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Compound Detail

CHEMBL4514780

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CC(C)(C)S(=O)(=O)c1cc2c(Nc3ccc4scnc4c3)ncnc2cc1OCCO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4514780
Phase Preclinical
Structure Type MOL
InChI Key UHDOJINBFLDQJM-UHFFFAOYSA-N
7
Targets
17
Activities
2
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

458.6
MW (Da)
3.93
ALogP
9
HBA
2
HBD
114.3
PSA (Ų)
0.45
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H22N4O4S2
MW 458.57
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -1.17

Activity Summary

IC50 16 meas. best 8.7
Ki 1 meas. best 5.09

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 2
Receptor-interacting serine/threonine-protein kinase 2
CHEMBL5014
 IC50 8.7 7.9067 2.0 6
Nucleotide-binding oligomerization domain-containing protein 2
CHEMBL1293266
 IC50 8.4 8.145 4.0 2
Intestinal mucosa
CHEMBL4651296
 IC50 8.0 8.0 10.0 4
Cyclin-G-associated kinase
CHEMBL4355
 Ki 5.09 5.09 8200.0 1
Unchecked
CHEMBL612545
 IC50 4.52 4.52 30000.0 1
LNCaP
CHEMBL612518
 IC50 4.0 4.0 99000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 460.0 ng.hr.mL-1 Rattus norvegicus
AUC 1800.0 ng.hr.mL-1 Canis lupus familiaris
AUC 85.0 ng.hr.mL-1 Sus scrofa
AUC 8800.0 ng.hr.mL-1 Rattus norvegicus
AUC 23400.0 ng.hr.mL-1 Rattus norvegicus
AUC 41400.0 ng.hr.mL-1 Rattus norvegicus
AUC 460.0 ng.hr.mL-1 Rattus norvegicus
CL 27.0 mL.min-1.kg-1 Rattus norvegicus
CL 9.9 mL.min-1.kg-1 Canis lupus familiaris
CL 18.0 mL.min-1.kg-1 Sus scrofa
CL 0.48 mL.min-1.g-1 Rattus norvegicus
CL 0.65 mL.min-1.g-1 Canis lupus familiaris
CL 0.55 mL.min-1.g-1 Sus scrofa
CL 0.48 mL.min-1.g-1 Homo sapiens
Cmax 261.68 nM Rattus norvegicus
Cmax 1024.93 nM Canis lupus familiaris
Cmax 67.6 nM Sus scrofa
Cmax 1962.62 nM Rattus norvegicus
Cmax 4579.45 nM Rattus norvegicus
Cmax 10685.39 nM Rattus norvegicus
F 39.0 % Rattus norvegicus
F 57.0 % Canis lupus familiaris
F 26.0 % Sus scrofa
Fu 0.11 - Rattus norvegicus
Fu 0.089 - Canis lupus familiaris
Fu 0.068 - Sus scrofa
Fu 0.069 - Homo sapiens
T1/2 4.4 hr Rattus norvegicus
T1/2 5.1 hr Canis lupus familiaris
T1/2 1.9 hr Sus scrofa

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 recombinant rat full-length FLAG/His-tagged RIP2 measured after 2 ... 31265286
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 2.0 nM 8.7 Displacement of fluorescent tracer from N-terminus of human RIPK2 expressed in H... 30768268
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 2.0 nM 8.7 Inhibition of fluorescent-labelled ligand binding to rat RIP2K preincubated for ... 31265286
Nucleotide-binding oligomerization domain-containing protein 2 IC50 = 4.0 nM 8.4 Inhibition of human NOD2 expressed in HEK293 cells assessed as reduction in MDP-... 31265286
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 4.0 nM 8.4 Inhibition of N-terminal poly his-tagged recombinant RIPK2 (8 to 310 residues) (... 38008339
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 5.0 nM 8.3 Inhibition of fluorescent-labelled ligand binding to human RIP2K preincubated fo... 31265286
Intestinal mucosa IC50 = 10.0 nM 8.0 Antiinflammatory activity in ulcerative colitis patient derived inflamed intesti... 31265286
Intestinal mucosa IC50 = 10.0 nM 8.0 Antiinflammatory activity in ulcerative colitis patient derived inflamed intesti... 31265286
Intestinal mucosa IC50 = 10.0 nM 8.0 Antiinflammatory activity in crohn's disease patient derived inflamed intestinal... 31265286
Intestinal mucosa IC50 = 10.0 nM 8.0 Antiinflammatory activity in crohn's disease patient derived inflamed intestinal... 31265286
Nucleotide-binding oligomerization domain-containing protein 2 IC50 = 13.0 nM 7.89 Inhibition of NOD2 in human monocytes assessed as reduction in MDP-induced TNFal... 31265286
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 26.0 nM 7.58 Inhibition of RIPK2 in human whole blood assessed as reduction in MDP-induced TN... 31265286
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 38.0 nM 7.42 Inhibition of RIPK2 in MDP stimulated NOD2 in human THP-1 cells expressing lucia... 38008339
Receptor-interacting serine/threonine-protein kinase 2 IC50 = 92.0 nM 7.04 Inhibition of RIPK2 in C14-Tri-LAN-Gly stimulated NOD1 in human THP-1 cells expr... 38008339
Cyclin-G-associated kinase Ki = 8200.0 nM 5.09 Binding affinity to C-terminal AVI-tagged GAK (unknown origin) (12 to 347 residu... 30768268
Unchecked IC50 = 30000.0 nM 4.52 Antiproliferative activity against human UCH2 cells measured after 72 hrs by ala... 30973735
LNCaP IC50 = 99000.0 nM 4.0 Cytotoxicity against human LNCAP cells after 72 hrs by MTS assay 30768268

Literature References

PubMed DOI Target Context # Activities
31265286 10.1021/acs.jmedchem.9b00575 ADMET 38
31265286 10.1021/acs.jmedchem.9b00575 Intestinal mucosa 8
38008339 10.1016/j.bmcl.2023.129567 Receptor-interacting serine/threonine-protein kinase 2 4
31265286 10.1021/acs.jmedchem.9b00575 Receptor-interacting serine/threonine-protein kinase 2 4
31265286 10.1021/acs.jmedchem.9b00575 Nucleotide-binding oligomerization domain-containing protein 2 4
30973735 10.1021/acs.jmedchem.9b00350 Unchecked 3
30768268 10.1021/acs.jmedchem.8b01213 Cyclin-G-associated kinase 2
30768268 10.1021/acs.jmedchem.8b01213 PC-3 2
30768268 10.1021/acs.jmedchem.8b01213 LNCaP 2
31265286 10.1021/acs.jmedchem.9b00575 Aldehyde oxidase 2
30768268 10.1021/acs.jmedchem.8b01213 DU-145 2
31265286 10.1021/acs.jmedchem.9b00575 Unchecked 2
30768268 10.1021/acs.jmedchem.8b01213 CWR22R 2
30768268 10.1021/acs.jmedchem.8b01213 VCaP 2
31265286 10.1021/acs.jmedchem.9b00575 Interleukin-1 receptor type 1 1
31265286 10.1021/acs.jmedchem.9b00575 Toll-like receptor 4 1
31265286 10.1021/acs.jmedchem.9b00575 Toll-like receptor 7 1
31265286 10.1021/acs.jmedchem.9b00575 Voltage-gated inwardly rectifying potassium channel KCNH2 1
31265286 10.1021/acs.jmedchem.9b00575 Vascular endothelial growth factor receptor 3 1
- 10.6019/CHEMBL5724564 Hepatocyte spheroids 1

Data from ChEMBL 36 via Core Engine