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

• ChemBase ID: 164180
• Molecular Formular: C9H11ClN2O5
• Molecular Mass: 262.64704
• Monoisotopic Mass: 262.03564914
• SMILES: C1(O)[C@@H](CO)O[C@H](C1)n1cc(c(=O)[nH]c1=O)Cl
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1cc(Cl)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11ClN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5?,6-,7-/m1/s1
• InChIKey: NJCXGFKPQSFZIB-JXBXZBNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-chloro-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 3'-epi-5-Chloro-2'-deoxyuridine; 5-Chloro-1-(2-deoxy-β-D-threo-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione

Database IDs

• CAS Number: 188559-94-6
• PubChem SID: 162258315
• PubChem CID: 71314711

CALCULATED PROPERTIES

• Acid pKa: 7.972004
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.85526407
• LogD (pH = 7.4): -0.95558345
• Log P: -0.8538184
• Molar Refractivity: 55.8462 cm^3
• Polarizability: 22.147081 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C365233

The 3’-enantiomer of 5-Chloro-2'-deoxyuridine (C365235). A halogenated uridine derivative used in pharmaceutical compositions.

REFERENCES

• Brammer, K., et al.: Biochim. Biophys. Acta, 72, 217 (1963)
• Uesugi, S., et al.: Chem. Pharm. Bull., 26, 3040 (1978)