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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:09 UTC
HMDB IDHMDB0000401
Secondary Accession Numbers
  • HMDB00401
Metabolite Identification
Common Name2,8-Dihydroxyadenine
Description2,8-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 ).
Structure
Data?1582752129
Synonyms
ValueSource
(6R)-2,6-2,8-DihydroxyadenineHMDB
2,8-DioxyadenineHMDB
6-Amino-1H-purine-2,8(3H,7H)-dioneHMDB
6-Amino-2,8-dihydroxypurineHMDB
6-Amino-7H-purine-2,8-diolHMDB
6-Amino-purine-2,8-diolHMDB
DimethyloctanoateHMDB
Dimethyloctanoic acidHMDB
2,8-DihydroxyadenineMeSH
Chemical FormulaC5H5N5O2
Average Molecular Weight167.1255
Monoisotopic Molecular Weight167.044324429
IUPAC Name6-amino-7H-purine-2,8-diol
Traditional Name6-amino-2,8-dihydroxypurine
CAS Registry Number30377-37-8
SMILES
NC1=NC(O)=NC2=C1NC(O)=N2
InChI Identifier
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)
InChI KeyXFBOJHLYDJZYSP-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurinones
Alternative Parents
Substituents
  • 6-aminopurine
  • Purinone
  • Aminopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.002 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.11 g/LALOGPS
logP-0.7ALOGPS
logP0.18ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.78ChemAxon
pKa (Strongest Basic)0.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.94 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.6 m³·mol⁻¹ChemAxon
Polarizability14.54 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01b9-2900000000-2a6ad00e5a61874dafbaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-5590000000-9a6615b1bb6baa991e39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-992c36bf805d3bd5b77cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0900000000-b0d2a41d5894b75e61baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc3-9500000000-094a0ab08df4cb8d66d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-73c402f938cd3d00ebbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2900000000-dfacf0b01ba05bd293a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-56660a79cc117195f3acSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022018
KNApSAcK IDNot Available
Chemspider ID83302
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,8-Dihydroxyadenine
METLIN ID5390
PubChem Compound92268
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceStevens, Marcus A.; Smith, Herman W.; Brown, George Bosworth. Purine N-oxides. VII. Reaction of aminopurine 1-N-oxides with acetic anhydride. Journal of the American Chemical Society (1960), 82 1148-52.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roth GJ, Moore GL, Kline WE, Poskitt TR: The renal effect of intravenous adenine in humans. Transfusion. 1975 Mar-Apr;15(2):116-23. [PubMed:1091029 ]
  2. Peck CC, Bailey FJ, Moore GL: Enhanced solubility of 2,8 dihydroxyadenine (DOA) in human urine. Transfusion. 1977 Jul-Aug;17(4):383-90. [PubMed:17934 ]
  3. Bartlett GR: Metabolism by man of intravenously administered adenine. Transfusion. 1977 Jul-Aug;17(4):367-73. [PubMed:878002 ]
  4. Hartmann S, Okun JG, Schmidt C, Langhans CD, Garbade SF, Burgard P, Haas D, Sass JO, Nyhan WL, Hoffmann GF: Comprehensive detection of disorders of purine and pyrimidine metabolism by HPLC with electrospray ionization tandem mass spectrometry. Clin Chem. 2006 Jun;52(6):1127-37. Epub 2006 Apr 13. [PubMed:16613999 ]
  5. Liang L, Chen J, Vittal R, Selvanayagam ZE, McAteer JA, Deng L, Tischfield J, Chin KV, Sahota A: Expression profiling of crystal-induced injury in human kidney epithelial cells. Nephron Physiol. 2006;103(1):p53-62. Epub 2005 Dec 21. [PubMed:16374038 ]
  6. Arnadottir M, Laxdal T, Halldorsdottir B: 2,8-dihydroxyadeninuria: are there no cases in Scandinavia? Scand J Urol Nephrol. 2005;39(1):82-6. [PubMed:15764278 ]