1-[(2R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 166038
• Molecular Formular: C9H12N2O5
• Molecular Mass: 228.20198
• Monoisotopic Mass: 228.07462149
• SMILES: [C@H]1(C([C@@H](O[C@@H]1C)n1c(=O)[nH]c(=O)cc1)O)O
• Canonical SMILES: C[C@H]1O[C@H](C([C@H]1O)O)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H12N2O5/c1-4-6(13)7(14)8(16-4)11-3-2-5(12)10-9(11)15/h2-4,6-8,13-14H,1H3,(H,10,12,15)/t4-,6+,7?,8-/m1/s1
• InChIKey: WUBAOANSQGKRHF-JDNPWWSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 5’-Deoxy-uridine; 5'-Deoxyuridine

Database IDs

• CAS Number: 15958-99-3
• PubChem SID: 162260171
• PubChem CID: 46781105

CALCULATED PROPERTIES

• Acid pKa: 9.70079
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.3683592
• LogD (pH = 7.4): -1.3704747
• Log P: -1.3683321
• Molar Refractivity: 51.0219 cm^3
• Polarizability: 20.191685 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288025

A uridine derivative used as a therapeutic agent for treating allergy, cancer, infection and autoimmune disease.

REFERENCES

• Vickers, M., et al.: Biochem. J., 339, 21 (1999)
• del Santo, B., et al.: J. Hepatol., 34, 873 (1999)
• Chang, C., et al.: Mol. Pharmacol., 65, 558 (1999)
• Visser, F., et al.: Mol. Pharmacol., 67, 1291 (1999)