pracinostat   Click here for help

GtoPdb Ligand ID: 8365

Synonyms: SB 939 | SB-939
Compound class: Synthetic organic
Comment: Pracinostat is an orally available, potent pan-HDAC inhibitor [3].
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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
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 CDK toolkit. 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 2
Rotatable bonds 11
Topological polar surface area 70.39
Molecular weight 358.24
XLogP 3.19
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCCCc1nc2c(n1CCN(CC)CC)ccc(c2)C=CC(=O)NO
Isomeric SMILES CCCCc1nc2c(n1CCN(CC)CC)ccc(c2)/C=C/C(=O)NO
InChI InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+
InChI Key JHDKZFFAIZKUCU-ZRDIBKRKSA-N
Bioactivity Comments
Pracinostat does not inhibit HDAC6 (IC50 1µM) or the class III isoenzyme SIRT1 (IC50 >100µM) [3]. We have included the four highest potency interactions in the table below, and have tagged HDAC10 as the primary target (as it is inhibited most by pracinostat) for data metrics purposes only. The IC50 values for the remaining HDACs range from 56-140nM and can be obtained from Novotny-Diermayr et al (2010) [3].
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 10 Primary target of this compound Hs Inhibitor Inhibition 7.4 pIC50 - 3
⤷ pIC50 7.4 (IC50 4x10-8 M) [3]
histone deacetylase 3 Hs Inhibitor Inhibition 7.4 pIC50 - 3
⤷ pIC50 7.4 (IC50 4.3x10-8 M) [3]
histone deacetylase 5 Hs Inhibitor Inhibition 7.3 pIC50 - 3
⤷ pIC50 7.3 (IC50 4.7x10-8 M) [3]
histone deacetylase 1 Hs Inhibitor Inhibition 7.3 pIC50 - 3
⤷ pIC50 7.3 (IC50 4.9x10-8 M) [3]