[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1H-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

• ChemBase ID: 177512
• Molecular Formular: C8H14N4O11P2
• Molecular Mass: 404.164482
• Monoisotopic Mass: 404.01343055
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1COP(=O)(O)OP(=O)(O)O)n1cnc(n1)C(=O)N)O)O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(O)O)O)O[C@H]([C@@H]1O)n1cnc(n1)C(=O)N
• InChI: InChI=1S/C8H14N4O11P2/c9-6(15)7-10-2-12(11-7)8-5(14)4(13)3(22-8)1-21-25(19,20)23-24(16,17)18/h2-5,8,13-14H,1H2,(H2,9,15)(H,19,20)(H2,16,17,18)/t3-,4-,5-,8-/m1/s1
• InChIKey: HWSPXPQHONXITJ-AFCXAGJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2R,3S,4R,5R)-5-(3-carbamoyl-1H-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: {[(2R,3S,4R,5R)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: 1-[5-O-[Hydroxy(phosphonooxy)phosphinyl]-β-D-ribofuranosyl]-1H-1,2,4-triazole-3-carboxamide; Ribavirin Diphosphate; Ribavirin 5'-DiphosphateDISCONTINUED

Database IDs

• CAS Number: 63142-70-1
• PubChem SID: 164233422
• PubChem CID: 124970

CALCULATED PROPERTIES

• Acid pKa: 1.772217
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -7.4620857
• LogD (pH = 7.4): -8.054146
• Log P: -3.1606042
• Molar Refractivity: 86.3202 cm^3
• Polarizability: 29.937458 Å^3
• Polar Surface Area: 236.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 140-143°C

DETAILS

Toronto Research Chemicals - R414495

A metabolite of Ribavirin.

REFERENCES

• Allen, L.B., et al.: J. Med. Chem., 21, 742 (1978)
• Zimmerman, T., et al.: Biochem. Pharmacol., 27, 709 (1978)
• Page, T., et al.: Int. J. Biochem., 22, 379 (1978)
• Lin, C., et al.: Antimicrob. Agents Chemother., 47, 1395 (1978)