3-{8-[(dimethylamino)methyl]-6H,7H,8H,9H-pyrido[1,2-a]indol-10-yl}-4-(1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione hydrochloride

• ChemBase ID: 162324
• Molecular Formular: C28H29ClN4O2
• Molecular Mass: 489.00846
• Monoisotopic Mass: 488.19790387
• SMILES: C1(=C(C(=O)NC1=O)c1c2c(n3c1CC(CC3)CN(C)C)cccc2)c1c2c(n(c1)C)cccc2.Cl
• Canonical SMILES: CN(CC1CCn2c(C1)c(C1=C(C(=O)NC1=O)c1cn(c3c1cccc3)C)c1c2cccc1)C.Cl
• InChI: InChI=1S/C28H28N4O2.ClH/c1-30(2)15-17-12-13-32-22-11-7-5-9-19(22)24(23(32)14-17)26-25(27(33)29-28(26)34)20-16-31(3)21-10-6-4-8-18(20)21;/h4-11,16-17H,12-15H2,1-3H3,(H,29,33,34);1H
• InChIKey: HSPRASOZRZDELU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{8-[(dimethylamino)methyl]-6H,7H,8H,9H-pyrido[1,2-a]indol-10-yl}-4-(1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione hydrochloride
• IUPAC Traditional name: 3-{8-[(dimethylamino)methyl]-6H,7H,8H,9H-pyrido[1,2-a]indol-10-yl}-4-(1-methylindol-3-yl)-1H-pyrrole-2,5-dione hydrochloride
• Synonyms: 3-[8-[(Dimethylamino)methyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione Hydrochloride; Ro 31-0432; Bisindolylmaleimide XI Hydrochloride

Database IDs

• PubChem SID: 162256459
• PubChem CID: 11605551

CALCULATED PROPERTIES

• Acid pKa: 9.450728
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.22966433
• LogD (pH = 7.4): 1.2452636
• Log P: 2.964238
• Molar Refractivity: 134.8922 cm^3
• Polarizability: 53.50053 Å^3
• Polar Surface Area: 59.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B448530

Bisindolylmaleimide XI is a potent and selective cell-permeable protein kinase C (PKC) inhibitor. Studies reveal that inhibition of PKCα by Bisindolylmaleimide XI and other similar PKC inhibitors has been associated with enhanced cardiac contractility and

REFERENCES

• Wilkinson, S.E. et al.: Biochem. J., 294, 335 (1993)
• Liu, Q., Chen, X. et al.: . Circ. Res. 105, 194 (1993)
• Birchall, A.M. et al.: J. Pharmacol. Exp. Ther., 268, 922 (1993)