8-Hydroxyadenine (CHEM034899)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:18:55 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034899
Identification
Common Name8-Hydroxyadenine
ClassSmall Molecule
DescriptionA oxopurine that is adenine bearing a single oxo substituent at position 8.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7,8-Dihydro-8-oxoadenineChEBI
8-oxo-7,8-DihydroadenineChEBI
8-OxoAChEBI
OxyadenineChEBI
6-Amino-1,7-dihydro-8H-purin-8-oneHMDB
6-Amino-8-hydroxypurineHMDB
6-Amino-purin-8(9H)-oneHMDB
6-Amino-purin-8-olHMDB
8-Hydroxy-1H-purin-6-amineHMDB
8-OxoadenineHMDB
OksadenHMDB
OxadenHMDB
7,8-DHOAHMDB
Chemical FormulaC5H5N5O
Average Molecular Mass151.126 g/mol
Monoisotopic Mass151.049 g/mol
CAS Registry Number21149-26-8
IUPAC Name6-amino-7H-purin-8-ol
Traditional Name6-amino-8-hydroxypurine
SMILESNC1=NC=NC2=C1NC(O)=N2
InChI IdentifierInChI=1S/C5H5N5O/c6-3-2-4(8-1-7-3)10-5(11)9-2/h1H,(H4,6,7,8,9,10,11)
InChI KeyRGKBRPAAQSHTED-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
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Urea
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.58 g/LALOGPS
logP-0.82ALOGPS
logP-0.19ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.89ChemAxon
pKa (Strongest Basic)5.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.71 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.67 m³·mol⁻¹ChemAxon
Polarizability13.45 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zmi-2900000000-15799f7dfde6b61d5e9dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0kmi-5930000000-e3d510cf39e85c0d6c20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-d209f35bcb47000991e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ccfafe3d723f793a566cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9500000000-8441670cd85efff4fc68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-7396c5f39ca266e16ca2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-fcac70e143de08e16c17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c317d7036a3bfb98fedbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-361a2474138028086bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-50d8e77d9b1fbd7cf4b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ai-7900000000-40365895919344706a26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-062eb4a75a9800bdbe07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ul0-0900000000-6b703dbbb8530abc9653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9200000000-5a08d4210b257200ae71Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000542
FooDB IDFDB022105
Phenol Explorer IDNot Available
KNApSAcK IDC00043227
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5527
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4511108
ChEBI ID134104
PubChem Compound ID95215
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10780366
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11747549
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12644468
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12688418
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15351402
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1851559
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21391900
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23209024
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23265901
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24692658
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25782998
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26188111
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26861551
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=2798767
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=8461291
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=8652548
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=9683192
18. Makarieva, Tatyana N.; Guzii, Alla G.; Dmitrenok, Andrei S.; Dmitrenok, Pavel S.; Krasokhin, Vladimir B.; Stonik, Valentin A. 8-Oxoadenine, 9-methyl-8-oxoadenine, and trihydroxylated sterols from a Far Eastern thorectidae sponge. Natural Product Communications (2006), 1(9), 711-714.
19. Ravanat JL, Guicherd P, Tuce Z, Cadet J: Simultaneous determination of five oxidative DNA lesions in human urine. Chem Res Toxicol. 1999 Sep;12(9):802-8.
20. Stillwell WG, Xu HX, Adkins JA, Wishnok JS, Tannenbaum SR: Analysis of methylated and oxidized purines in urine by capillary gas chromatography-mass spectrometry. Chem Res Toxicol. 1989 Mar-Apr;2(2):94-9.
21. Webb AL, Singh RH, Kennedy MJ, Elsas LJ: Verbal dyspraxia and galactosemia. Pediatr Res. 2003 Mar;53(3):396-402.
22. WYNGAARDEN JB, DUNN JT: 8-Hydroxyadenine as the intermediate in the oxidation of adenine to 2, 8-dihydroxyadenine by xanthine oxidase. Arch Biochem Biophys. 1957 Jul;70(1):150-6.
23. Bartlett GR: Metabolism by man of intravenously administered adenine. Transfusion. 1977 Jul-Aug;17(4):367-73.
24. Dizdaroglu M: Facts about the artifacts in the measurement of oxidative DNA base damage by gas chromatography-mass spectrometry. Free Radic Res. 1998 Dec;29(6):551-63.
25. Markesbery WR, Lovell MA: DNA oxidation in Alzheimer's disease. Antioxid Redox Signal. 2006 Nov-Dec;8(11-12):2039-45.