CHEBI:16072 - maleimide

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ChEBI Name maleimide
ChEBI ID CHEBI:16072
Definition A cyclic dicarboximide in which the two carboacyl groups on nitrogen together with the nitogen itself form a 1H-pyrrole-2,5-dione structure.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6654, CHEBI:14560
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Formula C4H3NO2
Net Charge 0
Average Mass 97.07210
Monoisotopic Mass 97.016
InChI InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
InChIKey PEEHTFAAVSWFBL-UHFFFAOYSA-N
SMILES O=C1NC(=O)C=C1
Roles Classification
Biological Role(s): EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
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ChEBI Ontology
Outgoing maleimide (CHEBI:16072) has functional parent maleic acid (CHEBI:18300)
maleimide (CHEBI:16072) has parent hydride 1H-pyrrole (CHEBI:19203)
maleimide (CHEBI:16072) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
maleimide (CHEBI:16072) is a dicarboximide (CHEBI:35356)
maleimide (CHEBI:16072) is a maleimides (CHEBI:55417)
Incoming 3-(1H-indol-3-yl)-4-(1-{2-[(2S)-1-methylpyrrolidin-2-yl]ethyl}-1H-indol-3-yl)-1H-pyrrole-2,5-dione (CHEBI:41168) has functional parent maleimide (CHEBI:16072)
3-(1H-indol-3-yl)-4-{1-[(2R)-2-(1-methylpyrrolidin-2-yl)ethyl]-1H-indol-3-yl}-1H-pyrrole-2,5-dione (CHEBI:41097) has functional parent maleimide (CHEBI:16072)
N-(2-ferrocenylethyl)maleimide (CHEBI:30735) has functional parent maleimide (CHEBI:16072)
N-ethylmaleimide (CHEBI:44485) has functional parent maleimide (CHEBI:16072)
bisindolylmaleimide III (CHEBI:41059) has functional parent maleimide (CHEBI:16072)
dipymetitrone (CHEBI:131600) has functional parent maleimide (CHEBI:16072)
lurasidone (CHEBI:70735) has functional parent maleimide (CHEBI:16072)
Ro 31-8220 (CHEBI:38912) has functional parent maleimide (CHEBI:16072)
IUPAC Name
1H-pyrrole-2,5-dione
Synonyms Sources
2,5-Pyrroledione KEGG COMPOUND
Maleic imide ChemIDplus
Maleimide KEGG COMPOUND
Database Links Databases
C07272 KEGG COMPOUND
Maleimide Wikipedia
MALEIMIDE MetaCyc
View more database links
Registry Numbers Types Sources
106910 Reaxys Registry Number Reaxys
541-59-3 CAS Registry Number KEGG COMPOUND
541-59-3 CAS Registry Number ChemIDplus
541-59-3 CAS Registry Number NIST Chemistry WebBook
Citation Waiting for Citations Type Source
11961142 PubMed citation Europe PMC
Last Modified
22 March 2016