oseltamivir acid

CHEBI:73139 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid which is substituted at positions 3, 4, and 5 by pentan-3-yloxy, acetamido, and amino groups, respectively (the 3R,4R,5S enantiomer). An antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza. — 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:23483 CHEBI:23483
CHEBI:33709 CHEBI:33709
CHEBI:47622 CHEBI:47622
CHEBI:50994 CHEBI:50994

Chemical structure

Computed structure properties
Molecular formula	C14H24N2O4
Charge	0
Average mass	284.356 Da
Monoisotopic mass	284.17361 Da
Source	ChEBI
InChIKey	NENPYTRHICXVCS-YNEHKIRRSA-N

SMILES

CCC(CC)O[C@@H]1C=C(C(=O)O)C[C@H](N)[C@H]1NC(C)=O

InChI

InChI=1S/C14H24N2O4/c1-4-10(5-2)20-12-7-9(14(18)19)6-11(15)13(12)16-8(3)17/h7,10-13H,4-6,15H2,1-3H3,(H,16,17)(H,18,19)/t11-,12+,13+/m0/s1

Also called

(3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid (EXACT_SYNONYM)— chebi
GS 4071 (EXACT_SYNONYM)— chebi
Ro 64-0802 (EXACT_SYNONYM)— chebi
oseltamivir carboxylate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:187227-45-8
reaxys:7714446

Activity roles

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

CHEBI:36044 CHEBI:36044
CHEBI:52425 CHEBI:52425

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:73139`	oseltamivir acid	`antibioticmech:chebi-af2ed73a2a`	2026-08-30

Mechanism summary

Mode of action: VIRAL_RELEASE_INHIBITION host shared target — Assigned from ChEBI role CHEBI:52425 (EC 3.2.1.18 (exo-α-sialidase) inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — 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.