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Compound Detail

CHEMBL392068

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C[C@H](NC(=O)[C@@H](O)c1cc(F)cc(F)c1)C(=O)N[C@@H]1C(=O)N(C)c2ccccc2-c2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL392068
Phase Preclinical
Structure Type MOL
InChI Key ULSSJYNJIZWPSB-CVRXJBIPSA-N
5
Targets
17
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

479.5
MW (Da)
3.00
ALogP
4
HBA
3
HBD
98.7
PSA (Ų)
0.52
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H23F2N3O4
MW 479.48
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.53

Activity Summary

IC50 12 meas. best 10.52
EC50 5 meas. best 9.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 10.52 9.33 0.0 4
Gamma-secretase
CHEMBL2094135
 IC50 10.1 8.92 0.1 6
Presenilin-1
CHEMBL2473
 EC50 9.94 9.905 0.1 2
Gamma-secretase
CHEMBL2094135
 EC50 9.92 9.92 0.1 1
Unchecked
CHEMBL612545
 EC50 9.45 9.45 0.4 2
Signal peptide peptidase-like 2A
CHEMBL4105833
 IC50 8.0 8.0 10.0 1
Plasmodium berghei
CHEMBL612653
 IC50 4.1 4.1 80000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 144.0 ng.hr.mL-1 Rattus norvegicus
AUC 386.0 ng.hr.mL-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.03 nM 10.52 Inhibition of gamma secretase-mediated amyloid beta (1 to 40) production 19694467
Gamma-secretase IC50 = 0.08 nM 10.1 Inhibition of gamma secretase in HEK293 cells expressing APP 695 assessed as red... 27045975
Unchecked IC50 = 0.082 nM 10.09 Inhibition of amyloid beta (unknown origin) production 35176561
Gamma-secretase IC50 = 0.082 nM 10.09 Inhibition of gamma secretase in HEK293 cells assessed as reduction in amyloid b... 32686940
Presenilin-1 EC50 = 0.114 nM 9.94 Reduction of human wild type PS1-induced amyloid beta-40 level in CHO cells over... 17573346
Gamma-secretase EC50 = 0.119 nM 9.92 Inhibition of gamma secretase in human HEK293 cells assessed as amyloid beta 40 ... 17573346
Presenilin-1 EC50 = 0.135 nM 9.87 Reduction of human wild type PS1-induced amyloid beta-42 level in CHO cells over... 17573346
Unchecked EC50 = 0.352 nM 9.45 Reduction of human PS1 delta exon9 mutant-induced amyloid beta-42 level in CHO c... 17573346
Unchecked EC50 = 0.358 nM 9.45 Reduction of human PS1 delta exon9 mutant-induced amyloid beta-40 level in CHO c... 17573346
Gamma-secretase IC50 = 0.39 nM 9.41 Inhibition of gamma secretase mediated Notch signaling in HEK293 cells after 5 h... 27045975
Unchecked IC50 = 0.39 nM 9.41 Inhibition of Notch cleavage in transgenic HEK293 cells 35176561
Gamma-secretase IC50 = 1.0 nM 9.0 Inhibition of gamma secretase-mediated amyloid beta (1 to 40) production in huma... 19694467
Gamma-secretase IC50 = 1.0 nM 9.0 Displacement of [3H]5-chloro-N-((2S,3R)-5,5,5-trifluoro-1-hydroxy-3-methylpentan... 19694467
Signal peptide peptidase-like 2A IC50 = 10.0 nM 8.0 Inhibition of human SPPL2a expressed in HEK293 cells using GAL4-VP16 fusedTNFalp... 29359565
Unchecked IC50 = 50.0 nM 7.3 Inhibition of human SPP expressed in human U2OS cells using EGFP-labeled EnvSigS... 29359565
Gamma-secretase IC50 = 1200.0 nM 5.92 Modulation of gamma-secretase in HEK293 cells expressing guinea pig Swedish muta... 24139583
Plasmodium berghei IC50 = 80000.0 nM 4.1 Antimalarial activity against Plasmodium berghei ANKA infected in human Huh7 cel... 22122518

Literature References

PubMed DOI Target Context # Activities
17573346 10.1074/jbc.m700618200 Presenilin-1 14
24139583 10.1016/j.bmcl.2013.09.041 Rattus norvegicus 12
17573346 10.1074/jbc.m700618200 Unchecked 8
17573346 10.1074/jbc.m700618200 Mus musculus 8
29359565 10.1021/acs.jmedchem.7b01371 Mus musculus 4
17827153 10.1074/jbc.m703649200 Mus musculus 3
29359565 10.1021/acs.jmedchem.7b01371 Unchecked 3
23181502 10.1021/jm301630s Gamma-secretase 3
27045975 10.1021/acs.jmedchem.5b01516 Gamma-secretase 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
24139583 10.1016/j.bmcl.2013.09.041 Plasma 2
22122518 10.1021/jm201095h Plasmodium berghei 2
19694467 10.1021/jm900188z Gamma-secretase 2
35176561 10.1016/j.ejmech.2022.114169 Unchecked 2
24139583 10.1016/j.bmcl.2013.09.041 Molecular identity unknown 1
19694467 10.1021/jm900188z Mus musculus 1
25575659 10.1016/j.bmcl.2014.12.073 Neurogenic locus notch homolog protein 1 1
19443228 10.1016/j.bmc.2009.04.052 Gamma-secretase 1
17573346 10.1074/jbc.m700618200 Gamma-secretase 1

Data from ChEMBL 36 via Core Engine