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Compound Detail

CHEMBL4125895

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

Basic Information

ChEMBL ID CHEMBL4125895
Phase Preclinical
Structure Type MOL
InChI Key PRVRMQAFLBOHCL-GEFXCWNQSA-N
8
Targets
27
Activities
2
Assay Types
7
PK Parameters
4
Publications
0
Known Names

Molecular Properties

313.2
MW (Da)
-1.92
ALogP
6
HBA
5
HBD
136.3
PSA (Ų)
0.41
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C11H17F2NO7
MW 313.25
Aromatic Rings 0
Heavy Atoms 21
NP-Likeness 0.78

Activity Summary

IC50 24 meas. best 5.35
EC50 3 meas. best 5.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuraminidase
CHEMBL4295840
 IC50 5.35 5.195 4480.0 2
Neuraminidase
CHEMBL6135
 IC50 5.35 4.85 4500.0 10
Influenza B virus
CHEMBL613129
 EC50 5.0 5.0 10000.0 1
Influenza A virus
CHEMBL613740
 EC50 5.0 4.5 10000.0 2
Unchecked
CHEMBL612545
 IC50 4.65 4.625 22240.0 2
Neuraminidase
CHEMBL1667684
 IC50 4.62 4.6 23770.0 2
Neuraminidase
CHEMBL6015
 IC50 4.58 4.475 25990.0 4
Neuraminidase
CHEMBL3377
 IC50 4.49 4.295 32230.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.625 hr Influenza A virus
T1/2 0.4083 hr Influenza A virus
T1/2 0.2867 hr Influenza A virus
T1/2 0.2817 hr Influenza A virus (A/chicken/Bangli/BBVD-563/2007(H5N1))
T1/2 0.495 hr Influenza A virus (A/Fukui/45/2004(H3N2))
T1/2 0.51 hr Influenza A virus (A/NWS/G70C(H1N9))
T1/2 4.0 hr Influenza B virus (B/Perth/211/2001)

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuraminidase IC50 = 4500.0 nM 5.35 Inhibition of Influenza A virus (A/Mississippi/03/01 (H1N1)) neuraminidase activ... 29397718
Neuraminidase IC50 = 4480.0 nM 5.35 Inhibition of Influenza B virus (B/Perth/211/2001) neuraminidase activity using ... 29397718
Neuraminidase IC50 = 4690.0 nM 5.33 Inhibition of Influenza A virus (A/Mississippi/03/01 (H1N1)) neuraminidase H274Y... 29397718
Neuraminidase IC50 = 6420.0 nM 5.19 Inhibition of Influenza A virus (A/Mississippi/03/01 (H1N1)) neuraminidase H274Y... 29397718
Neuraminidase IC50 = 9190.0 nM 5.04 Inhibition of Influenza B virus (B/Perth/211/2001) neuraminidase activity using ... 29397718
Influenza B virus EC50 = 10000.0 nM 5.0 Antiviral activity against Influenza B virus (B/Perth/211/2001) infected in MDCK... 29397718
Influenza A virus EC50 = 10000.0 nM 5.0 Antiviral activity against Influenza A virus (A/Mississippi/03/01 (H1N1)) infect... 29397718
Neuraminidase IC50 = 10760.0 nM 4.97 Inhibition of Influenza A virus (A/Mississippi/03/01 (H1N1)) neuraminidase activ... 29397718
Neuraminidase IC50 = 20960.0 nM 4.68 Inhibition of Influenza A virus (A/California/07/09 (H1N1)) neuraminidase activi... 29397718
Neuraminidase IC50 = 20680.0 nM 4.68 Inhibition of Influenza A virus (A/swine/Shepparton/6/2009 (H1N1)) neuraminidase... 29397718
Neuraminidase IC50 = 20680.0 nM 4.68 Inhibition of Influenza A virus (A/chicken/Vietnam/08/2004 (H5N1)) clade 1 neura... 29397718
Unchecked IC50 = 22240.0 nM 4.65 Inhibition of Influenza A virus (A/NWS/G70C(H1N9)) neuraminidase activity using ... 29397718
Neuraminidase IC50 = 23770.0 nM 4.62 Inhibition of Influenza A virus (A/chicken/Bangli/BBVD-563/2007(H5N1)) clade 2 n... 29397718
Unchecked IC50 = 25380.0 nM 4.6 Inhibition of Influenza A virus (A/NWS/G70C(H1N9)) neuraminidase activity using ... 29397718
Neuraminidase IC50 = 25400.0 nM 4.59 Inhibition of Influenza A virus (A/chicken/Vietnam/08/2004 (H5N1)) clade 1 neura... 29397718
Neuraminidase IC50 = 26100.0 nM 4.58 Inhibition of Influenza A virus (A/chicken/Bangli/BBVD-563/2007(H5N1)) clade 2 n... 29397718
Neuraminidase IC50 = 25990.0 nM 4.58 Inhibition of Influenza A virus (A/Fukui/45/04(H3N2)) neuraminidase E119V mutant... 29397718
Neuraminidase IC50 = 29640.0 nM 4.53 Inhibition of Influenza A virus (A/swine/Shepparton/6/2009 (H1N1)) neuraminidase... 29397718
Neuraminidase IC50 = 29510.0 nM 4.53 Inhibition of Influenza A virus (A/Fukui/45/04(H3N2)) neuraminidase activity usi... 29397718
Neuraminidase IC50 = 31710.0 nM 4.5 Inhibition of Influenza A virus (A/California/07/09 (H1N1)) neuraminidase activi... 29397718

Literature References

PubMed DOI Target Context # Activities
29397718 10.1021/acs.jmedchem.7b01467 Neuraminidase 39
29397718 10.1021/acs.jmedchem.7b01467 Unchecked 4
29397718 10.1021/acs.jmedchem.7b01467 Influenza A virus 4
29397718 10.1021/acs.jmedchem.7b01467 Influenza B virus 1

Data from ChEMBL 36 via Core Engine