1-[1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(pyrrolidin-1-yl)ethan-1-one

• ChemBase ID: 154898
• Molecular Formular: C18H21FN2O
• Molecular Mass: 300.3705432
• Monoisotopic Mass: 300.16379152
• SMILES: Cc1cc(c(n1c1ccc(cc1)F)C)C(=O)CN1CCCC1
• Canonical SMILES: Fc1ccc(cc1)n1c(C)cc(c1C)C(=O)CN1CCCC1
• InChI: InChI=1S/C18H21FN2O/c1-13-11-17(18(22)12-20-9-3-4-10-20)14(2)21(13)16-7-5-15(19)6-8-16/h5-8,11H,3-4,9-10,12H2,1-2H3
• InChIKey: JUWDSDKJBMFLHE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(pyrrolidin-1-yl)ethan-1-one
• IUPAC Traditional name: 1-[1-(4-fluorophenyl)-2,5-dimethylpyrrol-3-yl]-2-(pyrrolidin-1-yl)ethanone
• Synonyms: 1-[1-(4-Fluoro-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-pyrrolidin-1-yl-ethanone; IU1; IU1; 1-[1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(pyrrolidin-1-yl)ethan-1-one

Database IDs

• CAS Number: 314245-33-5
• MDL Number: MFCD01917473
• PubChem SID: 162249036
• PubChem CID: 675434

CALCULATED PROPERTIES

• Acid pKa: 16.99351
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6346332
• LogD (pH = 7.4): 3.1211221
• Log P: 3.3315325
• Molar Refractivity: 97.699 cm^3
• Polarizability: 33.385788 Å^3
• Polar Surface Area: 25.24 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white to light brown powder
• Hydrophobicity(logP): 4.73

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 61
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Proteasome

Product Information

• Purity: ≥98% (HPLC); 95%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H21FN2O

DETAILS

Sigma Aldrich - I1911

Biochem/physiol Actions
IU1 is an inhibitor of USP14, a deubiquitinating enzyme associated with the proteasome. The proteasome mediates the cellular degradation of oxidized, damaged and misfolded proteins which, if not removed, accumulate and become toxic to cells. Proteins targeted for proteasomal degradation are first ubiquitinated, with longer length ubiquitin chains interacting more strongly with the proteasome. Deubiquitinating enzymes (DUBs) such as USP14 interfere with the degradation process. IU1 inhibits USP14-mediated ubiquitin "chain-trimming" thereby enhancing substrate degradation by the proteasome. The compound may help to eliminate toxic proteins more effectively by enhancing their degradation.