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CHEBI:66239 - TMC-52B

Default Structure
ChEBI IDCHEBI:66239
ChEBI NameTMC-52B
Stars
DefinitionAn 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).
Last Modified1 November 2012
DownloadsMolfile
FormulaC20H30N4O6
Net Charge0
Average Mass422.482
Monoisotopic Mass422.21653
SMILESNCCCNCCCCNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)C1OC1C(=O)O
InChIInChI=1S/C20H30N4O6/c21-8-3-10-22-9-1-2-11-23-18(26)15(12-13-4-6-14(25)7-5-13)24-19(27)16-17(30-16)20(28)29/h4-7,15-17,22,25H,1-3,8-12,21H2,(H,23,26)(H,24,27)(H,28,29)/t15-,16?,17?/m0/s1
InChIKeyMQQOZPYNKMAOLT-GTPINHCMSA-N
Species of MetaboliteComponentSourceComments
Gliocladium (ncbitaxon:62887) - PubMed (9727388) Strain: F 2665
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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).
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 3.4.22.2 (papain) inhibitor  A cysteine protease inhibitor which inhibits papain (EC 3.4.22.2).
cathepsin B inhibitor  A cysteine protease inhibitor which inhibits cathepsin B (EC 3.4.22.1).
ChEBI Ontology
Outgoing Relation(s)
TMC-52B (CHEBI:66239) has role antimicrobial agent (CHEBI:33281)
TMC-52B (CHEBI:66239) has role cathepsin B inhibitor (CHEBI:64932)
TMC-52B (CHEBI:66239) has role cathepsin L (EC 3.4.22.15) inhibitor (CHEBI:70821)
TMC-52B (CHEBI:66239) has role EC 3.4.22.2 (papain) inhibitor (CHEBI:70822)
TMC-52B (CHEBI:66239) has role metabolite (CHEBI:25212)
TMC-52B (CHEBI:66239) is a epoxide (CHEBI:32955)
TMC-52B (CHEBI:66239) is a monocarboxylic acid (CHEBI:25384)
TMC-52B (CHEBI:66239) is a phenols (CHEBI:33853)
TMC-52B (CHEBI:66239) is a primary amino compound (CHEBI:50994)
TMC-52B (CHEBI:66239) is a secondary amino compound (CHEBI:50995)
IUPAC Name 
(2R*,3R*)-3-{[(2S)-1-({4-[(3-aminopropyl)amino]butyl}amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoyl}oxirane-2-carboxylic acid
Registry NumbersSources
Reaxys:8171475Reaxys
Citations