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

• ChemBase ID: 158869
• Molecular Formular: C18H20ClN5O8
• Molecular Mass: 469.8331
• Monoisotopic Mass: 469.10004031
• SMILES: n1c(nc2c(c1Cl)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1cnc2c1nc(NC(=O)C)nc2Cl)COC(=O)C
• InChI: InChI=1S/C18H20ClN5O8/c1-7(25)21-18-22-15(19)12-16(23-18)24(6-20-12)17-14(31-10(4)28)13(30-9(3)27)11(32-17)5-29-8(2)26/h6,11,13-14,17H,5H2,1-4H3,(H,21,22,23,25)/t11-,13-,14-,17-/m1/s1
• InChIKey: OVXYEIBYTBNNFE-LSCFUAHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(6-chloro-2-acetamido-9H-purin-9-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(6-chloro-2-acetamidopurin-9-yl)oxolan-2-yl]methyl acetate
• Synonyms: N-[6-Chloro-9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purin-2-yl]acetamide; 2-Acetamido-6-chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine

Database IDs

• CAS Number: 137896-02-7
• PubChem SID: 162253004
• PubChem CID: 11476924

CALCULATED PROPERTIES

• Acid pKa: 12.008876
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 0.20759845
• LogD (pH = 7.4): 0.20758887
• Log P: 0.20759903
• Molar Refractivity: 106.3113 cm^3
• Polarizability: 41.9547 Å^3
• Polar Surface Area: 160.83 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol
• Apperance: Light Orange Solid
• Melting Point: 71-73°C

Safety Information

• Storage Condition: Refrigerator

REFERENCES

• Matsuda, A., et al.: J. Med. Chem., 35, 241 (1992)