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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-27 20:30:03 UTC
HMDB IDHMDB0000786
Secondary Accession Numbers
  • HMDB00786
Metabolite Identification
Common NameOxypurinol
DescriptionOxypurinol, also known as oxoallopurinol or alloxanthine, 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. Oxypurinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Oxypurinol is found, on average, in the highest concentration within beers. This could make oxypurinol a potential biomarker for the consumption of these foods. A pyrazolopyrimidine that is 4,5,6,7-tetrahydro-H-pyrazolopyrimidine substituted by oxo groups at positions 4 and 6.
Structure
Data?1582752156
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 Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.58 g/LALOGPS
logP-2ALOGPS
logP-1.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)6.25ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalMetCCS_train_neg120.10330932474
DeepCCS[M+H]+ExperimentalMetCCS_train_pos126.68830932474
AllCCS[M-H]-ExperimentalNot Available120.103http://allccs.zhulab.cn/database/detail?ID=AllCCS00000331
AllCCS[M+H]+ExperimentalNot Available126.651http://allccs.zhulab.cn/database/detail?ID=AllCCS00000331
DarkChem[M+H]+PredictedNot Available131.37831661259
DarkChem[M-H]-PredictedNot Available130.71531661259
AllCCS[M+H]+PredictedNot Available132.17532859911
AllCCS[M-H]-PredictedNot Available125.49632859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zn9-4900000000-837f8f7de41a018a78682017-08-28View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0zn9-4900000000-cb382aeb6cd4f3d7e93b2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0w29-4900000000-2b2a5e7237cb7a9dd60e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ab9-9700000000-8017eefe2f766f6a33822012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0690-9100000000-b997025b96b7398143d22012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0f79-0900000000-3de88a143c5683886f8d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-cbc9adb0643d1712be572012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-cbc9adb0643d1712be572017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f79-0900000000-3de88a143c5683886f8d2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ca8f6a9e71c7b2514f302017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-2f457108cc7fec8527512017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-9d5c31601c46aa2e8eb62017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-a2f008eef4b535546f4f2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-7900000000-03e71b25e9d15486d84e2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c14d58288520ea2b76422017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-474318d91d8d19c998f52021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-7900000000-875d306636e2b3733f1f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-3d5fa40367b5b2bf21592021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ac450658003af6c0a1092021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2900000000-2d44e3bbdc52ac69a0642021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-1c88bcadaf84e60e72242021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, predicted)2012-12-05View Spectrum
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 Quantified19-37 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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 ]