EG-011   Click here for help

GtoPdb Ligand ID: 12315

Compound class: Synthetic organic
Comment: EG-001's chemical structure was derived from that of the Bruton's tyrosine kinase (BTK) inhibitor ibrutinib [1], but it does not inhibit BTK or any other kinase. It has potent anti-proliferative and anti-tumour effects in vivo, against a wide range of lymphomas and leukaemias. A preprint has reported the molecular mechanism of EG-001 [2]; it acts to convert the auto-inhibited (closed) form of the Wiskott-Aldrich syndrome protein (WASp; WAS; P42768) to its activated allosteric conformation. WASp is one of a family of actin/cytoskeleton-regulating proteins that is expressed only in cells of haematopoietic origin. Activated WASp increases actin polymerisation (via interactions with the Arp2/3 complex), induces cytoskeleton reorganisation, and promotes cell death.

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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 0
Rotatable bonds 7
Topological polar surface area 86.43
Molecular weight 482.2
XLogP 4.59
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)N1CCCC(C1)n1c(=O)n(Cc2ccc(cc2)Oc2ccccc2)c2c(c1=O)nccc2
Isomeric SMILES C=CC(=O)N1CCCC(C1)n1c(=O)n(Cc2ccc(Oc3ccccc3)cc2)c2c(nccc2)c1=O
InChI InChI=1S/C28H26N4O4/c1-2-25(33)30-17-7-8-21(19-30)32-27(34)26-24(11-6-16-29-26)31(28(32)35)18-20-12-14-23(15-13-20)36-22-9-4-3-5-10-22/h2-6,9-16,21H,1,7-8,17-19H2
InChI Key JBKILBGEQHFIOB-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/)

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Similar Ligands Click here for help
frevecitinib
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tolebrutinib
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Targets
Bruton tyrosine kinase
tirabrutinib
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Targets
Bruton tyrosine kinase