1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 145062
• Molecular Formular: C10H13FN2O4
• Molecular Mass: 244.2196232
• Monoisotopic Mass: 244.08593513
• SMILES: Cc1cn(c(=O)[nH]c1=O)[C@H]1C[C@@H]([C@H](O1)CO)F
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1F)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H13FN2O4/c1-5-3-13(10(16)12-9(5)15)8-2-6(11)7(4-14)17-8/h3,6-8,14H,2,4H2,1H3,(H,12,15,16)/t6-,7+,8+/m0/s1
• InChIKey: UXCAQJAQSWSNPQ-XLPZGREQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 3'-deoxy-3'-fluorothymidine
• Synonyms: 3′-Deoxy-3′-fluorothymidine; 3′-脱氧-3′-氟胸苷

Database IDs

• CAS Number: 25526-93-6
• MDL Number: MFCD00056058
• PubChem SID: 162239272; 24862180
• PubChem CID: 33039

CALCULATED PROPERTIES

• Acid pKa: 9.710306
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.22798827
• LogD (pH = 7.4): -0.23005797
• Log P: -0.22796181
• Molar Refractivity: 53.7199 cm^3
• Polarizability: 21.151886 Å^3
• Polar Surface Area: 78.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 176-178 °C(lit.)

Safety Information

• RTECS: XP2073000
• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... TK2(7084)

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C10H13FN2O4

DETAILS

Sigma Aldrich - 361275

Packaging
25 mg in glass bottle
Application
Promising antiviral agent possessing activity similar to other 3′-deoxy-3′-substituted thymidines.1,2