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

• ChemBase ID: 169508
• Molecular Formular: C13H14N2O6
• Molecular Mass: 294.26006
• Monoisotopic Mass: 294.08518618
• SMILES: C1C([C@H](O[C@H]1n1c(=O)[nH]c(=O)c(c1)c1ccco1)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1cc(c2ccco2)c(=O)[nH]c1=O
• InChI: InChI=1S/C13H14N2O6/c16-6-10-8(17)4-11(21-10)15-5-7(9-2-1-3-20-9)12(18)14-13(15)19/h1-3,5,8,10-11,16-17H,4,6H2,(H,14,18,19)/t8?,10-,11-/m1/s1
• InChIKey: IWTGFYBALHWJGB-GUJYYOPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(furan-2-yl)-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-(furan-2-yl)-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 2'-Deoxy-5-(2-furanyl)uridine; 5-(2-Furanyl)-2'-deoxyuridine

Database IDs

• CAS Number: 92233-50-6
• PubChem SID: 162263640
• PubChem CID: 71317010

CALCULATED PROPERTIES

• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 9.500859
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.78631246
• LogD (pH = 7.4): -0.7896597
• Log P: -0.78626966
• Molar Refractivity: 67.8979 cm^3
• Polarizability: 26.708612 Å^3
• Polar Surface Area: 112.24 Å^2

DETAILS

Toronto Research Chemicals - F864030

Several novel 5-substituted 2'-deoxyuridine (dUrd) analogs were evaluated as substrates for highly purified herpes simplex virus type 1 (HSV-1)-encoded thymidine kinase (TK) derived from HSV-1 TK gene-transfected murine mammary carcinoma FM3A cells, and h

REFERENCES

• Bohman, C., et al.: J. Biol. Chem., 269, 8036 (1994)