N-s-butyl-N-[(2R,3S)-3-({[(3aS,5R,6aR)-hexahydro-2H-cyclopenta[b]furan-5-yloxy]carbonyl}amino)-2-hydroxy-4-phenylbutyl]-4-(hydroxymethyl)benzenesulfonamide

CHEBI:46414 ·resolve ·ANTIVIRAL ·EXACT SEEDED

An N,N-disubstituted toluene-p-sulfonamaide, with a structure close to that of darunavir. It is found to inhibit dimerization of HIV-1 protease subunits. — 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:23003 CHEBI:23003
CHEBI:35358 CHEBI:35358
CHEBI:47783 CHEBI:47783

Chemical structure

Computed structure properties
Molecular formula	C29H40N2O7S
Charge	0
Average mass	560.713 Da
Monoisotopic mass	560.25562 Da
Source	ChEBI
InChIKey	VYBDPVQMILRSMK-GRXYLYAXSA-N

SMILES

[H][C@@]1(OC(=O)N[C@@H](Cc2ccccc2)[C@H](O)CN(CC(C)C)S(=O)(=O)c2ccc(CO)cc2)C[C@]2([H])CCO[C@]2([H])C1

InChI

InChI=1S/C29H40N2O7S/c1-20(2)17-31(39(35,36)25-10-8-22(19-32)9-11-25)18-27(33)26(14-21-6-4-3-5-7-21)30-29(34)38-24-15-23-12-13-37-28(23)16-24/h3-11,20,23-24,26-28,32-33H,12-19H2,1-2H3,(H,30,34)/t23-,24+,26-,27+,28+/m0/s1

Also called

(3aS,5R,6aR)-hexahydro-2H-cyclopenta[b]furan-5-yl {(2S,3R)-3-hydroxy-4-[{[4-(hydroxymethyl)phenyl]sulfonyl}(2-methylpropyl)amino]-1-phenylbutan-2-yl}carbamate (EXACT_SYNONYM)— chebi
(3AS,5R,6AR)-HEXAHYDRO-2H-CYCLOPENTA[B]FURAN-5-YL (2S,3S)-3-HYDROXY-4-(4-(HYDROXYMETHYL)-N-ISOBUTYLPHENYLSULFONAMIDO)-1-PHENYLBUTAN-2-YLCARBAMATE (EXACT_SYNONYM)— chebi
(3aS,5R,6aR)-hexahydro-2H-cyclopenta[b]furan-5-yl (2S,3R)-3-hydroxy-4-(4-(hydroxymethyl)-N-isobutylphenylsulfonamido)-1-phenylbutan-2-ylcarbamate (EXACT_SYNONYM)— chebi
(3aS,5R,6aR)-hexahydro-2H-cyclopenta[b]furan-5-yl {(1S,2R)-1-benzyl-2-hydroxy-3-[{[4-(hydroxymethyl)phenyl]sulfonyl}(2-methylpropyl)amino]propyl}carbamate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

pdb-ccd:GRL

Activity roles

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

CHEBI:35660 CHEBI:35660

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:46414`	N-s-butyl-N-[(2R,3S)-3-({[(3aS,5R,6aR)-hexahydro-2H-cyclopenta[b]furan-5-yloxy]carbonyl}amino)-2-hydroxy-4-phenylbutyl]-4-(hydroxymethyl)benzenesulfonamide	`antibioticmech:chebi-b986b3fb69`	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

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.