N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide

CHEBI:152560 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A secondary carboxamide resulting from the formal condensation of the carboxy group of 1H-indole-2-carboxylic acid with the primary amino group of 3-cyclohexyl-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-alaninamide. It is an inhibitor of SARS coronavirus main proteinase and inhibits SARS-CoV-2 replication in cell culture (EC50 = 0.53 μM). — 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.

CHEBI:140325 CHEBI:140325
CHEBI:17478 CHEBI:17478
CHEBI:25676 CHEBI:25676
CHEBI:46921 CHEBI:46921
CHEBI:74223 CHEBI:74223

Chemical structure

Computed structure properties
Molecular formula	C25H32N4O4
Charge	0
Average mass	452.555 Da
Monoisotopic mass	452.24236 Da
Source	ChEBI
InChIKey	HPKJGHVHQWJOOT-ZJOUEHCJSA-N

SMILES

[H]C(=O)[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](CC1CCCCC1)NC(=O)c1cc2ccccc2n1

InChI

InChI=1S/C25H32N4O4/c30-15-19(13-18-10-11-26-23(18)31)27-24(32)21(12-16-6-2-1-3-7-16)29-25(33)22-14-17-8-4-5-9-20(17)28-22/h4-5,8-9,14-16,18-19,21,28H,1-3,6-7,10-13H2,(H,26,31)(H,27,32)(H,29,33)/t18-,19-,21-/m0/s1

Cross-references

Equivalent identifiers for this same structure in other resources.

pdb-ccd:FHR

Activity roles

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

CHEBI:149553 CHEBI:149553

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:152560`	N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide	`antibioticmech:chebi-8f1d0c8718`	2026-08-30

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:147285 (EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

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.