1-[3-(dimethylamino)propyl]-5-fluoro-3-[(5-methoxy-1H-indol-3-yl)methylidene]-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 153277
• Molecular Formular: C23H24FN3O2
• Molecular Mass: 393.4539632
• Monoisotopic Mass: 393.18525524
• SMILES: CN(C)CCCN1c2ccc(cc2/C(=C/c2c[nH]c3c2cc(cc3)OC)/C1=O)F
• Canonical SMILES: COc1ccc2c(c1)c(c[nH]2)/C=C\1/c2cc(F)ccc2N(C1=O)CCCN(C)C
• InChI: InChI=1S/C23H24FN3O2/c1-26(2)9-4-10-27-22-8-5-16(24)12-19(22)20(23(27)28)11-15-14-25-21-7-6-17(29-3)13-18(15)21/h5-8,11-14,25H,4,9-10H2,1-3H3
• InChIKey: CQNOITUXWKRVMB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3-(dimethylamino)propyl]-5-fluoro-3-[(5-methoxy-1H-indol-3-yl)methylidene]-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 1-[3-(dimethylamino)propyl]-5-fluoro-3-[(5-methoxy-1H-indol-3-yl)methylidene]indol-2-one
• Synonyms: (Z)-5-Fluoro-1-(3′-dimethylamino)propyl-3-[(5′-methoxyindol-3-ylidene)methyl]-indolin-2-one; 1-[3-(dimethylamino)propyl]-5-fluoro-1,3-dihydro-3-[(5-methoxy-1H-indol-3-yl)methylene]-2H-Indol-2-one; Z36

Database IDs

• PubChem SID: 162247416
• PubChem CID: 71311634

CALCULATED PROPERTIES

• Acid pKa: 16.24457
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.031830322
• LogD (pH = 7.4): 1.3999835
• Log P: 3.2916932
• Molar Refractivity: 113.4978 cm^3
• Polarizability: 43.915257 Å^3
• Polar Surface Area: 48.57 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15 mg/mL
• Apperance: light yellow to dark yellow powder

Safety Information

• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H24FN3O2

DETAILS

Sigma Aldrich - SML0176

Biochem/physiol Actions
Z36 is a Bcl-XL inhibitor that induces autophagic cell death independent of apoptosis which distinguishes it from other Bcl-XL and Bcl-2 inhibitors that induce cancer cell death mainly through apoptosis. Z36 binds to the BH3 binding groove of BCL-XL where it is thought to induce autophagy through blocking the interaction between Bcl-XL/Bcl2 and Beclin 1.