ChemFOnt: Showing chemical card for Allopurinol riboside (CFc000000365)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:44 UTC

Chemfont ID

CFc000000365

Molecule Identification

Common Name

Allopurinol riboside

Definition

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy[3,4-D]pyrazolopyrimidine riboside	ChEBI
Allopurinol ribonucleoside	ChEBI
Allopurinol-1-ribonucleoside	ChEBI

Chemical Formula

C₁₀H₁₂N₄O₅

Average Molecular Weight

268.2261

Monoisotopic Molecular 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

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrazolo[3,4-d]pyrimidine glycosides

Sub Class

Not Available

Direct Parent

Pyrazolo[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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

nucleoside analogue (CHEBI:74074 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 838831)

Cellular substructure

Cytoplasm (HMDB: HMDB0000481)

Source

Endogenous

Endogenous (HMDB: HMDB0000481)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	14.8 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.32 m³·mol⁻¹	ChemAxon
Polarizability	24.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000481

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

METLIN ID

5468

PubChem Compound

5273534

PDB ID

Not Available

ChEBI ID

74074

Food Biomarker Ontology

Not Available

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.

Showing chemical card for Allopurinol riboside (CFc000000365)

MOL for CFc000000365 (Allopurinol riboside)

3D MOL for CFc000000365 (Allopurinol riboside)

3D SDF for CFc000000365 (Allopurinol riboside)

3D-SDF for CFc000000365 (Allopurinol riboside)

PDB for CFc000000365 (Allopurinol riboside)

3D PDB for CFc000000365 (Allopurinol riboside)

SMILES for CFc000000365 (Allopurinol riboside)

INCHI for CFc000000365 (Allopurinol riboside)

Structure for CFc000000365 (Allopurinol riboside)

3D Structure for CFc000000365 (Allopurinol riboside)