[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(3-carbamoyl-1H-1,2,4-triazol-1-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 177515
• Molecular Formular: C14H18N4O8
• Molecular Mass: 370.31472
• Monoisotopic Mass: 370.11246356
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1nc(nc1)C(=O)N)COC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1cnc(n1)C(=O)N)COC(=O)C
• InChI: InChI=1S/C14H18N4O8/c1-6(19)23-4-9-10(24-7(2)20)11(25-8(3)21)14(26-9)18-5-16-13(17-18)12(15)22/h5,9-11,14H,4H2,1-3H3,(H2,15,22)/t9-,10-,11-,14-/m1/s1
• InChIKey: XVXXBJKZJDPHAU-ZHSDAYTOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(3-carbamoyl-1H-1,2,4-triazol-1-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(3-carbamoyl-1,2,4-triazol-1-yl)oxolan-2-yl]methyl acetate
• Synonyms: 1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide; Tri-O-acetylribavirin; 1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide; Ribavirin 2,3,5-Tri-O-acetyl

Database IDs

• PubChem SID: 164233425
• PubChem CID: 3080793

CALCULATED PROPERTIES

• Acid pKa: 12.025573
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -1.5307606
• LogD (pH = 7.4): -1.5307671
• Log P: -1.5307604
• Molar Refractivity: 92.0289 cm^3
• Polarizability: 32.062107 Å^3
• Polar Surface Area: 161.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - R414515

Protected Ribavirin (R414475), a purine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Used as an antiviral agent.

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)