[3,4-bis(acetyloxy)-5-(6-chloro-9H-purin-9-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 178851
• Molecular Formular: C16H17ClN4O7
• Molecular Mass: 412.78178
• Monoisotopic Mass: 412.07857658
• SMILES: C1(C(C(C(O1)n1c2c(nc1)c(ncn2)Cl)OC(=O)C)OC(=O)C)COC(=O)C
• Canonical SMILES: CC(=O)OC1C(OC(=O)C)C(OC1n1cnc2c1ncnc2Cl)COC(=O)C
• InChI: InChI=1S/C16H17ClN4O7/c1-7(22)25-4-10-12(26-8(2)23)13(27-9(3)24)16(28-10)21-6-20-11-14(17)18-5-19-15(11)21/h5-6,10,12-13,16H,4H2,1-3H3
• InChIKey: INOTYVPMBNDAFK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3,4-bis(acetyloxy)-5-(6-chloro-9H-purin-9-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [3,4-bis(acetyloxy)-5-(6-chloropurin-9-yl)oxolan-2-yl]methyl acetate
• Synonyms: 6-Chloro-9-β-D-ribofuranosyl-9H-purine 2',3',5'-Triacetate; 2',3',5'-Tri-O-acetyl-6-chloronebularine; 6-Chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine; 6-Chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine; NSC 281799; 2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside

Database IDs

• CAS Number: 5987-73-5
• PubChem SID: 164234761
• PubChem CID: 323069

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 0.29095736
• LogD (pH = 7.4): 0.2911008
• Log P: 0.29110265
• Molar Refractivity: 91.5023 cm^3
• Polarizability: 36.99937 Å^3
• Polar Surface Area: 131.73 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Colourless Crystalline Powder
• Melting Point: 161-162°C

DETAILS

Toronto Research Chemicals - T736250

2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside is a nucleoside compound with inhibitory activity on a rho-GTPase cell protein.

REFERENCES

• Mounetou., et al.: J. Med. Chem., 40, 2902 (1997)
• Panero, J., et al.: Biotech. Lett., 28, 1077 (1997)