GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

E7820   Click here for help

GtoPdb Ligand ID: 14234

Synonyms: E-7820
PDB Ligand
Compound class: Synthetic organic
Comment: E7820 was initially reported as an integrin α2 inhibitor [1,3-4]. It has subsequently been identified to act as a molecular glue class degrader that promotes proteasome-dependent degradation of the splicing factor RBM39 by the DCAF15 cullin RING ligase complex CRL4DCAF15 [2].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 114.16
Molecular weight 336.37
XLogP 0.65
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
Click here for help

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/)

✖
Canonical SMILES CC1=CC=C(C2=C1C(=CN2)C#N)NS(=O)(=O)C3=CC(=CC=C3)C#N
Isomeric SMILES CC1=C2C(=CNC2=C(C=C1)NS(=O)(=O)C3=CC=CC(=C3)C#N)C#N
InChI InChI=1S/C17H12N4O2S/c1-11-5-6-15(17-16(11)13(9-19)10-20-17)21-24(22,23)14-4-2-3-12(7-14)8-18/h2-7,10,20-21H,1H3
InChI Key LWGUASZLXHYWIV-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/)
References
1. Łasiñska I, Mackiewicz J. (2019)
Integrins as A New Target for Cancer Treatment.
Anticancer Agents Med Chem, 19 (5): 580-586. [PMID:30451118]
2. Faust TB, Yoon H, Nowak RP, Donovan KA, Li Z, Cai Q, Eleuteri NA, Zhang T, Gray NS, Fischer ES. (2020)
Structural complementarity facilitates E7820-mediated degradation of RBM39 by DCAF15.
Nat Chem Biol, 16 (1): 7-14. [PMID:31686031]
3. Hülskamp MD, Kronenberg D, Stange R. (2021)
The small-molecule protein ligand interface stabiliser E7820 induces differential cell line specific responses of integrin α2 expression.
BMC Cancer, 21 (1): 571. [PMID:34006252]
4. Matsumoto Y, Kage H, Morota M, Zokumasu K, Ando T, Maemura K, Watanabe K, Kawakami M, Hinata M, Ushiku T et al.. (2023)
Integrin alpha 2 is associated with tumor progression and postoperative recurrence in non-small cell lung cancer.
Jpn J Clin Oncol, 53 (1): 63-73. [PMID:36151049]