(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl}amino)oxane-2-carboxylic acid

• ChemBase ID: 160310
• Molecular Formular: C19H20N4O6
• Molecular Mass: 400.3853
• Monoisotopic Mass: 400.13828438
• SMILES: c1(cnc2c(c1)n(c(n2)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)c1ccccc1
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Nc2nc3c(n2C)cc(cn3)c2ccccc2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C19H20N4O6/c1-23-11-7-10(9-5-3-2-4-6-9)8-20-16(11)21-19(23)22-17-14(26)12(24)13(25)15(29-17)18(27)28/h2-8,12-15,17,24-26H,1H3,(H,27,28)(H,20,21,22)/t12-,13-,14+,15-,17+/m0/s1
• InChIKey: SQVPGYDPSLNFET-KSXIZUIISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl}amino)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({1-methyl-6-phenylimidazo[4,5-b]pyridin-2-yl}amino)oxane-2-carboxylic acid
• Synonyms: 1-Deoxy-1-[(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)amino]-β-D-glucopyranuronic Acid; PhIP-N-β-D-glucuronide; 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine N-β-D-Glucuronide

Database IDs

• CAS Number: 133084-70-5
• PubChem SID: 162254445
• PubChem CID: 71313317

CALCULATED PROPERTIES

• Acid pKa: 3.2575505
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.6753533
• LogD (pH = 7.4): -3.062022
• Log P: -0.6945925
• Molar Refractivity: 101.6139 cm^3
• Polarizability: 40.36759 Å^3
• Polar Surface Area: 149.96 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A617005

Carcinogenic metabolite of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) (A617000).

REFERENCES

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