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Compound Detail

CHEMBL5170576

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COC(=O)Nc1cc(-c2ccc(OC[C@@](C)(N)CC(C)C)c(C)n2)ccn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5170576
Phase Preclinical
Structure Type MOL
InChI Key HINOQCZIDBNXEI-FQEVSTJZSA-N
11
Targets
19
Activities
2
Assay Types
9
PK Parameters
19
Publications
0
Known Names

Molecular Properties

372.5
MW (Da)
3.77
ALogP
6
HBA
2
HBD
99.4
PSA (Ų)
0.77
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H28N4O3
MW 372.47
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.79

Activity Summary

IC50 18 meas. best 8.96
Ki 1 meas. best 9.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
AP2-associated protein kinase 1
CHEMBL5169154
 Ki 9.54 9.54 0.3 1
AP2-associated protein kinase 1
CHEMBL3830
 IC50 8.96 8.9175 1.1 8
BMP-2-inducible protein kinase
CHEMBL4522
 IC50 7.05 7.05 90.0 1
MAP kinase-interacting serine/threonine-protein kinase 1
CHEMBL4718
 IC50 6.72 6.72 190.0 1
Cyclin-G-associated kinase
CHEMBL4355
 IC50 6.68 6.68 210.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 IC50 6.27 6.27 540.0 1
Death-associated protein kinase 1
CHEMBL2558
 IC50 5.85 5.85 1400.0 1
MAP kinase-interacting serine/threonine-protein kinase 2
CHEMBL4204
 IC50 5.82 5.82 1500.0 1
Myosin light chain kinase 2, skeletal/cardiac muscle
CHEMBL2777
 IC50 5.75 5.75 1800.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.23 5.23 5900.0 1
Unchecked
CHEMBL612545
 IC50 4.8 4.605 16000.0 2

Pharmacokinetic Data

Parameter Value Units Species
F 94.0 % Rattus norvegicus
Fu 0.18 - Homo sapiens
Fu 0.225 - Rattus norvegicus
T1/2 11.3 hr Rattus norvegicus
T1/2 2.0 hr Homo sapiens
T1/2 1.417 hr Rattus norvegicus
T1/2 1.533 hr Mus musculus
T1/2 0.85 hr Macaca fascicularis
T1/2 1.683 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
AP2-associated protein kinase 1 Ki = 0.29 nM 9.54 Displacement of 3H-LP-927443 from AAK1 in C57BL6 mouse brain homogenate assessed... 35261239
AP2-associated protein kinase 1 IC50 = 1.1 nM 8.96 AAK1 Kinase Assay: The assays were performed in U-bottom 384-well plates. The fi... -
AP2-associated protein kinase 1 IC50 = 1.1 nM 8.96 AAK1 Kinase Assay: The assays were performed in U-bottom 384-well plates. The fi... -
AP2-associated protein kinase 1 IC50 = 1.1 nM 8.96 Kinase Assay: The assays were performed in U-bottom 384-well plates. The final a... -
AP2-associated protein kinase 1 IC50 = 1.1 nM 8.96 AAK1 Kinase Assay: The assays were performed in U-bottom 384-well plates. The fi... -
AP2-associated protein kinase 1 IC50 = 1.1 nM 8.96 AAK1 Kinase Assay: The assays were performed in U-bottom 384-well plates. The fi... -
AP2-associated protein kinase 1 IC50 = 1.1 nM 8.96 Kinase Assay: The assays were performed in U-bottom 384-well plates. The final a... -
AP2-associated protein kinase 1 IC50 = 1.1 nM 8.96 Inhibition of bacterially expressed GST-Xa-tagged human AAK1 using 5-FAM-labelle... 35261239
AP2-associated protein kinase 1 IC50 = 2.4 nM 8.62 Inhibition of full length human AAK1 expressed in HEK293F cells assessed as supp... 35261239
BMP-2-inducible protein kinase IC50 = 90.0 nM 7.05 Inhibition of BIKE (unknown origin) 35261239
MAP kinase-interacting serine/threonine-protein kinase 1 IC50 = 190.0 nM 6.72 Inhibition of MNK1 (unknown origin) 35261239
Cyclin-G-associated kinase IC50 = 210.0 nM 6.68 Inhibition of GAK (unknown origin) 35261239
5-hydroxytryptamine receptor 2B IC50 = 540.0 nM 6.27 Inhibition of 5HT2B receptor (unknown origin) 35261239
Death-associated protein kinase 1 IC50 = 1400.0 nM 5.85 Inhibition of DAPK1 (unknown origin) 35261239
MAP kinase-interacting serine/threonine-protein kinase 2 IC50 = 1500.0 nM 5.82 Inhibition of MNK2 (unknown origin) 35261239
Myosin light chain kinase 2, skeletal/cardiac muscle IC50 = 1800.0 nM 5.75 Inhibition of MYLK2 (unknown origin) 35261239
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 5900.0 nM 5.23 Inhibition of human ERG by patch clamp assay 35261239
Unchecked IC50 = 16000.0 nM 4.8 Inhibition of calcium channel (unknown origin) 35261239
Unchecked IC50 = 39000.0 nM 4.41 Inhibition of sodium channel voltage-sensing domain (unknown origin) 35261239

Literature References

PubMed DOI Target Context # Activities
35261239 10.1021/acs.jmedchem.1c02132 ADMET 29
35261239 10.1021/acs.jmedchem.1c02132 No relevant target 11
35261239 10.1021/acs.jmedchem.1c02132 Rattus norvegicus 4
35261239 10.1021/acs.jmedchem.1c02132 AP2-associated protein kinase 1 3
35261239 10.1021/acs.jmedchem.1c02132 Cytochrome P450 3A4 2
35261239 10.1021/acs.jmedchem.1c02132 Unchecked 2
35261239 10.1021/acs.jmedchem.1c02132 Myosin light chain kinase 2, skeletal/cardiac muscle 1
35261239 10.1021/acs.jmedchem.1c02132 MAP kinase-interacting serine/threonine-protein kinase 2 1
35261239 10.1021/acs.jmedchem.1c02132 MAP kinase-interacting serine/threonine-protein kinase 1 1
35261239 10.1021/acs.jmedchem.1c02132 Cyclin-G-associated kinase 1
35261239 10.1021/acs.jmedchem.1c02132 Death-associated protein kinase 1 1
35261239 10.1021/acs.jmedchem.1c02132 BMP-2-inducible protein kinase 1
35261239 10.1021/acs.jmedchem.1c02132 5-hydroxytryptamine receptor 2B 1
35261239 10.1021/acs.jmedchem.1c02132 Voltage-gated inwardly rectifying potassium channel KCNH2 1
35261239 10.1021/acs.jmedchem.1c02132 Cytochrome P450 2B6 1
35261239 10.1021/acs.jmedchem.1c02132 Cytochrome P450 2D6 1
35261239 10.1021/acs.jmedchem.1c02132 Cytochrome P450 2C9 1
35261239 10.1021/acs.jmedchem.1c02132 Cytochrome P450 2C19 1
35261239 10.1021/acs.jmedchem.1c02132 Cytochrome P450 1A2 1

Data from ChEMBL 36 via Core Engine