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

• ChemBase ID: 169115
• Molecular Formular: C11H15FN2O5
• Molecular Mass: 274.2456032
• Monoisotopic Mass: 274.09649981
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)[nH]c(=O)c(c1)CCF)O
• Canonical SMILES: FCCc1cn([C@H]2C[C@H]([C@H](O2)CO)O)c(=O)[nH]c1=O
• InChI: InChI=1S/C11H15FN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h4,7-9,15-16H,1-3,5H2,(H,13,17,18)/t7-,8-,9-/m1/s1
• InChIKey: QURQCEKLDQAQFI-IWSPIJDZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 108008-61-3
• PubChem SID: 162263247
• PubChem CID: 71316819

CALCULATED PROPERTIES

• Acid pKa: 9.397661
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.2201262
• LogD (pH = 7.4): -1.2243665
• Log P: -1.2200718
• Molar Refractivity: 60.2496 cm^3
• Polarizability: 23.66532 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F591565

A deoxyuridine derivative as radiotracer for monitoring cancer gene therapy with PET.

REFERENCES

• Griengl, H., et al.: J. Med. Chem., 30, 1199 (1987)
• Devries, E., et al.: Curr. Pharm. Design, 8, 1435 (1987)