TMC-52C

Term ID

CHEBI:66240

Synonyms

(2R*,3R*)-3-{[(2S)-1-({3-[(4-aminobutyl)amino]propyl}amino)-1-oxo-3-phenylpropan-2-yl]carbamoyl}oxirane-2-carboxylic acid

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).

References

PMID:9727388
Reaxys:8169550

Ontology

ChEBI ( EBI )

Relationships

is a type of: dicarboxylic acid monoamide epoxide monocarboxylic acid primary amino compound secondary amino compound

dicarboxylic acid monoamide epoxide monocarboxylic acid primary amino compound secondary amino compound Show first 5 Terms
has_role: antimicrobial agent cathepsin B inhibitor cathepsin L (EC 3.4.22.15) inhibitor EC 3.4.22.2 (papain) inhibitor fungal metabolite

antimicrobial agent cathepsin B inhibitor cathepsin L (EC 3.4.22.15) inhibitor EC 3.4.22.2 (papain) inhibitor fungal metabolite Show first 5 Terms

Phenotype

Phenotype resulting from TMC-52C

Phenotype where environments contain TMC-52C

Phenotype modified by environments containing TMC-52C

Human Disease / Model Data

Citations