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

• ChemBase ID: 6085
• Molecular Formular: C12H12Cl2N2O4
• Molecular Mass: 319.14068
• Monoisotopic Mass: 318.01741223
• SMILES: c12cc(Cl)c(Cl)cc1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)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-DDHJBXDOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(5,6-dichloro-1H-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(5,6-dichloro-1,3-benzodiazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 5,6-Dichlorobenzimidazole riboside; 5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole; 5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside; 5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole; 5,6-dichloro-1-beta-D-ribofuranosyl-1H-benzimidazole; 5,6-DICHLOROBENZIMIDAZOLE RIBOSIDE; DRB; 5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole

Database IDs

• CAS Number: 53-85-0
• MDL Number: MFCD00036785
• Beilstein Number: 39123
• PubChem SID: 99444944; 24278361; 160969510; 24861801
• PubChem CID: 5894
• CHEMBL: 375530
• Chemspider ID: 5683
• DrugBank ID: DB08473
• Wikipedia Title: 5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.01
• LOG S: -2.09
• Solubility (Water): 2.59e+00 g/l

PROPERTIES

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen
• RTECS: DD7310000
• German water hazard class: 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CSNK2A1(1457), CSNK2B(1460)

Product Information

• Purity: ≥99.0% (HPLC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C12H12Cl2N2O4

DETAILS

MP Biomedicals - 02157639

Purity: 98%
Selectively inhibits casein kinase II. Blocks RNA synthesis by inhibiting RNA polymerase II transcription dependent on CK-II.

DrugBank - DB08473

Drug information: experimental

Sigma Aldrich - D1916

Biochem/physiol Actions
Inhibitor of RNA synthesis; causes premature termination of transcription. CK2 (casein kinase-2) inhibitor.

Sigma Aldrich - 35290

Biochem/physiol Actions
Inhibitor of RNA synthesis; causes premature termination of transcription. CK2 (casein kinase-2) inhibitor.

REFERENCES

• Zandomeni, R., et al., J. Biol. Chem. , 261 : 3414 (1986).