tucidinostat   Click here for help

GtoPdb Ligand ID: 8305

Synonyms: chidamide | CS-055 | CS055 | Epidaza® (China) | HBI-8000
Approved drug
tucidinostat is an approved drug (China)
Compound class: Synthetic organic
Comment: Tucidinostat (chidamide) is an orally active inhibitor of histone deacetylase (HDAC) enzymes [4]. It has some subtype selectivity for HDAC isoenzymes 1, 2, 3 and 10. Note that we show this compound with no specified stereochemistry.
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 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 97.11
Molecular weight 390.15
XLogP 2.47
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 O=C(C=Cc1cccnc1)NCc1ccc(cc1)C(=O)Nc1cc(F)ccc1N
Isomeric SMILES O=C(C=Cc1cccnc1)NCc1ccc(cc1)C(=O)Nc1cc(F)ccc1N
InChI InChI=1S/C22H19FN4O2/c23-18-8-9-19(24)20(12-18)27-22(29)17-6-3-16(4-7-17)14-26-21(28)10-5-15-2-1-11-25-13-15/h1-13H,14,24H2,(H,26,28)(H,27,29)
InChI Key WXHHICFWKXDFOW-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/)
Bioactivity Comments
Efficacy of chidamide has been measured using in vitro cytotoxicity, histone acetylation and signalling pathway activation assays. An IC50 or Ki for HDAC inhibition is not available. We have tagged HDAC1 as the pimary molecular target of this drug for data metrics purposes only, and in no way suggest that this in the only target of this drug.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
histone deacetylase 1 Primary target of this compound Hs Inhibitor Inhibition - - - 4
⤷ [4]
Ligand mentioned in the following text fields
3.5.1.- Histone deacetylases (HDACs) overview