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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:21 UTC
HMDB IDHMDB00786
Secondary Accession NumbersNone
Metabolite Identification
Common NameOxypurinol
DescriptionOxipurinol is a xanthine oxidase inhibitor. Oxipurinol is potentially used for treatment of congestive heart failure. PMID: 15139781 .
Structure
Thumb
Synonyms
ValueSource
OxipurinolChEBI
OxoallopurinolChEBI
OxypurinolChEBI
1H,3H,9H-AlloxanthineHMDB
1H-pyrazolo[3,4-D]Pyrimidin-4,6-diolHMDB
4,6-dihydroxypyrazolo[3,4-D]PyrimidineHMDB
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=C1NC2=C(C=NN2)C(=O)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 KeyInChIKey=HXNFUBHNUDHIGC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Xanthine
  • Pyrazolopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.35 m3·mol-1ChemAxon
Polarizability12.6 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0w29-4900000000-2b2a5e7237cb7a9dd60eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ab9-9700000000-8017eefe2f766f6a3382View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0690-9100000000-b997025b96b7398143d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0f79-0900000000-3de88a143c5683886f8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-cbc9adb0643d1712be57View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 IDNot Available
DrugBank Metabolite IDDBMET00414
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022242
KNApSAcK IDNot Available
Chemspider ID4483
KEGG Compound IDC07599
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00786
Metagene LinkHMDB00786
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. [6423323 ]
  2. Oxipurinol: alloxanthine, Oxyprim, oxypurinol. Drugs R D. 2004;5(3):171-5. [15139781 ]