TMC-52B

Term ID

CHEBI:66239

Synonyms

(2R*,3R*)-3-{[(2S)-1-({4-[(3-aminopropyl)amino]butyl}amino)-3-(4-hydroxyphenyl)-1-oxopropan-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-{4-[(3-aminopropyl)amino]butyl}-L-tyrosinamide. It is a natural product, isolated from Gliocladium sp. F-2665. TMC-52B 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); IC50 values are 200 nM, 10 nM, and 7 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:8171475

Ontology

ChEBI ( EBI )

Relationships

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

epoxide monocarboxylic acid phenols 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 metabolite

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

Phenotype

Phenotype resulting from TMC-52B

Phenotype where environments contain TMC-52B

Phenotype modified by environments containing TMC-52B

Human Disease Model