(2R,4R,5R)-2-{4-amino-6-chloro-1H-imidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 159940
• Molecular Formular: C11H13ClN4O4
• Molecular Mass: 300.69832
• Monoisotopic Mass: 300.0625326
• SMILES: n1c(cc2c(c1N)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O)Cl
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1cc(Cl)nc2N
• InChI: InChI=1S/C11H13ClN4O4/c12-6-1-4-7(10(13)15-6)14-3-16(4)11-9(19)8(18)5(2-17)20-11/h1,3,5,8-9,11,17-19H,2H2,(H2,13,15)/t5-,8+,9?,11-/m1/s1
• InChIKey: LIDWXUGNGGWNEU-QXBPSEORSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-{4-amino-6-chloro-1H-imidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-{4-amino-6-chloroimidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 6-Chloro-1-β-D-ribofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine; NSC 158900; 4-Amino-6-chloro-1-β-D-ribofuranosylimidazo[4,5-c]pyridine

Database IDs

• CAS Number: 40656-71-1
• PubChem SID: 162254075
• PubChem CID: 46780231

CALCULATED PROPERTIES

• Acid pKa: 12.4556
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.93712515
• LogD (pH = 7.4): -0.92848164
• Log P: -0.9283661
• Molar Refractivity: 70.2879 cm^3
• Polarizability: 28.001604 Å^3
• Polar Surface Area: 126.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Beige Solid
• Melting Point: 109-112°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A603514

Adenosine analog

REFERENCES

• Barbieri, D., et al.: Bioorg. Med. Chem. Lett., 8, 2533 (1998)