A cell-permeable bis-nitrobenzylidene-piperidinone that inhibits 19S deubiquitinase (DUB) activity (IC50 = 2.1 µM against Ub-AMC hydrolysis) in a reversible manner by directly targeting UCH37/UCH-L5 and USP14, while exhibiting little or no activity toward BAP1, UCH-L1, UCH-L3, USP2, USP7, USP8 (IC50 >100 µM), or POH1/PRN11. Dual UCH37 and USP14 inhibition by a-AP15 results in increased bulk cellular protein ubiquitination level and a blockage of protein proteasomal degradation (Effective conc. ≥770 nM in HCT-116 cells), exactly opposite to the effects seen with USP14 inhibition alone by IU1 (Cat. No. 662210). Effectively suppresses the growth of various tumors in mice (2.5 to 5 mg/kg, i.p. or s.c.) in vivo.

Specifications

Sinónimos

Especificaciones y pureza

≥97%(HPLC)

Mecanismos bioquímicos y fisiológicos

In Vitro：Purified 19S proteasomes (5 nM) are treated with indicated concentrations of b-AP15 and DUB activity is determined by detectionof Ub-AMC cleavage. The IC50 value (2.1±0.411 μM) is determined from log concentration curves in Graph Pad Prism using

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

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Pureza

≥97%(HPLC)

Nombres e identificadores

Pubchem Sid	504763648
Pubchem Sid Url	https://pubchem.ncbi.nlm.nih.gov/substance/504763648
Sonrisas canónicas	C=CC(=O)N1CC(=CC2=CC=C(C=C2)[N+](=O)[O-])C(=O)C(=CC3=CC=C(C=C3)[N+](=O)[O-])C1
IUPAC Name	(3E,5E)-3,5-bis[(4-nitrophenyl)methylidene]-1-prop-2-enoylpiperidin-4-one
InChIKey	GFARQYQBWJLZMW-JYFOCSDGSA-N
INCHI	1S/C22H17N3O6/c1-2-21(26)23-13-17(11-15-3-7-19(8-4-15)24(28)29)22(27)18(14-23)12-16-5-9-20(10-6-16)25(30)31/h2-12H,1,13-14H2/b17-11+,18-12+
Isómeros SMILES	C=CC(=O)N1C/C(=C\C2=CC=C(C=C2)[N+](=O)[O-])/C(=O)/C(=C/C3=CC=C(C=C3)[N+](=O)[O-])/C1
Peso molecular	419.39
Reaxy-Rn	28734978
Reaxys-RN_link_address	https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=28734978&ln=

Documentation

📋 Safety Data Sheet (SDS)

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✅ Certificate of Analysis (COA)

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Organoheterocyclic compounds
  - Clase Piperidines
    - Subclass N-acylpiperidines

Kingdom	Organic compounds
Superclass	Organoheterocyclic compounds
Clase	Piperidines
Subclass	N-acylpiperidines
Intermediate Tree Nodes	Not available
Direct Parent	N-acylpiperidines
Alternative Parents	Nitrobenzenes Nitroaromatic compounds Piperidinones Tertiary carboxylic acid amides Acrylic acids and derivatives Cyclic ketones Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
Molecular Framework	Aromatic heteromonocyclic compounds
Substituents	N-acyl-piperidine - Nitrobenzene - Nitroaromatic compound - Piperidinone - Monocyclic benzene moiety - Benzenoid - Acrylic acid or derivatives - Tertiary carboxylic acid amide - Carboxamide group - Ketone - C-nitro compound - Cyclic ketone - Organic nitro compound - Organic oxoazanium - Azacycle - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
Descripción	This compound belongs to the class of organic compounds known as n-acylpiperidines. These are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine.
External Descriptors	Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

Estructura 3D

Objetivos asociados (humanos)

A498 (42825 Activities)

Lot Number	Certificate Type	Fecha	Articulo
K2527162	Certificate of Analysis	Dec 13, 2025	N286763
J2129931	Certificate of Analysis	Aug 14, 2024	N286763
J2129932	Certificate of Analysis	Aug 14, 2024	N286763
J2129933	Certificate of Analysis	Aug 14, 2024	N286763

Solubilidad	insoluble in EtOH; insoluble in H2O
Peso molecular	419.400 g/mol
XLogP3	3.300
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	419.112 Da
Monoisotopic Mass	419.112 Da
Topological Polar Surface Area	129.000 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	750.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	2
Covalently-Bonded Unit Count	1

NSC 687852 - ≥97%(HPLC) , CAS No.1009817-63-3

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Descripción general

Specifications

Documentation

📋 Safety Data Sheet (SDS)

✅ Certificate of Analysis (COA)

📊 Datasheet

🔬 Specification Sheet

Advanced Data

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