1-[(2S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide

• ChemBase ID: 177509
• Molecular Formular: C8H12N4O5
• Molecular Mass: 244.20468
• Monoisotopic Mass: 244.0807695
• SMILES: [C@H]1(C([C@H](O[C@@H]1CO)n1cnc(n1)C(=O)N)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](C([C@H]1O)O)n1cnc(n1)C(=O)N
• InChI: InChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4+,5?,8+/m1/s1
• InChIKey: IWUCXVSUMQZMFG-AOKVRREPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
• IUPAC Traditional name: 1-[(2S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
• Synonyms: 1-α-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide; Ribavirin Impurity B; α-Ribavirin (Ribavirin Impurity B)

Database IDs

• CAS Number: 57198-02-4
• PubChem SID: 164233419
• PubChem CID: 46782878

CALCULATED PROPERTIES

• Acid pKa: 11.878701
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.7682977
• LogD (pH = 7.4): -2.7683082
• Log P: -2.7682974
• Molar Refractivity: 64.5744 cm^3
• Polarizability: 20.505037 Å^3
• Polar Surface Area: 143.72 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 152-155°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R414470

Ribavirin impurity B. The α-anomer of Ribavirin.

REFERENCES

• Fernandez, H., et al.: Eur. J. Epidemiol., 2, 1 (1986)
• Liao, H.J. and Stollar, V.: Antiviral Res., 22, 285 (1986)
• Honda, Y., et al.: Antimicrob. Agents Chemother., 38, 653 (1986)
• Reichard, O., et al.: Lancet, 351, 83 (1998)