tubastatin A   Click here for help

GtoPdb Ligand ID: 9702

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Tubastatin A is a selective histone deacetylase (HDAC) 6 inhibitor. It is claimed as example 6 in patent US8748451 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 57.5
Molecular weight 335.16
XLogP 2.99
No. Lipinski's rules broken 0
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Canonical SMILES ONC(=O)c1ccc(cc1)Cn1c2ccccc2c2c1CCN(C2)C
Isomeric SMILES ONC(=O)c1ccc(cc1)Cn1c2ccccc2c2c1CCN(C2)C
InChI InChI=1S/C20H21N3O2/c1-22-11-10-19-17(13-22)16-4-2-3-5-18(16)23(19)12-14-6-8-15(9-7-14)20(24)21-25/h2-9,25H,10-13H2,1H3,(H,21,24)
Bioactivity Comments
Tubastatin A exhibits >1000-fold selectivity for HDAC6 compared to all other isozymes excluding HDAC8 (58-fold selectivity) [1].
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 6 Primary target of this compound Hs Inhibitor Inhibition 7.8 pIC50 - 1
pIC50 7.8 (IC50 1.4x10-8 M) [1]
histone deacetylase 8 Hs Inhibitor Inhibition 6.1 pIC50 - 1
pIC50 6.1 (IC50 8.14x10-7 M) [1]
histone deacetylase 1 Hs Inhibitor Inhibition 4.9 pIC50 - 1
pIC50 4.9 (IC50 1.38x10-5 M) [1]