3-{1-[3-(dimethylamino)propyl]-1H-indol-3-yl}-4-(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 3426
• Molecular Formular: C25H24N4O2
• Molecular Mass: 412.48366
• Monoisotopic Mass: 412.18992603
• SMILES: CN(C)CCCn1cc(c2c1cccc2)C1=C(C(=O)NC1=O)c1c2ccccc2[nH]c1
• Canonical SMILES: CN(CCCn1cc(c2c1cccc2)C1=C(C(=O)NC1=O)c1c[nH]c2c1cccc2)C
• InChI: InChI=1S/C25H24N4O2/c1-28(2)12-7-13-29-15-19(17-9-4-6-11-21(17)29)23-22(24(30)27-25(23)31)18-14-26-20-10-5-3-8-16(18)20/h3-6,8-11,14-15,26H,7,12-13H2,1-2H3,(H,27,30,31)
• InChIKey: QMGUOJYZJKLOLH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{1-[3-(dimethylamino)propyl]-1H-indol-3-yl}-4-(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 3-{1-[3-(dimethylamino)propyl]indol-3-yl}-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione; bisindolylmaleimide
• Synonyms: Rbt205 Inhibitor; GF109203X; BISINDOLYLMALEIMIDE I; 3-(N-[Dimethylamino]propyl-3-indolyl)-4-(3-indolyl)maleimide; 3-[1-[3-(Dimethylamino)propyl]1H-indol-3-yl]-4-(1Hindol-3-yl)1H-pyrrole-2,5dione; Bisindolylmaleimide I; GF 109203X

Database IDs

• CAS Number: 133052-90-1
• MDL Number: MFCD00236428
• PubChem SID: 160966865; 46507495
• PubChem CID: 2396

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.989128
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.21542445
• LogD (pH = 7.4): 0.95865685
• Log P: 2.578337
• Molar Refractivity: 122.2098 cm^3
• Polarizability: 48.86856 Å^3
• Polar Surface Area: 70.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.39
• LOG S: -4.7
• Solubility (Water): 8.24e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble (~1 mg/ml)

Safety Information

• Storage Condition: 2-8°C
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 36/37
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; ≥90% (HPLC)
• Biological Source: synthetic
• Empirical Formula (Hill Notation): C25H24N4O2

DETAILS

MP Biomedicals - 02194138

Purity:>95%
Highly selective Protein Kinase C inhibitor.

DrugBank - DB03777

Drug information: experimental

Sigma Aldrich - G2911

Biochem/physiol Actions
A potent and selective competitive inhibitor of protein kinase C (PKC) and of glycogen synthase kinase-3 (GSK-3). In certain cells, inhibition of PKC leads to an increase in autophagy. For PKC inhibition, typically used at a concentration of 0.1-10 μM.
A potent and selective competitive inhibitor of protein kinase C (PKC) and of glycogen synthase kinase-3 (GSK-3). Inhibits parathyroid hormone-induced Ca2+ resorption from isolated bone tissue, Staurosporine, another protein kinase inhibitor, actually enhanced Ca2+ resorption elicited by a number of agents, but GF109203X counteracted that enhancement.1
Quantity
For PKC inhibition, typically used at a concentration of 0.1-10 μM.

REFERENCES

• Toullec, D., et al., J. Biol. Chem. , 266 : 15771, (1991).