CHEBI:94186 - tubastatin A

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ChEBI Name tubastatin A
ChEBI ID CHEBI:94186
Definition A pyridoindole that is 1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indole which is substituted on the tetrahydropyridine nitrogen by a methyl group and on the indole nitrogen by a p-[N-(hydroxy)aminocarbonyl]benzyl group. It is a histone deacetylase 6 (HDAC6) inhibitor that is selective against all the other isozymes (1000-fold) except HDAC8 (57-fold).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H21N3O2
Net Charge 0
Average Mass 335.400
Monoisotopic Mass 335.163
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)
InChIKey GOVYBPLHWIEHEJ-UHFFFAOYSA-N
SMILES CN1CCC2=C(C1)C3=CC=CC=C3N2CC4=CC=C(C=C4)C(=O)NO
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tubastatin A (CHEBI:94186) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115)
tubastatin A (CHEBI:94186) is a hydroxamic acid (CHEBI:24650)
tubastatin A (CHEBI:94186) is a pyridoindole (CHEBI:48888)
tubastatin A (CHEBI:94186) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
N-hydroxy-4-[(2-methyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide
Synonyms Sources
N-hydroxy-4-[(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl)methyl]benzamide LINCS
tubastatin-a LINCS
Manual Xref Database
LSM-4806 LINCS
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Registry Numbers Types Sources
1252003-15-8 CAS Registry Number ChEBI
20796421 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20614936 PubMed citation Europe PMC
23541634 PubMed citation Europe PMC
24844691 PubMed citation Europe PMC
24909686 PubMed citation Europe PMC
25108326 PubMed citation Europe PMC
25921924 PubMed citation Europe PMC
26647018 PubMed citation Europe PMC
26790818 PubMed citation Europe PMC
Last Modified
01 June 2016