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

• ChemBase ID: 179261
• Molecular Formular: C12H20N2O5Sn
• Molecular Mass: 390.9986
• Monoisotopic Mass: 392.03941575
• SMILES: C1C([C@H](O[C@H]1n1c(=O)[nH]c(=O)c(c1)[Sn](C)(C)C)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1cc(c(=O)[nH]c1=O)[Sn](C)(C)C
• InChI: InChI=1S/C9H11N2O5.3CH3.Sn/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15;;;;/h2,5-6,8,12-13H,3-4H2,(H,10,14,15);3*1H3;/t5?,6-,8-;;;;/m1..../s1
• InChIKey: OQDVZLNWCJTGNH-QFRWVEFESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 146629-34-7
• PubChem SID: 164235171
• PubChem CID: 71752841

CALCULATED PROPERTIES

• Acid pKa: 9.800924
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.7577784
• LogD (pH = 7.4): 1.7560905
• Log P: 1.7578
• Molar Refractivity: 67.105 cm^3
• Polarizability: 31.334406 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T797200

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)