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CHEBI:183641 - 2,8-dihydroxyadenine

Default Structure
ChEBI IDCHEBI:183641
ChEBI Name2,8-dihydroxyadenine
Stars
DefinitionA 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.
Last Modified11 November 2021
SubmitterAdnan
DownloadsMolfile
FormulaC5H5N5O2
Net Charge0
Average Mass167.128
Monoisotopic Mass167.04432
SMILESNc1nc(O)nc2nc(O)nc12
InChIInChI=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)
InChIKeyXFBOJHLYDJZYSP-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) urine (BTO:0001419) PubMed (29861153)
Mus musculus (ncbitaxon:10090) - PubMed (32859011)
Roles Classification
Biological Roles:
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
nephrotoxic agent  A role played by any chemical compound (natural or synthetic) exhibiting itself through the ability to induce damage to the kidneys.
human urinary metabolite  Any metabolite (endogenous or exogenous) found in human urine samples.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
2,8-dioxoadenine (CHEBI:179632) is tautomer of 2,8-dihydroxyadenine (CHEBI:183641)
IUPAC Name 
6-amino-9H-purine-2,8-diol
Synonyms  Source
2,8-DHAChEBI
6-amino-2,8-dihydroxypurineChemIDplus
6-amino-purine-2,8-diolChEBI
Manual XrefsDatabases
2,8-DihydroxyadenineWikipedia
FDB022018FooDB
HMDB0000401HMDB
Registry NumbersSources
CAS:30377-37-8ChemIDplus
Citations