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Compound Detail

CHEMBL196945

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O=C(O)C1(c2ccc(-c3ccc(Cl)c(Cl)c3)c(F)c2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL196945
Phase Preclinical
Structure Type MOL
InChI Key LIYLTQQDABRNRX-UHFFFAOYSA-N
8
Targets
12
Activities
2
Assay Types
13
PK Parameters
20
Publications
0
Known Names

Molecular Properties

325.2
MW (Da)
4.92
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.87
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H11Cl2FO2
MW 325.17
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.64

Activity Summary

IC50 10 meas. best 6.66
EC50 2 meas. best 4.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aldo-keto reductase family 1 member C3
CHEMBL4681
 IC50 6.66 6.66 220.0 1
Aldo-keto reductase family 1 member C2
CHEMBL5847
 IC50 5.96 5.96 1100.0 1
Unchecked
CHEMBL612545
 IC50 5.44 4.92 3600.0 2
Amyloid-beta precursor protein
CHEMBL2487
 IC50 4.85 4.62 14000.0 2
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.6 4.6 25000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.42 4.42 38000.0 1
Gamma-secretase
CHEMBL2094135
 IC50 4.4 4.4 40000.0 1
Unchecked
CHEMBL612545
 EC50 4.4 4.4 40000.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 4.32 4.32 48000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 435000.0 ng.hr.mL-1 Rattus norvegicus
AUC 173000.0 ng.hr.mL-1 Rattus norvegicus
CL 0.04833 mL.min-1.kg-1 Rattus norvegicus
CL 38.9 uL.min-1.(10^6cells)-1 Homo sapiens
Cmax 18759.42 nM Rattus norvegicus
Cmax 49820.09 nM Rattus norvegicus
F 50.2 % Rattus norvegicus
F 50.0 % Rattus norvegicus
T1/2 20.7 hr Rattus norvegicus
T1/2 29.4 hr Rattus norvegicus
T1/2 20.0 hr Rattus norvegicus
Tmax 4.0 hr Rattus norvegicus
Tmax 0.08 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aldo-keto reductase family 1 member C3 IC50 = 220.0 nM 6.66 Inhibition of human recombinant AKR1C3 transfected in Escherichia coli BL21 (DE3... 37409679
Aldo-keto reductase family 1 member C2 IC50 = 1100.0 nM 5.96 Inhibition of human recombinant AKR1C2 transfected in Escherichia coli BL21 (DE3... 37409679
Unchecked IC50 = 3600.0 nM 5.44 Modulation of gamma-secretase in human H4 cells expressing APPswe mutant assesse... 35176561
Amyloid-beta precursor protein IC50 = 14000.0 nM 4.85 Concentration required to inhibit A beta 40 peptide 100 uM 16134939
Cytochrome P450 2C19 IC50 = 25000.0 nM 4.6 Interaction with human cytochrome P450 isoform 2C19 expressed in baculovirus-ins... 16134939
Cytochrome P450 2C9 IC50 = 38000.0 nM 4.42 Interaction with human cytochrome P450 isoform 2C9 expressed in baculovirus-inse... 16134939
Unchecked EC50 = 40000.0 nM 4.4 Modulation of gamma-secretase-mediated cleavage of APP assessed as reduction in ... 22061640
Unchecked EC50 = 40000.0 nM 4.4 Modulation of gamma-secretase 24900267
Unchecked IC50 = 40000.0 nM 4.4 Inhibition of gamma secretase assessed as reduction in Abeta42 production 21141968
Gamma-secretase IC50 = 40000.0 nM 4.4 Inhibition of gamma-secretase (unknown origin) 29477076
Amyloid-beta precursor protein IC50 = 41000.0 nM 4.39 Inhibitory concentration against beta-amyloid-42 (Abeta42) secretion was evaluat... 16134939
Cytochrome P450 3A4 IC50 = 48000.0 nM 4.32 Interaction with human cytochrome P450 isoform 3A4 expressed in baculovirus-inse... 16134939

Literature References

PubMed DOI Target Context # Activities
16134939 10.1021/jm0502541 ADMET 12
21141968 10.1021/jm101168r Mus musculus 7
16134939 10.1021/jm0502541 Amyloid-beta precursor protein 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
35176561 10.1016/j.ejmech.2022.114169 ADMET 2
21141968 10.1021/jm101168r Brain 2
24900267 10.1021/ml200175q Unchecked 2
21405086 10.1021/jm101450p RAW264.7 2
21405086 10.1021/jm101450p N2a 1
22061640 10.1016/j.bmcl.2011.10.047 Unchecked 1
21141968 10.1021/jm101168r Unchecked 1
16134939 10.1021/jm0502541 Caco-2 1
16134939 10.1021/jm0502541 Cytochrome P450 3A4 1
21141968 10.1021/jm101168r Plasma 1
21141968 10.1021/jm101168r Homo sapiens 1
37409679 10.1021/acs.jmedchem.3c00213 Unchecked 1
29477076 10.1016/j.ejmech.2018.02.035 Gamma-secretase 1
16134939 10.1021/jm0502541 Cytochrome P450 2C19 1
16134939 10.1021/jm0502541 Cytochrome P450 2C9 1

Data from ChEMBL 36 via Core Engine