Structure Database (LMSD)

Common Name
Trichostatin
Systematic Name
Synonyms
LM ID
LMPK01000055
Formula
C17H22N2O3
Exact Mass
Calculate m/z
302.163043
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Linear polyketides [PK01]

Biological Context

Trichostatin A is a potent, reversible inhibitor of class I, II, and IV histone deacetylases (HDACs). In human Jurkat T cells, trichostatin A arrests cell cycle progression in G1 and inhibits the activity of HDAC1 with an IC50 value of 70 nM.1 Trichostatin A selectively inhibits the removal of acetyl groups from the amino-terminal lysine residues of core histones, which modulates the access of transcription factors to the underlying genomic DNA.2

This information has been provided by Cayman Chemical

References

1. Taunton, J., Hassig, C.A., and Schreiber, S.L. A mammalian histone deacetylase related to the yeast transcriptional regulator Rpd3p. Science 272(5260), 408-411 (1996).
2. Hoshikawa, Y., Kwon, H.J., Yoshida, M., et al. Trichostatin A induces morphological changes and gelsolin expression by inhibiting histone deacetylase in human carcinoma cell lines. Exp. Cell Res. 214, 189-197 (1994).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Streptomyces hygroscopicus (#1912)
Actinomycetes (#1760)
A new antifungal antibiotic, trichostatin,
J Antibiot (Tokyo), 1976
Pubmed ID: 931784

String Representations

InChiKey (Click to copy)
RTKIYFITIVXBLE-QEQCGCAPSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1=CC(C(=O)[C@H](C)/C=C(\C)/C=C/C(=O)NO)=CC=C1N(C)C

Other Databases

Wikipedia
Trichostatin_A
CHEBI ID
46024
PubChem CID
444732
Cayman ID
89730
PDB ID
TSN
GuidePharm ID
7005

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 1
Aromatic Rings 1
Rotatable Bonds 6
Van der Waals Molecular Volume 309.29
Topological Polar Surface Area 69.64
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 2.75
Molar Refractivity 86.95

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Created at
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Updated at
18th May 2021