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

• ChemBase ID: 153740
• Molecular Formular: C26H26N4O3
• Molecular Mass: 442.50964
• Monoisotopic Mass: 442.20049071
• SMILES: CN(C)CCCn1cc(c2c1ccc(c2)OC)C1=C(C(=O)NC1=O)c1c[nH]c2c1cccc2
• Canonical SMILES: COc1ccc2c(c1)c(cn2CCCN(C)C)C1=C(C(=O)NC1=O)c1c[nH]c2c1cccc2
• InChI: InChI=1S/C26H26N4O3/c1-29(2)11-6-12-30-15-20(18-13-16(33-3)9-10-22(18)30)24-23(25(31)28-26(24)32)19-14-27-21-8-5-4-7-17(19)21/h4-5,7-10,13-15,27H,6,11-12H2,1-3H3,(H,28,31,32)
• InChIKey: LLJJDLHGZUOMQP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{1-[3-(dimethylamino)propyl]-5-methoxy-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]-5-methoxyindol-3-yl}-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione
• Synonyms: 3-[1-[3-(Dimethylamino)propyl]-5-methoxy-1H-indol-3-yl]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione; Gö 6983; Go 6983

Database IDs

• CAS Number: 133053-19-7
• MDL Number: MFCD04040031
• PubChem SID: 24894916; 162247879
• PubChem CID: 3499

CALCULATED PROPERTIES

• Acid pKa: 9.989258
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.37309587
• LogD (pH = 7.4): 0.8009858
• Log P: 2.420821
• Molar Refractivity: 128.673 cm^3
• Polarizability: 51.352863 Å^3
• Polar Surface Area: 79.36 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: red powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Target: PKC

Product Information

• Purity: ≥97%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C26H26N4O3

DETAILS

Sigma Aldrich - G1918

Biochem/physiol Actions
Protein kinase C (PKC) inhibitor that selectively inhibits several PKC isozymes (IC50 = 7 nM for PKCα and PKCβ; 6 nM for PKCγ; 10 nM for PKCδ; and 60 nM for PKCζ), but does not inhibit PKCμ (IC50 = 20 mM).