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EN67   Click here for help

GtoPdb Ligand ID: 12637

Synonyms: EN-67
Compound class: Synthetic organic
Comment: EN67 is a molecular glue type protein degrader [1]. It is a derivative of EN450, and like its predecsor EN67 forms a covalent bond with the allosteric C111 residue on UBE2D E2 ubiquitin-conjugating enzymes. Direct interaction with the UBE2D2 isozyme has been demonstrated.

EN67 has been conjudated to the BRD4 inhibitor (+)-JQ1, to generate a PROTAC class degrader (named NF90), which demonstrates that E2 ubiquitin ligase components can be recruited by such molecules to promote degradation of neo-substrates, in addition to the many previously reported recruiters that target E3 components of the ubiquitin-proteasome system.
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 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 59.92
Molecular weight 278.28
XLogP 1.25
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)NCC1CC(=NO1)C2=CC(=C(C=C2)OC)F
Isomeric SMILES COC1=CC=C(C=C1F)C2=NOC(CNC(=O)C=C)C2
InChI InChI=1S/C14H15FN2O3/c1-3-14(18)16-8-10-7-12(17-20-10)9-4-5-13(19-2)11(15)6-9/h3-6,10H,1,7-8H2,2H3,(H,16,18)
InChI Key YHMCRSNQSHQSSZ-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-[[3-(3-fluoro-4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl]prop-2-enamide
Synonyms Click here for help
EN-67
Database Links Click here for help
GtoPdb PubChem SID 479821427
PubChem CID 132362390
Search Google for chemical match using the InChIKey YHMCRSNQSHQSSZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YHMCRSNQSHQSSZ
UniChem Compound Search for chemical match using the InChIKey YHMCRSNQSHQSSZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YHMCRSNQSHQSSZ-UHFFFAOYSA-N