3-[1-(3-aminopropyl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 1713
• Molecular Formular: C24H22N4O2
• Molecular Mass: 398.45708
• Monoisotopic Mass: 398.17427596
• SMILES: Cn1c2c(c(C3=C(c4cn(CCCN)c5ccccc45)C(=O)NC3=O)c1)cccc2
• Canonical SMILES: NCCCn1cc(c2c1cccc2)C1=C(C(=O)NC1=O)c1cn(c2c1cccc2)C
• InChI: InChI=1S/C24H22N4O2/c1-27-13-17(15-7-2-4-9-19(15)27)21-22(24(30)26-23(21)29)18-14-28(12-6-11-25)20-10-5-3-8-16(18)20/h2-5,7-10,13-14H,6,11-12,25H2,1H3,(H,26,29,30)
• InChIKey: UQHKJRCFSLMWIA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[1-(3-aminopropyl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 3-[1-(3-aminopropyl)indol-3-yl]-4-(1-methylindol-3-yl)-1H-pyrrole-2,5-dione
• Synonyms: 3-[1-(3-Aminopropyl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione; Ro 31-7549; Ro 31-7549/001; Bisindolylmaleimide VIII; 3-[1-(3-Aminopropyl)-1h-Indol-3-Yl]-4-(1-Methyl-1h-Indol-3-Yl)-1h-Pyrrole-2,5-Dione

Database IDs

• CAS Number: 125313-65-7
• PubChem SID: 46508045; 160965169
• PubChem CID: 2403

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.613818
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.41742817
• LogD (pH = 7.4): -0.047081724
• Log P: 1.6893204
• Molar Refractivity: 117.0372 cm^3
• Polarizability: 46.937805 Å^3
• Polar Surface Area: 82.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.25
• LOG S: -4.1
• Solubility (Water): 3.18e-02 g/l

DETAILS

DrugBank - DB01946

Drug information: experimental

Toronto Research Chemicals - B448500

It is a potent inhibitor of protein kinase C (PKC) activity. Bisindolylmaleimide VIII (Bis VIII) has been previously shown to enhance Fas-mediated apoptosis through a protein kinase C-independent mechanism.

REFERENCES

• Emery, J., et al.: J. Biol. Chem., 273, 14363 (1998)
• Wiley, S., et al.: Immunity, 3, 673 (1998)
• MacFarlane, M., et al.: Biochem. J., 348, 93 (1998)