trichostatin A   

GtoPdb Ligand ID: 7005

Abbreviated name: TSA
Compound class: Synthetic organic
Comment: Trichostatin A Inhibits Class I and II histone deacetylases (HDACs), but NOT the Class III HDACs (sirtuins (SIRTs) 1-7), so is therefore a useful probe of histone deacetylase activity. HDAC1 has been tagged as the drug's primary target for data retrieval purposes only and in no way infers that this is the only target of this drug.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 69.64
Molecular weight 302.16
XLogP 2.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES ONC(=O)C=CC(=CC(C(=O)c1ccc(cc1)N(C)C)C)C
Isomeric SMILES ONC(=O)/C=C/C(=C/[C@H](C(=O)c1ccc(cc1)N(C)C)C)/C
InChI InChI=1S/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)/b10-5+,12-11+/t13-/m1/s1
InChI Key RTKIYFITIVXBLE-QEQCGCAPSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
Database Links
CAS Registry No. 58880-19-6
ChEMBL Ligand CHEMBL99
DrugBank Ligand DB04297
GtoPdb PubChem SID 178103584
PubChem CID 444732
RCSB PDB Ligand TSN
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SynPHARM 79159 (in complex with histone deacetylase 6)
79163 (in complex with histone deacetylase 8)
Wikipedia Trichostatin_A

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Tocris
Trichostatin A
Cat. No. 1406