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TMC-52D
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-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).

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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > enzyme inhibitor [CHEBI:23924] > protease inhibitor [CHEBI:37670] > cysteine protease inhibitor [CHEBI:64152] > cathepsin B inhibitor [CHEBI:64932] > TMC-52D [CHEBI:66241]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 enzyme inhibitor [CHEBI:23924] (825) 
 protease inhibitor [CHEBI:37670] (37) 
 cysteine protease inhibitor [CHEBI:64152] (11) 
 cathepsin B inhibitor [CHEBI:64932] (5) 
 TMC-52D [CHEBI:66241] (1)
 cathepsin L inhibitor [CHEBI:70821] (4) 
 TMC-52D [CHEBI:66241] (1)
 papain inhibitor [CHEBI:70822] (4) 
 TMC-52D [CHEBI:66241] (1)
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 TMC-52D [CHEBI:66241] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antibiotic [CHEBI:22582] (193) 
 TMC-52D [CHEBI:66241] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Fungi, Yeasts, Molds and Mildews (348) 
 Deuteromycotina (255) 
 Hyphomycetes (137) 
 Gliocladium (4)
07. Part of Biological Source of Chemical 
07. Part of Biological Source of Chemical
 unspecified structure [PO:0000004] (703)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 amide [CHEBI:32988] (1863) 
 primary amide [CHEBI:33256] (1586) 
 carboxamide [CHEBI:37622] (1381) 
 TMC-52D [CHEBI:66241] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 carboxamide [CHEBI:37622] (1381) 
 TMC-52D [CHEBI:66241] (1)
 organic amino compound [CHEBI:50047] (2472) 
 primary amino compound [CHEBI:50994] (104) 
 TMC-52D [CHEBI:66241] (1)
 secondary amino compound [CHEBI:50995] (110) 
 TMC-52D [CHEBI:66241] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 carboxamide [CHEBI:37622] (1381) 
 TMC-52D [CHEBI:66241] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 carboxamide [CHEBI:37622] (1381) 
 TMC-52D [CHEBI:66241] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 carboxamide [CHEBI:37622] (1381) 
 TMC-52D [CHEBI:66241] (1)
 organic amino compound [CHEBI:50047] (2472) 
 primary amino compound [CHEBI:50994] (104) 
 TMC-52D [CHEBI:66241] (1)
 secondary amino compound [CHEBI:50995] (110) 
 TMC-52D [CHEBI:66241] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 carboxamide [CHEBI:37622] (1381) 
 TMC-52D [CHEBI:66241] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 organic amino compound [CHEBI:50047] (2472) 
 primary amino compound [CHEBI:50994] (104) 
 TMC-52D [CHEBI:66241] (1)
 secondary amino compound [CHEBI:50995] (110) 
 TMC-52D [CHEBI:66241] (1)
 organic acid [CHEBI:64709] (3008) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 TMC-52D [CHEBI:66241] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 oxoacid [CHEBI:24833] (3119) 
 carbon oxoacid [CHEBI:35605] (3012) 
 carboxylic acid [CHEBI:33575] (3005) 
 monocarboxylic acid [CHEBI:25384] (1620) 
 TMC-52D [CHEBI:66241] (1)
ChEBI Compound Accession Identifier:   [CHEBI:66241]
ChEBI Compound Description:   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-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).
ChEBI Compound Identification Number:   66241
ChEBI InChI Value:   InChI=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
ChEBI InChIKey Value:   VMUJCCBLIGGNAX-GTPINHCMSA-N
ChEBI Compound Name:   TMC-52D
ChEBI SMILES Value:   NCCCNCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)C1OC1C(O)=O
ChEBI Substance ID:   160645217
ChEBI URL:   ChEBI:66241
ChemSpider ID:   28533025
Ontomatica Chemical Accession Key (OnChAKey):   VMUJCCBLIGGNAX_GTPINHCMSA_N_000_000000
PubChem Compound ID:   70678747