5-benzyl-3-[1-(phenylamino)ethylidene]pyrrolidine-2,4-dione

• ChemBase ID: 155069
• Molecular Formular: C19H18N2O2
• Molecular Mass: 306.35842
• Monoisotopic Mass: 306.13682783
• SMILES: C/C(=C/1\C(=O)C(NC1=O)Cc1ccccc1)/Nc1ccccc1
• Canonical SMILES: O=C1NC(C(=O)/C/1=C(/Nc1ccccc1)\C)Cc1ccccc1
• InChI: InChI=1S/C19H18N2O2/c1-13(20-15-10-6-3-7-11-15)17-18(22)16(21-19(17)23)12-14-8-4-2-5-9-14/h2-11,16,20H,12H2,1H3,(H,21,23)
• InChIKey: KWSXUGYAGMSUTN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-benzyl-3-[1-(phenylamino)ethylidene]pyrrolidine-2,4-dione
• IUPAC Traditional name: 5-benzyl-3-[1-(phenylamino)ethylidene]pyrrolidine-2,4-dione
• Synonyms: 3-[1-(Phenylamino)ethylidene]-5-(phenylmethyl)-2,4-pyrrolidinedione; NSC 239274; TN-16

Database IDs

• CAS Number: 33016-12-5
• PubChem SID: 162249207
• PubChem CID: 5354005

CALCULATED PROPERTIES

• Acid pKa: 11.510488
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.709197
• LogD (pH = 7.4): 2.7091677
• Log P: 2.7091978
• Molar Refractivity: 91.9768 cm^3
• Polarizability: 34.264652 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥17 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43-50/53
• Safety Statements: 36/37-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H400
• GHS Precautionary statements: P273-P280
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H18N2O2

DETAILS

Sigma Aldrich - T7580

Biochem/physiol Actions
Inhibitor of microtubule assembly
TN-16 is a synthetic compound that blocks the assembly, and promotes the dissociation of microtubules. Recently, TN-16 has been shown to prevent the b-TrCP-mediated degradation of the transcription factor Gli2, leading to the up-regulation of BMP-2 and supporting a role for microtubule formation in the regulation of bone formation.