MC1568 (CHEBI:140475)

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ChEBI Name	MC1568

ChEBI ID	CHEBI:140475

Definition	A hydroxamic acid that is N-methylpyrrole which is substituted at positions 2 and 5 by 3-(hydroxyamino)-3-oxoprop-1-en-1-yl and 3-(m-fluorophenyl)-3-oxoprop-1-en-1-yl groups, respectively. It is a potent and selective inhibitor of class II (IIa) histone deacetylase (HDAC II).

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

Submitter	TheOtherDave

Supplier Information

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Formula

C17H15FN2O3

Net Charge

Average Mass

314.312

Monoisotopic Mass

314.10667

InChI

InChI=1S/C17H15FN2O3/c1-20-14(5-6-15(20)8-10-17(22)19-23)7-9-16(21)12-3-2-4-13(18)11-12/h2-11,23H,1H3,(H,19,22)

InChIKey

QQDIFLSJMFDTCQ-UHFFFAOYSA-N

SMILES

N1(C(=CC=C1C(=C(C(C2=CC(=CC=C2)F)=O)[H])[H])C(=C(C(=O)NO)[H])[H])C

Roles Classification
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	MC1568 (CHEBI:140475) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115) MC1568 (CHEBI:140475) is a aromatic ketone (CHEBI:76224) MC1568 (CHEBI:140475) is a enone (CHEBI:51689) MC1568 (CHEBI:140475) is a hydroxamic acid (CHEBI:24650) MC1568 (CHEBI:140475) is a monofluorobenzenes (CHEBI:83575) MC1568 (CHEBI:140475) is a pyrroles (CHEBI:26455)

IUPAC Name

3-{5-[3-(3-fluorophenyl)-3-oxoprop-1-en-1-yl]-1-methyl-1H-pyrrol-2-yl}-N-hydroxyacrylamide

Synonym	Source
MC-1568	ChEBI

Last Modified

26 March 2018

General Comment
2018-03-26	This compound was originally believed to be a 2,4-disubstituted N-methylpyrrole, but was later reassigned as the 2,5-disubstituted isomer (see J. Med. Chem., 2014, 57, 1132-1135).