| Common Name |
Allopurinol riboside
| Description |
Allopurinol is an analog of the natural purines in the body, and is quickly metabolized to oxypurines which is also a xanthine oxidase inhibitor. Allopurinol is a white, powdery drug used to treat gout. Its use in the United States was started in 1964. It is an isomer of hypoxanthine and inhibits the production of uric acid, the metabolite responsible for gout, by inhibiting the enzyme xanthine oxidase. The side effects of high levels of precursors are usually minor. A small percentage of people develop a rash and must discontinue this drug. The most serious adverse event is a hypersensitivity syndrome consisting of fever, skin rash, eosinophilia, hepatitis, and worsening renal function. In some cases, allopurinol hypersensitivity syndrome.
| Structure |
| Synonyms |
| Value |
Source |
4-Hydroxy[3,4-D]pyrazolopyrimidine ribosideChEBI
Allopurinol ribonucleosideChEBI
Allopurinol-1-ribonucleosideChEBI
| Chemical Formlia |
C10H12N4O5
| Average Molecliar Weight |
268.2261
| Monoisotopic Molecliar Weight |
268.080769514
| IUPAC Name |
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one
| Traditional Name |
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrazolo[3,4-d]pyrimidin-4-one
| CAS Registry Number |
16220-07-8
| 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 Key |
KFQUAMTWOJHPEJ-DAGMQNCNSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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 moleclie.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Nucleosides, nucleotides, and analogues
| Sub Class |
Pyrazolo[3,4-d]pyrimidine glycosides
| Direct Parent |
Pyrazolo[3,4-d]pyrimidine glycosides
| Alternative Parents |
Glycosylamines
Pentoses
Pyrazolo[3,4-d]pyrimidines
Pyrimidones
Vinylogous amides
Heteroaromatic compounds
Oxolanes
Pyrazoles
Secondary alcohols
Oxacyclic compounds
Azacyclic compounds
Organopnictogen compounds
Organonitrogen compounds
Organic oxides
Primary alcohols
Hydrocarbon derivatives
| Substituents |
Pyrazolo[3,4-d]pyrimidine glycoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Pyrazolo[3,4-d]pyrimidine
Pyrazolopyrimidine
Pyrimidone
Monosaccharide
Pyrimidine
Azole
Oxolane
Pyrazole
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Primary alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
nucleoside analogue (CHEBI:74074 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility14.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity72.32 m3·mol-1ChemAxon
Polarizability24.35 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified5.0 (0.05-10.0) uMAdlit (>18 years old)BothNormal
838831
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022067
| KNApSAcK ID |
Not Available
| Chemspider ID |
18512601
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00481
| Metagene Link |
HMDB00481
| METLIN ID |
5468
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: VU0364770
References |
| Synthesis Reference |
Korbukh, 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 References |
- Ledvinova J, Poupetova H, Hanackova A, Pisacka M, Elleder M: Blood group B glycosphingolipids in alpha-galactosidase deficiency (Fabry disease): influence of secretor status. Biochim Biophys Acta. 1997 Apr 1;1345(2):180-7. [PubMed:9106497 ]
- Nelson DJ, Elion GB: Metabolic studies of high doses of allopurinol in humans. Adv Exp Med Biol. 1984;165 Pt A:167-70. [PubMed:6720373 ]
|
PMID: 18998663