1.0 2011-09-21 00:07:04 UTC 2015-07-21 06:56:56 UTC FDB022018 2,8-Dihydroxyadenine 2,8-Dihydroxyadenine is a Purine metabolite usually not detectable in biofluids of normal individuals; this insoluble metabolite (at physiological urinary pH) cause urinary tract calculi and arthritis, and is identified in Adenine phosphoribosyltransferase deficiency (APRT, OMIM 102600). (PMID 16613999) In APRT, 2,8-dihydroxyadenine (DHA) accumulates in crystals within the tubular lumens (a feature of many kidney stone diseases) creating crystal-induced injury in human kidney epithelial cells. (PMID 16374038) Urinary DHA crystals are easily recognized under a microscope, and effective treatment can be offered and therefore the prognosis depends upon the renal function at diagnosis; treatment consists of adequate fluid intake, a low-purine diet and administration of allopurinol. (PMID 15764278) [HMDB] (6R)-2,6-2,8-Dihydroxyadenine 2,8-Dihydroxyadenine 2,8-Dioxyadenine 6-Amino-1H-purine-2,8(3H,7H)-dione 6-Amino-2,8-dihydroxypurine 6-amino-7H-purine-2,8-diol 6-amino-purine-2,8-diol dimethyloctanoate dimethyloctanoic acid C5H5N5O2 167.1255 167.044324429 6-amino-7H-purine-2,8-diol 6-amino-2,8-dihydroxypurine 30377-37-8 NC1=NC(O)=NC2=C1NC(O)=N2 InChI=1S/C5H5N5O2/c6-2-1-3(9-4(11)7-1)10-5(12)8-2/h(H5,6,7,8,9,10,11,12) XFBOJHLYDJZYSP-UHFFFAOYSA-N belongs to the class of organic compounds known as purinones. These are purines in which the purine moiety bears a C=O group. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Purinones Organic compounds Organoheterocyclic compounds Imidazopyrimidines Purines and purine derivatives Aromatic heteropolycyclic compounds 6-aminopurines Aminopyrimidines and derivatives Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Imidazoles Organic oxides Organooxygen compounds Organopnictogen compounds Primary amines Pyrimidones Ureas 6-aminopurine Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Heteroaromatic compound Hydrocarbon derivative Imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary amine Purinone Pyrimidine Pyrimidone Urea Solid logp -0.70 ALOGPS logs -1.37 ALOGPS solubility 7.11e+00 g/l ALOGPS logp 0.18 ChemAxon pka_strongest_acidic 8.78 ChemAxon pka_strongest_basic 0.7 ChemAxon iupac 6-amino-7H-purine-2,8-diol ChemAxon average_mass 167.1255 ChemAxon mono_mass 167.044324429 ChemAxon smiles NC1=NC(O)=NC2=C1NC(O)=N2 ChemAxon formula C5H5N5O2 ChemAxon inchi InChI=1S/C5H5N5O2/c6-2-1-3(9-4(11)7-1)10-5(12)8-2/h(H5,6,7,8,9,10,11,12) ChemAxon inchikey XFBOJHLYDJZYSP-UHFFFAOYSA-N ChemAxon polar_surface_area 120.94 ChemAxon refractivity 41.6 ChemAxon polarizability 14.54 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 478 Specdb::MsIr 479 Specdb::MsIr 480 Specdb::CMs 23268 Specdb::CMs 37501 Specdb::CMs 154061 Specdb::CMs 1060655 Specdb::CMs 1060656 Specdb::CMs 1060658 Specdb::CMs 1060660 Specdb::CMs 1060662 Specdb::CMs 1060664 Specdb::CMs 1060665 Specdb::CMs 1060667 Specdb::CMs 1060669 Specdb::CMs 1060670 Specdb::CMs 1060672 Specdb::CMs 1060674 Specdb::CMs 1060676 Specdb::CMs 1060677 Specdb::CMs 1060679 Specdb::CMs 1060681 Specdb::CMs 1060683 Specdb::CMs 1060685 Specdb::CMs 1060686 Specdb::CMs 1060688 Specdb::CMs 1060690 Specdb::MsMs 317629 Specdb::MsMs 317630 Specdb::MsMs 317631 Specdb::MsMs 364138 Specdb::MsMs 364139 Specdb::MsMs 364140 Specdb::MsMs 2781790 Specdb::MsMs 2781791 Specdb::MsMs 2781792 Specdb::MsMs 2927104 Specdb::MsMs 2927105 Specdb::MsMs 2927106 HMDB00401 #<Reference:0x000055ce32449d40> #<Reference:0x000055ce32449b60> #<Reference:0x000055ce32449908> #<Reference:0x000055ce32449750> #<Reference:0x000055ce32449570> #<Reference:0x000055ce32449318> 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