinol riboside Allopurinol is an analog of the natural purines in the body, and is quickly metabolized to oxypurines which is also a xanthine oxidase inhibitor. Allopurinol is a white, powdery drug used to treat gout. Its use in the United States was started in 1964. It is an isomer of hypoxanthine and inhibits the production of uric acid, the metabolite responsible for gout, by inhibiting the enzyme xanthine oxidase. The side effects of high levels of precursors are usually minor. A small percentage of people develop a rash and must discontinue this drug. The most serious adverse event is a hypersensitivity syndrome consisting of fever, skin rash, eosinophilia, hepatitis, and worsening renal function. In some cases, allopurinol hypersensitivity syndrome. [HMDB] 4-Hydroxy[3,4-d]pyrazolopyrimidine riboside Allopurinol ribonucleoside Allopurinol riboside Allopurinol-1-ribonucleoside C10H12N4O5 268.2261 268.080769514 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrazolo[3,4-d]pyrimidin-4-one 16220-07-8 OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1 KFQUAMTWOJHPEJ-DAGMQNCNSA-N belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidine glycosides. These are nucleosides or derivatives thereof that consist of a pyazolo[3,2-d]pyrimidine ring system that is N-glycosidically linked to a ribose or deoxyribose. They bear the sugar moiety on the pyrimidine part of the molecule. Pyrazolo[3,4-d]pyrimidine glycosides Organic compounds Nucleosides, nucleotides, and analogues Pyrazolo[3,4-d]pyrimidine glycosides Aromatic heteropolycyclic compounds Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Pyrazoles Pyrazolo[3,4-d]pyrimidines Pyrimidones Secondary alcohols Tetrahydrofurans Vinylogous amides Alcohol Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Monosaccharide N-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Pyrazole Pyrazolo[3,4-d]pyrimidine Pyrazolo[3,4-d]pyrimidine glycoside Pyrazolopyrimidine Pyrimidine Pyrimidone Secondary alcohol Tetrahydrofuran Vinylogous amide nucleoside analogue Solid logp -1.70 ALOGPS logs -1.26 ALOGPS solubility 1.48e+01 g/l ALOGPS logp -2 ChemAxon pka_strongest_acidic 7.36 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one ChemAxon average_mass 268.2261 ChemAxon mono_mass 268.080769514 ChemAxon smiles OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O ChemAxon formula C10H12N4O5 ChemAxon inchi InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1 ChemAxon inchikey KFQUAMTWOJHPEJ-DAGMQNCNSA-N ChemAxon polar_surface_area 129.2 ChemAxon refractivity 72.32 ChemAxon polarizability 24.35 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20116 Specdb::CMs 37559 Specdb::CMs 134036 Specdb::CMs 141770 Specdb::CMs 1063219 Specdb::CMs 1063221 Specdb::CMs 1063223 Specdb::CMs 1063224 Specdb::CMs 1063226 Specdb::CMs 1063228 Specdb::CMs 1063230 Specdb::CMs 1063232 Specdb::CMs 1063234 Specdb::CMs 1063236 Specdb::CMs 1063238 Specdb::CMs 1063240 Specdb::CMs 1063242 Specdb::CMs 1063244 Specdb::CMs 1063246 Specdb::CMs 1063248 Specdb::CMs 1063250 Specdb::CMs 1063252 Specdb::CMs 1063254 Specdb::CMs 1063255 Specdb::CMs 1063257 Specdb::MsMs 310831 Specdb::MsMs 310832 Specdb::MsMs 310833 Specdb::MsMs 355684 Specdb::MsMs 355685 Specdb::MsMs 355686 Specdb::MsMs 2275791 Specdb::MsMs 2275792 Specdb::MsMs 2275793 Specdb::MsMs 3093559 Specdb::MsMs 3093560 Specdb::MsMs 3093561 Specdb::NmrOneD 6842 Specdb::NmrOneD 6843 Specdb::NmrOneD 6844 Specdb::NmrOneD 6845 Specdb::NmrOneD 6846 Specdb::NmrOneD 6847 Specdb::NmrOneD 6848 Specdb::NmrOneD 6849 Specdb::NmrOneD 6850 Specdb::NmrOneD 6851 Specdb::NmrOneD 6852 Specdb::NmrOneD 6853 Specdb::NmrOneD 6854 Specdb::NmrOneD 6855 Specdb::NmrOneD 6856 Specdb::NmrOneD 6857 Specdb::NmrOneD 6858 Specdb::NmrOneD 6859 Specdb::NmrOneD 6860 Specdb::NmrOneD 6861 HMDB00481 #<Reference:0x000055ce33083840> #<Reference:0x000055ce33083688> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823