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

• ChemBase ID: 164007
• Molecular Formular: C17H16Br2N4O2
• Molecular Mass: 468.14254
• Monoisotopic Mass: 465.96399977
• SMILES: c12c(c(c(=O)n(cc1)C)Cc1cc(c(c(c1)Br)OC)Br)nc(n2)NC
• Canonical SMILES: CNc1nc2c(n1)c(Cc1cc(Br)c(c(c1)Br)OC)c(=O)n(cc2)C
• InChI: InChI=1S/C17H16Br2N4O2/c1-20-17-21-13-4-5-23(2)16(24)10(14(13)22-17)6-9-7-11(18)15(25-3)12(19)8-9/h4-5,7-8H,6H2,1-3H3,(H,20,22)
• InChIKey: HAIJSTYZBPUVSG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 634151-15-8
• PubChem SID: 162258142
• PubChem CID: 11488186

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.7246523
• LogD (pH = 7.4): 2.1301577
• Log P: 2.9414577
• Molar Refractivity: 104.756 cm^3
• Polarizability: 38.895996 Å^3
• Polar Surface Area: 66.29 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C265500

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