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Compound Detail

CHEMBL4128362

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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](O)CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4128362
Phase Preclinical
Structure Type MOL
InChI Key HMALKZAXODOYOP-DAXAGCIGSA-N
8
Targets
29
Activities
2
Assay Types
7
PK Parameters
4
Publications
0
Known Names

Molecular Properties

329.2
MW (Da)
-2.95
ALogP
7
HBA
6
HBD
156.6
PSA (Ų)
0.31
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C11H17F2NO8
MW 329.25
Aromatic Rings 0
Heavy Atoms 22
NP-Likeness 0.94

Activity Summary

IC50 24 meas. best 7.19
EC50 5 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuraminidase
CHEMBL4295840
 IC50 7.19 6.785 65.0 2
Neuraminidase
CHEMBL6135
 IC50 7.1 6.3242 80.0 12
Neuraminidase
CHEMBL3377
 IC50 6.76 6.33 174.0 2
Neuraminidase
CHEMBL6015
 IC50 6.62 6.1475 238.0 4
Neuraminidase
CHEMBL1667684
 IC50 6.06 6.055 863.0 2
Influenza B virus
CHEMBL613129
 EC50 6.0 6.0 1000.0 1
Influenza A virus
CHEMBL613740
 EC50 6.0 5.0 1000.0 4
Unchecked
CHEMBL612545
 IC50 5.96 5.94 1103.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.4133 hr Influenza A virus
T1/2 0.1967 hr Influenza A virus
T1/2 0.2 hr Influenza A virus
T1/2 0.1417 hr Influenza A virus (A/chicken/Bangli/BBVD-563/2007(H5N1))
T1/2 0.2933 hr Influenza A virus (A/Fukui/45/2004(H3N2))
T1/2 0.185 hr Influenza A virus (A/NWS/G70C(H1N9))
T1/2 0.7267 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 = 65.0 nM 7.19 Inhibition of Influenza B virus (B/Perth/211/2001) neuraminidase activity using ... 29397718
Neuraminidase IC50 = 80.0 nM 7.1 Inhibition of Influenza A virus (A/Mississippi/03/01 (H1N1)) neuraminidase activ... 29397718
Neuraminidase IC50 = 116.0 nM 6.94 Inhibition of Influenza A virus (A/Mississippi/03/01 (H1N1)) neuraminidase H274Y... 29397718
Neuraminidase IC50 = 116.0 nM 6.94 Inhibition of Influenza A virus (A/Mississippi/03/01 (H1N1)) neuraminidase activ... 29397718
Neuraminidase IC50 = 139.0 nM 6.86 Inhibition of Influenza A virus (A/Mississippi/03/01 (H1N1)) neuraminidase H274Y... 29397718
Neuraminidase IC50 = 174.0 nM 6.76 Inhibition of Influenza B virus (B/Perth/211/2001) neuraminidase D197E mutant ac... 29397718
Neuraminidase IC50 = 238.0 nM 6.62 Inhibition of Influenza A virus (A/Fukui/45/04(H3N2)) neuraminidase E119V mutant... 29397718
Neuraminidase IC50 = 414.0 nM 6.38 Inhibition of Influenza B virus (B/Perth/211/2001) neuraminidase activity using ... 29397718
Neuraminidase IC50 = 470.0 nM 6.33 Inhibition of Influenza A virus (A/swine/Shepparton/6/2009 (H1N1)) neuraminidase... 29397718
Neuraminidase IC50 = 465.0 nM 6.33 Inhibition of Influenza A virus (A/Fukui/45/04(H3N2)) neuraminidase E119V mutant... 29397718
Neuraminidase IC50 = 601.0 nM 6.22 Inhibition of Influenza A virus (A/California/07/09 (H1N1)) neuraminidase activi... 29397718
Neuraminidase IC50 = 791.0 nM 6.1 Inhibition of Influenza A virus (A/swine/Shepparton/6/2009 (H1N1)) neuraminidase... 29397718
Neuraminidase IC50 = 791.0 nM 6.1 Inhibition of Influenza A virus (A/California/07/09 (H1N1)) neuraminidase activi... 29397718
Neuraminidase IC50 = 863.0 nM 6.06 Inhibition of Influenza A virus (A/chicken/Bangli/BBVD-563/2007(H5N1)) clade 2 n... 29397718
Neuraminidase IC50 = 889.0 nM 6.05 Inhibition of Influenza A virus (A/chicken/Bangli/BBVD-563/2007(H5N1)) clade 2 n... 29397718
Influenza A virus EC50 = 1000.0 nM 6.0 Antiviral activity against Influenza A virus (A/NWS/G70C(H1N9)) infected in MDCK... 29397718
Influenza B virus EC50 = 1000.0 nM 6.0 Antiviral activity against Influenza B virus (B/Perth/211/2001) infected in MDCK... 29397718
Influenza A virus EC50 = 1000.0 nM 6.0 Antiviral activity against Influenza A virus (A/Mississippi/03/01 (H1N1)) infect... 29397718
Unchecked IC50 = 1103.0 nM 5.96 Inhibition of Influenza A virus (A/NWS/G70C(H1N9)) neuraminidase activity using ... 29397718
Neuraminidase IC50 = 1148.0 nM 5.94 Inhibition of Influenza A virus (A/NWS/G70C(H1N9)) neuraminidase E119G mutant ac... 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