CAS 133052-90-1|3-{1-[3-(dimethylamino)propyl]-1H-indol-3-yl}-4-(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione|Rbt205 Inhibitor|3-{1-[3-(dimethylamino)propyl]indol-3-yl}-4-(1H-indol-3-yl)-1H-pyrro...

General Information

Structure

Molecular Formula

C₂₅H₂₄N₄O₂

Molecular Mass

412.48366

Exact Mass

412.18992603

Charge

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

Canonic Smiles

CN(CCCn1cc(c2c1cccc2)C1=C(C(=O)NC1=O)c1c[nH]c2c1cccc2)C

Isomeric Smiles

CN(C)CCCn1cc(c2c1cccc2)C1=C(C(=O)NC1=O)c1c2ccccc2[nH]c1

Calculated Properties

JChem

Acid pKa

9.989128

H Acceptors

H Donor

LogD (pH = 5.5)

-0.21542445

LogD (pH = 7.4)

0.95865685

Log P

2.578337

Molar Refractivity

122.2098

Polarizability

48.86856

Polar Surface Area

70.13

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

4.39

LOG S

-4.7

Solubility (Water)

8.24e-03 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

Rbt205 Inhibitor3-(N-[Dimethylamino]propyl-3-indolyl)-4-(3-indolyl)maleimideBISINDOLYLMALEIMIDE IGF 109203X3-[1-[3-(Dimethylamino)propyl]1H-indol-3-yl]-4-(1Hindol-3-yl)1H-pyrrole-2,5dioneGF109203XBisindolylmaleimide I

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem CID

PubChem SID

Registration numbers

Properties

Product Information

Purity

≥95%

≥90% (HPLC)

Certificate of Analysis

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Biological Source

synthetic

Empirical Formula (Hill Notation)

C25H24N4O2

Physical Property

Solubility

DMSO: soluble (~1 mg/ml)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB03777

Drug information: experimental

MP Biomedicals

02194138

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

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.

Molecule Details

References

PubChem Literature

From Data Sources

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

References

Bioactivity

PubChem BioAssay

Bioactivity