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CHEMBL81717

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

Basic Information

ChEMBL ID CHEMBL81717
Phase Preclinical
Structure Type MOL
InChI Key TXXPTEJSSVMAFL-YNEHKIRRSA-N

Known Names

Guanidino-Oseltamivir Carboxylicacid
8
Targets
31
Activities
3
Assay Types
17
PK Parameters
20
Publications
1
Known Names

Molecular Properties

326.4
MW (Da)
0.33
ALogP
4
HBA
5
HBD
137.5
PSA (Ų)
0.34
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H26N4O4
MW 326.40
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness 1.07

Activity Summary

IC50 24 meas. best 9.82
EC50 6 meas. best 8.15
Ki 1 meas. best 7.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuraminidase
CHEMBL6135
 IC50 9.82 8.8662 0.1 13
Influenza A virus
CHEMBL613740
 IC50 9.66 9.38 0.2 2
Neuraminidase
CHEMBL2051
 IC50 9.3 9.15 0.5 2
Sialidase
CHEMBL5189
 IC50 9.3 9.3 0.5 1
Neuraminidase
CHEMBL1287610
 IC50 9.0 9.0 1.0 1
Neuraminidase
CHEMBL3559643
 IC50 8.64 8.3967 2.3 3
Neuraminidase
CHEMBL1667684
 IC50 8.16 8.16 6.9 1
Influenza A virus
CHEMBL613740
 EC50 8.15 6.795 7.0 6
Unchecked
CHEMBL612545
 Ki 7.34 7.34 46.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4800.0 ng.hr.mL-1 Rattus norvegicus
AUC 450.0 ng.hr.mL-1 Rattus norvegicus
Cmax 919.12 nM Rattus norvegicus
F 4.0 % Rattus norvegicus
F 100.0 % Rattus norvegicus
F 48.0 % Mus musculus
F 23.0 % Mus musculus
F 4.0 % Rattus norvegicus
F 1.9 % Rattus norvegicus
F 5.0 % Rattus norvegicus
F 2.1 % Rattus norvegicus
MRT 2.2 hr Rattus norvegicus
MRT 0.9833 hr Rattus norvegicus
T1/2 20.1 hr Rattus norvegicus
T1/2 1.567 hr Rattus norvegicus
T1/2 1.217 hr Rattus norvegicus
Tmax 1.717 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuraminidase IC50 = 0.15 nM 9.82 Inhibition of neuraminidase in Influenza A virus A/HH/1580/09(H1N1) using Na-sta... 24422530
Neuraminidase IC50 = 0.19 nM 9.72 Inhibition of neuraminidase in Influenza A virus A/Jena/5258/2009(H1N1) using Na... 24422530
Influenza A virus IC50 = 0.22 nM 9.66 Antiviral activity against Influenza A virus H1N1 24422530
Neuraminidase IC50 = 0.31 nM 9.51 Inhibition of neuraminidase in Influenza A virus A/Jena/5555/09(H1N1) using Na-s... 24422530
Sialidase IC50 = 0.5 nM 9.3 Inhibition of Clostridium perfringenes neuraminidase activity using 4-methylumbe... 29141777
Neuraminidase IC50 = 0.5 nM 9.3 Inhibition of Influenza virus neuraminidase A -
Neuraminidase IC50 = 0.5 nM 9.3 Inhibitory activity against influenza A neuraminidase from influenza A/PR/8/34 (... 9651151
Neuraminidase IC50 = 0.63 nM 9.2 Inhibition of neuraminidase in Influenza A virus A/Rheinland-Pfalz/3911/03(H3N2)... 24422530
Neuraminidase IC50 = 0.75 nM 9.12 Inhibition of neuraminidase in Influenza A virus A/Berlin/10/04(H3N2) using Na-s... 24422530
Influenza A virus IC50 = 0.8 nM 9.1 Antiviral activity against Influenza A virus H3N2 24422530
Neuraminidase IC50 = 0.83 nM 9.08 Inhibition of neuraminidase in Influenza A virus A/Hong Kong/68(H3N2) using Na-s... 24422530
Neuraminidase IC50 = 0.99 nM 9.0 Inhibition of neuraminidase in Influenza A virus A/Sachsen/6/02(H3N2) using Na-s... 24422530
Neuraminidase IC50 = 1.0 nM 9.0 Inhibition of Influenza A virus (A/WSN/1933(H1N1)) wild type neuraminidase using... 29843102
Neuraminidase IC50 = 1.0 nM 9.0 Inhibition of influenza A virus (A/WSN/1933(H1N1)) neuraminidase using MUNANA as... 30576902
Neuraminidase IC50 = 1.4 nM 8.85 Inhibition of influenza A/WSN/1933 (H1N1) virus neuraminidase N1 using MUNANA su... 21778065
Neuraminidase IC50 = 2.0 nM 8.7 Inhibition of Influenza A virus (A/WSN/1933(H1N1)) neuraminidase H275Y mutant us... 29843102
Neuraminidase IC50 = 2.3 nM 8.64 Inhibition of Influenza A virus A/duck/china/1206/2012(H5N1) Neuraminidase 25255388
Neuraminidase IC50 = 2.6 nM 8.59 Inhibition of Influenza A virus A/duck/china/QJ/01(H5N1) Neuraminidase 25255388
Neuraminidase IC50 = 3.4 nM 8.47 Inhibition of neuraminidase H274Y mutant in Oseltamivir-resistant Influenza A vi... 24422530
Neuraminidase IC50 = 6.4 nM 8.19 Inhibition of Influenza A virus A/chicken/china/415/2013(H9N2) Neuraminidase N2 25255388

Literature References

PubMed DOI Target Context # Activities
24422530 10.1021/jm401492x Rattus norvegicus 11
24422530 10.1021/jm401492x Neuraminidase 8
25255388 10.1021/jm500892k Neuraminidase 5
24422530 10.1021/jm401492x No relevant target 4
24422530 10.1021/jm401492x Influenza A virus 4
29843102 10.1016/j.ejmech.2018.05.030 Influenza A virus 2
29843102 10.1016/j.ejmech.2018.05.030 Neuraminidase 2
23009169 10.1021/jm3008486 Rattus norvegicus 2
24422530 10.1021/jm401492x Mus musculus 2
- 10.1039/C1MD00050K Neuraminidase 2
24422530 10.1021/jm401492x Molecular identity unknown 1
32512482 10.1016/j.ejmech.2020.112423 ADMET 1
27236066 10.1016/j.ejmech.2016.05.016 Unchecked 1
24422530 10.1021/jm401492x Albumin 1
24422530 10.1021/jm401492x MDCK 1
9651151 10.1021/jm980162u Neuraminidase 1
23009169 10.1021/jm3008486 No relevant target 1
21778065 10.1016/j.bmc.2011.06.080 Influenza A virus 1
21778065 10.1016/j.bmc.2011.06.080 Neuraminidase 1
21778065 10.1016/j.bmc.2011.06.080 No relevant target 1

Data from ChEMBL 36 via Core Engine