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Compound Detail

CHEMBL3823499

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CC(C)(C)S(=O)(=O)c1ccc2nccc(Nc3n[nH]c4ccc(F)cc34)c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3823499
Phase Preclinical
Structure Type MOL
InChI Key XLOGLWKOHPIJLV-UHFFFAOYSA-N
13
Targets
18
Activities
2
Assay Types
17
PK Parameters
20
Publications
0
Known Names

Molecular Properties

398.5
MW (Da)
4.57
ALogP
5
HBA
2
HBD
87.7
PSA (Ų)
0.53
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C20H19FN4O2S
MW 398.46
Aromatic Rings 4
Heavy Atoms 28
NP-Likeness -1.56

Activity Summary

IC50 17 meas. best 8.7
Ki 1 meas. best 6.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Receptor-interacting serine/threonine-protein kinase 2
CHEMBL3822350
 IC50 8.7 8.7 2.0 1
Receptor-interacting serine/threonine-protein kinase 2
CHEMBL5014
 IC50 8.3 7.9283 5.0 6
Monocyte
CHEMBL614076
 IC50 8.1 8.1 8.0 1
Receptor-interacting serine/threonine-protein kinase 3
CHEMBL1795199
 IC50 7.8 7.8 16.0 1
Mus musculus
CHEMBL375
 IC50 7.43 7.43 37.0 1
Rattus norvegicus
CHEMBL376
 IC50 7.3 7.3 50.0 1
Whole blood
CHEMBL2367373
 IC50 6.88 6.88 133.0 1
Cyclin-G-associated kinase
CHEMBL4355
 Ki 6.66 6.66 220.0 1
Whole blood
CHEMBL2367389
 IC50 6.62 6.62 237.0 1
TGF-beta receptor type-1
CHEMBL4439
 IC50 5.5 5.5 3160.0 1
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 5.29 5.29 5119.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.13 5.13 7445.0 1
Tyrosine-protein kinase Lck
CHEMBL258
 IC50 4.9 4.9 12600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 980.0 ng.hr.mL-1 Rattus norvegicus
AUC 860.0 ng.hr.mL-1 Mus musculus
AUC 980.0 ng.hr.mL-1 Rattus norvegicus
CL 15.0 mL.min-1.kg-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Mus musculus
CL 15.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 652.51 nM Rattus norvegicus
Cmax 853.29 nM Mus musculus
Cmax 652.51 nM Rattus norvegicus
F 39.0 % Rattus norvegicus
F 34.0 % Mus musculus
F 39.0 % Rattus norvegicus
Fu 0.026 - Rattus norvegicus
Fu 0.026 - Rattus norvegicus
T1/2 3.1 hr Rattus norvegicus
T1/2 2.1 hr Mus musculus
T1/2 7.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 2.0 nM 8.7 Inhibition of rat RIPK2 preincubated for 10 mins followed by addition of fluores... 27109867
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 5.0 nM 8.3 Competitive inhibition of full length FLAG-His-tagged RIP2K (unknown origin) exp... 27109867
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 5.0 nM 8.3 Inhibition of full length His/flag-tagged RIPK2 (unknown origin) expressed in ba... 30344914
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 5.0 nM 8.3 Inhibition of full length FLAG His-tagged RIPK2 (unknown origin) expressed in Ba... 37531744
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 5.0 nM 8.3 Inhibition of wildtype RIPK2 (unknown origin) by ADP-Glo assay 37531744
Monocyte IC50 = 8.0 nM 8.1 Inhibition of MDP-stimulated TNF-alpha release in human monocytes preincubated f... 27109867
Receptor-interacting serine/threonine-protein kinase 3 IC50 = 16.0 nM 7.8 Inhibition of RIPK3 (unknown origin) preincubated for 10 mins followed by additi... 27109867
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 18.0 nM 7.75 Inhibition of RIP2K in MDP-stimulated HEK-293 cells over-expressing NOD2 assesse... 27109867
Mus musculus IC50 = 37.0 nM 7.43 Antiinflammatory activity in Balb/c mouse model of L18-MDP-induced inflammatory ... 27109867
Rattus norvegicus IC50 = 50.0 nM 7.3 Antiinflammatory activity in Crl:CD Sprague-Dawley rat model of L18-MDP-induced ... 27109867
Whole blood IC50 = 133.0 nM 6.88 Inhibition of MDP-stimulated TNF-alpha release in rat whole blood preincubated f... 27109867
Cyclin-G-associated kinase Ki = 220.0 nM 6.66 Binding affinity to C-terminal AVI-tagged GAK (unknown origin) (12 to 347 residu... 30768268
Whole blood IC50 = 237.0 nM 6.62 Inhibition of MDP-stimulated TNF-alpha release in human whole blood preincubated... 27109867
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 237.0 nM 6.62 Inhibition of RIPK2 in human whole blood assessed as reduction in MDP-stimulated... 30344914
TGF-beta receptor type-1 IC50 = 3160.0 nM 5.5 Inhibition of full length GST-tagged ALK5 (unknown origin) expressed in baculovi... 31749904
Mitogen-activated protein kinase 14 IC50 = 5119.0 nM 5.29 Inhibition of p38alpha (unknown origin) 27109867
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 7445.0 nM 5.13 Inhibition of human ERG expressed in CHO cells by Qpatch clamp assay 30344914
Tyrosine-protein kinase Lck IC50 = 12600.0 nM 4.9 Inhibition of full length His-Tev-tagged LCK (unknown origin) expressed in bacul... 31749904

Literature References

PubMed DOI Target Context # Activities
27109867 10.1021/acs.jmedchem.6b00211 Mus musculus 11
- 10.6019/CHEMBL5303304 U2OS 9
27109867 10.1021/acs.jmedchem.6b00211 Rattus norvegicus 8
- 10.6019/CHEMBL5303304 HEK-293T 8
30344914 10.1021/acsmedchemlett.8b00344 Rattus norvegicus 7
- 10.6019/CHEMBL5303304 Fibroblast 7
27109867 10.1021/acs.jmedchem.6b00211 Receptor-interacting serine/threonine-protein kinase 2 5
27109867 10.1021/acs.jmedchem.6b00211 Intestinal mucosa 4
30344914 10.1021/acsmedchemlett.8b00344 Receptor-interacting serine/threonine-protein kinase 2 2
27109867 10.1021/acs.jmedchem.6b00211 Receptor-interacting serine/threonine-protein kinase 3 2
37531744 10.1016/j.ejmech.2023.115683 Receptor-interacting serine/threonine-protein kinase 2 2
27109867 10.1021/acs.jmedchem.6b00211 Whole blood 2
30768268 10.1021/acs.jmedchem.8b01213 Cyclin-G-associated kinase 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
27109867 10.1021/acs.jmedchem.6b00211 Nucleotide-binding oligomerization domain-containing protein 2 1
27109867 10.1021/acs.jmedchem.6b00211 Toll-like receptor 7 1
27109867 10.1021/acs.jmedchem.6b00211 Toll-like receptor 4 1
27109867 10.1021/acs.jmedchem.6b00211 Toll-like receptor 2 1
27109867 10.1021/acs.jmedchem.6b00211 Aurora kinase A 1
27109867 10.1021/acs.jmedchem.6b00211 Protein-tyrosine kinase 6 1

Data from ChEMBL 36 via Core Engine