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Compound Detail

CHEMBL5394880

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COc1cc(-c2cnc(Nc3cc(N4CCN(C)CC4)nc(C)n3)s2)cc2c1C(=O)N(CC(F)(F)F)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5394880
Phase Preclinical
Structure Type MOL
InChI Key WCLYSPWUHSZWOR-UHFFFAOYSA-N
6
Targets
10
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

547.6
MW (Da)
3.97
ALogP
9
HBA
1
HBD
86.7
PSA (Ų)
0.50
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H28F3N7O2S
MW 547.61
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness -1.38

Activity Summary

IC50 9 meas. best 9.22
EC50 1 meas. best 6.83

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase SIK2
CHEMBL5699
 IC50 9.22 9.185 0.6 2
Serine/threonine-protein kinase SIK3
CHEMBL6149
 IC50 8.23 8.0 5.9 2
Unchecked
CHEMBL612545
 IC50 7.52 7.52 30.0 1
Serine/threonine-protein kinase SIK1
CHEMBL6082
 IC50 7.48 7.165 33.0 2
Unchecked
CHEMBL612545
 EC50 6.83 6.83 148.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.31 4.31 48900.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.3 4.3 50000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1014.0 ng.hr.mL-1 Mus musculus
CL 64.8 mL.min-1.kg-1 Mus musculus
F 38.0 % Mus musculus
T1/2 0.35 hr Homo sapiens
T1/2 0.2917 hr Mus musculus
T1/2 3.03 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine/threonine-protein kinase SIK2 IC50 = 0.6 nM 9.22 Inhibition of SIK2 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Serine/threonine-protein kinase SIK2 IC50 = 0.7 nM 9.15 Inhibition of SIK2 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Serine/threonine-protein kinase SIK3 IC50 = 5.9 nM 8.23 Inhibition of SIK3 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Serine/threonine-protein kinase SIK3 IC50 = 17.0 nM 7.77 Inhibition of SIK3 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Unchecked IC50 = 30.0 nM 7.52 Reduction in LPS-stimulated TNFalpha production in human CD14+ monocytes isolate... 37467565
Serine/threonine-protein kinase SIK1 IC50 = 33.0 nM 7.48 Inhibition of SIK1 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Serine/threonine-protein kinase SIK1 IC50 = 140.0 nM 6.85 Inhibition of SIK1 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Unchecked EC50 = 148.0 nM 6.83 Induction of IL-10 expression in human CD14+ monocytes isolated from PBMC measur... 37467565
Cytochrome P450 2C19 IC50 = 48900.0 nM 4.31 Inhibition of human CYP2C19 by LC-MS/MS analysis 37467565
Cytochrome P450 2C9 IC50 = 50000.0 nM 4.3 Inhibition of human CYP2C9 by LC-MS/MS analysis 37467565

Literature References

PubMed DOI Target Context # Activities
37467565 10.1016/j.bmc.2023.117414 ADMET 8
37467565 10.1016/j.bmc.2023.117414 No relevant target 3
37467565 10.1016/j.bmc.2023.117414 Unchecked 3
37467565 10.1016/j.bmc.2023.117414 Serine/threonine-protein kinase SIK2 2
37467565 10.1016/j.bmc.2023.117414 Serine/threonine-protein kinase SIK1 2
37467565 10.1016/j.bmc.2023.117414 Serine/threonine-protein kinase SIK3 2
37467565 10.1016/j.bmc.2023.117414 Cytochrome P450 3A4 1
37467565 10.1016/j.bmc.2023.117414 AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 1
37467565 10.1016/j.bmc.2023.117414 Cytochrome P450 2C19 1
37467565 10.1016/j.bmc.2023.117414 Cytochrome P450 2C9 1
37467565 10.1016/j.bmc.2023.117414 Cytochrome P450 1A2 1
37467565 10.1016/j.bmc.2023.117414 Maternal embryonic leucine zipper kinase 1
37467565 10.1016/j.bmc.2023.117414 NUAK family SNF1-like kinase 2 1
37467565 10.1016/j.bmc.2023.117414 NUAK family SNF1-like kinase 1 1
37467565 10.1016/j.bmc.2023.117414 Serine/threonine-protein kinase BRSK1 1
37467565 10.1016/j.bmc.2023.117414 MAP/microtubule affinity-regulating kinase 4 1
37467565 10.1016/j.bmc.2023.117414 MAP/microtubule affinity-regulating kinase 3 1
37467565 10.1016/j.bmc.2023.117414 Serine/threonine-protein kinase MARK2 1
37467565 10.1016/j.bmc.2023.117414 Serine/threonine-protein kinase MARK1 1
37467565 10.1016/j.bmc.2023.117414 AMPK alpha2/beta1/gamma1 1

Data from ChEMBL 36 via Core Engine