CHEBI:73139 - oseltamivir acid

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ChEBI Name oseltamivir acid
ChEBI ID CHEBI:73139
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C14H24N2O4
Net Charge 0
Average Mass 284.35140
Monoisotopic Mass 284.17361
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
InChIKey NENPYTRHICXVCS-YNEHKIRRSA-N
SMILES CCC(CC)O[C@@H]1C=C(C[C@H](N)[C@H]1NC(C)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
marine xenobiotic metabolite
Any metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oseltamivir acid (CHEBI:73139) has role antiviral drug (CHEBI:36044)
oseltamivir acid (CHEBI:73139) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425)
oseltamivir acid (CHEBI:73139) has role marine xenobiotic metabolite (CHEBI:83399)
oseltamivir acid (CHEBI:73139) is a acetate ester (CHEBI:47622)
oseltamivir acid (CHEBI:73139) is a amino acid (CHEBI:33709)
oseltamivir acid (CHEBI:73139) is a cyclohexenecarboxylic acid (CHEBI:23483)
oseltamivir acid (CHEBI:73139) is a primary amino compound (CHEBI:50994)
IUPAC Name
(3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid
Synonyms Sources
GS 4071 ChemIDplus
oseltamivir carboxylate ChemIDplus
Ro 64-0802 ChemIDplus
Registry Numbers Types Sources
187227-45-8 CAS Registry Number ChemIDplus
7714446 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10628898 PubMed citation Europe PMC
21338262 PubMed citation Europe PMC
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Last Modified
10 November 2014