CHEBI:66240 - TMC-52C

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ChEBI Name TMC-52C
ChEBI ID CHEBI:66240
Definition An epoxide which is a carboxamide obtained by the formal condensation of one of the carboxy groups of oxirane-2,3-dicarboxylic acid with N-{3-[(4-aminobutyl)amino]propyl}-L-phenylalaninamide. It is a natural product, isolated from Gliocladium sp. F-2665. TMC-52C acts as an inhibitor of cysteine proteinases, particularly cathepsin B (EC 3.4.22.1), cathepsin L (EC 3.4.22.15), and papain (EC 3.4.22.2), with IC50 values of 460 nM, 10 nM, and 88 nM, respectively. The epoxide group has trans configuration but its exact stereochemistry is uncertain: it is either (2R,3R) or (2S,3S).
Stars This entity has been manually annotated by the ChEBI Team.
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Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): cathepsin B inhibitor
A cysteine protease inhibitor which inhibits cathepsin B (EC 3.4.22.1).
cathepsin L (EC 3.4.22.15) inhibitor
An EC 3.4.22.* (cysteine endopeptidase) inhibitor which interferes with the action of cathepsin L (EC 3.4.22.15).
EC 3.4.22.2 (papain) inhibitor
A cysteine protease inhibitor which inhibits papain (EC 3.4.22.2).
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Related Structures
TMC-52C is a Structural Derivative of
ammonia
Mass : 17.03056
Formula : H3N
16134 		oxirane
Mass : 44.05256
Formula : C2H4O
27561
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Relationship Types
is a
has part
is conjugate base of
is conjugate acid of
is tautomer of
is enantiomer of
has functional parent
has parent hydride
is substituent group from
has role
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