Compound: 2,8-Dihydroxyadenine
SMILES: O=c1nc2[nH]c(=O)[nH]c2c([nH]1)N
InChIKey: XFBOJHLYDJZYSP-UHFFFAOYSA-N
Synonyms: 2,8-Dihydroxyadenine, 30377-37-8, 6-Amino-1H-purine-2,8(3H,7H)-dione, 6-Amino-2,8-dihydroxypurine, 6-amino-7H-purine-2,8-diol, 2,8-Dioxyadenine, MYE4YC3VKU, DTXSID80184453, CHEBI:183641, RefChem:908928, DTXCID90106944, 250-158-1, 6-Amino-7,9-dihydro-2H-purine-2,8(3H)-dione, 6-amino-7,9-dihydro-1H-purine-2,8-dione, Dimethyloctanoic acid, 2H-Purine-2,8(3H)-dione, 6-amino-7,9-dihydro-, 1H-Purine-2,8(3H,7H)-dione, 6-amino-, 6-amino-purine-2,8-diol, 6-amino-2,3,7,8-tetrahydro-1H-purine-2,8-dione, 1022140-21-1, EINECS 250-158-1, dimethyloctanoate, 6-amino-9H-purine-2,8-diol, XFBOJHLYDJZYSP-UHFFFAOYSA-N, UNII-MYE4YC3VKU, 6-amino-2,8-purinedione, SCHEMBL524228, SCHEMBL524229, SCHEMBL524230, orb1690631, Purine-2,8-diol, 6-amino-, SCHEMBL7113565, SCHEMBL15713240, SCHEMBL20135741, SCHEMBL29394441, 2,8-DHA, CHEBI:179632, (6R)-2,6-2,8-Dihydroxyadenine, HY-N9941, AKOS006273192, AKOS015998758, AKOS040758027, 6-Amino-1H-purine-2,8(7H,9H)-dione, MS-22911, PD215204, DB-350318, CS-0226279, NS00028912, 6-Amino-79-dihydro-2H-purine-28(3H)-dione, C22500, EN300-251404, G91354, Q4596812
Theoretical properties:
molecular_formula: C5H5N5O2
molecular_weight: 167.13 g/mol
exact_mass: 167.04432442 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 12
topological_polar_surface_area: 109 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 0.002 mg/mL
Descriptions:
pubchem: 2,8-dioxoadenine is an oxopurine that is adenine bearing two oxo substituents at positions 2 and 8. It has a role as a nephrotoxic agent, a mammalian metabolite and a human urinary metabolite. It is a member of 6-aminopurines and an oxopurine. It is functionally related to an adenine. It is a tautomer of a 2,8-dihydroxyadenine.
chebi: An oxopurine that is adenine bearing two oxo substituents at positions 2 and 8.
wikipedia: Adenine phosphoribosyltransferase deficiency is a rare autosomal recessive metabolic disorder caused by mutations of the APRT gene. Adenine phosphoribosyltransferase (APRT) catalyzes the creation of pyrophosphate and adenosine monophosphate from 5-phosphoribosyl-1-pyrophosphate and adenine. Adenine phosphoribosyltransferase is a purine salvage enzyme. Genetic mutations of adenine phosphoribosyltransferase make large amounts of 2,8-Dihydroxyadenine causing urolithiasis and renal failure.
Adenine phosphoribosyltransferase deficiency has been classified into two types. Type one is caused by mutant alleles of APRT*Q0 and is found in individuals from many different countries. Type one causes a complete deficiency in vivo or in vitro. Type two adenine phosphoribosyltransferase deficiency is caused by mutant alleles of APRT*J results in a full enzyme defiency in vivo but only a partial deficiency in cell extracts. Type two is mainly seen in Japan.
APRT deficiency is often identified by the presence of dihydroxyadenine in urine and kidney stones. Other diagnostic tests for APRT deficiency include urine microscopy, kidney stone analysis, renal biopsy, APRT activity, and genetic testing. Treatment of adenine phosphoribosyltransferase deficiency includes allopurinol and can prevent kidney stones and chronic kidney disease in most patients.