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Compound Detail

CHEMBL4475494

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CC(C)(O)[C@H](F)CN1Cc2cc(NC(=O)c3cnn4cccnc34)c(N3CCOCC3)cc2C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4475494
Phase Preclinical
Structure Type MOL
InChI Key AUYCSWFYKYVCLD-HXUWFJFHSA-N
12
Targets
37
Activities
3
Assay Types
17
PK Parameters
20
Publications
0
Known Names

Molecular Properties

482.5
MW (Da)
1.88
ALogP
8
HBA
2
HBD
112.3
PSA (Ų)
0.55
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C24H27FN6O4
MW 482.52
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -1.48

Activity Summary

IC50 23 meas. best 9.72
EC50 8 meas. best 8.52
Ki 6 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Interleukin-1 receptor-associated kinase 4
CHEMBL3778
 IC50 9.72 8.22 0.2 2
Interleukin-1 receptor-associated kinase 4
CHEMBL3778
 Ki 8.85 8.8425 1.4 4
Unchecked
CHEMBL612545
 EC50 8.52 8.52 3.0 1
Interleukin-1 receptor-associated kinase 4
CHEMBL3778
 EC50 8.52 8.52 3.0 1
Unchecked
CHEMBL612545
 IC50 8.48 6.9375 3.3 4
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 6.75 6.75 177.0 2
Leucine-rich repeat serine/threonine-protein kinase 2
CHEMBL1075104
 IC50 6.7 6.7 198.0 2
BDNF/NT-3 growth factors receptor
CHEMBL4898
 IC50 6.59 6.59 259.0 2
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 6.55 6.55 282.0 2
High affinity nerve growth factor receptor
CHEMBL2815
 IC50 6.5 6.5 313.0 2
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 6.31 6.31 486.0 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.29 6.29 509.4 2
Mitogen-activated protein kinase kinase kinase kinase 4
CHEMBL6166
 IC50 6.17 6.17 680.0 2
Misshapen-like kinase 1
CHEMBL5518
 IC50 6.06 6.06 879.0 2
Cyclin-dependent kinase 9
CHEMBL3116
 IC50 6.01 6.01 966.0 1
Leucine-rich repeat serine/threonine-protein kinase 2
CHEMBL1075104
 EC50 5.28 5.28 5200.0 2
BDNF/NT-3 growth factors receptor
CHEMBL4898
 EC50 5.25 5.1533 5600.0 3
High affinity nerve growth factor receptor
CHEMBL2815
 EC50 4.96 4.96 11000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 579.02 ng.hr.mL-1 Mus musculus
AUC 1833.58 ng.hr.mL-1 Rattus norvegicus
AUC 1495.81 ng.hr.mL-1 Canis lupus familiaris
AUC 1061.54 ng.hr.mL-1 Macaca fascicularis
CL 29.0 mL.min-1.kg-1 Mus musculus
CL 9.2 mL.min-1.kg-1 Rattus norvegicus
CL 11.3 mL.min-1.kg-1 Canis lupus familiaris
CL 15.8 mL.min-1.kg-1 Macaca fascicularis
F 34.0 % Mus musculus
F 31.0 % Rattus norvegicus
F 109.0 % Canis lupus familiaris
F 47.0 % Macaca fascicularis
Fu 0.01 - Homo sapiens
T1/2 1.9 hr Mus musculus
T1/2 1.6 hr Rattus norvegicus
T1/2 4.1 hr Canis lupus familiaris
T1/2 5.4 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Interleukin-1 receptor-associated kinase 4 IC50 = 0.19 nM 9.72 Inhibition of IRAK4 in human whole blood assessed as inhibition of R848-induced ... 32184965
Interleukin-1 receptor-associated kinase 4 Ki = 1.4 nM 8.85 Affinity Biochemical interaction: (Biochemical assay) EUB0001558a IRAK4 -
Interleukin-1 receptor-associated kinase 4 Ki = 1.4 nM 8.85 IRAK4 biochemical assay -
Interleukin-1 receptor-associated kinase 4 Ki = 1.4 nM 8.85 Inhibition of recombinant full-length N-terminal His6-tagged human IRAK4 express... 32184965
Interleukin-1 receptor-associated kinase 4 Ki = 1.5 nM 8.82 Biological Assay: Kinase activities were assayed using the Transcreener-Fluorece... -
Interleukin-1 receptor-associated kinase 4 EC50 = 3.0 nM 8.52 Affinity On-target Cellular interaction: (NanoBRET assay (HEK293T cells)) EUB000... -
Unchecked EC50 = 3.0 nM 8.52 NanoBRET assay (IRAK4, SGC Frankfurt) -
Unchecked IC50 = 3.3 nM 8.48 NanoBRET assay (IRAK4, SGC Frankfurt) -
Receptor-type tyrosine-protein kinase FLT3 IC50 = 177.0 nM 6.75 Flt3 Kinase panel -
Receptor-type tyrosine-protein kinase FLT3 IC50 = 177.0 nM 6.75 Selectivity interaction (Z-Lyte kinase biochemical assay, conc. ATP = Km(app), T... -
Unchecked IC50 = 190.0 nM 6.72 R848-induced IL-6 production in human whole blood -
Interleukin-1 receptor-associated kinase 4 IC50 = 190.0 nM 6.72 Affinity Phenotypic Cellular interaction: (R848-induced IL-6 production in human... -
Leucine-rich repeat serine/threonine-protein kinase 2 IC50 = 198.0 nM 6.7 LRRK2 Kinase panel -
Leucine-rich repeat serine/threonine-protein kinase 2 IC50 = 198.0 nM 6.7 Selectivity interaction (Z-Lyte kinase biochemical assay, conc. ATP = Km(app), T... -
BDNF/NT-3 growth factors receptor IC50 = 259.0 nM 6.59 TrkB Kinase panel -
BDNF/NT-3 growth factors receptor IC50 = 259.0 nM 6.59 Selectivity interaction (Z-Lyte kinase biochemical assay, conc. ATP = Km(app), T... -
Tyrosine-protein kinase JAK1 IC50 = 282.0 nM 6.55 Selectivity interaction (Z-Lyte kinase biochemical assay, conc. ATP = Km(app), T... -
Tyrosine-protein kinase JAK1 IC50 = 282.0 nM 6.55 JAK1 Kinase panel -
Unchecked IC50 = 290.0 nM 6.54 IFNalpha human whole blood assay -
High affinity nerve growth factor receptor IC50 = 313.0 nM 6.5 TrkA Kinase panel -

Literature References

PubMed DOI Target Context # Activities
32184965 10.1021/acsmedchemlett.9b00380 ADMET 25
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
32184965 10.1021/acsmedchemlett.9b00380 Mus musculus 11
- 10.6019/CHEMBL4879554 Unchecked 10
- 10.6019/CHEMBL5303304 HEK-293T 8
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
- 10.6019/CHEMBL5303304 U2OS 4
- 10.6019/CHEMBL5465560 BDNF/NT-3 growth factors receptor 4
- 10.6019/CHEMBL4879554 5-hydroxytryptamine receptor 2B 3
- 10.6019/CHEMBL5465560 Tyrosine-protein kinase JAK2 3
- 10.6019/CHEMBL4879554 Receptor-type tyrosine-protein kinase FLT3 3
- 10.6019/CHEMBL4879554 High affinity nerve growth factor receptor 3
- 10.6019/CHEMBL5465560 Receptor-type tyrosine-protein kinase FLT3 3
- 10.6019/CHEMBL4879554 Leucine-rich repeat serine/threonine-protein kinase 2 3
- 10.6019/CHEMBL4879554 Tyrosine-protein kinase JAK1 3
- 10.6019/CHEMBL4879554 BDNF/NT-3 growth factors receptor 3
- 10.6019/CHEMBL4879554 Tyrosine-protein kinase JAK2 3
- 10.6019/CHEMBL5465560 Leucine-rich repeat serine/threonine-protein kinase 2 3

Data from ChEMBL 36 via Core Engine