EN450   Click here for help

GtoPdb Ligand ID: 12636

Synonyms: EN-450
Compound class: Synthetic organic
Comment: A chemoproteomic approach identified EN450 as a molecular glue type degrader of the (oncogenic) transcription factor NF-κB1 [1]. It binds covalently to an E2 ubiquitin-conjugating enzyme (most likely UBE2D1 and UBE2D4), and this initiates the formation of a ternary complex with NF-κB1 that ultimately promotes proteasome-dependent degradation of NF-κB1. This mechanism impairs viability of leukemia cells in vitro.

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 74.86
Molecular weight 288.75
XLogP 0.31
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C=CC(=O)NC1=CC(=CC=C1Cl)S(=O)(=O)N(C)C
Isomeric SMILES CN(C)S(=O)(=O)C1=CC=C(Cl)C(NC(=O)C=C)=C1
InChI InChI=1S/C11H13ClN2O3S/c1-4-11(15)13-10-7-8(5-6-9(10)12)18(16,17)14(2)3/h4-7H,1H2,2-3H3,(H,13,15)
InChI Key OXFXDOLAQBMOPH-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
N-[2-chloro-5-(dimethylsulfamoyl)phenyl]prop-2-enamide
Synonyms Click here for help
EN-450
Database Links Click here for help
CAS Registry No. 793719-01-4 (source: PubChem)
GtoPdb PubChem SID 479821426
PubChem CID 4877041
Search Google for chemical match using the InChIKey OXFXDOLAQBMOPH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OXFXDOLAQBMOPH
UniChem Compound Search for chemical match using the InChIKey OXFXDOLAQBMOPH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OXFXDOLAQBMOPH-UHFFFAOYSA-N

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MedChemExpress
EN450 (links to external site)
Cat. No. HY-49444