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Compound Detail

CHEMBL4105032

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O=C(O)c1c[nH]c2cc(F)c(-c3ccc([C@@H]4CCCCO4)cc3)c(F)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4105032
Phase Preclinical
Structure Type MOL
InChI Key JQJNGAWEMYQJIQ-INIZCTEOSA-N
2
Targets
5
Activities
2
Assay Types
18
PK Parameters
20
Publications
0
Known Names

Molecular Properties

357.4
MW (Da)
5.05
ALogP
2
HBA
2
HBD
62.3
PSA (Ų)
0.69
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H17F2NO3
MW 357.36
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.22

Activity Summary

EC50 3 meas. best 8.22
Kd 2 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
AMPK alpha2/beta1/gamma1
CHEMBL3038455
 EC50 8.22 8.22 6.0 1
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1
CHEMBL2111345
 EC50 8.1 7.88 8.0 2
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1
CHEMBL2111345
 Kd 7.85 7.845 14.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 16400.0 ng.hr.mL-1 Rattus norvegicus
AUC 12800.0 ng.hr.mL-1 Rattus norvegicus
AUC 35900.0 ng.hr.mL-1 Macaca fascicularis
AUC 91600.0 ng.hr.mL-1 Macaca fascicularis
CL 10.0 mL.min-1.kg-1 Rattus norvegicus
CL 0.03 mL.min-1.kg-1 Rattus norvegicus
CL 1.15 mL.min-1.kg-1 Rattus norvegicus
CL 1.15 mL.min-1.kg-1 Rattus norvegicus
CL 0.38 mL.min-1.kg-1 Macaca fascicularis
Cmax 5288.78 nM Rattus norvegicus
Cmax 22890.08 nM Macaca fascicularis
F 26.0 % Rattus norvegicus
F 85.0 % Macaca fascicularis
T1/2 4.95 hr Rattus norvegicus
T1/2 12.0 hr Macaca fascicularis
T1/2 0.01887 hr Homo sapiens
Tmax 2.7 hr Rattus norvegicus
Tmax 2.0 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
AMPK alpha2/beta1/gamma1 EC50 = 6.0 nM 8.22 Activation of full-length recombinant N-terminal His-tagged human AMPKalpha2beta... 30036059
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 EC50 = 8.0 nM 8.1 Activation of full-length recombinant N-terminal His-tagged human AMPKalpha1beta... 30036059
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 Kd = 14.0 nM 7.85 Binding affinity to human BAP-tagged AMPK alpha1/beta1/gamma1 by SPR assay 29466005
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 Kd = 14.4 nM 7.84 Binding affinity to Bap-tagged human AMPKalpha1beta1gamma1 expressed in Escheric... 30036059
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 EC50 = 22.0 nM 7.66 Allosteric activation of human AMPK alpha1/beta1/gamma1 by TR-FRET assay 29466005

Literature References

PubMed DOI Target Context # Activities
29466005 10.1021/acs.jmedchem.7b01641 Rattus norvegicus 11
29466005 10.1021/acs.jmedchem.7b01641 Cynomolgus monkey 8
30036059 10.1021/acs.jmedchem.8b00807 AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 6
29466005 10.1021/acs.jmedchem.7b01641 ADMET 3
29466005 10.1021/acs.jmedchem.7b01641 No relevant target 3
29466005 10.1021/acs.jmedchem.7b01641 AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 3
29466005 10.1021/acs.jmedchem.7b01641 Organic anion transporter 3 2
30036059 10.1021/acs.jmedchem.8b00807 AMPK alpha2/beta2/gamma3 2
30036059 10.1021/acs.jmedchem.8b00807 AMPK alpha2/beta2/gamma1 2
30036059 10.1021/acs.jmedchem.8b00807 AMPK alpha1/beta2/gamma1 2
30036059 10.1021/acs.jmedchem.8b00807 AMPK alpha2/beta1/gamma1 2
30036059 10.1021/acs.jmedchem.8b00807 ADMET 2
30036059 10.1021/acs.jmedchem.8b00807 No relevant target 1
30036059 10.1021/acs.jmedchem.8b00807 Hepatocyte 1
29466005 10.1021/acs.jmedchem.7b01641 AMPK alpha2/beta1/gamma1 1
29466005 10.1021/acs.jmedchem.7b01641 AMPK alpha2/beta2/gamma3 1
29466005 10.1021/acs.jmedchem.7b01641 AMPK alpha2/beta2/gamma1 1
29466005 10.1021/acs.jmedchem.7b01641 AMPK alpha1/beta2/gamma1 1
29466005 10.1021/acs.jmedchem.7b01641 Solute carrier family 22 member 6 1
29466005 10.1021/acs.jmedchem.7b01641 MDCKII-LE 1

Data from ChEMBL 36 via Core Engine