trichostatin A (CHEBI:46024)

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CHEBI:46024 - trichostatin A

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ChEBI Name	trichostatin A

ChEBI ID	CHEBI:46024

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:39145, CHEBI:46022

Supplier Information	ChemicalBook:CB0506416, ChemicalBook:CB9667842, ChemicalBook:CB8117582, eMolecules:492467, ZINC000001700075

Download	Molfile XML SDF

more structures >>

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reading 44 atoms

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44 atoms created

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Molfile expand

Wikipedia	License
Trichostatin A (TSA) is an organic compound that serves as an antifungal antibiotic and selectively inhibits the class I and II mammalian histone deacetylase (HDAC) families of enzymes, but not class III HDACs (i.e., sirtuins). However, there are recent reports of the interactions of this molecule with Sirt 6 protein. TSA inhibits the eukaryotic cell cycle during the beginning of the growth stage. TSA can be used to alter gene expression by interfering with the removal of acetyl groups from histones (histone deacetylases, HDAC) and therefore altering the ability of DNA transcription factors to access the DNA molecules inside chromatin. It is a member of a larger class of histone deacetylase inhibitors (HDIs or HDACIs) that have a broad spectrum of epigenetic activities. Thus, TSA has some potential as an anti-cancer drug. One suggested mechanism is that TSA promotes the expression of apoptosis-related genes, leading to cancerous cells surviving at lower rates, thus slowing the progression of cancer. Other mechanisms may include the activity of HDIs to induce cell differentiation, thus acting to "mature" some of the de-differentiated cells found in tumors. HDIs have multiple effects on non-histone effector molecules, so the anti-cancer mechanisms are truly not understood at this time. TSA inhibits HDACs 1, 3, 4, 6 and 10 with IC50 values around 20 nM. TSA represses IL (interleukin)-1β/LPS (lipopolysaccharide)/IFNγ (interferon γ)-induced nitric oxide synthase 2 (NOS2) expression in murine macrophage-like cells but increases LPS-stimulated NOS2 expression in murine N9 and primary rat microglial cells. Vorinostat is structurally related to trichostatin A and used to treat cutaneous T cell lymphoma.
Read full article at Wikipedia

Formula

C17H22N2O3

Net Charge

Average Mass

302.36826

Monoisotopic Mass

302.16304

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

InChIKey

RTKIYFITIVXBLE-QEQCGCAPSA-N

SMILES

C[C@@H](C(=O)c1ccc(cc1)N(C)C)\C=C(C)\C=C\C(=O)NO

Metabolite of Species	Details
Streptomyces hygroscopicus (NCBI:txid1912)	See: PubMed

Roles Classification
Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. EC 3.5.1.98 (histone deacetylase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98). antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via antibiotic antifungal agent ) antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via carbocyclic antibiotic )

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	trichostatin A (CHEBI:46024) has functional parent (R)-trichostatic acid (CHEBI:39158) trichostatin A (CHEBI:46024) has role bacterial metabolite (CHEBI:76969) trichostatin A (CHEBI:46024) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115) trichostatin A (CHEBI:46024) has role geroprotector (CHEBI:176497) trichostatin A (CHEBI:46024) is a antibiotic antifungal agent (CHEBI:86478) trichostatin A (CHEBI:46024) is a hydroxamic acid (CHEBI:24650) trichostatin A (CHEBI:46024) is a trichostatin (CHEBI:39146)

Incoming	trichostatin C (CHEBI:39147) has functional parent trichostatin A (CHEBI:46024) trichostatin D (CHEBI:39160) has functional parent trichostatin A (CHEBI:46024)

IUPAC Name

(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

Synonyms	Sources
(2E,4E,6R)-7-(4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide	ChemIDplus
TRICHOSTATIN A	PDBeChem
TSA	ChemIDplus

Manual Xrefs	Databases
C00016002	KNApSAcK
DB04297	DrugBank
HMDB0259177	HMDB
Trichostatin_A	Wikipedia
TSN	PDBeChem
View more database links

Registry Numbers	Types	Sources
5291761	Beilstein Registry Number	Beilstein
58880-19-6	CAS Registry Number	ChemIDplus

Citations

Last Modified

27 October 2021

CHEBI:46024 - trichostatin A

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