2-amino-8-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4H,8H-imidazo[1,2-a][1,3,5]triazin-4-one

• ChemBase ID: 160462
• Molecular Formular: C10H13N5O5
• Molecular Mass: 283.24072
• Monoisotopic Mass: 283.09166854
• SMILES: n1c(nc2n(c1=O)ccn2[C@H]1[C@H](C(O)[C@@H](CO)O1)O)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1ccn2c1nc(N)nc2=O
• InChI: InChI=1S/C10H13N5O5/c11-8-12-9-14(1-2-15(9)10(19)13-8)7-6(18)5(17)4(3-16)20-7/h1-2,4-7,16-18H,3H2,(H2,11,13,19)/t4-,5?,6+,7-/m1/s1
• InChIKey: ZQUTYCUKRGSIGL-ZFGFBIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-8-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4H,8H-imidazo[1,2-a][1,3,5]triazin-4-one
• IUPAC Traditional name: 2-amino-8-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazo[1,2-a][1,3,5]triazin-4-one
• Synonyms: 2-Amino-8-β-D-ribofuranosylimidazo[1,2-a]-1,3,5-triazin-4(8H)-one; NSC 344511; ZX 2401; 5-Aza-7-deaza Guanosine

Database IDs

• CAS Number: 67410-65-5
• PubChem SID: 162254597
• PubChem CID: 46783528

CALCULATED PROPERTIES

• Acid pKa: 12.555566
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -2.566692
• LogD (pH = 7.4): -2.566691
• Log P: -2.5666878
• Molar Refractivity: 62.9604 cm^3
• Polarizability: 24.538849 Å^3
• Polar Surface Area: 144.21 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 233-237°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A628915

Nucleosides as antiviral agent for the treatment of influenza; broad-spectrum inhibitor of viruses in the Flaviviridae family.

REFERENCES

• Sidwell, R.W., et al.: Appl. Microbiol., 22, 797 (1971)
• Allen, B., et al.: J. Med. Che,., 18, 721 (1971)