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Compound Detail

CHEMBL1224151

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COc1cc(/C=C2\CCCN([C@@H](C)c3ccc(F)cc3)C2=O)ccc1-n1cnc(C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1224151
Phase Preclinical
Structure Type MOL
InChI Key PUOAETJYKQITMO-LANLRWRYSA-N
3
Targets
21
Activities
2
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

419.5
MW (Da)
5.10
ALogP
4
HBA
0
HBD
47.4
PSA (Ų)
0.54
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H26FN3O2
MW 419.50
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.94

Activity Summary

IC50 19 meas. best 7.38
EC50 2 meas. best 7.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 7.38 7.002 42.0 5
Gamma-secretase
CHEMBL2094135
 IC50 7.19 6.7292 64.0 13
Gamma-secretase
CHEMBL2094135
 EC50 7.08 7.08 83.0 1
Unchecked
CHEMBL612545
 EC50 7.08 7.08 83.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.92 5.92 1200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 25337.8 ng.hr.mL-1 Rattus norvegicus
CL 37.1 mL.min-1.g-1 Homo sapiens
Fu 0.00363 - Rattus norvegicus
Fu 0.00429 - Rattus norvegicus
Fu 0.00185 - Rattus norvegicus
Fu 0.00785 - Rattus norvegicus
Fu 0.00939 - Rattus norvegicus
Fu 0.0012 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 42.0 nM 7.38 Inhibition of gamma secretase in rat primary neurons assessed as reduction in am... 21924610
Unchecked IC50 = 62.0 nM 7.21 Modulation of gamma-secretase assessed as reduction in amyloid beta 42 level by ... 23030762
Gamma-secretase IC50 = 64.0 nM 7.19 Inhibition of gamma secretase-mediated amyloid beta42 production in HEK293 cells 20724152
Gamma-secretase IC50 = 64.0 nM 7.19 Inhibition of gamma secretase-mediated amyloid beta42 production in HEK293 cells... 21195610
Gamma-secretase IC50 = 64.0 nM 7.19 Modulation of gamma-secretase-mediated cleavage of human APP Swedish and London ... 22098494
Gamma-secretase IC50 = 64.0 nM 7.19 Modulation of gamma secretase in HEK293 cells transfected with human APP with Sw... 32786237
Gamma-secretase IC50 = 80.0 nM 7.1 Modulation of gamma-secretase (unknown origin) assessed as reduction in amyloid ... 29057041
Gamma-secretase IC50 = 81.0 nM 7.09 Modulation of gamma-secretase in human SK-N-BE(2) cells expressing wild type APP... 22650177
Gamma-secretase EC50 = 83.0 nM 7.08 Modulation of human gamma-secretase assessed as inhibition of amyloid beta (1 to... 27007185
Gamma-secretase IC50 = 83.0 nM 7.08 Inhibition of gamma-secretase (unknown origin) 29477076
Unchecked EC50 = 83.0 nM 7.08 Modulation of gamma-secretase (unknown origin) 28230986
Gamma-secretase IC50 = 85.0 nM 7.07 Modulation of gamma-secretase in HEK293 cells expressing Swedish mutant APP asse... 26142947
Unchecked IC50 = 93.0 nM 7.03 Modulation of gamma secretase in Wistar rat fetal brain-derived neuronal cell in... 33479693
Unchecked IC50 = 143.0 nM 6.84 Inhibition of gamma secretase expressed in CHO cells expressing APP assessed as ... 22429469
Gamma-secretase IC50 = 143.0 nM 6.84 Modulation of human gamma-secretase assessed as reduction in amyloidbeta42 level... 38848667
Gamma-secretase IC50 = 160.0 nM 6.8 Modulation of gamma-secretase in HEK293 cells expressing guinea pig Swedish muta... 24139583
Unchecked IC50 = 280.0 nM 6.55 Modulation of gamma-secretase assessed as reduction in amyloid beta 40 level by ... 23030762
Gamma-secretase IC50 = 560.0 nM 6.25 Modulation of gamma-secretase in HEK293 cells expressing Swedish mutant APP asse... 26142947
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 1200.0 nM 5.92 Inhibition of human ERG by cell based voltage clamp assay 22098494
Gamma-secretase IC50 = 2300.0 nM 5.64 Modulation of gamma-secretase-mediated cleavage of human APP Swedish and London ... 22098494

Literature References

PubMed DOI Target Context # Activities
31732255 10.1016/j.ejmech.2019.111813 ADMET 18
38059872 10.1021/acs.jmedchem.3c01480 Gamma-secretase 6
22098494 10.1021/jm201407j Gamma-secretase 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
23030762 10.1021/jm300976b Unchecked 3
22098494 10.1021/jm201407j Rattus norvegicus 2
26142947 10.1016/j.bmcl.2015.06.032 Gamma-secretase 2
29057041 10.1021/acsmedchemlett.7b00178 Gamma-secretase 2
22650177 10.1021/jm201710f Gamma-secretase 2
29249626 10.1016/j.bmc.2017.11.049 Cytochrome P450 3A4 2
22650177 10.1021/jm201710f Mus musculus 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
22098494 10.1021/jm201407j Caco-2 2
21195610 10.1016/j.bmcl.2010.12.012 Rattus norvegicus 2
21195610 10.1016/j.bmcl.2010.12.012 Gamma-secretase 2
22429469 10.1016/j.bmcl.2012.02.059 MDCK 1
22429469 10.1016/j.bmcl.2012.02.059 Unchecked 1
21924610 10.1016/j.bmcl.2011.08.060 Unchecked 1
20724152 10.1016/j.bmcl.2010.07.121 ADMET 1

Data from ChEMBL 36 via Core Engine