4-[(3,5-dibromo-4-methoxyphenyl)methyl]-2-(methylamino)-5H,6H-imidazo[4,5-d]azepin-5-one

• ChemBase ID: 164008
• Molecular Formular: C16H14Br2N4O2
• Molecular Mass: 454.11596
• Monoisotopic Mass: 451.94834971
• SMILES: c12c(c(c(=O)[nH]cc1)Cc1cc(c(c(c1)Br)OC)Br)nc(n2)NC
• Canonical SMILES: CNc1nc2c(n1)c(Cc1cc(Br)c(c(c1)Br)OC)c(=O)[nH]cc2
• InChI: InChI=1S/C16H14Br2N4O2/c1-19-16-21-12-3-4-20-15(23)9(13(12)22-16)5-8-6-10(17)14(24-2)11(18)7-8/h3-4,6-7H,5H2,1-2H3,(H,20,23)(H,19,21,22)
• InChIKey: UCJCVNFPNDGXHS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(3,5-dibromo-4-methoxyphenyl)methyl]-2-(methylamino)-5H,6H-imidazo[4,5-d]azepin-5-one
• IUPAC Traditional name: 4-[(3,5-dibromo-4-methoxyphenyl)methyl]-2-(methylamino)-6H-imidazo[4,5-d]azepin-5-one
• Synonyms: 4-[(3,5-Dibromo-4-methoxyphenyl)methyl]-2-(methylamino)imidazo[4,5-d]azepin-5(6H)-one; Ceratamine B

Database IDs

• CAS Number: 634151-16-9
• PubChem SID: 162258143
• PubChem CID: 11201846

CALCULATED PROPERTIES

• Acid pKa: 11.456507
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.49655172
• LogD (pH = 7.4): 1.896356
• Log P: 2.7177818
• Molar Refractivity: 99.8593 cm^3
• Polarizability: 37.090775 Å^3
• Polar Surface Area: 75.08 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C265510

An antimitotic heterocyclic alkaloid isolated from the marine sponge Pseudoceratina sp. collected in Papua New Guinea.

REFERENCES

• Anderson, H., et al.: Cancer Chemother. Pharmacol., 39, 223 (1997)
• Roberge, M., et al.: Cancer Res., 60, 5052 (1997)
• Kavallaris, M., et al.: Drug Resist. Update, 4, 392 (1997)
• Rundle, N., et al.: J. Biol. Chem., 276, 48231 (1997)
• Nieman, J., et al.: J