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CHEBI:94186 - tubastatin A

ChEBI IDCHEBI:94186
ChEBI Nametubastatin A
Stars
DefinitionA 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).
Last Modified1 June 2016
DownloadsMolfile
FormulaC20H21N3O2
Net Charge0
Average Mass335.407
Monoisotopic Mass335.16338
SMILESCN1CCc2c(c3ccccc3n2Cc2ccc(C(=O)NO)cc2)C1
InChIInChI=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)
InChIKeyGOVYBPLHWIEHEJ-UHFFFAOYSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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 Relation(s)
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  Source
N-hydroxy-4-[(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl)methyl]benzamideLINCS
tubastatin-aLINCS
Manual XrefsDatabases
LSM-4806LINCS
Registry NumbersSources
Reaxys:20796421Reaxys
CAS:1252003-15-8ChEBI
Citations