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Compound Detail

CHEMBL5181864

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CCC(CC)O[C@@H]1C=C(C(=O)O)C[C@H](NCc2ccc3sc4ccccc4c3c2)[C@H]1NC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5181864
Phase Preclinical
Structure Type MOL
InChI Key HLHDCHXBXBBXLH-PPJWLVRDSA-N
7
Targets
13
Activities
2
Assay Types
16
PK Parameters
10
Publications
0
Known Names

Molecular Properties

480.6
MW (Da)
5.01
ALogP
5
HBA
3
HBD
87.7
PSA (Ų)
0.40
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H32N2O4S
MW 480.63
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness 0.07

Activity Summary

IC50 9 meas. best 9.57
EC50 4 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.57 7.5125 0.3 4
Neuraminidase
CHEMBL2051
 IC50 9.14 9.14 0.7 1
Influenza A virus
CHEMBL613740
 EC50 7.7 6.585 20.0 4
Neuraminidase
CHEMBL1667685
 IC50 5.19 5.19 6500.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.23 4.23 58900.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.22 4.22 60800.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.05 4.05 89400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4279.0 ng.hr.mL-1 Rattus norvegicus
AUC 5834.0 ng.hr.mL-1 Rattus norvegicus
AUC 4286.0 ng.hr.mL-1 Rattus norvegicus
AUC 5854.0 ng.hr.mL-1 Rattus norvegicus
CL 7.8 mL.min-1.kg-1 Rattus norvegicus
CL 9.6 mL.min-1.g-1 Homo sapiens
CL 8.6 mL.min-1.kg-1 Homo sapiens
Cmax 27027.03 nM Rattus norvegicus
Cmax 13097.39 nM Rattus norvegicus
F 13.7 % Rattus norvegicus
T1/2 0.743 hr Rattus norvegicus
T1/2 1.03 hr Rattus norvegicus
T1/2 145.0 hr Homo sapiens
Tmax 0.083 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus
Vd 0.161 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.27 nM 9.57 Inhibition of Influenza A virus A/Goose/Guangdong/SH7/2013 (H5N1) neuraminidase ... 34735766
Unchecked IC50 = 0.63 nM 9.2 Inhibition of Influenza A virus A/Goose/Jiangsu/1306/2014 (H5N8) neuraminidase u... 34735766
Neuraminidase IC50 = 0.73 nM 9.14 Inhibition of Influenza A virus A/PR/8/1934 (H1N1) neuraminidase using 2(4-methy... 34735766
Influenza A virus EC50 = 20.0 nM 7.7 Antiviral activity against Influenza A virus A/PR/8/34 (H1N1) infected in dog MD... 34735766
Influenza A virus EC50 = 340.0 nM 6.47 Antiviral activity against Influenza A virus A/Goose/Guangdong/SH7/2013 (H5N1) i... 34735766
Influenza A virus EC50 = 570.0 nM 6.24 Antiviral activity against Influenza A virus A/Goose/Jiangsu/1306/2014 (H5N8) in... 34735766
Influenza A virus EC50 = 1170.0 nM 5.93 Antiviral activity against Influenza A virus A/Wisconsin/67/05 (H3N2) infected i... 34735766
Unchecked IC50 = 1359.0 nM 5.87 Inhibition of Influenza A virus A/Babol/36/2005 (H3N2) neuraminidase using using... 34735766
Unchecked IC50 = 3900.0 nM 5.41 Inhibition of Influenza A virus (A/California/07/2009 (H1N1)) neuraminidase H275... 34735766
Neuraminidase IC50 = 6500.0 nM 5.19 Inhibition of Influenza A virus A/Anhui/1/2005 (H5N1) Neuraminidase H274Y mutant... 34735766
Cytochrome P450 2D6 IC50 = 58900.0 nM 4.23 Inhibition of CYP2D6 in human liver microsomes incubated for 20 mins in presence... 34735766
Cytochrome P450 2C9 IC50 = 60800.0 nM 4.22 Inhibition of CYP2C9 in human liver microsomes incubated for 20 mins in presence... 34735766
Cytochrome P450 1A2 IC50 = 89400.0 nM 4.05 Inhibition of CYP1A2 in human liver microsomes incubated for 20 mins in presence... 34735766

Literature References

PubMed DOI Target Context # Activities
34735766 10.1021/acs.jmedchem.1c01366 ADMET 31
34735766 10.1021/acs.jmedchem.1c01366 Influenza A virus 26
34735766 10.1021/acs.jmedchem.1c01366 Unchecked 8
34735766 10.1021/acs.jmedchem.1c01366 Neuraminidase 4
34735766 10.1021/acs.jmedchem.1c01366 MDCK 1
34735766 10.1021/acs.jmedchem.1c01366 Cytochrome P450 1A2 1
34735766 10.1021/acs.jmedchem.1c01366 Cytochrome P450 2C19 1
34735766 10.1021/acs.jmedchem.1c01366 Cytochrome P450 2D6 1
34735766 10.1021/acs.jmedchem.1c01366 Cytochrome P450 3A4 1
34735766 10.1021/acs.jmedchem.1c01366 Cytochrome P450 2C9 1

Data from ChEMBL 36 via Core Engine