2-amino-5-[2-bromo-8-oxo(5,5,6,6-2H4)-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-ylidene]-4,5-dihydro-1H-imidazol-4-one

• ChemBase ID: 171470
• Molecular Formular: C11H10BrN5O2
• Molecular Mass: 324.1334
• Monoisotopic Mass: 323.00178659
• SMILES: c1c2c([nH]c1Br)C(=O)NCC/C/2=C/1\C(=O)N=C(N1)N
• Canonical SMILES: NC1=NC(=O)/C(=C/2\CCNC(=O)c3c2cc([nH]3)Br)/N1
• InChI: InChI=1S/C11H10BrN5O2/c12-6-3-5-4(7-10(19)17-11(13)16-7)1-2-14-9(18)8(5)15-6/h3,15H,1-2H2,(H,14,18)(H3,13,16,17,19)/b7-4-
• InChIKey: ATBAETXFFCOZOY-DAXSKMNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-5-[2-bromo-8-oxo(5,5,6,6-^2H₄)-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-ylidene]-4,5-dihydro-1H-imidazol-4-one
• IUPAC Traditional name: 2-amino-5-[2-bromo-8-oxo(5,5,6,6-^2H₄)-1H,7H-pyrrolo[2,3-c]azepin-4-ylidene]-1H-imidazol-4-one
• Synonyms: (4Z)-4-(2-Amino-1,5-dihydro-5-oxo-4H-imidazol-4-ylidene)-2-bromo-4,5,6,7-tetrahydro-pyrrolo[2,3-c]azepin-8(1H)-one-d4; (Z)-Hymenialdisine-d4; Hymenialdisine-d4

Database IDs

• CAS Number: 1185240-30-5
• PubChem SID: 164227380
• PubChem CID: 46781930

CALCULATED PROPERTIES

• Acid pKa: 11.058585
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.2247736
• LogD (pH = 7.4): -1.224588
• Log P: -1.2245009
• Molar Refractivity: 72.2733 cm^3
• Polarizability: 26.4678 Å^3
• Polar Surface Area: 112.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H998002

A potent inhibitor of a variety of kinases including MEK-1, GSK-3Β, and CKI. It also exhibits inhibition of the G2 cell cycle checkpoint at the micromolar concentrations. A marine sponge alkaloid, a natural product.

REFERENCES

• Cheetham, G., et al.: J. Biol. Chem., 277, 42419 (2002)
• Bain, J., et al.: Biochem. J., 371, 199 (2002)
• Sharma, V., et al.: Bioorg. Med. Chem. Lett., 14, 4319 (2002)
• Anamika, et al.: Proteins, 58, 180 (2002)
• Birault, V., et al.: Curr. Med. Chem., 13, 1