8-bromo-1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 119346
• Molecular Formular: C8H9BrN4O2
• Molecular Mass: 273.08666
• Monoisotopic Mass: 271.99088755
• SMILES: c12c(c(=O)n(c(=O)n2C)C)n(c(n1)Br)C
• Canonical SMILES: Brc1nc2c(n1C)c(=O)n(c(=O)n2C)C
• InChI: InChI=1S/C8H9BrN4O2/c1-11-4-5(10-7(11)9)12(2)8(15)13(3)6(4)14/h1-3H3
• InChIKey: YRLRORFORQUTKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-bromo-1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 8-bromo-1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione; 8-bromo-1,3,7-trimethylpurine-2,6-dione
• Synonyms: Xanthobin; Xantobin; 8-Bromocaffeine; Xanthobine; 8-bromo-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione

Database IDs

• CAS Number: 10381-82-5
• PubChem SID: 162107533
• PubChem CID: 64127

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.51842153
• LogD (pH = 7.4): 0.51842153
• Log P: 0.51842153
• Molar Refractivity: 57.456 cm^3
• Polarizability: 21.005934 Å^3
• Polar Surface Area: 58.44 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Adenosine A1, A2 receptor antagonist; Radiosensitizer

Product Information

• Application(s): Radiosensitizer

REFERENCES

• 1. Jacobson KA,Shi D,Gallo-Rodriguez C,Manning M Jr,Muller C,Daly JW,Neumeyer JL,Kiriasis L,Pfleiderer W (1993)
• Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors.
• Journal of medicinal chemistry 36, 2639-44