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CHEBI:66238 - TMC-52A

ChEBI IDCHEBI:66238
ChEBI NameTMC-52A
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-{3-[(4-aminobutyl)amino]propyl}-L-tyrosinamide. It is a natural product, isolated from Gliocladium sp. F-2665. TMC-52A 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 320 nM, 13 nM, and 44 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
FormulaC20H30N4O6
Net Charge0
Average Mass422.482
Monoisotopic Mass422.21653
SMILESNCCCCNCCCNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)C1OC1C(=O)O
InChIInChI=1S/C20H30N4O6/c21-8-1-2-9-22-10-3-11-23-18(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
InChIKeyPRCZPOBZJVCPKL-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-52A (CHEBI:66238) has role antimicrobial agent (CHEBI:33281)
TMC-52A (CHEBI:66238) has role cathepsin B inhibitor (CHEBI:64932)
TMC-52A (CHEBI:66238) has role cathepsin L (EC 3.4.22.15) inhibitor (CHEBI:70821)
TMC-52A (CHEBI:66238) has role EC 3.4.22.2 (papain) inhibitor (CHEBI:70822)
TMC-52A (CHEBI:66238) has role fungal metabolite (CHEBI:76946)
TMC-52A (CHEBI:66238) is a dicarboxylic acid monoamide (CHEBI:35735)
TMC-52A (CHEBI:66238) is a epoxide (CHEBI:32955)
TMC-52A (CHEBI:66238) is a monocarboxylic acid (CHEBI:25384)
TMC-52A (CHEBI:66238) is a phenols (CHEBI:33853)
TMC-52A (CHEBI:66238) is a primary amino compound (CHEBI:50994)
TMC-52A (CHEBI:66238) is a secondary amino compound (CHEBI:50995)
IUPAC Name 
(2R*,3R*)-3-{[(2S)-1-({3-[(4-aminobutyl)amino]propyl}amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoyl}oxirane-2-carboxylic acid
Registry NumbersSources
Reaxys:8171444Reaxys
Citations