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Compound Detail

CHEMBL3670375

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C[C@@]1(c2nc(NC(=O)c3ncc(C(F)(F)F)cc3Cl)ccc2F)CO[C@@](C)(C(F)(F)F)C(N)=N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3670375
Phase Preclinical
Structure Type MOL
InChI Key PSBBWFNMHDUTRH-DLBZAZTESA-N
9
Targets
27
Activities
1
Assay Types
15
PK Parameters
15
Publications
0
Known Names

Molecular Properties

513.8
MW (Da)
4.46
ALogP
6
HBA
2
HBD
102.5
PSA (Ų)
0.59
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H15ClF7N5O2
MW 513.80
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness -1.10

Activity Summary

IC50 27 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amyloid-beta precursor protein
CHEMBL2487
 IC50 8.52 8.49 3.0 4
Beta-secretase 1
CHEMBL3297642
 IC50 8.52 8.52 3.0 1
Unchecked
CHEMBL612545
 IC50 8.52 7.94 3.0 2
Beta-secretase 1
CHEMBL4822
 IC50 8.15 8.055 7.0 6
Beta-secretase 2
CHEMBL2525
 IC50 7.52 7.52 30.0 7
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.5 5.5 3200.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.96 4.96 10900.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.87 4.87 13400.0 1
Cathepsin E
CHEMBL3092
 IC50 4.18 4.18 66400.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 1050.72 ng.hr.mL-1 Rattus norvegicus
AUC 596.01 ng.hr.mL-1 Mus musculus
AUC 3980.41 ng.hr.mL-1 Canis lupus familiaris
CL 9.0 mL.min-1.kg-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Mus musculus
CL 2.0 mL.min-1.kg-1 Canis lupus familiaris
Cmax 146.0 nM Rattus norvegicus
Cmax 82.0 nM Mus musculus
Cmax 257.0 nM Canis lupus familiaris
F 60.0 % Rattus norvegicus
F 48.0 % Mus musculus
F 57.0 % Canis lupus familiaris
T1/2 13.3 hr Rattus norvegicus
T1/2 9.5 hr Mus musculus
T1/2 23.4 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amyloid-beta precursor protein IC50 = 3.0 nM 8.52 Inhibition of wild type APP751 (unknown origin) expressed in CHO cells 34648711
Amyloid-beta precursor protein IC50 = 3.0 nM 8.52 Inhibition of wild type human APP751 expressed in CHO cells assessed as reductio... 34648711
Amyloid-beta precursor protein IC50 = 3.0 nM 8.52 Inhibition of wild type human APP751 expressed in CHO cells assessed as reductio... 34648711
Unchecked IC50 = 3.0 nM 8.52 Inhibition of Cellular Release of Amyloid Peptide 1-40: Chinese hamster ovary ce... -
Beta-secretase 1 IC50 = 3.0 nM 8.52 Inhibition of BACE1 in CHO cells expressing human APP assessed as reduction in a... 30709653
Amyloid-beta precursor protein IC50 = 4.0 nM 8.4 Inhibition of wild type human APP751 expressed in CHO cells assessed as reductio... 34648711
Beta-secretase 1 IC50 = 7.0 nM 8.15 Inhibition Assay: Recombinant BACE-1 (extracellular domain, expressed in baculov... -
Beta-secretase 1 IC50 = 7.0 nM 8.15 Inhibition of Human BACE-1: Recombinant BACE-1 (extracellular domain, expressed ... -
Beta-secretase 1 IC50 = 7.0 nM 8.15 Inhibition Assay: Recombinant BACE-1 (extracellular domain, expressed in baculov... -
Beta-secretase 1 IC50 = 11.0 nM 7.96 Inhibition of human BACE1 by FRET assay 30709653
Beta-secretase 1 IC50 = 11.0 nM 7.96 Inhibition of human recombinant BACE1 catalytic domain using FRET substrate with... 34648711
Beta-secretase 1 IC50 = 11.0 nM 7.96 Inhibition of human BACE1 34648711
Beta-secretase 2 IC50 = 30.0 nM 7.52 Inhibition Assay: Recombinant BACE-2 (extracellular domain, expressed in baculov... -
Beta-secretase 2 IC50 = 30.0 nM 7.52 Inhibition Assay: Recombinant BACE-2 (extracellular domain, expressed in baculov... -
Beta-secretase 2 IC50 = 30.0 nM 7.52 Inhibition of Human BACE-2: Recombinant BACE-2 (extracellular domain, expressed ... -
Beta-secretase 2 IC50 = 30.0 nM 7.52 Inhibition Assay: Recombinant BACE-2 (extracellular domain, expressed in baculov... -
Beta-secretase 2 IC50 = 30.0 nM 7.52 Inhibition of human BACE2 34648711
Beta-secretase 2 IC50 = 30.0 nM 7.52 Inhibition of human recombinant BACE2 catalytic domain using FRET substrate with... 34648711
Beta-secretase 2 IC50 = 30.0 nM 7.52 Inhibition of human BACE2 by FRET assay 30709653
Unchecked IC50 = 44.0 nM 7.36 Inhibition of human APP751swedish mutant expressed in CHO cells assessed as redu... 34648711

Literature References

PubMed DOI Target Context # Activities
34648711 10.1021/acs.jmedchem.1c01300 ADMET 42
34648711 10.1021/acs.jmedchem.1c01300 Unchecked 13
34648711 10.1021/acs.jmedchem.1c01300 No relevant target 6
34648711 10.1021/acs.jmedchem.1c01300 Amyloid-beta precursor protein 4
30709653 10.1016/j.bmcl.2018.12.049 Beta-secretase 1 2
34648711 10.1021/acs.jmedchem.1c01300 Beta-secretase 1 2
34648711 10.1021/acs.jmedchem.1c01300 Beta-secretase 2 2
34648711 10.1021/acs.jmedchem.1c01300 Cathepsin D 2
34648711 10.1021/acs.jmedchem.1c01300 Cathepsin E 2
34648711 10.1021/acs.jmedchem.1c01300 Voltage-gated inwardly rectifying potassium channel KCNH2 2
30709653 10.1016/j.bmcl.2018.12.049 Homo sapiens 1
30709653 10.1016/j.bmcl.2018.12.049 Beta-secretase 2 1
34648711 10.1021/acs.jmedchem.1c01300 Cytochrome P450 3A4 1
34648711 10.1021/acs.jmedchem.1c01300 Cytochrome P450 2D6 1
34648711 10.1021/acs.jmedchem.1c01300 Cytochrome P450 2C9 1

Data from ChEMBL 36 via Core Engine