6,8-Purinediol (CHEM033455)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:10:55 UTC
Update Date2016-11-09 01:20:55 UTC
Accession NumberCHEM033455
Identification
Common Name6,8-Purinediol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6,8-PurinediolHMDB
7,9-Dihydro-1H-purine-6,8-dioneHMDB
7,9-Dihydro-8H-purin-8-oneHMDB
8-OxohypoxanthineHMDB
Purine-6,8(1H,9H)-dioneHMDB
Purine-6,8-diolHMDB
Purine-6,8-dioneHMDB
Chemical FormulaC25H20N20O10
Average Molecular Mass760.554 g/mol
Monoisotopic Mass760.167 g/mol
CAS Registry Number13231-00-0
IUPAC Name6,7,8,9-tetrahydro-3H-purine-6,8-dione
Traditional Name7,9-dihydro-3H-purine-6,8-dione
SMILESOC1=NC2=C(N1)NC=NC2=O.OC1=NC2=C(N1)N=CN=C2O.OC1=NC2=C(O)N=CNC2=N1.O=C1NC2=C(N1)C(=O)N=CN2.O=C1NC2=C(N1)C(=O)NC=N2
InChI IdentifierInChI=1S/5C5H4N4O2/c5*10-4-2-3(6-1-7-4)9-5(11)8-2/h5*1H,(H3,6,7,8,9,10,11)
InChI KeyZHWYDMYXJSUNAJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. 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 ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen 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 Solubility1.75 g/LALOGPS
logP-1ALOGPS
logP-1.6ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)7.63ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.59 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.32 m³·mol⁻¹ChemAxon
Polarizability12.68 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, Positivesplash10-0zi1-6900000000-b597900216a7c18ff4ecSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-73408e2a019cf6145389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-4ec7e27bd75758d5243dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9400000000-4b36792f2a9b31c0e39fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0c74ea3af474d10b7ea8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-30080f0e6c244018af86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-9600000000-23699c571e13d9a8c982Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ac450658003af6c0a109Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-00ec07b7bda30887c327Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ai-9200000000-f8c6511273a5bfd31f74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-757517510c89a3191171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-2900000000-b1f56627b7499b83ee76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5b696d1d5422470c88eaSpectrum
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
1D NMR13C 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 IDHMDB0001182
FooDB IDFDB112171
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID75117
ChEBI IDNot Available
PubChem Compound ID83252
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ohtsuka, Yozo; Sugimoto, Kikuo. Oxazolopyrimidines. III. Formation of 6,8-dihydroxypurine by the oxidation of 7-aminooxazolo[5,4-d]pyrimidine with hydrogen peroxide-acetic acid. Bulletin of the Chemical Society of Japan (1970), 43(7), 2281.
2. Ohtsuka, Yozo; Sugimoto, Kikuo. Oxazolopyrimidines. III. Formation of 6,8-dihydroxypurine by the oxidation of 7-aminooxazolo[5,4-d]pyrimidine with hydrogen peroxide-acetic acid. Bulletin of the Chemical Society of Japan (1970), 43(7), 2281.
3. Davies RJ: Complexes of poly(adenylic acid) with complementary monomers. Eur J Biochem. 1976 Jan 2;61(1):225-36.
4. TRICERRI S, BRASCHI A: [Quantitative spectrophotometric determination of 6-hydroxypurine in the presence of 2, 6-dihydroxypurine]. Farmaco Sci. 1957;12(1):28-33.
5. Smith M, Sullivan C: Germination of Clostridium cylindrosporum Spores on Medium Containing Uric Acid. Appl Environ Microbiol. 1989 Jun;55(6):1380-5.
6. Montero-Moran GM, Li M, Rendon-Huerta E, Jourdan F, Lowe DJ, Stumpff-Kane AW, Feig M, Scazzocchio C, Hausinger RP: Purification and characterization of the FeII- and alpha-ketoglutarate-dependent xanthine hydroxylase from Aspergillus nidulans. Biochemistry. 2007 May 8;46(18):5293-304. Epub 2007 Apr 13.
7. Salas JA, Johnstone K, Ellar DJ: Role of uricase in the triggering of germination of Bacillus fastidiosus spores. Biochem J. 1985 Jul 1;229(1):241-9.
8. Yamane I, Murakami O: 6,8-Dihydroxypurine: a novel growth factor for mammalian cells in vitro, isolated from a commercial peptone. J Cell Physiol. 1973 Apr;81(2):281-4.
9. Ohe T, Watanabe Y: Purification and properties of xanthine dehydrogenase from Streptomyces cyanogenus. J Biochem. 1979 Jul;86(1):45-53.
10. Simmonds HA, Sneddon W: Identification of 6,8-dihydroxypurine in the urine of a gouty patient treated with allopurinol. Clin Chim Acta. 1970 Nov;30(2):421-7.
11. Middelhoven WJ, Hoogkamer-Te Niet MC, Kreger-Van Rij NJ: Trichosporon adeninovorans sp. nov., a yeast species utilizing adenine, xanthine, uric acid, putrescine and primary n-alkylamines as the sole source of carbon, nitrogen and energy. Antonie Van Leeuwenhoek. 1984;50(4):369-78.
12. Durre P, Andreesen JR: Purine and glycine metabolism by purinolytic clostridia. J Bacteriol. 1983 Apr;154(1):192-9.
13. Kraushar MF, Nussbaum P, Kisch AL: Anaphylactic reaction to intravitreal cefazolin. Retina. 1994;14(2):187-8.
14. Keuzenkamp-Jansen CW, van Baal JM, De Abreu RA, de Jong JG, Zuiderent R, Trijbels JM: Detection and identification of 6-methylmercapto-8-hydoxypurine, a major metabolite of 6-mercaptopurine, in plasma during intravenous administration. Clin Chem. 1996 Mar;42(3):380-6.
15. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18.
16. Yang TH, Hu ML: Intracellular levels of S-adenosylhomocysteine but not homocysteine are highly correlated to the expression of nm23-H1 and the level of 5-methyldeoxycytidine in human hepatoma cells with different invasion activities. Nutr Cancer. 2006;55(2):224-31.
17. Liu Z, Liu S, Xie Z, Blum W, Perrotti D, Paschka P, Klisovic R, Byrd J, Chan KK, Marcucci G: Characterization of in vitro and in vivo hypomethylating effects of decitabine in acute myeloid leukemia by a rapid, specific and sensitive LC-MS/MS method. Nucleic Acids Res. 2007;35(5):e31. Epub 2007 Jan 30.
18. Cho SH, Jung BH, Lee SH, Lee WY, Kong G, Chung BC: Direct determination of nucleosides in the urine of patients with breast cancer using column-switching liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2006 Nov;20(11):1229-36.