1-[(2R,3R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidine-2,4-dione

• ChemBase ID: 168915
• Molecular Formular: C9H10FIN2O5
• Molecular Mass: 375.06844583
• Monoisotopic Mass: 374.95927227
• SMILES: [15nH]1[13c](=O)[15n](cc(c1=O)I)[C@H]1[C@H](C(O)[C@@H](CO)O1)F
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)F)[15n]1cc(I)c(=O)[15nH][13c]1=O
• InChI: InChI=1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5-,6?,8-/m1/s1/i9+1,12+1,13+1
• InChIKey: IPVFGAYTKQKGBM-WLHWJJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo(2-^1^3C,1,3-^1^5N₂)-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-2,4(1H,3H-pyrimi- dinedione-15N2,13C; 1-(2'-Deoxy-2'-fluoro-β-D-arabinofuranosyl) -5-iodouracil-15N2,13C; 5-Iodo-2'-fluoroarauracil-15N2,13C; FIAU-15N2,13C; Fialuridine-15N2,13C

Database IDs

• PubChem SID: 162263047
• PubChem CID: 46781575

CALCULATED PROPERTIES

• Acid pKa: 7.8011513
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.5406056
• LogD (pH = 7.4): -0.68171644
• Log P: -0.5384649
• Molar Refractivity: 64.2225 cm^3
• Polarizability: 25.498547 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F335002

An antiviral agent; nucleoside analog with antihepatitis B activity.

REFERENCES

• Watanabe A., et al.: J. Med. Chem., 22, 21 (1979)
• Colacino, J.M., et al.: Antimicrob. Agents Chemother., 24, 505 (1979)
• Staschke, K.A., et al.: Antiviral Res., 23, 45 (1979)
• Cui, L., et al.: J. Clin. Invest., 95, 555 (1979)