1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one

• ChemBase ID: 133547
• Molecular Formular: C10H12N4O5
• Molecular Mass: 268.22608
• Monoisotopic Mass: 268.0807695
• SMILES: c1c2c([nH]cnc2=O)n(n1)C1C(C(C(O1)CO)O)O
• Canonical SMILES: OCC1OC(C(C1O)O)n1ncc2c1[nH]cnc2=O
• InChI: 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)
• InChIKey: KFQUAMTWOJHPEJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one
• IUPAC Traditional name: 1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrazolo[3,4-d]pyrimidin-4-one
• Synonyms: 1-β-D-Ribofuranosyl-1H-pyrazolo[3,4-d]pyrimidine-4-one; Allopurinol riboside

Database IDs

• CAS Number: 16220-07-8
• MDL Number: MFCD00057096
• PubChem SID: 162227824; 24890617
• PubChem CID: 283570

CALCULATED PROPERTIES

• Acid pKa: 7.3612595
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.029763
• LogD (pH = 7.4): -2.3219225
• Log P: -2.0241234
• Molar Refractivity: 72.3223 cm^3
• Polarizability: 23.332998 Å^3
• Polar Surface Area: 129.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - A2026

Biochem/physiol Actions
An anti-leishmanial agent
Application
Allopurinol riboside is an experimental agent for the treatment of leishmaniasis and American trypanosomiasis. Allopurinol riboside is an inhibitor of orotidine 5′-monophosphate (OMP) decarboxylase from Plasmodium falciparum ((PfODCase, EC 4.1.1.23).