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Compound Detail

CHEMBL2152944

Skepinone-L
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O=C1c2ccc(Nc3ccc(F)cc3F)cc2CCc2ccc(OC[C@H](O)CO)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2152944
Name Skepinone-L
Phase Preclinical
Structure Type MOL
InChI Key HXMGCTFLLWPVFM-GOSISDBHSA-N
8
Targets
52
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

425.4
MW (Da)
3.77
ALogP
5
HBA
3
HBD
78.8
PSA (Ų)
0.56
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C24H21F2NO4
MW 425.43
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.64

Activity Summary

IC50 42 meas. best 8.55
Ki 9 meas. best 6.78
Kd 1 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mitogen-activated protein kinase 14
CHEMBL260
 Kd 8.82 8.82 1.5 1
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 8.55 7.9915 2.8 13
MAP kinase p38
CHEMBL2094115
 IC50 7.6 7.6 25.0 1
Mitogen-activated protein kinase 11
CHEMBL3961
 IC50 7.6 7.4667 25.0 3
Heat shock protein beta-1
CHEMBL5976
 IC50 7.6 7.6 25.0 1
Unchecked
CHEMBL612545
 IC50 7.52 6.4759 30.0 22
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.78 6.7667 166.0 3
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 5.49 5.4767 3235.9 3
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.47 5.4433 3388.4 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mitogen-activated protein kinase 14 Kd = 1.5 nM 8.82 Inhibition of non-phosphorylated human N-terminal His-P38alpha overexpressed in ... 22198732
Mitogen-activated protein kinase 14 IC50 = 2.8 nM 8.55 Inhibition of human p38alpha using ATF2 as substrate in presence of 33P-ATP by P... 22198732
Mitogen-activated protein kinase 14 IC50 = 5.0 nM 8.3 Inhibition of activated human P38alpha 22198732
Mitogen-activated protein kinase 14 IC50 = 5.0 nM 8.3 Affinity Biochemical interaction (ELISA (cell free)) EUB0000717a MAPK14 -
Mitogen-activated protein kinase 14 IC50 = 5.0 nM 8.3 Inhibition of human p38 MAPK alpha 33974419
Mitogen-activated protein kinase 14 IC50 = 5.0 nM 8.3 Biochemical assay: cell free ELISA -
Mitogen-activated protein kinase 14 IC50 = 5.0 nM 8.3 Inhibition of p38alpha MAP kinase (unknown origin) by ELISA 23270382
Mitogen-activated protein kinase 14 IC50 = 5.0 nM 8.3 Inhibition of p38alpha by immunosorbent based kinase assay 22676210
Mitogen-activated protein kinase 14 IC50 = 13.6 nM 7.87 NanoBRET (MAPK14) -
Mitogen-activated protein kinase 14 IC50 = 13.6 nM 7.87 Affinity On-target Cellular interaction (NanoBRET assay (HEK293T cells)) EUB0000... -
Mitogen-activated protein kinase 14 IC50 = 25.0 nM 7.6 Affinity Phenotypic Cellular interaction (Western Blot (HSP27 phosph. in anisomy... -
MAP kinase p38 IC50 = 25.0 nM 7.6 Inhibition of p38-MAPK in human HeLa cells assessed as HSP27 phosphorylation at ... 22198732
Mitogen-activated protein kinase 11 IC50 = 25.0 nM 7.6 Affinity Phenotypic Cellular interaction (Western Blot (HSP27 phosph. in anisomy... -
Heat shock protein beta-1 IC50 = 25.0 nM 7.6 Inhibition of HSP27 (Ser82) (Western blot) -
Unchecked IC50 = 30.0 nM 7.52 Anti-inflammatory activity against human derived high respond PBMC cells assesse... 22198732
Mitogen-activated protein kinase 14 IC50 = 40.0 nM 7.4 Inhibition of p38alpha MAP kinase in whole blood (unknown origin) assessed as li... 23270382
Mitogen-activated protein kinase 14 IC50 = 40.0 nM 7.4 Inhibition of P38alpha in human THP-1 cells incubated for 30 mins by whole blood... 22198732
Mitogen-activated protein kinase 11 IC50 = 40.2 nM 7.4 NanoBRET (MAPK11) -
Mitogen-activated protein kinase 14 IC50 = 40.0 nM 7.4 Inhibition of p38alpha-dependent TNFalpha production in human whole blood 22676210
Mitogen-activated protein kinase 11 IC50 = 40.2 nM 7.4 Affinity On-target Cellular interaction (NanoBRET assay (HEK293T cells)) EUB0000... -

Literature References

PubMed DOI Target Context # Activities
22198732 10.1038/nchembio.761 Unchecked 35
22198732 10.1038/nchembio.761 Epidermal growth factor receptor 22
22198732 10.1038/nchembio.761 Tyrosine-protein kinase ABL1 18
22198732 10.1038/nchembio.761 Hepatocyte growth factor receptor 13
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL4507316 Epidermal growth factor receptor 11
- 10.6019/CHEMBL4507316 Hepatocyte growth factor receptor 10
- 10.6019/CHEMBL4689842 U2OS 10
22198732 10.1038/nchembio.761 Receptor-type tyrosine-protein kinase FLT3 9
- 10.6019/CHEMBL4507316 Tyrosine-protein kinase ABL1 9
22198732 10.1038/nchembio.761 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 9
- 10.6019/CHEMBL4689842 Fibroblast 8
22198732 10.1038/nchembio.761 Mast/stem cell growth factor receptor Kit 8
22198732 10.1038/nchembio.761 Proto-oncogene tyrosine-protein kinase receptor Ret 7
22198732 10.1038/nchembio.761 Mitogen-activated protein kinase 14 6
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
22198732 10.1038/nchembio.761 Platelet-derived growth factor receptor alpha 5
- 10.6019/CHEMBL4507316 Leucine-rich repeat serine/threonine-protein kinase 2 4

Data from ChEMBL 36 via Core Engine