daclatasvir

CHEBI:82977 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A member of the class of biphenyls that is a potent inhibitor of nonstructural protein 5A and is used (as its hydrochloride salt) for treatment of hepatitis C. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:22888
Label unavailable CHEBI:23003
Label unavailable CHEBI:24780
Label unavailable CHEBI:27267
Label unavailable CHEBI:37622

Chemical structure

Computed structure properties
Molecular formula	C40H50N8O6
Charge	0
Average mass	738.89 Da
Monoisotopic mass	738.38533 Da
Source	ChEBI
InChIKey	FKRSSPOQAMALKA-CUPIEXAXSA-N

SMILES

COC(=O)N[C@H](C(=O)N1CCC[C@H]1c1ncc(-c2ccc(-c3ccc(-c4cnc([C@@H]5CCCN5C(=O)[C@@H](NC(=O)OC)C(C)C)n4)cc3)cc2)n1)C(C)C

InChI

InChI=1S/C40H50N8O6/c1-23(2)33(45-39(51)53-5)37(49)47-19-7-9-31(47)35-41-21-29(43-35)27-15-11-25(12-16-27)26-13-17-28(18-14-26)30-22-42-36(44-30)32-10-8-20-48(32)38(50)34(24(3)4)46-40(52)54-6/h11-18,21-24,31-34H,7-10,19-20H2,1-6H3,(H,41,43)(H,42,44)(H,45,51)(H,46,52)/t31-,32-,33-,34-/m0/s1

Also called

methyl [(2S)-1-{(2S)-2-[4-(4'-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}biphenyl-4-yl)-1H-imidazol-2-yl]pyrrolidin-1-yl}-3-methyl-1-oxobutan-2-yl]carbamate (EXACT_SYNONYM)— chebi
BMS 790052 (EXACT_SYNONYM)— chebi
BMS-790052 (EXACT_SYNONYM)— chebi
BMS790052 (EXACT_SYNONYM)— chebi
Dimethyl N,N'-(biphenyl-4,4'-diylbis{1H-imidazole-5,2-diyl-((2S)-pyrrolidine-2,1- diyl)((1S)-1-(1-methylethyl)-2-oxoethane-2,1-diyl)})dicarbamate (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:1009119-64-5
reaxys:13077731

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Daclatasvir

Activity roles

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

antiviral drug CHEBI:36044
nonstructural protein 5A inhibitor CHEBI:83799

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:82977`	daclatasvir	`antibioticmech:chebi-4adeb1f061`	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.

hepatitis C virus nonstructural protein 5A (NS5A) VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

HCV genotype replicons, resistance selection, viral-kinetic modeling, and cell experiments associated daclatasvir with NS5A-dependent replication and assembly; direct binding was not established. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2012-10; 2013-02 (retrieved 2026-09-02).

PMID:23089758 (Primary genotype-3 NS5A replicon and resistance-selection study (DOI:10.1128/AAC.01874-12).)
PMID:23431163 (Primary multiscale-model and in-vitro dual-mechanism study (DOI:10.1073/pnas.1203110110).)

Mechanism summary

Mode of action: MULTIPLE microbial target — CURATOR: PMID:23089758 measured picomolar daclatasvir activity against HCV NS5A genotype-3 replicons and selected NS5A resistance at residues 31 and 93. PMID:23431163 combined viral-kinetic modeling with cell experiments and supported two effects: inhibition of viral RNA synthesis and of virion assembly/secretion. Direct compound-NS5A binding was not established.

Resistance mechanisms

1 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
HCV NS5A substitutions at M28, Q30, L31, and Y93 Clinical sequencing after 14-day monotherapy identified genotype-dependent NS5A variants; phenotypes were assessed separately in H77c and Con1 reference replicons. Variant populations, not every individual substitution, persisted for up to six months. Taxon grounding only: no patient-specific protein, strain TaxID, genome, normalized allele or new quantitative endpoint assigned. This review does not establish the administered compound form.	—	Orthohepacivirus hominis `NCBITaxon:3052230`	HCV NS5A	PMID:23403428 (Primary daclatasvir monotherapy sequencing and resistance-persistence study (DOI:10.1128/AAC.02494-12).) https://rest.uniprot.org/taxonomy/3052230 (Taxonomic identity only: active species, UniProt release 2026_03; retrieved 2026-10-08 UTC.)

Record-level evidence

PMID:23089758 (Primary daclatasvir NS5A replicon and resistance study.)
PMID:23431163 (Primary daclatasvir dual-mechanism modeling and cell study.)
PMID:23403428 (Primary clinical resistance-persistence 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 free-base ChEBI identity distinct from the administered salt, structure, roles, and antiviral class; corrected the assembly-only seed to MULTIPLE, added the evidence-calibrated NS5A association, and added target-alteration resistance.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
GROUNDED_RESISTANCE_CONTEXT 2026-10-08 · codex · LLM-assisted
Grounded the existing aggregate claim to a verified species and clarified experimental versus reference context. No exact mutant protein, strain TaxID, genome, variant normalization or quantitative endpoint added.

Provenance

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

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