CHEBI:167893 - SID 26681509

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ChEBI Name SID 26681509
ChEBI ID CHEBI:167893
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Supplier Information ChemicalBook:CB94798094, ChemicalBook:CB52622685, ChemicalBook:CB5274961, ChemicalBook:CB1252206, eMolecules:31226118, eMolecules:2736271, Selleckchem:fluticasone-propionate-Flonase-Veramyst, ZINC000003920027
Download Molfile XML SDF
Formula C27H33N5O5S
Net Charge 0
Average Mass 539.650
Monoisotopic Mass 539.22024
InChI InChI=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
InChIKey OTIWAYTTYNFEKL-QFIPXVFZSA-N
SMILES CCC1=C(NC(=O)CSC(=O)NNC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC(=O)OC(C)(C)C)C=CC=C1
Roles Classification
Biological Role(s): 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.
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).
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
N-[(1,1-dimethylethoxy)carbonyl]-L-tryptophan-2-[[[2-[(2-ethylphenyl)amino]-2-oxoethyl]thio]carbonyl]hydrazide ChEBI
S-[2-(2-ethylanilino)-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazine-1-carbothioate IUPAC
SID26681509 ChEBI
tert-butyl N-[(2S)-1-[2-[2-(2-ethylanilino)-2-oxoethyl]sulfanylcarbonylhydrazinyl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate ChEBI
Registry Number Type Source
958772-66-2 CAS Registry Number ChEBI
Citations Types Sources
18060772 PubMed citation Europe PMC
18403718 PubMed citation Europe PMC
18499453 PubMed citation Europe PMC
22589721 PubMed citation Europe PMC
26349060 PubMed citation Europe PMC
33774649 PubMed citation SUBMITTER
Last Modified
06 April 2021