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

• ChemBase ID: 166035
• Molecular Formular: C9H12N2O5
• Molecular Mass: 228.20198
• Monoisotopic Mass: 228.07462149
• SMILES: [nH]1c(=O)n(ccc1=O)[C@H]1C[C@H]([C@H](O1)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6-,8-/m1/s1
• InChIKey: MXHRCPNRJAMMIM-ATRFCDNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2-Deoxy-β-D-erythro-pentofuranosyl)uracil; 2'-Desoxyuridine; Deoxyribose Uracil; Deoxyuridine; NSC 23615; Uracil Deoxyriboside; 2'-Deoxyuridine

Database IDs

• CAS Number: 951-78-0
• PubChem SID: 162260168
• PubChem CID: 13048618

CALCULATED PROPERTIES

• Acid pKa: 9.7057295
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.5146308
• LogD (pH = 7.4): -1.5167224
• Log P: -1.5146041
• Molar Refractivity: 51.0549 cm^3
• Polarizability: 20.191685 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Silfoxode; Methanol
• Apperance: White Solid
• Melting Point: 160-162°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D288010

An uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease.

REFERENCES

• Fu, M., et al.: J. Biol. Chem., 271, 9982 (1996)
• Thornalley, P., et al.: Biochem. J., et al.: 344, 109 (1996)
• Munter, T., et al.: Chem. Res. Toxicol., 15, 1549 (2002)