2-({2-amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-5-yl}amino)-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 160044
• Molecular Formular: C21H22N10O4
• Molecular Mass: 478.46398
• Monoisotopic Mass: 478.18254923
• SMILES: C1C([C@H](O[C@H]1n1c2c(nc1)c(=O)[nH]c(n2)Nc1c2c(c3c(c1)n(c(n3)N)C)nc(cn2)C)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1cnc2c1nc([nH]c2=O)Nc1cc2c(c3c1ncc(n3)C)nc(n2C)N
• InChI: InChI=1S/C21H22N10O4/c1-8-5-23-14-9(3-10-15(16(14)25-8)27-20(22)30(10)2)26-21-28-18-17(19(34)29-21)24-7-31(18)13-4-11(33)12(6-32)35-13/h3,5,7,11-13,32-33H,4,6H2,1-2H3,(H2,22,27)(H2,26,28,29,34)/t11?,12-,13-/m1/s1
• InChIKey: OYDMPQZHCQFIDK-VFRRUGBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({2-amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-5-yl}amino)-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-({2-amino-3,8-dimethylimidazo[4,5-f]quinoxalin-5-yl}amino)-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: N-(2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-5-yl)-2'-deoxyguanosine; N2-MeIQx-Deoxyguanosine; N-(2-Amino-3,8-dimethylimidazo[4,5-f]quinoxalin-5-yl) 2'-Deoxyguanosine

Database IDs

• CAS Number: 142038-30-0
• PubChem SID: 162254179
• PubChem CID: 71313210

CALCULATED PROPERTIES

• Acid pKa: 9.369281
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.93603164
• LogD (pH = 7.4): -0.8051976
• Log P: -0.7990413
• Molar Refractivity: 123.4082 cm^3
• Polarizability: 47.73191 Å^3
• Polar Surface Area: 190.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A606815

Heterocyclic amines, such as 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), are mutagenic/carcinogenic compounds formed during the cooking of protein-rich foods. An adduct of the potent dietary mutagen MeIQx.

REFERENCES

• Farmer, P., et al.: Arch. Toxicol., 60, 251 (1987)
• Chou, H., et al.: Cancer Res., 55, 525 (1987)
• Frantz, C., et al.: Carcinogenesis, 16, 367 (1987)