SID 26681509

CHEBI:167893 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

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). — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140325
Label unavailable CHEBI:140402
Label unavailable CHEBI:35363
Label unavailable CHEBI:47994
Label unavailable CHEBI:51277

Chemical structure

Computed structure properties
Molecular formula	C27H33N5O5S
Charge	0
Average mass	539.658 Da
Monoisotopic mass	539.22024 Da
Source	ChEBI
InChIKey	OTIWAYTTYNFEKL-QFIPXVFZSA-N

SMILES

CCc1ccccc1NC(=O)CSC(=O)NNC(=O)[C@H](Cc1cnc2ccccc12)NC(=O)OC(C)(C)C

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

Also called

S-[2-(2-ethylanilino)-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate (EXACT_SYNONYM)— chebi
N-[(1,1-dimethylethoxy)carbonyl]-L-tryptophan-2-[[[2-[(2-ethylphenyl)amino]-2-oxoethyl]thio]carbonyl]hydrazide (EXACT_SYNONYM)— chebi
S-[2-(2-ethylanilino)-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazine-1-carbothioate (EXACT_SYNONYM)— chebi
SID26681509 (EXACT_SYNONYM)— chebi
tert-butyl N-[(2S)-1-[2-[2-(2-ethylanilino)-2-oxoethyl]sulfanylcarbonylhydrazinyl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

cas:958772-66-2

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antiplasmodial drug CHEBI:64915

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:167893`	SID 26681509	`antibioticmech:chebi-0aa8494bfa`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (SID 26681509) · CultureMech · NaturalProductMech · PathwayMech · TraitMech