3-{[2-(4-fluorophenyl)ethyl]amino}-1-methyl-4-(2-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 155055
• Molecular Formular: C22H20FN3O2
• Molecular Mass: 377.4115032
• Monoisotopic Mass: 377.15395512
• SMILES: Cc1c(c2ccccc2[nH]1)C1=C(C(=O)N(C1=O)C)NCCc1ccc(cc1)F
• Canonical SMILES: Fc1ccc(cc1)CCNC1=C(C(=O)N(C1=O)C)c1c(C)[nH]c2c1cccc2
• InChI: InChI=1S/C22H20FN3O2/c1-13-18(16-5-3-4-6-17(16)25-13)19-20(22(28)26(2)21(19)27)24-12-11-14-7-9-15(23)10-8-14/h3-10,24-25H,11-12H2,1-2H3
• InChIKey: ZKJAZFUFPPSFCO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[2-(4-fluorophenyl)ethyl]amino}-1-methyl-4-(2-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 3-{[2-(4-fluorophenyl)ethyl]amino}-1-methyl-4-(2-methyl-1H-indol-3-yl)pyrrole-2,5-dione
• Synonyms: 3-(4-Fluorophenylethylamino)-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione; IM-12

Database IDs

• CAS Number: 1129669-05-1
• MDL Number: MFCD20527313
• PubChem SID: 162249193
• PubChem CID: 25209788

CALCULATED PROPERTIES

• Acid pKa: 14.68175
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.986755
• LogD (pH = 7.4): 2.9867623
• Log P: 2.9867623
• Molar Refractivity: 106.9199 cm^3
• Polarizability: 40.86248 Å^3
• Polar Surface Area: 65.2 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥9 mg/mL
• Apperance: yellow-orange powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H20FN3O2

DETAILS

Sigma Aldrich - SML0084

Biochem/physiol Actions
IM-12 is a cell-permeable indolylmaleimide that acts as a Glycogen synthase kinase 3β (GSK-3β) inhibitor, activating downstream components of canonical Wnt signaling. IM-12 significantly increased β-catenin levels. When used to treat human neural progenitor cells, IM-12 promoted neuronal differentiation resulting in an increase of neuronal cells. It has an IC50 of 53 nM in an in vitro binding assay, compared with 92 nM for SB-216763 in the same assay condition.