U100313

CHEBI:46238 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pyranone that is 4-hydroxy-3-methyl-2H-pyran-2-one in which two of the hydrogens of the methyl group are replaced by a cycloprop-2-en-1-yl group and a 3-{[N-(tert-butoxycarbonyl)-β-alanyl]amino}phenyl group (S-configuration) and in which the hydrogen at position 6 is replaced by a 1-phenylbutan-2-yl group (R-configuration). — 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:13248 CHEBI:13248
CHEBI:23003 CHEBI:23003
CHEBI:29347 CHEBI:29347
CHEBI:51455 CHEBI:51455
CHEBI:75885 CHEBI:75885

Chemical structure

Computed structure properties
Molecular formula	C33H38N2O6
Charge	0
Average mass	558.675 Da
Monoisotopic mass	558.27299 Da
Source	ChEBI
InChIKey	OORLDLMDGJZAFM-MNNSJKJDSA-N

SMILES

[H][C@](c1cccc(NC(=O)CCNC(=O)OC(C)(C)C)c1)(c1c(O)cc([C@H](CC)Cc2ccccc2)oc1=O)C1C=C1

InChI

InChI=1S/C33H38N2O6/c1-5-22(18-21-10-7-6-8-11-21)27-20-26(36)30(31(38)40-27)29(23-14-15-23)24-12-9-13-25(19-24)35-28(37)16-17-34-32(39)41-33(2,3)4/h6-15,19-20,22-23,29,36H,5,16-18H2,1-4H3,(H,34,39)(H,35,37)/t22-,29+/m1/s1

Also called

tert-butyl [3-({3-[(S)-cycloprop-2-en-1-yl{4-hydroxy-2-oxo-6-[(2R)-1-phenylbutan-2-yl]-2H-pyran-3-yl}methyl]phenyl}amino)-3-oxopropyl]carbamate (EXACT_SYNONYM)— chebi
tert-butyl [3-({3-[(S)-{6-[(1R)-1-benzylpropyl]-4-hydroxy-2-oxo-2H-pyran-3-yl}(cycloprop-2-en-1-yl)methyl]phenyl}amino)-3-oxopropyl]carbamate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

pdb-ccd:U02

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:46238`	U100313	`antibioticmech:chebi-83ef4e7237`	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.