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

• ChemBase ID: 165470
• Molecular Formular: C11H14N4O4
• Molecular Mass: 266.25326
• Monoisotopic Mass: 266.10150495
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(ncc2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1ccnc2N
• InChI: InChI=1S/C11H14N4O4/c12-10-7-5(1-2-13-10)15(4-14-7)11-9(18)8(17)6(3-16)19-11/h1-2,4,6,8-9,11,16-18H,3H2,(H2,12,13)/t6-,8?,9+,11-/m1/s1
• InChIKey: DBZQFUNLCALWDY-DZNMIZDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-{4-amino-1H-imidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,5R)-2-{4-aminoimidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 4-Amino-1-(β-D-ribofuranosyl)-1H-imidazo(4,5)-pyridine; 3-Deaza Adenosine

Database IDs

• CAS Number: 6736-58-9
• PubChem SID: 162259603
• PubChem CID: 59036309

CALCULATED PROPERTIES

• Acid pKa: 12.455601
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.7644441
• LogD (pH = 7.4): -1.7527436
• Log P: -1.752588
• Molar Refractivity: 64.4218 cm^3
• Polarizability: 26.000923 Å^3
• Polar Surface Area: 126.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White to Off-White SolidSolid
• Melting Point: 228-229°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D200875

Possesses antiviral activity. It is an inhibitor of leukocyte adhesion to TNF-treated endothelial cells.

REFERENCES

• Jurgensen, C.H., et al.: J. Immunol., 144, 653 (1990)
• Flexner, C.W., et al.: Lancet, 339, 438 (1990)
• Reddy, M., et al.: Prot. Sci., 17 2134 (1990)