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Compound Detail

CHEMBL4744680

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O=C(N[C@@H](C1CC1)C(F)(F)F)c1cc(-c2cnn3cc(-c4ccc(F)cc4)cnc23)cs1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4744680
Phase Preclinical
Structure Type MOL
InChI Key PFZRXJIYAFANHP-IBGZPJMESA-N
9
Targets
21
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

460.5
MW (Da)
5.33
ALogP
5
HBA
1
HBD
59.3
PSA (Ų)
0.41
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C22H16F4N4OS
MW 460.46
Aromatic Rings 4
Heavy Atoms 32
NP-Likeness -1.49

Activity Summary

EC50 12 meas. best 6.41
IC50 9 meas. best 8.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase ULK1
CHEMBL6006
 IC50 8.08 7.848 8.3 5
Serine/threonine-protein kinase 17A
CHEMBL4525
 IC50 7.85 7.85 14.0 1
MAP kinase-interacting serine/threonine-protein kinase 2
CHEMBL4204
 IC50 7.66 7.66 22.0 1
Serine/threonine-protein kinase ULK2
CHEMBL5435
 IC50 7.52 7.52 30.0 2
Serine/threonine-protein kinase ULK1
CHEMBL6006
 EC50 6.41 6.41 390.0 1
U2OS
CHEMBL615023
 EC50 6.16 5.3367 700.0 3
NCI-H838
CHEMBL1075547
 EC50 5.92 5.435 1200.0 2
NCI-H727
CHEMBL1075545
 EC50 5.52 5.055 3000.0 2
NCI-H2030
CHEMBL1075530
 EC50 5.44 5.065 3600.0 2
A549
CHEMBL392
 EC50 5.0 4.625 10000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 68.0 mL.min-1.g-1 Homo sapiens
CL 38.0 mL.min-1.g-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine/threonine-protein kinase ULK1 IC50 = 8.3 nM 8.08 Inhibition of human ULK1 30292171
Serine/threonine-protein kinase ULK1 IC50 = 8.3 nM 8.08 Inhibition of ULK1 (unknown origin) 38432059
Serine/threonine-protein kinase ULK1 IC50 = 8.3 nM 8.08 Inhibition of human ULK1 by discoverX kinome scan assay 38295689
Serine/threonine-protein kinase ULK1 IC50 = 10.0 nM 8.0 Binding affinity to GST tagged ULK1 kinase domain (1 to 283 residues) (unknown o... 38232465
Serine/threonine-protein kinase 17A IC50 = 14.0 nM 7.85 Inhibition of human recombinant DRAK1 30292171
MAP kinase-interacting serine/threonine-protein kinase 2 IC50 = 22.0 nM 7.66 Inhibition of human recombinant MNK2 30292171
Serine/threonine-protein kinase ULK2 IC50 = 30.0 nM 7.52 Inhibition of human ULK2 30292171
Serine/threonine-protein kinase ULK2 IC50 = 30.0 nM 7.52 Inhibition of human ULK2 by discoverX kinome scan assay 38295689
Serine/threonine-protein kinase ULK1 IC50 = 100.0 nM 7.0 Inhibition of NanoLuc fused ULK1 (unknown origin) transfected in NCI-H2030 cells... 38232465
Serine/threonine-protein kinase ULK1 EC50 = 390.0 nM 6.41 Inhibition of ULK1 phosphorylation at Ser15 residue in HEK293 cells incubated fo... 30292171
U2OS EC50 = 700.0 nM 6.16 Inhibition of autophagy in human U2OS cells assessed as BafA1-induced LC3B-II ac... 30292171
NCI-H838 EC50 = 1200.0 nM 5.92 Cytotoxicity against human NCI-H838 cells harboring KRAS mutant assessed as redu... 30292171
NCI-H727 EC50 = 3000.0 nM 5.52 Cytotoxicity against human NCI-H727 cells harboring KRAS G12V mutant assessed as... 30292171
NCI-H2030 EC50 = 3600.0 nM 5.44 Cytotoxicity against human NCI-H2030 cells harboring KRAS G12C mutant assessed a... 30292171
U2OS EC50 = 6300.0 nM 5.2 Cytotoxicity against human U2OS cells assessed as reduction in cell viability pr... 30292171
A549 EC50 = 10000.0 nM 5.0 Cytotoxicity against human A549 cells harboring KRAS G12S mutant assessed as red... 30292171
NCI-H838 EC50 = 11300.0 nM 4.95 Cytotoxicity against human NCI-H838 cells harboring KRAS mutant assessed as redu... 30292171
NCI-H2030 EC50 = 20300.0 nM 4.69 Cytotoxicity against human NCI-H2030 cells harboring KRAS G12C mutant assessed a... 30292171
U2OS EC50 = 22300.0 nM 4.65 Cytotoxicity against human U2OS cells assessed as reduction in cell viability pr... 30292171
NCI-H727 EC50 = 25600.0 nM 4.59 Cytotoxicity against human NCI-H727 cells harboring KRAS G12V mutant assessed as... 30292171

Literature References

PubMed DOI Target Context # Activities
30292171 10.1016/j.isci.2018.09.012 Unchecked 13
30292171 10.1016/j.isci.2018.09.012 U2OS 10
- 10.6019/CHEMBL4689842 U2OS 9
- 10.6019/CHEMBL4689842 Fibroblast 9
- 10.6019/CHEMBL4689842 HEK-293T 5
30292171 10.1016/j.isci.2018.09.012 MAP kinase-interacting serine/threonine-protein kinase 2 5
30292171 10.1016/j.isci.2018.09.012 Serine/threonine-protein kinase ULK1 4
30292171 10.1016/j.isci.2018.09.012 Serine/threonine-protein kinase N1 4
30292171 10.1016/j.isci.2018.09.012 Serine/threonine-protein kinase 17A 3
38232465 10.1016/j.ejmech.2023.116101 Serine/threonine-protein kinase ULK1 3
38232465 10.1016/j.ejmech.2023.116101 ADMET 3
30292171 10.1016/j.isci.2018.09.012 Serine/threonine-protein kinase ULK2 3
30292171 10.1016/j.isci.2018.09.012 Tyrosine-protein kinase ZAP-70 2
30292171 10.1016/j.isci.2018.09.012 Tyrosine-protein kinase ABL2 2
30292171 10.1016/j.isci.2018.09.012 NCI-H2030 2
30292171 10.1016/j.isci.2018.09.012 Actin-related protein 2 2
30292171 10.1016/j.isci.2018.09.012 A549 2
30292171 10.1016/j.isci.2018.09.012 NCI-H838 2
30292171 10.1016/j.isci.2018.09.012 Activated CDC42 kinase 1 2
38232465 10.1016/j.ejmech.2023.116101 No relevant target 2

Data from ChEMBL 36 via Core Engine