Showing metabocard for Allopurinol riboside (BMDB0000481)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:31:23 UTC
Update Date2020-04-22 15:03:47 UTC
BMDB IDBMDB0000481
Secondary Accession Numbers
  • BMDB00481
Metabolite Identification
Common NameAllopurinol riboside
DescriptionAllopurinol riboside belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidine glycosides. These are nucleosides or derivatives thereof that consist of a pyazolo[3,2-d]pyrimidine ring system that is N-glycosidically linked to a ribose or deoxyribose. They bear the sugar moiety on the pyrimidine part of the molecule. Based on a literature review a significant number of articles have been published on Allopurinol riboside.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Hydroxy[3,4-D]pyrazolopyrimidine ribosideChEBI
Allopurinol ribonucleosideChEBI
Allopurinol-1-ribonucleosideChEBI
Chemical FormulaC10H12N4O5
Average Molecular Weight268.2261
Monoisotopic Molecular Weight268.080769514
IUPAC Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one
Traditional Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrazolo[3,4-d]pyrimidin-4-one
CAS Registry Number16220-07-8
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O
InChI Identifier
InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1
InChI KeyKFQUAMTWOJHPEJ-DAGMQNCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidine glycosides. These are nucleosides or derivatives thereof that consist of a pyazolo[3,2-d]pyrimidine ring system that is N-glycosidically linked to a ribose or deoxyribose. They bear the sugar moiety on the pyrimidine part of the molecule.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrazolo[3,4-d]pyrimidine glycosides
Sub ClassNot Available
Direct ParentPyrazolo[3,4-d]pyrimidine glycosides
Alternative Parents
Substituents
  • Pyrazolo[3,4-d]pyrimidine glycoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Pyrazolo[3,4-d]pyrimidine
  • Pyrazolopyrimidine
  • Pyrimidone
  • Monosaccharide
  • Pyrimidine
  • Azole
  • Heteroaromatic compound
  • Pyrazole
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.7ALOGPS
logP-2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)7.36ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity72.32 m³·mol⁻¹ChemAxon
Polarizability24.35 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000481
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022067
KNApSAcK IDNot Available
Chemspider ID18512601
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5468
PubChem Compound5273534
PDB IDNot Available
ChEBI ID74074
References
Synthesis ReferenceKorbukh, I. A.; Yakunina, N. G.; Preobrazhenskaya, M. N. Synthesis and reactions of 4- and 4,6-substituted pyrazolo[3,4-d]pyrimidine nucleosides. Bioorganicheskaya Khimiya (1980), 6(11), 1632-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available