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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:06 UTC
HMDB IDHMDB0000786
Secondary Accession Numbers
  • HMDB00786
Metabolite Identification
Common NameOxypurinol
DescriptionOxipurinol is a xanthine oxidase inhibitor. Oxipurinol is potentially used for treatment of congestive heart failure. PMID: 15139781 .
Structure
Data?1547234106
Synonyms
ValueSource
OxipurinolChEBI
OxoallopurinolChEBI
1H,3H,9H-AlloxanthineHMDB
1H-Pyrazolo[3,4-D]pyrimidin-4,6-diolHMDB
4,6-Dihydroxypyrazolo[3,4-D]pyrimidineHMDB
AlloxanthineHMDB
Chemical FormulaC5H4N4O2
Average Molecular Weight152.1109
Monoisotopic Molecular Weight152.033425392
IUPAC Name1H,2H,4H,5H,6H-pyrazolo[3,4-d]pyrimidine-4,6-dione
Traditional Nameoxypurinol
CAS Registry Number2465-59-0
SMILES
O=C1NC(=O)C2=CNNC2=N1
InChI Identifier
InChI=1S/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)
InChI KeyHXNFUBHNUDHIGC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • Pyrazolopyrimidine
  • Pyrazolo[3,4-d]pyrimidine
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Pyrazole
  • Vinylogous amide
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.58 g/LALOGPS
logP-2ALOGPS
logP-1.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.19ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.59 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.35 m³·mol⁻¹ChemAxon
Polarizability12.6 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zn9-4900000000-837f8f7de41a018a7868JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0w29-4900000000-2b2a5e7237cb7a9dd60eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ab9-9700000000-8017eefe2f766f6a3382JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0690-9100000000-b997025b96b7398143d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0f79-0900000000-3de88a143c5683886f8dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-cbc9adb0643d1712be57JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-cbc9adb0643d1712be57JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f79-0900000000-3de88a143c5683886f8dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ca8f6a9e71c7b2514f30JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-2f457108cc7fec852751JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-9d5c31601c46aa2e8eb6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-a2f008eef4b535546f4fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-7900000000-03e71b25e9d15486d84eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c14d58288520ea2b7642JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified50.0 (0.5-100.0) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified13.3 (5.1-29.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.29 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05262
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022242
KNApSAcK IDNot Available
Chemspider ID4483
KEGG Compound IDC07599
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxypurinol
METLIN ID5752
PubChem Compound4644
PDB IDNot Available
ChEBI ID28315
References
Synthesis ReferenceBoudet Nadege; Knochel Paul Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine. Organic letters (2006), 8(17), 3737-40.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kojima T, Nishina T, Kitamura M, Hosoya T, Nishioka K: Biochemical studies on the purine metabolism of four cases with hereditary xanthinuria. Clin Chim Acta. 1984 Feb 28;137(2):189-98. [PubMed:6423323 ]
  2. Authors unspecified: Oxipurinol: alloxanthine, Oxyprim, oxypurinol. Drugs R D. 2004;5(3):171-5. [PubMed:15139781 ]