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Compound Detail

CHEMBL4287425

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CCC(CC)O[C@@H]1C=C(C(=O)O)C[C@H](NCc2ccc(Sc3ccccc3)cc2)[C@H]1NC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4287425
Phase Preclinical
Structure Type MOL
InChI Key UNXXHRRIIASFMJ-JIMJEQGWSA-N
9
Targets
22
Activities
2
Assay Types
22
PK Parameters
13
Publications
0
Known Names

Molecular Properties

482.6
MW (Da)
4.79
ALogP
5
HBA
3
HBD
87.7
PSA (Ų)
0.43
QED
0
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H34N2O4S
MW 482.65
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness 0.18

Activity Summary

IC50 15 meas. best 9.08
EC50 7 meas. best 7.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.08 7.5956 0.8 9
Neuraminidase
CHEMBL2051
 IC50 8.73 8.73 1.9 1
Neuraminidase
CHEMBL4295592
 IC50 8.72 8.72 1.9 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 8.25 8.25 5.6 1
Neuraminidase
CHEMBL1667685
 IC50 7.49 7.49 32.2 1
Neuraminidase
CHEMBL1667684
 IC50 7.48 7.48 32.8 1
Influenza A virus
CHEMBL613740
 EC50 7.25 6.3933 56.0 6
Neuraminidase
CHEMBL4295612
 IC50 5.51 5.51 3065.0 1
Influenza B virus
CHEMBL613129
 EC50 4.72 4.72 19000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1460.84 ng.hr.mL-1 Rattus norvegicus
AUC 1464.41 ng.hr.mL-1 Rattus norvegicus
AUC 1504.43 ng.hr.mL-1 Rattus norvegicus
AUC 1558.63 ng.hr.mL-1 Rattus norvegicus
AUC 1504.0 ng.hr.mL-1 Rattus norvegicus
CL 0.0235 mL.min-1.kg-1 Rattus norvegicus
CL 9.6 mL.min-1.g-1 Homo sapiens
CL 0.0086 mL.min-1.kg-1 Homo sapiens
Cmax 3924168.65 nM Rattus norvegicus
Cmax 843261.16 nM Rattus norvegicus
Cmax 843.26 nM Rattus norvegicus
F 100.0 % Rattus norvegicus
F 10.3 % Rattus norvegicus
MRT 2.03 hr Rattus norvegicus
MRT 4.05 hr Rattus norvegicus
T1/2 4.818 hr Homo sapiens
T1/2 1.76 hr Rattus norvegicus
T1/2 2.417 hr Homo sapiens
T1/2 3.82 hr Rattus norvegicus
Tmax 0.083 hr Rattus norvegicus
Tmax 0.83 hr Rattus norvegicus
Vd 3.51 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.83 nM 9.08 Inhibition of Influenza A virus A/Goose/Jiangsu/1306/2014 (H5N8) neuraminidase u... 34735766
Unchecked IC50 = 0.94 nM 9.03 Inhibition of Influenza A virus A/Goose/Guangdong/SH7/2013 (H5N1) neuraminidase ... 34735766
Unchecked IC50 = 0.96 nM 9.02 Inhibition of Influenza A virus A/goose/Guangdong/SH7/2013(H5N1) neuraminidase N... 30365885
Unchecked IC50 = 0.96 nM 9.02 Inhibition of Influenza A virus H5N1 Neuraminidase 34735766
Neuraminidase IC50 = 1.88 nM 8.73 Inhibition of Influenza A virus A/PR/8/1934 (H1N1) neuraminidase using 2(4-methy... 34735766
Neuraminidase IC50 = 1.89 nM 8.72 Inhibition of Influenza A virus A/goose/Jiangsu/1306/2014(H5N8) neuraminidase N8... 30365885
Human immunodeficiency virus type 1 integrase IC50 = 5.57 nM 8.25 Inhibition of Influenza A virus H1N1 Neuraminidase 34735766
Unchecked IC50 = 5.57 nM 8.25 Inhibition of Influenza A virus A/California/04/2009 neuraminidase N1 using fluo... 30365885
Neuraminidase IC50 = 32.18 nM 7.49 Inhibition of Influenza A virus H5N1 Neuraminidase H274Y mutant 34735766
Neuraminidase IC50 = 32.81 nM 7.48 Inhibition of Influenza A virus A/Anhui/1/2005(H5N1) neuraminidase N1 H274Y muta... 30365885
Influenza A virus EC50 = 56.0 nM 7.25 Antiviral activity against Influenza A virus A/goose/Jiangsu/1306/2014(H5N8) inf... 30365885
Influenza A virus EC50 = 60.0 nM 7.22 Antiviral activity against Influenza A virus (A/Puerto Rico/8/34(H1N1)) infected... 30365885
Influenza A virus EC50 = 90.0 nM 7.05 Antiviral activity against Influenza A virus A/Chicken/Hebei/LZF/2014(H5N2) infe... 30365885
Influenza A virus EC50 = 390.0 nM 6.41 Antiviral activity against Influenza A virus A/goose/Guangdong/SH7/2013(H5N1) in... 30365885
Unchecked IC50 = 457.6 nM 6.34 Inhibition of Influenza A virus A/Babol/36/2005 (H3N2) neuraminidase using using... 34735766
Influenza A virus EC50 = 520.0 nM 6.28 Antiviral activity against Influenza A virus A/duck/Guangdong/674/2014(H5N6) inf... 30365885
Unchecked IC50 = 869.0 nM 6.06 Inhibition of Influenza A virus H5N2 Neuraminidase 34735766
Unchecked IC50 = 896.9 nM 6.05 Inhibition of Influenza A virus A/Chicken/Hebei/LZF/2014(H5N2) neuraminidase N2 ... 30365885
Neuraminidase IC50 = 3065.0 nM 5.51 Inhibition of Influenza A virus A/duck/Guangdong/674/2014(H5N6) neuraminidase N6... 30365885
Unchecked IC50 = 3065.0 nM 5.51 Inhibition of Influenza A virus H5N6 Neuraminidase 34735766

Literature References

PubMed DOI Target Context # Activities
30365885 10.1021/acs.jmedchem.8b01065 Influenza A virus 18
30365885 10.1021/acs.jmedchem.8b01065 Rattus norvegicus 16
30365885 10.1021/acs.jmedchem.8b01065 ADMET 10
34735766 10.1021/acs.jmedchem.1c01366 Unchecked 6
30365885 10.1021/acs.jmedchem.8b01065 Unchecked 4
30365885 10.1021/acs.jmedchem.8b01065 Neuraminidase 4
30365885 10.1021/acs.jmedchem.8b01065 Mus musculus 2
34735766 10.1021/acs.jmedchem.1c01366 Neuraminidase 2
36055001 10.1016/j.ejmech.2022.114711 ADMET 2
30365885 10.1021/acs.jmedchem.8b01065 Fibroblast 1
30365885 10.1021/acs.jmedchem.8b01065 Influenza B virus 1
30365885 10.1021/acs.jmedchem.8b01065 MDCK 1
34735766 10.1021/acs.jmedchem.1c01366 Human immunodeficiency virus type 1 integrase 1

Data from ChEMBL 36 via Core Engine