tazemetostat   Click here for help

GtoPdb Ligand ID: 7011

Synonyms: E-7438 | EPZ 6438 | EPZ-6438 | EPZ6438 | Tazverik®
Approved drug
tazemetostat is an approved drug (FDA (2020))
Compound class: Synthetic organic
Comment: Tazemetostat is an oral, potent, first-in-class inhibitor of the histone methyltransferase, enhancer of zeste 2 polycomb repressive complex 2 subunit (EZH2) that was developed by Epizyme as anovel drug for the treatment of solid tumours and lymphomas with speciific genetic alterations. Link to Epizyme's tazemetostat webpage here.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

tazemetostat is commercially available from our sponsors

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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Click here for structure editor
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 7
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 86.9
Molecular weight 572.34
XLogP 5.61
No. Lipinski's rules broken 1

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 CCN(c1cc(cc(c1C)C(=O)NCc1c(C)cc([nH]c1=O)C)c1ccc(cc1)CN1CCOCC1)C1CCOCC1
Isomeric SMILES CCN(c1cc(cc(c1C)C(=O)NCc1c(C)cc([nH]c1=O)C)c1ccc(cc1)CN1CCOCC1)C1CCOCC1
InChI InChI=1S/C34H44N4O4/c1-5-38(29-10-14-41-15-11-29)32-20-28(27-8-6-26(7-9-27)22-37-12-16-42-17-13-37)19-30(25(32)4)33(39)35-21-31-23(2)18-24(3)36-34(31)40/h6-9,18-20,29H,5,10-17,21-22H2,1-4H3,(H,35,39)(H,36,40)
InChI Key NSQSAUGJQHDYNO-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. Hornick JL, Dal Cin P, Fletcher CD. (2009)
Loss of INI1 expression is characteristic of both conventional and proximal-type epithelioid sarcoma.
Am J Surg Pathol, 33 (4): 542-50. [PMID:19033866]
2. Knutson SK, Warholic NM, Wigle TJ, Klaus CR, Allain CJ, Raimondi A, Porter Scott M, Chesworth R, Moyer MP, Copeland RA et al.. (2013)
Durable tumor regression in genetically altered malignant rhabdoid tumors by inhibition of methyltransferase EZH2.
Proc Natl Acad Sci USA, 110 (19): 7922-7. [PMID:23620515]
3. Patil PA, Lombardo K, Sturtevant A, Mangray S, Yakirevich E. (2018)
Loss of Expression of a Novel Chromatin Remodeler SMARCA1 in Soft Tissue Sarcoma.
J Cytol Histol, 9 (6): 524. DOI: 10.4172/2157-7099.1000524 [PMID:31093468]