1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2H3)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 178117
• Molecular Formular: C10H14N2O5
• Molecular Mass: 242.22856
• Monoisotopic Mass: 242.09027156
• SMILES: C1[C@H]([C@@H](O[C@@H]1n1cc(c(=O)[nH]c1=O)C)CO)O
• Canonical SMILES: OC[C@@H]1O[C@@H](C[C@H]1O)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m1/s1
• InChIKey: IQFYYKKMVGJFEH-CSMHCCOUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(^2H₃)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(^2H₃)methyl-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2-Deoxy-β-L-erythro-pentofuranosyl)-5-(methyl-d3)-2,4(1H,3H)-pyrimidinedione-d3; 1-(2-deoxy-β-L-erythro-pentofuranosyl)thymine-d3; β-L-Thymidine-d3; 2'-Deoxy-L-thymidine-d3; Epavudine-d3; L-Thymidine-d3; NV 02B-d3; Telbivudine-d3

Database IDs

• PubChem SID: 164234027
• PubChem CID: 71752342

CALCULATED PROPERTIES

• Acid pKa: 9.960277
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.1190685
• LogD (pH = 7.4): -1.1202337
• Log P: -1.1190536
• Molar Refractivity: 55.412 cm^3
• Polarizability: 22.001661 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 184-186°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T016002

Labelled nucleoside analog; specific inhibitor of hepatitis B virus (HBV) replication. Antiviral.

REFERENCES

• Standring, D.N., et al.: Antiviral. Chem. Chemother., 12, 119 (2001)
• Hernandez-Santiago, B., et al.: Antimicrob. Agents Chemother., 46, 1728 (2001)
• Lai, C.-L., et al.: Hepatology, 40, 719 (2001)
• Han, S.-H.B., et al.: Expert Opin. Invest. Drugs, 14, 51