2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-({1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl}amino)-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 165973
• Molecular Formular: C23H23N9O4
• Molecular Mass: 489.48662
• Monoisotopic Mass: 489.18730026
• SMILES: [nH]1c(nc2c(c1=O)nc(n2[C@H]1C[C@H]([C@H](O1)CO)O)Nc1nc2ncc(cc2n1C)c1ccccc1)N
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1c(nc2c1nc(N)[nH]c2=O)Nc1nc2c(n1C)cc(cn2)c1ccccc1
• InChI: InChI=1S/C23H23N9O4/c1-31-13-7-12(11-5-3-2-4-6-11)9-25-18(13)27-22(31)30-23-26-17-19(28-21(24)29-20(17)35)32(23)16-8-14(34)15(10-33)36-16/h2-7,9,14-16,33-34H,8,10H2,1H3,(H3,24,28,29,35)(H,25,26,27,30)/t14-,15-,16-/m1/s1
• InChIKey: UHVGJHQDVDVQHH-BZUAXINKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-({1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl}amino)-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-({1-methyl-6-phenylimidazo[4,5-b]pyridin-2-yl}amino)-1H-purin-6-one
• Synonyms: 2'-Deoxy-8-[(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)amino]guanosine; dG-C8-PhIP; N-(Deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo[4,5-β]pyridine

Database IDs

• CAS Number: 142784-25-6
• PubChem SID: 162260106
• PubChem CID: 29977094

CALCULATED PROPERTIES

• Acid pKa: 10.157412
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 1.2636085
• LogD (pH = 7.4): 1.2666184
• Log P: 1.2673374
• Molar Refractivity: 128.9025 cm^3
• Polarizability: 49.603176 Å^3
• Polar Surface Area: 177.73 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO
• Apperance: Brownish Yellow Solid
• Melting Point: >270°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D239630

The DNA adduct formed from N-Hydroxy-PHIP. Mutagenic nucleotide incorporation and hindered translocation by a food carcinogen C8-dG adduct in Sulfolobus solfataricus P2 DNA polymerase IV (Dpo4).

REFERENCES

• Frandsen, H., et al.: Carcinogenesis, 13, 4, 629 (1992)
• Lin, D., et al.: Chem. Res. Toxicol., 5, 691 (1992)
• Mizukami, S., et al.: Biochemistry, 45, 2772 (1992)