ChemFOnt: Showing chemical card for Oseltamivir (CFc000008740)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:39 UTC

Chemfont ID

CFc000008740

Molecule Identification

Common Name

Oseltamivir

Definition

Oseltamivir is only found in individuals that have used or taken this drug. It is an acetamido cyclohexene that is a structural homolog of sialic acid and inhibits neuraminidase. [PubChem]Oseltamivir is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. The proposed mechanism of action of oseltamivir is inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Oseltamivir	ChEBI
Agucort	ChEBI
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate	ChEBI
GS-4104	ChEBI
HSDB 7433	ChEBI
Oseltamivirum	ChEBI
Tamiflu	ChEBI
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid	Generator
Oseltamivir phosphate	HMDB

Chemical Formula

C₁₆H₂₈N₂O₄

Average Molecular Weight

312.4045

Monoisotopic Molecular Weight

312.204907394

IUPAC Name

ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Traditional Name

oseltamivir

CAS Registry Number

204255-11-8

SMILES

CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1

InChI Identifier

InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1

InChI Key

VSZGPKBBMSAYNT-RRFJBIMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Enoate ester
Acetamide
Alpha,beta-unsaturated carboxylic ester
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Carbonyl group
Primary aliphatic amine
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

diester (CHEBI:7798 )
primary amino compound (CHEBI:7798 )
acetamides (CHEBI:7798 )
amino acid ester (CHEBI:7798 )
cyclohexenecarboxylate ester (CHEBI:7798 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014343)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.69 g/L	ALOGPS
logP	1.3	ALOGPS
logP	1.16	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.65 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	84.2 m³·mol⁻¹	ChemAxon
Polarizability	34.65 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon