2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-{[3-(2H3)methyl-8-methyl-3H-imidazo[4,5-f]quinoxalin-2-yl]amino}-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 165972
• Molecular Formular: C21H22N10O4
• Molecular Mass: 478.46398
• Monoisotopic Mass: 478.18254923
• SMILES: [nH]1c(nc2c(c1=O)nc(n2[C@H]1C[C@@H]([C@H](O1)CO)O)Nc1nc2c3c(ccc2n1C)ncc(n3)C)N
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1c(nc2c1nc(N)[nH]c2=O)Nc1nc2c(n1C)ccc1c2nc(C)cn1
• InChI: InChI=1S/C21H22N10O4/c1-8-6-23-9-3-4-10-15(14(9)24-8)25-20(30(10)2)29-21-26-16-17(27-19(22)28-18(16)34)31(21)13-5-11(33)12(7-32)35-13/h3-4,6,11-13,32-33H,5,7H2,1-2H3,(H,25,26,29)(H3,22,27,28,34)/t11-,12+,13+/m0/s1
• InChIKey: ATNHUXHBJPMSBV-YNEHKIRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-{[3-(^2H₃)methyl-8-methyl-3H-imidazo[4,5-f]quinoxalin-2-yl]amino}-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-{[3-(^2H₃)methyl-8-methylimidazo[4,5-f]quinoxalin-2-yl]amino}-1H-purin-6-one
• Synonyms: 2'-Deoxy-8-[(3-(methyl-d3)-8-methyl-3H-imidazo[4,5-f]quinoxalin-2-yl)amino]guanosine; dG-C8-MeIQx-d3; N2-(Deoxyguanosin-8-yl)-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline-d3

Database IDs

• PubChem SID: 162260105
• PubChem CID: 71315485

CALCULATED PROPERTIES

• Acid pKa: 10.157411
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.030676842
• LogD (pH = 7.4): -0.030697571
• Log P: -0.030017376
• Molar Refractivity: 120.3343 cm^3
• Polarizability: 47.811867 Å^3
• Polar Surface Area: 190.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Brownish Yellow Solid
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D239617

Labelled dG-C8-MeIQx (D239615). MeIQx-DNA adducts exist in human tissues and this adduct formation may be involved in human cancer development.

REFERENCES

• Ohshima, H., et al.: Mutat. Res., 305, 253 (1994)
• Pais, P., et al.: J. Agric. Food Chem., 47, 1098 (1994)
• Lakshmi, V., et al.: Chem. Res. Toxicol., 18, 1038 (1994)