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Compound Detail

CHEMBL4468760

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C[C@H]1c2cccc(-c3cnn(C)c3)c2C[C@H](CO)N1C(=O)Cc1c(Cl)cccc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4468760
Phase Preclinical
Structure Type MOL
InChI Key MJDOWJUPBHLXIH-GOEBONIOSA-N
6
Targets
9
Activities
2
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

444.4
MW (Da)
4.44
ALogP
4
HBA
1
HBD
58.4
PSA (Ų)
0.65
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H23Cl2N3O2
MW 444.36
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.91

Activity Summary

EC50 8 meas. best 7.93
IC50 1 meas. best 5.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(1A) dopamine receptor
CHEMBL2056
 EC50 7.93 7.8367 11.7 3
D(1A) dopamine receptor
CHEMBL3071
 EC50 6.82 6.82 151.0 1
D(1B) dopamine receptor
CHEMBL2737
 EC50 6.32 6.035 480.0 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
 EC50 6.0 6.0 1000.0 1
Cytochrome P450 3A4
CHEMBL340
 EC50 5.5 5.5 3200.0 1
Voltage-dependent N-type calcium channel subunit alpha-1B
CHEMBL4478
 IC50 5.21 5.21 6200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1075.35 ng.hr.mL-1 Rattus norvegicus
AUC 31771.74 ng.hr.mL-1 Canis lupus familiaris
AUC 1879.64 ng.hr.mL-1 Macaca fascicularis
CL 40.0 mL.min-1.kg-1 Homo sapiens
CL 27.2 mL.min-1.kg-1 Rattus norvegicus
CL 0.268 mL.min-1.kg-1 Canis lupus familiaris
CL 11.9 mL.min-1.kg-1 Macaca fascicularis
Cmax 459.0 nM Rattus norvegicus
Cmax 8700.0 nM Canis lupus familiaris
Cmax 870.0 nM Macaca fascicularis
F 57.8 % Rattus norvegicus
F 20.4 % Canis lupus familiaris
F 26.0 % Macaca fascicularis
T1/2 1.81 hr Rattus norvegicus
T1/2 20.1 hr Canis lupus familiaris
T1/2 4.96 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(1A) dopamine receptor EC50 = 11.7 nM 7.93 Positive allosteric modulation of human D1 receptor in HEK293 cells assessed as ... 35175768
D(1A) dopamine receptor EC50 = 16.4 nM 7.79 Positive allosteric modulation of human D1 receptor expressed in HEK293 assessed... 31938453
D(1A) dopamine receptor EC50 = 16.4 nM 7.79 Human D1 Receptor PAM Assay: The PAM activity of the compounds of the present in... -
D(1A) dopamine receptor EC50 = 151.0 nM 6.82 Positive allosteric modulation of mouse D1 receptor expressed in HEK293 cells as... 35175768
D(1B) dopamine receptor EC50 = 480.0 nM 6.32 Positive allosteric modulation of mouse D5 receptor expressed in HEK293 cells as... 35175768
5-hydroxytryptamine receptor 2B EC50 = 1000.0 nM 6.0 Agonist activity at human 5HT2b 35175768
D(1B) dopamine receptor EC50 = 1800.0 nM 5.75 Agonist activity at mouse D5 receptor expressed in HEK293 cells assessed as incr... 35175768
Cytochrome P450 3A4 EC50 = 3200.0 nM 5.5 Induction of CYP3A4 in human hepatocytes 35175768
Voltage-dependent N-type calcium channel subunit alpha-1B IC50 = 6200.0 nM 5.21 Inhibition of human Cav2.2 35175768

Literature References

PubMed DOI Target Context # Activities
35175768 10.1021/acs.jmedchem.1c01887 ADMET 31
35175768 10.1021/acs.jmedchem.1c01887 D(1A) dopamine receptor 17
35175768 10.1021/acs.jmedchem.1c01887 Unchecked 14
35175768 10.1021/acs.jmedchem.1c01887 Mus musculus 6
35175768 10.1021/acs.jmedchem.1c01887 D(1B) dopamine receptor 6
35175768 10.1021/acs.jmedchem.1c01887 Cytochrome P450 3A4 3
35175768 10.1021/acs.jmedchem.1c01887 No relevant target 3
35175768 10.1021/acs.jmedchem.1c01887 Sodium-dependent dopamine transporter 2
35175768 10.1021/acs.jmedchem.1c01887 5-hydroxytryptamine receptor 2B 2
35175768 10.1021/acs.jmedchem.1c01887 D(2) dopamine receptor 2
31938453 10.1021/acsmedchemlett.9b00547 D(1A) dopamine receptor 2
35175768 10.1021/acs.jmedchem.1c01887 Translocator protein 1
35175768 10.1021/acs.jmedchem.1c01887 Cannabinoid receptor 1 1
35175768 10.1021/acs.jmedchem.1c01887 Cytochrome P450 1
35175768 10.1021/acs.jmedchem.1c01887 Gamma-aminobutyric acid receptor subunit alpha-1 1
35175768 10.1021/acs.jmedchem.1c01887 Glutamate [NMDA] receptor 1
35175768 10.1021/acs.jmedchem.1c01887 Neuronal acetylcholine receptor; alpha4/beta2 1
35175768 10.1021/acs.jmedchem.1c01887 Cytochrome P450 2C19 1
35175768 10.1021/acs.jmedchem.1c01887 5-hydroxytryptamine receptor 2A 1
35175768 10.1021/acs.jmedchem.1c01887 Cytochrome P450 2C9 1

Data from ChEMBL 36 via Core Engine