EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:73139 - oseltamivir acid

ChEBI IDCHEBI:73139
ChEBI Nameoseltamivir acid
Stars
DefinitionA 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.
Last Modified10 November 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC14H24N2O4
Net Charge0
Average Mass284.356
Monoisotopic Mass284.17361
SMILESCCC(CC)O[C@@H]1C=C(C(=O)O)C[C@H](N)[C@H]1NC(C)=O
InChIInChI=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
InChIKeyNENPYTRHICXVCS-YNEHKIRRSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
marine xenobiotic metabolite  Any metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
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.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
GS 4071ChemIDplus
oseltamivir carboxylateChemIDplus
Ro 64-0802ChemIDplus
Registry NumbersSources
Reaxys:7714446Reaxys
CAS:187227-45-8ChemIDplus
Citations