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CHEBI:167893 - SID 26681509

ChEBI IDCHEBI:167893
ChEBI NameSID 26681509
Stars
DefinitionA carbohydrazide that is L-tryptophan in which the amino and carboxy groups are substituted by tert-butoxycarbonyl and 2-({[2-(2-ethylanilino)-2-oxoethyl]sulfanyl}carbonyl)hydrazinyl groups, respectively. It is a potent and reversible inhibitor of human cathepsin L (IC50 = 56 nM).
Last Modified6 April 2021
SubmitterMargaret Duesbury
DownloadsMolfile
FormulaC27H33N5O5S
Net Charge0
Average Mass539.658
Monoisotopic Mass539.22024
SMILESCCc1ccccc1NC(=O)CSC(=O)NNC(=O)[C@H](Cc1cnc2ccccc12)NC(=O)OC(C)(C)C
InChIInChI=1S/C27H33N5O5S/c1-5-17-10-6-8-12-20(17)29-23(33)16-38-26(36)32-31-24(34)22(30-25(35)37-27(2,3)4)14-18-15-28-21-13-9-7-11-19(18)21/h6-13,15,22,28H,5,14,16H2,1-4H3,(H,29,33)(H,30,35)(H,31,34)(H,32,36)/t22-/m0/s1
InChIKeyOTIWAYTTYNFEKL-QFIPXVFZSA-N
Roles Classification
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).
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
Application:
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
ChEBI Ontology
Outgoing Relation(s)
SID 26681509 (CHEBI:167893) has role antiplasmodial drug (CHEBI:64915)
SID 26681509 (CHEBI:167893) has role cathepsin L (EC 3.4.22.15) inhibitor (CHEBI:70821)
SID 26681509 (CHEBI:167893) is a tert-butyl ester (CHEBI:140402)
SID 26681509 (CHEBI:167893) is a L-tryptophan derivative (CHEBI:47994)
SID 26681509 (CHEBI:167893) is a carbohydrazide (CHEBI:35363)
SID 26681509 (CHEBI:167893) is a secondary carboxamide (CHEBI:140325)
SID 26681509 (CHEBI:167893) is a thioester (CHEBI:51277)
IUPAC Name 
S-[2-(2-ethylanilino)-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate
Synonyms  Source
S-[2-(2-ethylanilino)-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazine-1-carbothioateIUPAC
tert-butyl N-[(2S)-1-[2-[2-(2-ethylanilino)-2-oxoethyl]sulfanylcarbonylhydrazinyl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamateChEBI
N-[(1,1-dimethylethoxy)carbonyl]-L-tryptophan-2-[[[2-[(2-ethylphenyl)amino]-2-oxoethyl]thio]carbonyl]hydrazideChEBI
SID26681509ChEBI
Registry NumbersSources
CAS:958772-66-2ChEBI
Citations