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.

Label unavailable CHEBI:23483
Label unavailable CHEBI:33709
Label unavailable CHEBI:47622
Label unavailable 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

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:187227-45-8
reaxys:7714446

Activity roles

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

antiviral drug CHEBI:36044
EC 3.2.1.18 (exo-α-sialidase) inhibitor 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 (YAML).

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