3-{[4-(dimethylamino)naphthalen-1-yl]methylidene}-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 153157
• Molecular Formular: C21H18N2O
• Molecular Mass: 314.38042
• Monoisotopic Mass: 314.14191321
• SMILES: CN(C)c1ccc(c2c1cccc2)/C=C/1\c2ccccc2NC1=O
• Canonical SMILES: O=C1Nc2c(/C/1=C\c1ccc(c3c1cccc3)N(C)C)cccc2
• InChI: InChI=1S/C21H18N2O/c1-23(2)20-12-11-14(15-7-3-4-9-17(15)20)13-18-16-8-5-6-10-19(16)22-21(18)24/h3-13H,1-2H3,(H,22,24)
• InChIKey: VFCXONOPGCDDBQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[4-(dimethylamino)naphthalen-1-yl]methylidene}-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 3-{[4-(dimethylamino)naphthalen-1-yl]methylidene}-1H-indol-2-one
• Synonyms: 3-(4-Dimethylaminonaphthalen-1-ylmethylene)-1,3-dihydroindol-2-one; MAZ51

Database IDs

• CAS Number: 163655-37-6
• MDL Number: MFCD04036983
• PubChem SID: 162247297; 24724533
• PubChem CID: 53230017

CALCULATED PROPERTIES

• Acid pKa: 11.312146
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.268081
• LogD (pH = 7.4): 4.36137
• Log P: 4.3627505
• Molar Refractivity: 100.6101 cm^3
• Polarizability: 38.234695 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble11 mg/mL
• Apperance: orange solid

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-37/38-41-51/53
• Safety Statements: 26-39-61
• GHS Pictograms: GHS05; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335-H411
• GHS Precautionary statements: P261-P273-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H18N2O

DETAILS

Sigma Aldrich - M1695

Biochem/physiol Actions
Cell-permeable VEGFR-3 inhibitor. At low concentration ≥ 5 μM), it specifically blocks VEGF-C- and VEGF-D-induced phosphorylation of VEGFR-3, but not VEGFR-2, in PAE cells. It partially blocks VEGFR-2 phosphorylation only at higher concentrations (50 μM).