tubastatin A (CHEBI:94186)

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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	ChemicalBook:CB32667491, Selleckchem:tubastatin-a, ZINC000051951670

Download	Molfile XML SDF

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Formula

C20H21N3O2

Net Charge

Average Mass

335.400

Monoisotopic Mass

335.16338

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).

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

Citations

Last Modified

01 June 2016