3-nitro-N-(4-phenoxyphenyl)benzamide

• ChemBase ID: 154746
• Molecular Formular: C19H14N2O4
• Molecular Mass: 334.32546
• Monoisotopic Mass: 334.09535694
• SMILES: c1ccc(cc1)Oc1ccc(cc1)NC(=O)c1cccc(c1)[N+](=O)[O-]
• Canonical SMILES: O=C(c1cccc(c1)[N+](=O)[O-])Nc1ccc(cc1)Oc1ccccc1
• InChI: InChI=1S/C19H14N2O4/c22-19(14-5-4-6-16(13-14)21(23)24)20-15-9-11-18(12-10-15)25-17-7-2-1-3-8-17/h1-13H,(H,20,22)
• InChIKey: GDWKBKTVROCPNZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-nitro-N-(4-phenoxyphenyl)benzamide
• IUPAC Traditional name: 3-nitro-N-(4-phenoxyphenyl)benzamide
• Synonyms: 3-nitro-N-(4-phenoxyphenyl)-benzamide; ICA-105574

Database IDs

• CAS Number: 316146-57-3
• MDL Number: MFCD01596399
• PubChem SID: 162248884
• PubChem CID: 715924

CALCULATED PROPERTIES

• Acid pKa: 11.4297285
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.5054016
• LogD (pH = 7.4): 4.5053635
• Log P: 4.505402
• Molar Refractivity: 95.157 cm^3
• Polarizability: 35.120335 Å^3
• Polar Surface Area: 84.15 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: off-white to light tan powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36-43-50/53
• Safety Statements: 26-36/37-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319-H400
• GHS Precautionary statements: P273-P280-P305 + P351 + P338
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H14N2O4

DETAILS

Sigma Aldrich - I1661

Biochem/physiol Actions
hERG (Kv11.1) is a voltage-gated potassium channel with important cardiovascular function. Many potential and marketed drugs bind to and inhibit hERG function, causing prolongation of the electrocardiogram QT interval, which leads to life-threatening ventricular arrhythmias. Understanding of hERG function is critical for drug discovery and development. hERG exhibits a unique bell-shaped current-voltage relationship which is a result of very rapid inactivation of the channel upon voltage activation. ICA-105574 is a small molecule activator of hERG that binds to the channel to remove inactivation, thereby increasing peak current amplitude and shortening the action potential. It also modulates activation kinetics of the channel. ICA-105574 differs in efficacy, mechanism of action, and/or binding site from other known hERG activators and enhancers. This compound is a valuable tool for furthering understanding of hERG biophysics and physiology, expecially the structural transitions that occur during inactivation.