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Compound Detail

CHEMBL5393771

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COc1cc(-c2cnc3cc(OCCN4CCOCC4)ccn23)cc2c1C(=O)N(CC(F)(F)F)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5393771
Phase Preclinical
Structure Type MOL
InChI Key XASOHFCUIQARJT-UHFFFAOYSA-N
9
Targets
22
Activities
2
Assay Types
27
PK Parameters
20
Publications
0
Known Names

Molecular Properties

504.5
MW (Da)
3.28
ALogP
7
HBA
0
HBD
68.5
PSA (Ų)
0.49
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H27F3N4O4
MW 504.51
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness -1.01

Activity Summary

IC50 20 meas. best 8.42
EC50 2 meas. best 5.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase SIK3
CHEMBL6149
 IC50 8.42 7.6925 3.8 4
Serine/threonine-protein kinase SIK2
CHEMBL5699
 IC50 8.11 7.3325 7.8 4
Unchecked
CHEMBL612545
 IC50 7.17 6.7825 67.0 4
Receptor-interacting serine/threonine-protein kinase 2
CHEMBL5014
 IC50 7.11 7.11 78.4 1
Serine/threonine-protein kinase SIK1
CHEMBL6082
 IC50 6.55 6.0267 282.8 3
Blood
CHEMBL613416
 IC50 6.0 6.0 1000.0 1
MAP kinase-interacting serine/threonine-protein kinase 2
CHEMBL4204
 IC50 5.97 5.97 1074.0 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 5.96 5.96 1095.0 1
Unchecked
CHEMBL612545
 EC50 5.96 5.865 1087.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.82 4.82 15300.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 402.0 ng.hr.mL-1 Mus musculus
AUC 1380.0 ng.hr.mL-1 Mus musculus
AUC 759.0 ng.hr.mL-1 Rattus norvegicus
AUC 2120.0 ng.hr.mL-1 Rattus norvegicus
AUC 897.0 ng.hr.mL-1 Canis lupus familiaris
AUC 1840.0 ng.hr.mL-1 Canis lupus familiaris
AUC 2490.0 ng.hr.mL-1 Mus musculus
AUC 13900.0 ng.hr.mL-1 Mus musculus
AUC 86800.0 ng.hr.mL-1 Mus musculus
CL 41.33 mL.min-1.kg-1 Mus musculus
CL 92.83 mL.min-1.kg-1 Mus musculus
CL 31.5 mL.min-1.kg-1 Rattus norvegicus
CL 127.33 mL.min-1.kg-1 Rattus norvegicus
CL 12.78 mL.min-1.kg-1 Canis lupus familiaris
CL 26.17 mL.min-1.kg-1 Canis lupus familiaris
Cmax 1397.4 nM Mus musculus
Cmax 7095.99 nM Mus musculus
Cmax 42219.18 nM Mus musculus
F 68.7 % Mus musculus
F 55.9 % Rattus norvegicus
F 41.0 % Canis lupus familiaris
T1/2 0.555 hr Mus musculus
T1/2 1.28 hr Mus musculus
T1/2 1.42 hr Rattus norvegicus
T1/2 3.61 hr Rattus norvegicus
T1/2 4.28 hr Canis lupus familiaris
T1/2 4.63 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine/threonine-protein kinase SIK3 IC50 = 3.8 nM 8.42 Inhibition of full length SIK3 (unknown origin) using AMARA peptide as substrate... 38552030
Serine/threonine-protein kinase SIK2 IC50 = 7.8 nM 8.11 Inhibition of full length human SIK2 using AMARA peptide as substrate incubated ... 38552030
Serine/threonine-protein kinase SIK3 IC50 = 16.4 nM 7.79 Inhibition of SIK3 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Serine/threonine-protein kinase SIK2 IC50 = 20.4 nM 7.69 Inhibition of SIK2 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Serine/threonine-protein kinase SIK3 IC50 = 35.0 nM 7.46 Inhibition of SIK3 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Unchecked IC50 = 67.0 nM 7.17 Antiinflammatory activity against LPS-stimulated human CD14+ monocytes assessed ... 38552030
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 78.4 nM 7.11 Inhibition of human RIPK2 38552030
Serine/threonine-protein kinase SIK3 IC50 = 79.0 nM 7.1 Inhibition of NanoLuc-fused SIK3 (unknown origin) expressed in HEK293 cells meas... 38552030
Serine/threonine-protein kinase SIK2 IC50 = 114.0 nM 6.94 Inhibition of SIK2 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Unchecked IC50 = 133.0 nM 6.88 Reduction in LPS-stimulated TNFalpha production in human CD14+ monocytes isolate... 37467565
Unchecked IC50 = 231.0 nM 6.64 Antiinflammatory activity against LPS-stimulated human CD14+ monocytes assessed ... 38552030
Serine/threonine-protein kinase SIK2 IC50 = 254.0 nM 6.59 Inhibition of NanoLuc-fused SIK2 (unknown origin) expressed in HEK293 cells meas... 38552030
Serine/threonine-protein kinase SIK1 IC50 = 282.8 nM 6.55 Inhibition of N-terminal GST-tagged wild type human SIK1 (1 to 783 residues) exp... 38552030
Unchecked IC50 = 365.0 nM 6.44 Antiinflammatory activity against LPS-stimulated human MdM cells assessed as inh... 38552030
Serine/threonine-protein kinase SIK1 IC50 = 591.0 nM 6.23 Inhibition of SIK1 (unknown origin) using AMARA as substrate buffer incubated fo... 37467565
Blood IC50 = 1000.0 nM 6.0 Antiinflammatory activity against LPS-stimulated human whole blood assessed as i... 38552030
MAP kinase-interacting serine/threonine-protein kinase 2 IC50 = 1074.0 nM 5.97 Inhibition of human MKNK2 38552030
Tyrosine-protein kinase ABL1 IC50 = 1095.0 nM 5.96 Inhibition of human ABL1 38552030
Unchecked EC50 = 1087.0 nM 5.96 Induction of IL-10 expression in human CD14+ monocytes isolated from PBMC measur... 37467565
Unchecked EC50 = 1703.0 nM 5.77 Inhibition of SIK in human U2OS cells assessed as CRTC3 nuclear translocation me... 38552030

Literature References

PubMed DOI Target Context # Activities
38552030 10.1021/acs.jmedchem.3c02246 ADMET 49
38552030 10.1021/acs.jmedchem.3c02246 Mus musculus 20
38552030 10.1021/acs.jmedchem.3c02246 Unchecked 12
37467565 10.1016/j.bmc.2023.117414 Unchecked 3
37467565 10.1016/j.bmc.2023.117414 Serine/threonine-protein kinase SIK1 2
38552030 10.1021/acs.jmedchem.3c02246 Blood 2
38552030 10.1021/acs.jmedchem.3c02246 MAP kinase-interacting serine/threonine-protein kinase 2 2
38552030 10.1021/acs.jmedchem.3c02246 Tyrosine-protein kinase ABL1 2
38552030 10.1021/acs.jmedchem.3c02246 Receptor-interacting serine/threonine-protein kinase 2 2
38552030 10.1021/acs.jmedchem.3c02246 Cytochrome P450 2
38552030 10.1021/acs.jmedchem.3c02246 Serine/threonine-protein kinase SIK3 2
38552030 10.1021/acs.jmedchem.3c02246 Serine/threonine-protein kinase SIK2 2
38552030 10.1021/acs.jmedchem.3c02246 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 Serine/threonine-protein kinase SIK2 2
38552030 10.1021/acs.jmedchem.3c02246 Plasma 1
38552030 10.1021/acs.jmedchem.3c02246 Cytochrome P450 2C19 1
38552030 10.1021/acs.jmedchem.3c02246 Cytochrome P450 2C9 1
38552030 10.1021/acs.jmedchem.3c02246 Cytochrome P450 3A4 1
38552030 10.1021/acs.jmedchem.3c02246 Cytochrome P450 2D6 1

Data from ChEMBL 36 via Core Engine