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Compound Detail

CHEMBL523586

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NC[C@H](Cc1cccc(F)c1)NC(=O)c1cc(Br)c(-c2ccnc3[nH]ccc23)s1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL523586
Phase Preclinical
Structure Type MOL
InChI Key KEBMSGAJMPWLNS-AWEZNQCLSA-N
15
Targets
17
Activities
2
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

473.4
MW (Da)
4.49
ALogP
4
HBA
3
HBD
83.8
PSA (Ų)
0.39
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H18BrFN4OS
MW 473.37
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -1.08

Activity Summary

IC50 15 meas. best 9.0
Ki 2 meas. best 10.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 Ki 10.52 10.52 0.0 1
RAC-beta serine/threonine-protein kinase
CHEMBL2431
 Ki 9.2 9.2 0.6 1
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 IC50 9.0 9.0 1.0 1
RAC-gamma serine/threonine-protein kinase
CHEMBL4816
 IC50 8.7 8.7 2.0 1
Rho-associated protein kinase 1
CHEMBL3231
 IC50 8.7 8.7 2.0 1
RAC-beta serine/threonine-protein kinase
CHEMBL2431
 IC50 8.05 8.05 9.0 1
LNCaP
CHEMBL612518
 IC50 7.75 7.75 18.0 1
Protein kinase C alpha type
CHEMBL299
 IC50 7.4 7.4 40.0 1
Unchecked
CHEMBL612545
 IC50 7.05 7.05 90.0 1
BT-474
CHEMBL614529
 IC50 6.62 6.62 240.0 1
HFF
CHEMBL614071
 IC50 6.58 6.58 260.0 1
Serine/threonine-protein kinase pim-1
CHEMBL2147
 IC50 6.1 6.1 794.0 1
MAP kinase-activated protein kinase 2
CHEMBL2208
 IC50 5.6 5.6 2500.0 1
Epidermal growth factor receptor
CHEMBL203
 IC50 5.0 5.0 10000.0 1
Glycogen synthase kinase-3 beta
CHEMBL262
 IC50 4.7 4.7 20000.0 1
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 4.6 4.6 25000.0 1
Tyrosine-protein kinase SYK
CHEMBL2599
 IC50 4.6 4.6 25000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
RAC-alpha serine/threonine-protein kinase Ki = 0.03 nM 10.52 Inhibition of AKT1 19285393
RAC-beta serine/threonine-protein kinase Ki = 0.63 nM 9.2 Inhibition of AKT2 19285393
RAC-alpha serine/threonine-protein kinase IC50 = 1.0 nM 9.0 Inhibition of AKT1 19285393
RAC-gamma serine/threonine-protein kinase IC50 = 2.0 nM 8.7 Inhibition of AKT3 19285393
Rho-associated protein kinase 1 IC50 = 2.0 nM 8.7 Inhibition of ROCK1 19285393
RAC-beta serine/threonine-protein kinase IC50 = 9.0 nM 8.05 Inhibition of AKT2 19285393
LNCaP IC50 = 18.0 nM 7.75 Cytotoxicity against human LNCAP cells 19285393
Protein kinase C alpha type IC50 = 40.0 nM 7.4 Inhibition of PKCalpha 19285393
Unchecked IC50 = 90.0 nM 7.05 Inhibition of AKT-mediated GSK3-beta phosphorylation in human BT474 cells by mec... 19285393
BT-474 IC50 = 240.0 nM 6.62 Cytotoxicity against human BT474 cells 19285393
HFF IC50 = 260.0 nM 6.58 Cytotoxicity against human HFF cells 19285393
Serine/threonine-protein kinase pim-1 IC50 = 794.0 nM 6.1 Inhibition of PIM1 19285393
MAP kinase-activated protein kinase 2 IC50 = 2500.0 nM 5.6 Inhibition of MAPKAPK2 19285393
Epidermal growth factor receptor IC50 = 10000.0 nM 5.0 Inhibition of EGFR 19285393
Glycogen synthase kinase-3 beta IC50 = 20000.0 nM 4.7 Inhibition of GSK3-beta 19285393
Mitogen-activated protein kinase 14 IC50 = 25000.0 nM 4.6 Inhibition of P38alpha 19285393
Tyrosine-protein kinase SYK IC50 = 25000.0 nM 4.6 Inhibition of SYK 19285393

Literature References

PubMed DOI Target Context # Activities
19285393 10.1016/j.bmcl.2009.02.094 RAC-alpha serine/threonine-protein kinase 2
19285393 10.1016/j.bmcl.2009.02.094 RAC-beta serine/threonine-protein kinase 2
19285393 10.1016/j.bmcl.2009.02.094 Unchecked 1
19285393 10.1016/j.bmcl.2009.02.094 Mus musculus 1
19285393 10.1016/j.bmcl.2009.02.094 RAC-gamma serine/threonine-protein kinase 1
19285393 10.1016/j.bmcl.2009.02.094 BT-474 1
19285393 10.1016/j.bmcl.2009.02.094 LNCaP 1
19285393 10.1016/j.bmcl.2009.02.094 HFF 1
19285393 10.1016/j.bmcl.2009.02.094 Protein kinase C alpha type 1
19285393 10.1016/j.bmcl.2009.02.094 Rho-associated protein kinase 1 1
19285393 10.1016/j.bmcl.2009.02.094 Glycogen synthase kinase-3 beta 1
19285393 10.1016/j.bmcl.2009.02.094 Mitogen-activated protein kinase 14 1
19285393 10.1016/j.bmcl.2009.02.094 MAP kinase-activated protein kinase 2 1
19285393 10.1016/j.bmcl.2009.02.094 Serine/threonine-protein kinase pim-1 1
19285393 10.1016/j.bmcl.2009.02.094 Epidermal growth factor receptor 1
19285393 10.1016/j.bmcl.2009.02.094 Tyrosine-protein kinase SYK 1

Data from ChEMBL 36 via Core Engine