Record Information
Version1.0
Creation date2011-09-21 00:10:46 UTC
Update date2015-10-09 22:30:38 UTC
Primary IDFDB022242
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 found, on average, in the highest concentration within beer. This could make oxypurinol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Oxypurinol.
CAS Number2465-59-0
Structure
Thumb
Synonyms
SynonymSource
OxipurinolChEBI
OxoallopurinolChEBI
1H,3H,9H-AlloxanthineHMDB
1H-Pyrazolo[3,4-D]pyrimidin-4,6-diolHMDB
4,6-Dihydroxypyrazolo[3,4-D]pyrimidineHMDB
AlloxanthineHMDB
1H-Pyrazolo[3,4-d]pyrimidin-4,6-diolhmdb
4,6-Dihydroxypyrazolo[3,4-d]pyrimidinehmdb
Predicted Properties
PropertyValueSource
Water Solubility2.32 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
Chemical FormulaC5H4N4O2
IUPAC name1H,2H,4H,5H,6H-pyrazolo[3,4-d]pyrimidine-4,6-dione
InChI IdentifierInChI=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
Isomeric SMILESO=C1NC(=O)C2=CNNC2=N1
Average Molecular Weight152.1109
Monoisotopic Molecular Weight152.033425392
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSOxypurinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zn9-4900000000-837f8f7de41a018a7868Spectrum
Predicted GC-MSOxypurinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOxypurinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0w29-4900000000-2b2a5e7237cb7a9dd60e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ab9-9700000000-8017eefe2f766f6a33822012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0690-9100000000-b997025b96b7398143d22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0f79-0900000000-3de88a143c5683886f8d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-cbc9adb0643d1712be572012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-cbc9adb0643d1712be572017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f79-0900000000-3de88a143c5683886f8d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9000000000-3ce669d763865167a4022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-e36d8a77fa2e2a31b5432021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-275c9502306d49a7f8872021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f55bc1d37afe8f28c3542021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udr-9700000000-bd486884d4915c23b1a52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-066r-9700000000-c8f39d076fdf79f2bd282021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-c55a17ac9c4a712652a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0udi-0900000000-048462704a3cd891924f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0udi-0900000000-09b723a1bae058dd1de62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-7b5346a657416f2ca8aa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-9000000000-514523b07285f885cc272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0zfr-2900000000-6b3927234159e81b70b72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ca8f6a9e71c7b2514f302017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-2f457108cc7fec8527512017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-9d5c31601c46aa2e8eb62017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-a2f008eef4b535546f4f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-7900000000-03e71b25e9d15486d84e2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c14d58288520ea2b76422017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID4483
ChEMBL IDCHEMBL859
KEGG Compound IDC07599
Pubchem Compound ID4644
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB05262
HMDB IDHMDB00786
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference