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Compound Detail

CHEMBL674

OSELTAMIVIR CARBOXYLATE
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CCC(CC)O[C@@H]1C=C(C(=O)O)C[C@H](N)[C@H]1NC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL674
Name OSELTAMIVIR CARBOXYLATE
Phase Preclinical
Structure Type MOL
InChI Key NENPYTRHICXVCS-YNEHKIRRSA-N

Known Names

GS 4071 GS-4071 GS4071 Oseltamivir acid Oseltamivir acid, (-)- Oseltamivir carboxylate Oseltamivir free acid RO-64-0802 RO-640802
23
Targets
254
Activities
3
Assay Types
30
PK Parameters
20
Publications
9
Known Names

Molecular Properties

284.4
MW (Da)
0.81
ALogP
4
HBA
3
HBD
101.7
PSA (Ų)
0.67
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vir

Extended Properties

Molecular Formula C14H24N2O4
MW 284.36
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 1.43

Activity Summary

IC50 175 meas. best 10.8
EC50 73 meas. best 8.85
Ki 6 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 10.8 7.5608 0.0 53
Neuraminidase
CHEMBL6135
 IC50 10.0 7.7789 0.1 46
Neuraminidase
CHEMBL6015
 IC50 9.96 8.64 0.1 4
Influenza A virus
CHEMBL613740
 IC50 9.92 7.8615 0.1 13
H2N2 subtype
CHEMBL612765
 IC50 9.77 9.77 0.2 1
Influenza A virus H3N2
CHEMBL2366902
 IC50 9.22 9.22 0.6 1
Neuraminidase
CHEMBL2051
 IC50 9.19 7.9263 0.6 19
Neuraminidase
CHEMBL1667683
 IC50 9.14 9.14 0.7 1
Sialidase
CHEMBL5189
 IC50 9.0 9.0 1.0 1
Neuraminidase
CHEMBL1287610
 IC50 9.0 7.6225 1.0 4
Influenza A virus
CHEMBL613740
 EC50 8.85 6.4538 1.4 63
Neuraminidase
CHEMBL3559643
 IC50 8.75 7.6925 1.8 4
Neuraminidase
CHEMBL2046263
 IC50 8.54 7.39 2.9 2
Neuraminidase
CHEMBL3377
 IC50 8.52 8.0983 3.0 6
Influenza B virus
CHEMBL613129
 IC50 8.4 7.9067 4.0 3
Influenza A virus H3N2
CHEMBL2366902
 EC50 8.15 7.535 7.1 2
Neuraminidase
CHEMBL4295592
 IC50 8.05 8.05 8.9 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 8.0 6.725 10.0 2
Neuraminidase
CHEMBL2051
 Ki 8.0 8.0 10.0 1
Neuraminidase
CHEMBL4295612
 IC50 7.82 7.82 15.2 1
Neuraminidase
CHEMBL1667684
 IC50 7.77 6.66 17.0 2
Unchecked
CHEMBL612545
 Ki 7.62 7.54 24.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.55 6.255 28.2 2
Unchecked
CHEMBL612545
 EC50 7.52 6.705 30.0 2
H5N1 subtype
CHEMBL613845
 EC50 6.12 6.12 750.0 1
Neuraminidase
CHEMBL1667685
 IC50 5.8 4.975 1600.0 6
Neuraminidase
CHEMBL1667686
 IC50 5.79 5.79 1630.0 1
Influenza B virus
CHEMBL613129
 EC50 5.54 5.54 2900.0 1
Influenza A virus (A/Puerto Rico/8/1934(H1N1))
CHEMBL612610
 EC50 5.51 5.455 3070.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 6069.0 ng.hr.mL-1 Homo sapiens
AUC 5064.0 ng.hr.mL-1 Homo sapiens
AUC 6218.0 ng.hr.mL-1 Homo sapiens
AUC 5543.0 ng.hr.mL-1 Homo sapiens
AUC 10900.0 ng.hr.mL-1 Rattus norvegicus
AUC 9260.0 ng.hr.mL-1 Rattus norvegicus
AUC 12100.0 ng.hr.mL-1 Rattus norvegicus
AUC 5070.0 ng.hr.mL-1 Rattus norvegicus
AUC 4870.0 ng.hr.mL-1 Rattus norvegicus
AUC 4860.0 ng.hr.mL-1 Rattus norvegicus
AUC 2960.0 ng.hr.mL-1 Rattus norvegicus
AUC 6340.0 ng.hr.mL-1 Rattus norvegicus
AUC 6330.0 ng.hr.mL-1 Rattus norvegicus
AUC 4510.0 ng.hr.mL-1 Rattus norvegicus
AUC 5290.0 ng.hr.mL-1 Rattus norvegicus
AUC 5280.0 ng.hr.mL-1 Rattus norvegicus
AUC 3540.0 ng.hr.mL-1 Rattus norvegicus
AUC 8860.0 ng.hr.mL-1 Rattus norvegicus
AUC 8350.0 ng.hr.mL-1 Rattus norvegicus
AUC 6300.0 ng.hr.mL-1 Rattus norvegicus
AUC 5810.0 ng.hr.mL-1 Rattus norvegicus
AUC 6140.0 ng.hr.mL-1 Rattus norvegicus
AUC 5910.0 ng.hr.mL-1 Rattus norvegicus
AUC 8400.0 ng.hr.mL-1 Rattus norvegicus
AUC 300.0 ng.hr.mL-1 Rattus norvegicus
CL 4.8 mL.min-1.kg-1 Homo sapiens
CL 4.8 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 4.8 mL.min-1.kg-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.016 nM 10.8 Inhibition of Influenza A virus (A/Babo1/36/2005 (H3N2)) Neuraminidase N2 preinc... 32092589
Unchecked IC50 = 0.041 nM 10.39 Inhibition of Influenza A virus (A/California/04/2009(H1N1)) pdm09 Neuraminidase... 32092589
Neuraminidase IC50 = 0.1 nM 10.0 Inhibition of neuraminidase in Influenza A virus A/Jena/5555/09(H1N1) using Na-s... 24422530
Neuraminidase IC50 = 0.11 nM 9.96 Inhibition of influenza A virus H3N2 clinical isolate neuraminidase using NA-Flu... 31493744
Influenza A virus IC50 = 0.12 nM 9.92 Antiviral activity against Influenza A virus H1N1 24422530
Neuraminidase IC50 = 0.12 nM 9.92 Inhibition of neuraminidase in Influenza A virus A/Jena/5258/2009(H1N1) using Na... 24422530
Neuraminidase IC50 = 0.14 nM 9.85 Inhibition of neuraminidase in Influenza A virus A/HH/1580/09(H1N1) using Na-sta... 24422530
Neuraminidase IC50 = 0.15 nM 9.82 Inhibition of neuraminidase in Influenza A virus A/Berlin/10/04(H3N2) using Na-s... 24422530
H2N2 subtype IC50 = 0.17 nM 9.77 Antiviral activity against influenza H2N2 virus 19112024
Neuraminidase IC50 = 0.17 nM 9.77 Inhibition of neuraminidase in Influenza A virus A/Rheinland-Pfalz/3911/03(H3N2)... 24422530
Neuraminidase IC50 = 0.18 nM 9.74 Inhibition of neuraminidase in Influenza A virus A/Sachsen/6/02(H3N2) using Na-s... 24422530
Influenza A virus IC50 = 0.24 nM 9.62 Antiviral activity against Influenza A virus H3N2 24422530
Unchecked IC50 = 0.4 nM 9.4 Inhibition of recombinant Influenza A virus (A/Moscow/10/99(H3N2)) Neuraminidase... 27341624
Neuraminidase IC50 = 0.4 nM 9.4 Inhibition of oseltamivir-resistant Influenza A virus A/WSN/1933(H1N1) recombina... 27167096
Neuraminidase IC50 = 0.44 nM 9.36 Inhibition of neuraminidase in Influenza A virus A/Hong Kong/68(H3N2) using Na-s... 24422530
Unchecked IC50 = 0.5 nM 9.3 Inhibition of Influenza A virus (A/Moscow/10/99(H3N2)) neuraminidase N2 using MU... 34797984
Influenza A virus H3N2 IC50 = 0.6 nM 9.22 Antiviral activity against influenza H3N2 virus 19112024
Neuraminidase IC50 = 0.6 nM 9.22 Inhibition of Influenza A virus A/Brisbane/10/2007(H3N2) recombinant wild type n... 27167096
Neuraminidase IC50 = 0.648 nM 9.19 Inhibition of Influenza A virus (H1N1) neuraminidase 31744778
Neuraminidase IC50 = 0.73 nM 9.14 Inhibition of Influenza A virus (A/reassortant/NIBRG-14(Viet Nam/1194/2004 x Pue... 23009169

Literature References

PubMed DOI Target Context # Activities
22584254 10.1124/dmd.112.044990 Rattus norvegicus 39
34735766 10.1021/acs.jmedchem.1c01366 Influenza A virus 25
36931117 10.1016/j.ejmech.2023.115275 Influenza A virus 24
35939763 10.1021/acs.jmedchem.1c01970 ADMET 20
30365885 10.1021/acs.jmedchem.8b01065 Influenza A virus 16
19721074 10.1128/aac.01541-08 Brain 16
32069052 10.1021/acs.jmedchem.9b01900 Influenza A virus 15
22584254 10.1124/dmd.112.044990 Homo sapiens 14
19721074 10.1128/aac.01541-08 Cerebrospinal fluid 14
19721074 10.1128/aac.01541-08 Plasma 14
19721074 10.1128/aac.01541-08 ADMET 13
22584254 10.1124/dmd.112.044990 ADMET 12
29965752 10.1021/acs.jmedchem.8b00929 Neuraminidase 12
30429954 10.1021/acsmedchemlett.8b00336 Influenza A virus 10
23009169 10.1021/jm3008486 Influenza A virus 10
29407952 10.1016/j.ejmech.2018.01.050 Influenza A virus 10
32512482 10.1016/j.ejmech.2020.112423 ADMET 9
24422530 10.1021/jm401492x Neuraminidase 9
37804770 10.1016/j.ejmech.2023.115845 Influenza A virus 9
27167096 10.1021/acs.jmedchem.6b00029 Neuraminidase 8

Data from ChEMBL 36 via Core Engine