2,8-dihydroxyadenine (CHEBI:183641)

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ChEBI Name	2,8-dihydroxyadenine

ChEBI ID	CHEBI:183641

Definition	A member of the class of 6-aminopurines that is adenine bearing two hydroxy substituents at positions 2 and 8. It is a highly insoluble metabolite of adenine that causes radiolucent urolithiasis. It is produced by individuals who suffer from adenine phosphoribosyltransferase (APRT) deficiency, a rare autosomal recessive error of purine metabolism.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C5H5N5O2

Net Charge

Average Mass

167.128

Monoisotopic Mass

167.04432

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)

InChIKey

XFBOJHLYDJZYSP-UHFFFAOYSA-N

SMILES

NC1=NC(O)=NC2=C1N=C(O)N2

Roles Classification
Biological Role(s):	human urinary metabolite Any metabolite (endogenous or exogenous) found in human urine samples. nephrotoxic agent A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

ChEBI Ontology
Outgoing	2,8-dihydroxyadenine (CHEBI:183641) has functional parent adenine (CHEBI:16708) 2,8-dihydroxyadenine (CHEBI:183641) has role human urinary metabolite (CHEBI:84087) 2,8-dihydroxyadenine (CHEBI:183641) has role mouse metabolite (CHEBI:75771) 2,8-dihydroxyadenine (CHEBI:183641) has role nephrotoxic agent (CHEBI:50909) 2,8-dihydroxyadenine (CHEBI:183641) is a 6-aminopurines (CHEBI:20706) 2,8-dihydroxyadenine (CHEBI:183641) is a diol (CHEBI:23824) 2,8-dihydroxyadenine (CHEBI:183641) is a heteroaryl hydroxy compound (CHEBI:74818) 2,8-dihydroxyadenine (CHEBI:183641) is tautomer of 2,8-dioxoadenine (CHEBI:179632)

Incoming	2,8-dioxoadenine (CHEBI:179632) is tautomer of 2,8-dihydroxyadenine (CHEBI:183641)

IUPAC Name

6-amino-9H-purine-2,8-diol

Registry Number	Type	Source
30377-37-8	CAS Registry Number	ChemIDplus

Last Modified

11 November 2021