1-[4-(phenylamino)naphthalen-1-yl]-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 153104
• Molecular Formular: C20H14N2O2
• Molecular Mass: 314.33736
• Monoisotopic Mass: 314.1055277
• SMILES: c1ccc(cc1)Nc1ccc(c2c1cccc2)N1C(=O)C=CC1=O
• Canonical SMILES: O=C1C=CC(=O)N1c1ccc(c2c1cccc2)Nc1ccccc1
• InChI: InChI=1S/C20H14N2O2/c23-19-12-13-20(24)22(19)18-11-10-17(15-8-4-5-9-16(15)18)21-14-6-2-1-3-7-14/h1-13,21H
• InChIKey: DUFUXAHBRPMOFG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(phenylamino)naphthalen-1-yl]-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 1-[4-(phenylamino)naphthalen-1-yl]pyrrole-2,5-dione
• Synonyms: 1-(4-Anilino-1-naphtyl)-3-pyrroline-2,5-dione; 1-[4-(phenylamino)naphthalen-1-yl]-2,5-dihydro-1H-pyrrole-2,5-dione; 1-[4-(phenylamino)naphthyl]-1H-pyrrole-2,5-dione; ANM; N-(1-Anilinonaphthyl-4)-maleimide; N-(1-Anilinophenyl)maleimide; N-[4-(Phenylamino)-1-naphtyl]maleimide; N-(4-Anilino-1-naphthyl)maleimide

Database IDs

• CAS Number: 50539-45-2
• EC Number: 256-618-8
• MDL Number: MFCD00042694
• Beilstein Number: 1487865
• PubChem SID: 24846431; 162247244
• PubChem CID: 121973

CALCULATED PROPERTIES

• Acid pKa: 19.300749
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.6751323
• LogD (pH = 7.4): 3.6751342
• Log P: 3.6751342
• Molar Refractivity: 92.9621 cm^3
• Polarizability: 36.259148 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

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

Product Information

• Purity: ≥99.0% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C20H14N2O2

DETAILS

Sigma Aldrich - 10420

Other Notes
Fluorescent hydrophobic probe for thiol groups in proteins; Review7,8
Application
ANM has been used to label muscle fibers to determine the conformational changes between the rigor state and the relaxed state 1>. This probe provides an excellent signal for monitoring changes in environment during protein refolding 2 because it′s fluorescence quantum yield is highly sensitive to solvent polarity 3. A non fluorescent compound which becomes strongly fluorescent upon selective reaction wih thiols 3. ANM can be used to monitor heterodimerization of the α and β subunits of luciferase. 2. Applied to monitor protein interactions using FRET 4 and protein conformational changes using nanosecond time-resolved fluorescence experiments 5. This probe has been used to determine the reactivity of the sulphydrl groups in tryptophanse 6.