AntibioticMech

lopinavir

CHEBI:31781 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A dicarboxylic acid diamide that is amphetamine is substituted on nitrogen by a (2,6-dimethylphenoxy)acetyl group and on the carbon α- to nitrogen by a (1S,3S)-1-hydroxy-3-{[(2S)-3-methyl-2-(2-oxotetrahydropyrimidin-1-yl)butanoyl]amino}-4-phenylbutyl group. An antiretroviral of the protease inhibitor class, it is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:35338 CHEBI:35338
• CHEBI:35779 CHEBI:35779

Chemical structure

Computed structure properties

Molecular formula	C37H48N4O5
Charge	0
Average mass	628.814 Da
Monoisotopic mass	628.36247 Da
Source	ChEBI
InChIKey	KJHKTHWMRKYKJE-SUGCFTRWSA-N

SMILES

Cc1cccc(C)c1OCC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)C[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)N1CCCNC1=O

InChI

InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1

Also called

• (2S)-N-[(2S,4S,5S)-5-{[(2,6-dimethylphenoxy)acetyl]amino}-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide (EXACT_SYNONYM)— chebi
• Lopinavir (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• cas:192725-17-0
• drugbank:DB01601
• drugcentral:1601
• hmdb:HMDB0015539
• kegg.compound:C12871
• kegg.drug:D01425
• lincs.smallmolecule:LSM-6027
• pdb-ccd:AB1
• reaxys:9309881

Activity roles

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

• CHEBI:149553 CHEBI:149553
• CHEBI:35660 CHEBI:35660
• CHEBI:36044 CHEBI:36044

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:31781	lopinavir	antibioticmech:chebi-f20bf39533	2026-08-30

Mechanism summary

Mode of action

VIRAL_PROTEASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:35660 (HIV protease 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

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. 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.