2-amino-4-{1-oxo-1H,2H,3H,4H,5H,10H-azepino[3,4-b]indol-5-ylidene}-4,5-dihydro-1H-imidazol-5-one

• ChemBase ID: 171471
• Molecular Formular: C15H13N5O2
• Molecular Mass: 295.29602
• Monoisotopic Mass: 295.10692468
• SMILES: c1ccc2c(c1)c1c([nH]2)C(=O)NCC/C/1=C/1\C(=O)NC(=N1)N
• Canonical SMILES: NC1=N/C(=C\2/CCNC(=O)c3c2c2ccccc2[nH]3)/C(=O)N1
• InChI: InChI=1S/C15H13N5O2/c16-15-19-11(14(22)20-15)8-5-6-17-13(21)12-10(8)7-3-1-2-4-9(7)18-12/h1-4,18H,5-6H2,(H,17,21)(H3,16,19,20,22)/b11-8-
• InChIKey: SMPPSGXPGZSJCP-FLIBITNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-{1-oxo-1H,2H,3H,4H,5H,10H-azepino[3,4-b]indol-5-ylidene}-4,5-dihydro-1H-imidazol-5-one
• IUPAC Traditional name: 2-amino-5-{1-oxo-2H,3H,4H,10H-azepino[3,4-b]indol-5-ylidene}-3H-imidazol-4-one
• Synonyms: 5-(2-Amino-5-oxo-1,5-dihydroimidazol-4-ylidene)-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one; Hymenialdisine Analogue #1

Database IDs

• CAS Number: 693222-51-4
• PubChem SID: 164227381
• PubChem CID: 9882612

CALCULATED PROPERTIES

• Acid pKa: 10.968279
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.33379224
• LogD (pH = 7.4): -0.33383247
• Log P: -0.33372787
• Molar Refractivity: 81.3962 cm^3
• Polarizability: 30.868979 Å^3
• Polar Surface Area: 112.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Butanol; DMSO
• Apperance: Light Yellow Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H998025

The indole derivative of Hymenialdisine, 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. This compound exhibits very potent inhibi

REFERENCES

• Sharma, V., and Tepe, J.J.: Bioorg. & Medicinal Chem. Letters, 14, 4319 (2004)
• Sharma, V., et al.: J. Med. Chem., 47, 3700 (2004)