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133052-90-1 molecular structure
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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 and InChIs

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

Cite this record

CBID:3426 http://www.chembase.cn/molecule-3426.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
133052-90-1
MDL Number
MFCD00236428
PubChem SID
160966865
46507495
PubChem CID
2396

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
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 cm3 Polarizability 48.86856 Å3
Polar Surface Area 70.13 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.39  LOG S -4.7 
Solubility (Water) 8.24e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: soluble (~1 mg/ml) expand Show data source
Storage Condition
2-8°C expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
40 expand Show data source
Safety Statements
36/37 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95% expand Show data source
≥90% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
synthetic expand Show data source
Empirical Formula (Hill Notation)
C25H24N4O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02194138 external link
Purity:>95%
Highly selective Protein Kinase C inhibitor.
DrugBank - DB03777 external link
Drug information: experimental
Sigma Aldrich - G2911 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Toullec, D., et al., J. Biol. Chem. , 266 : 15771, (1991).
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PATENTS

PATENTS

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INTERNET

INTERNET

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