2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-5-ol

• ChemBase ID: 171088
• Molecular Formular: C13H12N4O
• Molecular Mass: 240.26058
• Monoisotopic Mass: 240.10111102
• SMILES: c1(c(nc2c(c1)n(c(n2)N)C)O)c1ccccc1
• Canonical SMILES: Oc1nc2nc(n(c2cc1c1ccccc1)C)N
• InChI: InChI=1S/C13H12N4O/c1-17-10-7-9(8-5-3-2-4-6-8)12(18)15-11(10)16-13(17)14/h2-7H,1H3,(H3,14,15,16,18)
• InChIKey: VFOYOLOUKGRSJB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-5-ol
• IUPAC Traditional name: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridin-5-ol
• Synonyms: 1-Methyl-5-hydroxy-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine; 2-Amino-1,4-dihydro-1-methyl-6-phenyl-5H-imidazo[4,5-b]pyridin-5-one; 5-Hydroxy-PhIP

Database IDs

• CAS Number: 159471-46-2
• PubChem SID: 164226998
• PubChem CID: 71749254

CALCULATED PROPERTIES

• Acid pKa: 12.217019
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.1565387
• LogD (pH = 7.4): 2.3800895
• Log P: 2.3839538
• Molar Refractivity: 70.8854 cm^3
• Polarizability: 27.560476 Å^3
• Polar Surface Area: 76.96 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H950765

A carcinogenic metabolite of PhIP (A617000).

REFERENCES

• Turesky, R., et al.: Mutat. Res., 506, 187 (2002)
• Felton, J., et al.: Toxicology, 198, 135 (2002)
• Sugimura, T., et al.: Cancer Sci., 95, 290 (2002)