GRL-0617

CHEBI:167176 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A benzamide resulting from the formal condensation of the carboxy group of 5-amino-2-methylbenzoic acid with the amino group of (1R)-1-(naphthalen-1-yl)ethan-1-amine. It is a potent noncovalent inhibitor (IC50 = 600 nM) of severe acute respiratory syndrome-coronavirus papain-like protease (SARS-CoV PLpro). — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140325
Label unavailable CHEBI:22702
Label unavailable CHEBI:25477
Label unavailable CHEBI:48975

Chemical structure

Computed structure properties
Molecular formula	C20H20N2O
Charge	0
Average mass	304.393 Da
Monoisotopic mass	304.15756 Da
Source	ChEBI
InChIKey	UVERBUNNCOKGNZ-CQSZACIVSA-N

SMILES

Cc1ccc(N)cc1C(=O)N[C@H](C)c1cccc2ccccc12

InChI

InChI=1S/C20H20N2O/c1-13-10-11-16(21)12-19(13)20(23)22-14(2)17-9-5-7-15-6-3-4-8-18(15)17/h3-12,14H,21H2,1-2H3,(H,22,23)/t14-/m1/s1

Also called

5-amino-2-methyl-N-[(1R)-1-(naphthalen-1-yl)ethyl]benzamide (EXACT_SYNONYM)— chebi
5-amino-2-methyl-N-[(1R)-1-(1-naphthalenyl)ethyl]benzamide (EXACT_SYNONYM)— chebi
5-amino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide (EXACT_SYNONYM)— chebi
GRL 0617 (EXACT_SYNONYM)— chebi
GRL0617 (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.

Activity roles

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

anticoronaviral agent 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:167176`	GRL-0617	`antibioticmech:chebi-c97057ae5c`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

SARS-CoV-2 papain-like protease (PLpro) VIRAL_PROTEIN DIRECT_BINDING_TARGET

A 2.6-angstrom GRL-0617-PLpro cocrystal localized the inhibitor in the S3-S4 substrate pockets; biochemical and infected-cell assays measured protease and antiviral effects. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2020-07; 2020-09 (retrieved 2026-09-02).

Severe acute respiratory syndrome coronavirus 2 NCBITaxon:2697049

Organism-specific examples
Protein	Gene	Organism	Entry
Replicase polyprotein 1ab `UniProtKB:P0DTD1` SARS-CoV-2 replicase polyprotein 1ab encoding the nsp3 papain-like protease (PLpro) domain crystallized in complex with GRL-0617 (PMID:32895623, PDB 7CJM).	rep	Severe acute respiratory syndrome coronavirus 2 `NCBITaxon:2697049`	REVIEWED

PMID:32895623 (Primary GRL-0617-bound SARS-CoV-2 PLpro structural and enzyme study (DOI:10.1016/j.apsb.2020.08.014).)
PMID:32726803 (Primary PLpro biochemical, structural, and infected-cell study (DOI:10.1038/s41586-020-2601-5).)

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — CURATOR: PMID:32895623 determined a SARS-CoV-2 papain-like protease complex with GRL-0617 and measured protease inhibition. The inhibitor occupies the S3-S4 pockets and closes the BL2 loop over the substrate cleft. PMID:32726803 further linked PLpro inhibition to reduced viral replication and preserved host antiviral signaling in infected cells.

Record-level evidence

PMID:32895623 (Primary GRL-0617-bound PLpro structure and inhibition study.)
PMID:32726803 (Primary infected-cell PLpro inhibition study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, antiviral role, and class; added viral-protease inhibition, the directly bound SARS-CoV-2 PLpro target, and infected-cell antiviral context.
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated SARS-CoV-2 replicase polyprotein 1ab (P0DTD1) UniProtKB protein example on the PRIMARY_LITERATURE SARS-CoV-2 papain-like protease (PLpro) molecular target.

Provenance

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

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