1-methyl-N-{2-methyl-4-[2-(2-methylphenyl)diazen-1-yl]phenyl}-1H-pyrazole-5-carboxamide

• ChemBase ID: 154773
• Molecular Formular: C19H19N5O
• Molecular Mass: 333.38706
• Monoisotopic Mass: 333.15896025
• SMILES: Cc1ccccc1/N=N/c1ccc(c(c1)C)NC(=O)c1ccnn1C
• Canonical SMILES: Cc1cc(ccc1NC(=O)c1ccnn1C)/N=N/c1ccccc1C
• InChI: InChI=1S/C19H19N5O/c1-13-6-4-5-7-17(13)23-22-15-8-9-16(14(2)12-15)21-19(25)18-10-11-20-24(18)3/h4-12H,1-3H3,(H,21,25)
• InChIKey: LKTNEXPODAWWFM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-N-{2-methyl-4-[2-(2-methylphenyl)diazen-1-yl]phenyl}-1H-pyrazole-5-carboxamide
• IUPAC Traditional name: 2-methyl-N-{2-methyl-4-[2-(2-methylphenyl)diazen-1-yl]phenyl}pyrazole-3-carboxamide
• Synonyms: 1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phen yl-1H-pyrazole-5-carboxamide; 2-Methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)-amide; CH-223191

Database IDs

• CAS Number: 301326-22-7
• MDL Number: MFCD00377884
• PubChem SID: 162248911
• PubChem CID: 3091786

CALCULATED PROPERTIES

• Acid pKa: 11.522657
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.8457136
• LogD (pH = 7.4): 4.845697
• Log P: 4.8457284
• Molar Refractivity: 114.7738 cm^3
• Polarizability: 36.277466 Å^3
• Polar Surface Area: 71.64 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: orange powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H19N5O

DETAILS

Sigma Aldrich - C8124

Biochem/physiol Actions
CH-223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist. It inhibited TCDD-mediated nuclear translocation and DNA binding of AhR, and inhibited TCDD-induced luciferase activity with an IC50 of 30nM. Unlike some other AhR antagonists which display agonist activity at high concentrations, CH-223191 did not stimulate AhR-dependent transcription even at 100 micromolar. It is also specific for AhR, displaying no affinity for the estrogen receptor, as some other antagonists do.