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Compound Detail

CHEMBL3785703

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CN1C(=O)[C@@H](NC(=O)c2cc(Cc3ccccc3)on2)COc2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3785703
Phase Preclinical
Structure Type MOL
InChI Key KNOUWGGQMADIBV-KRWDZBQOSA-N
4
Targets
17
Activities
2
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

377.4
MW (Da)
2.42
ALogP
5
HBA
1
HBD
84.7
PSA (Ų)
0.75
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C21H19N3O4
MW 377.40
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.96

Activity Summary

IC50 16 meas. best 8.8
Ki 1 meas. best 9.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Receptor-interacting serine/threonine-protein kinase 1
CHEMBL5464
 Ki 9.1 9.1 0.8 1
Receptor-interacting serine/threonine-protein kinase 1
CHEMBL5464
 IC50 8.8 8.375 1.6 6
U-937
CHEMBL612794
 IC50 8.0 8.0 10.0 1
Unchecked
CHEMBL612545
 IC50 7.92 6.545 12.0 6
Receptor-interacting serine/threonine-protein kinase 1
CHEMBL3784911
 IC50 6.96 5.9867 110.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 380.0 ng.hr.mL-1 Rattus norvegicus
AUC 380.0 ng.hr.mL-1 Rattus norvegicus
CL 69.0 mL.min-1.kg-1 Rattus norvegicus
T1/2 1.067 hr Homo sapiens
Vd 8.5 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Receptor-interacting serine/threonine-protein kinase 1 Ki = 0.8 nM 9.1 Competitive inhibition of human RIP1 (1 to 375 residues) in presence of increasi... 26854747
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 1.6 nM 8.8 Inhibition of pDEST8HisGSTTev-tagged human RIP1 (1 to 375 residues) expressed in... 31223438
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 1.6 nM 8.8 Inhibition of human RIP1 (1 to 375 residues) after 4 hrs by ADP-Glo reagent base... 26854747
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 2.8 nM 8.55 Inhibition of human WT RIP1 infected in HEK293T cells assessed as reduction in S... 26854747
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 7.9 nM 8.1 Inhibition of RIP1 in human U937 cells assessed as reduction in necroptosis incu... 31223438
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 10.0 nM 8.0 Inhibition of human RIP1 in human U937 cells assessed as inhibition of TNF/zVAD.... 26854747
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 10.0 nM 8.0 Binding affinity to human RIP1 (1 to 375 residues) preincubated for 10 mins meas... 26854747
U-937 IC50 = 10.0 nM 8.0 Anti-necroptotic activity against TNFalph/Z-VAD-FMK-induced human U-937 cells as... 33964444
Unchecked IC50 = 12.0 nM 7.92 Inhibition of mouse RIP1 V159L/T164M/Q176L/S180D/S181G mutant transfected in HEK... 26854747
Unchecked IC50 = 18.0 nM 7.75 Inhibition of mouse RIP1 15 point mutant transfected in HEK293T cells assessed a... 26854747
Unchecked IC50 = 25.0 nM 7.6 Binding affinity to cynomolgus monkey RIP1 (1 to 379 residues) preincubated for ... 26854747
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 110.0 nM 6.96 Inhibition of mouse RIP1 V159L mutant transfected in HEK293T cells assessed as r... 26854747
Unchecked IC50 = 2000.0 nM 5.7 Binding affinity to rabbit RIP1 (1 to 371 residues) preincubated for 10 mins mea... 26854747
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 3200.0 nM 5.5 Binding affinity to mouse RIP1 (1 to 378 residues) preincubated for 10 mins meas... 26854747
Receptor-interacting serine/threonine-protein kinase 1 IC50 = 3200.0 nM 5.5 Inhibition of mouse RIP1 in mouse L929 cells assessed as inhibition of TNF/zVAD.... 26854747
Unchecked IC50 = 6300.0 nM 5.2 Binding affinity to rat RIP1 (1 to 377 residues) preincubated for 10 mins measur... 26854747
Unchecked IC50 = 7900.0 nM 5.1 Binding affinity to dog RIP1 (1 to 373 residues) preincubated for 10 mins measur... 26854747

Literature References

PubMed DOI Target Context # Activities
26854747 10.1021/acs.jmedchem.5b01898 Unchecked 16
26854747 10.1021/acs.jmedchem.5b01898 Receptor-interacting serine/threonine-protein kinase 1 13
28151659 10.1021/acs.jmedchem.6b01751 Rattus norvegicus 3
28151659 10.1021/acs.jmedchem.6b01751 No relevant target 2
31223438 10.1021/acsmedchemlett.9b00108 Receptor-interacting serine/threonine-protein kinase 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5308504 Bromodomain-containing protein 4 1
- 10.6019/CHEMBL5308504 Transcription intermediary factor 1-alpha 1
- 10.6019/CHEMBL5308504 Peregrin 1
- 10.6019/CHEMBL5308504 Fibroblast growth factor receptor 3 1
- 10.6019/CHEMBL5308504 Tyrosine-protein kinase ABL1 1
- 10.6019/CHEMBL5308504 Aurora kinase A 1
- 10.6019/CHEMBL5308504 Mitogen-activated protein kinase 1 1
- 10.6019/CHEMBL5308504 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5308504 Cyclin-dependent kinase 2 1
- 10.6019/CHEMBL5308504 Casein kinase I isoform delta 1
33964444 10.1016/j.bmcl.2021.128084 U-937 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
31223438 10.1021/acsmedchemlett.9b00108 ADMET 1
31223438 10.1021/acsmedchemlett.9b00108 No relevant target 1

Data from ChEMBL 36 via Core Engine