(8R)-3-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol

• ChemBase ID: 176274
• Molecular Formular: C11H16N4O4
• Molecular Mass: 268.26914
• Monoisotopic Mass: 268.11715501
• SMILES: c12c(N=CNC[C@H]1O)n(cn2)[C@H]1C[C@H]([C@H](O1)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1N=CNC[C@H]2O
• InChI: InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7-,8-,9-/m1/s1
• InChIKey: FPVKHBSQESCIEP-FNCVBFRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R)-3-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol
• IUPAC Traditional name: (8R)-3-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol
• Synonyms: (8R)-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydro-imidazo[4,5-d][1,3]diazepin-8-ol; (R)-; 2'-DCF; 2'-Deoxycoformycin; CI 825; CL 67310465; Cl 825; Co-V; Co-Vidarabine; Coforin; NSC 218321; NSC 247520; Nipent; PD-ADI; Vira A Deaminase Inhibitor; Pentostatin

Database IDs

• CAS Number: 53910-25-1
• PubChem SID: 164232184
• PubChem CID: 44283251

CALCULATED PROPERTIES

• Acid pKa: 13.062051
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.7633858
• LogD (pH = 7.4): -2.9345255
• Log P: -2.016391
• Molar Refractivity: 64.9814 cm^3
• Polarizability: 24.982864 Å^3
• Polar Surface Area: 112.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 225-227°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P227350

An adenosine deaminase inhibitor used as an anti-cancer therapeutic drug. Shown to be effective in the treatment of hairy cell leukemia as well as having use in the treatment of other types of cancer such as chronic lymphocytic leukemia.

REFERENCES

• Rogler-Brown, T. et al.: Biochem. Pharmacol., 28, 201 (1979)
• Johnston, J.B. et al.: J. Natl. Canvcer Inst., 80, 765 (1979)
• Fortune, A.F. et al.: Leuk. and Lymph., 51, 839 (1979)
• Robak, T. et al.: Drugs, 69, 2415 (1979)