trisodium ({[(2R,3S,4R,5R)-5-(3-carbamoyl-1H-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(hydrogen phosphonatooxy)phosphinate

• ChemBase ID: 177514
• Molecular Formular: C8H12N4Na3O14P3
• Molecular Mass: 550.089873
• Monoisotopic Mass: 549.92559382
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1COP(=O)(OP(=O)(OP(=O)(O)[O-])[O-])[O-])n1cnc(n1)C(=O)N)O)O.[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc(n1)C(=O)N.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C8H15N4O14P3.3Na/c9-6(15)7-10-2-12(11-7)8-5(14)4(13)3(24-8)1-23-28(19,20)26-29(21,22)25-27(16,17)18;;;/h2-5,8,13-14H,1H2,(H2,9,15)(H,19,20)(H,21,22)(H2,16,17,18);;;/q;3*+1/p-3/t3-,4-,5-,8-;;;/m1.../s1
• InChIKey: BRRJCRUTNWTKKX-JWYZMMGYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium ({[(2R,3S,4R,5R)-5-(3-carbamoyl-1H-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(hydrogen phosphonatooxy)phosphinate
• IUPAC Traditional name: trisodium {[(2R,3S,4R,5R)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy(hydrogen phosphonatooxy)phosphinate
• Synonyms: 1-[5-O-[Hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-β-D-ribofuranosyl]-1H-1,2,4-triazole-3-carboxamide Trisodium; Ribavirin Triphosphate Trisodium; Virazole 5'-Triphosphate Trisodium; Ribavirin 5'-Triphosphate Trisodium Salt

Database IDs

• CAS Number: 63142-71-2
• PubChem SID: 164233424
• PubChem CID: 71752068

CALCULATED PROPERTIES

• Acid pKa: 0.89883524
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): -9.920693
• LogD (pH = 7.4): -10.601975
• Log P: -3.402514
• Molar Refractivity: 93.828 cm^3
• Polarizability: 34.40236 Å^3
• Polar Surface Area: 291.8 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Brown Solid
• Melting Point: 132-135°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R414505

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)