[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(5,6-dichloro-1H-1,3-benzodiazol-1-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 167163
• Molecular Formular: C18H18Cl2N2O7
• Molecular Mass: 445.25072
• Monoisotopic Mass: 444.04910629
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1c2c(nc1)cc(c(c2)Cl)Cl)COC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1cnc2c1cc(Cl)c(c2)Cl)COC(=O)C
• InChI: InChI=1S/C18H18Cl2N2O7/c1-8(23)26-6-15-16(27-9(2)24)17(28-10(3)25)18(29-15)22-7-21-13-4-11(19)12(20)5-14(13)22/h4-5,7,15-18H,6H2,1-3H3/t15-,16-,17-,18-/m1/s1
• InChIKey: LAILZPSFJJOYLV-BRSBDYLESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(5,6-dichloro-1H-1,3-benzodiazol-1-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(5,6-dichloro-1,3-benzodiazol-1-yl)oxolan-2-yl]methyl acetate
• Synonyms: 5,6-Dichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-benzimidazole; 5,6-Dichloropurine-1-(2,3,5-tri-O-acetyl-β-D-ribofuanosyl)-1H-benzimidazole

Database IDs

• CAS Number: 443678-71-5
• PubChem SID: 162261296
• PubChem CID: 70023290

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.0682147
• LogD (pH = 7.4): 2.2283888
• Log P: 2.2310185
• Molar Refractivity: 98.6289 cm^3
• Polarizability: 41.152035 Å^3
• Polar Surface Area: 105.95 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Yellow Oil

DETAILS

Toronto Research Chemicals - D435935

A protected 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)