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CHEBI:66241 - TMC-52D

ChEBI IDCHEBI:66241
ChEBI NameTMC-52D
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-phenylalaninamide. It is a natural product, isolated from Gliocladium sp. F-2665. TMC-52D 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 280 nM, 6 nM, and 49 nM, respectively. The epoxide group has trans configuration but its exact stereochemistry is uncertain: it is either (2R,3R) or (2S,3S).
Last Modified6 March 2014
DownloadsMolfile
FormulaC20H30N4O5
Net Charge0
Average Mass406.483
Monoisotopic Mass406.22162
SMILESNCCCNCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)C1OC1C(=O)O
InChIInChI=1S/C20H30N4O5/c21-9-6-11-22-10-4-5-12-23-18(25)15(13-14-7-2-1-3-8-14)24-19(26)16-17(29-16)20(27)28/h1-3,7-8,15-17,22H,4-6,9-13,21H2,(H,23,25)(H,24,26)(H,27,28)/t15-,16?,17?/m0/s1
InChIKeyVMUJCCBLIGGNAX-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).
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
EC 3.4.22.2 (papain) inhibitor  A cysteine protease inhibitor which inhibits papain (EC 3.4.22.2).
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
cathepsin B inhibitor  A cysteine protease inhibitor which inhibits cathepsin B (EC 3.4.22.1).
ChEBI Ontology
Outgoing Relation(s)
TMC-52D (CHEBI:66241) has role antimicrobial agent (CHEBI:33281)
TMC-52D (CHEBI:66241) has role cathepsin B inhibitor (CHEBI:64932)
TMC-52D (CHEBI:66241) has role cathepsin L (EC 3.4.22.15) inhibitor (CHEBI:70821)
TMC-52D (CHEBI:66241) has role EC 3.4.22.2 (papain) inhibitor (CHEBI:70822)
TMC-52D (CHEBI:66241) has role fungal metabolite (CHEBI:76946)
TMC-52D (CHEBI:66241) is a dicarboxylic acid monoamide (CHEBI:35735)
TMC-52D (CHEBI:66241) is a epoxide (CHEBI:32955)
TMC-52D (CHEBI:66241) is a monocarboxylic acid (CHEBI:25384)
TMC-52D (CHEBI:66241) is a primary amino compound (CHEBI:50994)
TMC-52D (CHEBI:66241) is a secondary amino compound (CHEBI:50995)
IUPAC Name 
(2R*,3R*)-3-{[(2S)-1-({4-[(3-aminopropyl)amino]butyl}amino)-1-oxo-3-phenylpropan-2-yl]carbamoyl}oxirane-2-carboxylic acid
Registry NumbersSources
Reaxys:8169487Reaxys
Citations