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

• ChemBase ID: 165906
• 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)Nc1nc2cc3c(cc2n1C)ncc(n3)C)N
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1c(Nc2nc3c(n2C)cc2c(c3)nc(cn2)C)nc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C21H22N10O4/c1-8-6-23-9-4-12-11(3-10(9)24-8)25-20(30(12)2)29-21-26-16-17(27-19(22)28-18(16)34)31(21)15-5-13(33)14(7-32)35-15/h3-4,6,13-15,32-33H,5,7H2,1-2H3,(H,25,26,29)(H3,22,27,28,34)/t13-,14-,15-/m1/s1
• InChIKey: WVEUJGXCHJHAOX-RBSFLKMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-8-({1,6-dimethyl-1H-imidazo[4,5-g]quinoxalin-2-yl}amino)-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-8-({1,6-dimethylimidazo[4,5-g]quinoxalin-2-yl}amino)-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• Synonyms: 2-Deoxy-2,2-difluoro-4,5-O-(1-methylethylidene)-D-erythro-pentonic Acid Ethyl Ester; 2-Deoxy-2,2-difluoro-4,5-O-isopropylidene-D-erythro-pentonic Acid Ethyl Ester; 2'-Deoxy-8-[(3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-yl)amino]guanosine; dG-C8-MeIQx; N2-(Deoxyguanosin-8-yl)-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline

Database IDs

• CAS Number: 142038-31-1; 95058-92-7
• PubChem SID: 162260039
• PubChem CID: 71315448

CALCULATED PROPERTIES

• Acid pKa: 10.157431
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.39602292
• LogD (pH = 7.4): -0.038238578
• Log P: -0.030017376
• Molar Refractivity: 120.3343 cm^3
• Polarizability: 47.72599 Å^3
• Polar Surface Area: 190.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 220°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D239615

MeIQx-DNA adducts exist in human tissues and this adduct formation may be involved in human cancer development.

Toronto Research Chemicals - D232831

Intermediate in the preparation of ribose sugar derivatives.

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)