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Compound Detail

CHEMBL2206459

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

Basic Information

ChEMBL ID CHEMBL2206459
Phase Preclinical
Structure Type MOL
InChI Key NLOONHWUUBBYCD-YNEHKIRRSA-N
6
Targets
15
Activities
3
Assay Types
24
PK Parameters
14
Publications
0
Known Names

Molecular Properties

362.4
MW (Da)
0.38
ALogP
4
HBA
6
HBD
157.8
PSA (Ų)
0.22
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H27N4O5P
MW 362.37
Aromatic Rings 0
Heavy Atoms 24
NP-Likeness 0.79

Activity Summary

EC50 8 meas. best 8.42
IC50 6 meas. best 10.4
Ki 1 meas. best 6.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuraminidase
CHEMBL1667683
 IC50 10.4 10.4 0.0 1
Neuraminidase
CHEMBL1287610
 IC50 10.05 9.725 0.1 2
Neuraminidase
CHEMBL6135
 IC50 9.52 9.52 0.3 1
Neuraminidase
CHEMBL2046263
 IC50 9.46 9.46 0.3 1
Unchecked
CHEMBL612545
 IC50 8.68 8.68 2.1 1
Influenza A virus
CHEMBL613740
 EC50 8.42 6.6338 3.8 8
Unchecked
CHEMBL612545
 Ki 6.85 6.85 140.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1050.0 ng.hr.mL-1 Mus musculus
AUC 939.0 ng.hr.mL-1 Mus musculus
AUC 669.0 ng.hr.mL-1 Rattus norvegicus
AUC 666.0 ng.hr.mL-1 Rattus norvegicus
AUC 373.0 ng.hr.mL-1 Mus musculus
AUC 354.0 ng.hr.mL-1 Mus musculus
AUC 128.4 ng.hr.mL-1 Rattus norvegicus
AUC 116.7 ng.hr.mL-1 Rattus norvegicus
Cmax 929.99 nM Mus musculus
Cmax 201.73 nM Rattus norvegicus
F 100.0 % Mus musculus
F 100.0 % Rattus norvegicus
F 7.0 % Mus musculus
F 3.2 % Rattus norvegicus
MRT 3.61 hr Mus musculus
MRT 2.4 hr Rattus norvegicus
MRT 0.66 hr Rattus norvegicus
MRT 0.58 hr Mus musculus
T1/2 2.44 hr Mus musculus
T1/2 1.47 hr Rattus norvegicus
T1/2 0.83 hr Rattus norvegicus
T1/2 0.53 hr Mus musculus
Tmax 1.33 hr Mus musculus
Tmax 0.88 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuraminidase IC50 = 0.04 nM 10.4 Inhibition of Influenza A virus (A/reassortant/NIBRG-14(Viet Nam/1194/2004 x Pue... 23009169
Neuraminidase IC50 = 0.09 nM 10.05 Inhibition of wild type Influenza A virus A/WSN/1933(H1N1) neuraminidase in viru... 23009169
Neuraminidase IC50 = 0.3 nM 9.52 Inhibition of Influenza A virus A/Taiwan/3446/2002(H3N2) neuraminidase in virus-... 23009169
Neuraminidase IC50 = 0.35 nM 9.46 Inhibition of Influenza A virus A/Udorn/1972(H3N2) neuraminidase in virus-infect... 23009169
Neuraminidase IC50 = 0.4 nM 9.4 Inhibition of oseltamivir-resistant Influenza A virus A/WSN/1933/H275Y(H1N1) neu... 23009169
Unchecked IC50 = 2.1 nM 8.68 Inhibition of Influenza B virus B/Taiwan/70641/2004 neuraminidase in virus-infec... 23009169
Influenza A virus EC50 = 3.8 nM 8.42 Antiviral activity against Influenza A virus (A/WSN/1933(H1N1)) infected in MDCK... 29843102
Influenza A virus EC50 = 7.0 nM 8.15 Antiviral activity against Influenza A virus A/Panama/2007/99(H3N2) infected in ... 23009169
Influenza A virus EC50 = 35.0 nM 7.46 Antiviral activity against Influenza A virus A/Victoria/3/75(H3N2) infected in M... 23009169
Unchecked Ki = 140.0 nM 6.85 Inhibition of Influenza A virus (A/California/07/2009(H1N1)) recombinant wild ty... 27236066
Influenza A virus EC50 = 360.0 nM 6.44 Antiviral activity against influenza A virus A/WSN/1933(H1N1) infected in MDCK c... 23009169
Influenza A virus EC50 = 475.0 nM 6.32 Antiviral activity against Influenza A virus A/Duck/MN/1525/81(H5N1) infected in... 23009169
Influenza A virus EC50 = 3200.0 nM 5.5 Antiviral activity against oseltamivir-resistant Influenza A virus A/WSN/1933/H2... 23009169
Influenza A virus EC50 = 3600.0 nM 5.44 Antiviral activity against influenza A virus A/CA/07/2009 (pandemic H1N1) infect... 23009169
Influenza A virus EC50 = 4600.0 nM 5.34 Antiviral activity against oseltamivir-resistant Influenza A virus A/Hong Kong/2... 23009169

Literature References

PubMed DOI Target Context # Activities
23009169 10.1021/jm3008486 Influenza A virus 27
23009169 10.1021/jm3008486 Rattus norvegicus 16
23009169 10.1021/jm3008486 Mus musculus 16
23009169 10.1021/jm3008486 Neuraminidase 5
23009169 10.1021/jm3008486 Liver microsomes 4
23009169 10.1021/jm3008486 ADMET 3
23009169 10.1021/jm3008486 Blood 2
23009169 10.1021/jm3008486 Influenza B virus 2
23009169 10.1021/jm3008486 Liver 1
23009169 10.1021/jm3008486 No relevant target 1
23009169 10.1021/jm3008486 Unchecked 1
23009169 10.1021/jm3008486 MDCK 1
27236066 10.1016/j.ejmech.2016.05.016 Unchecked 1
29843102 10.1016/j.ejmech.2018.05.030 Influenza A virus 1

Data from ChEMBL 36 via Core Engine