(2R,3S,5R)-2-(5,6-dichloro-1H-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 167149
• Molecular Formular: C12H12Cl2N2O4
• Molecular Mass: 319.14068
• Monoisotopic Mass: 318.01741223
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)cc(c(c2)Cl)Cl)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1cc(Cl)c(c2)Cl
• InChI: InChI=1S/C12H12Cl2N2O4/c13-5-1-7-8(2-6(5)14)16(4-15-7)12-11(19)10(18)9(3-17)20-12/h1-2,4,9-12,17-19H,3H2/t9-,10?,11+,12-/m1/s1
• InChIKey: XHSQDZXAVJRBMX-SGUBAKSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-(5,6-dichloro-1H-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-(5,6-dichloro-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 5,6-Dichlorobenzimidazole 1-β-D-Ribofuranoside; 1-β-D-Ribofuranosyl-5,6-dichlorobenzimidazole; 5,6-Dichloro-1-(β-D-ribofuranosyl)benzimidazole; DRB; NSC 401575; 5,6-Dichloropurine-1-β-D-ribofuanosyl-H-benzimidazole

Database IDs

• CAS Number: 53-85-0
• PubChem SID: 162261282
• PubChem CID: 59910845

CALCULATED PROPERTIES

• Acid pKa: 12.455603
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.7447811
• LogD (pH = 7.4): 0.9050076
• Log P: 0.9076422
• Molar Refractivity: 71.1744 cm^3
• Polarizability: 29.581772 Å^3
• Polar Surface Area: 87.74 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Light Beige Solid
• Melting Point: 213-216°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D435820

An inhibitor of RNA synthesis (causes premature termination of transcription).

REFERENCES

• Braedlye, J. and Sporns, O.: Brain Res., 815, 140 (1999)
• Ljungman, M., et al.: Oncogene, 18, 583 (1999)
• Roele, R.H., et al.: Oncogene, 18, 5765 (1999)