3-(1H-imidazol-5-ylmethylidene)-5-methoxy-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 153177
• Molecular Formular: C13H11N3O2
• Molecular Mass: 241.24534
• Monoisotopic Mass: 241.08512661
• SMILES: COc1ccc2c(c1)/C(=C\c1cnc[nH]1)/C(=O)N2
• Canonical SMILES: COc1ccc2c(c1)/C(=C\c1cnc[nH]1)/C(=O)N2
• InChI: InChI=1S/C13H11N3O2/c1-18-9-2-3-12-10(5-9)11(13(17)16-12)4-8-6-14-7-15-8/h2-7H,1H3,(H,14,15)(H,16,17)
• InChIKey: QNUKRWAIZMBVCU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(1H-imidazol-5-ylmethylidene)-5-methoxy-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 3-(3H-imidazol-4-ylmethylidene)-5-methoxy-1H-indol-2-one
• Synonyms: SU 9516

Database IDs

• CAS Number: 377090-84-1
• MDL Number: MFCD05865243
• PubChem SID: 162247316; 24278633
• PubChem CID: 57511258

CALCULATED PROPERTIES

• Acid pKa: 11.594566
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.39677572
• LogD (pH = 7.4): 0.8587423
• Log P: 0.90909
• Molar Refractivity: 69.0268 cm^3
• Polarizability: 25.148487 Å^3
• Polar Surface Area: 67.01 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~17 mg/mL; H2O: insoluble
• Apperance: brown crystalline

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CDK2(1017), PDGFRB(5159), SRC(6714)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H11N3O2

DETAILS

Sigma Aldrich - S1693

Application
Identified through a high-throughput screening with Cdk2. IC50=22 nM.
Biochem/physiol Actions
3-substituted indoline cyclin-dependent kinase-2 (Cdk2) inhibitor. Induces apoptosis in colon carcinoma cells.