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Compound Detail

CHEMBL576138

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Cc1ccc(N(C)C(=O)c2c(-c3ccccc3Cl)noc2C)cc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL576138
Phase Preclinical
Structure Type MOL
InChI Key WRRGABWWSIAMMJ-UHFFFAOYSA-N
7
Targets
14
Activities
2
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

375.3
MW (Da)
5.54
ALogP
3
HBA
0
HBD
46.3
PSA (Ų)
0.60
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 C19H16Cl2N2O2
MW 375.26
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.85

Activity Summary

EC50 12 meas. best 7.64
IC50 2 meas. best 6.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 7.64 6.9429 23.0 7
Unchecked
CHEMBL612545
 EC50 7.5 6.925 31.6 2
Cytochrome P450 2C19
CHEMBL3622
 IC50 6.5 6.5 316.2 1
Homo sapiens
CHEMBL372
 EC50 6.22 6.22 600.0 1
G-protein coupled bile acid receptor 1
CHEMBL1075223
 EC50 6.2 6.2 631.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.9 5.9 1258.9 1
Melanophore
CHEMBL614313
 EC50 4.5 4.5 31622.8 1

Pharmacokinetic Data

Parameter Value Units Species
CL 148.0 mL.min-1.kg-1 Rattus norvegicus
CL 54.0 mL.min-1.kg-1 Rattus norvegicus
CL 111.0 mL.min-1.kg-1 Canis lupus familiaris
CL 39.0 mL.min-1.kg-1 Canis lupus familiaris
CL 320.0 mL.min-1.g-1 Homo sapiens
F 1.0 % Rattus norvegicus
F 0.3 % Canis lupus familiaris
T1/2 8.7 hr Rattus norvegicus
T1/2 5.2 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
G-protein coupled bile acid receptor 1 EC50 = 23.0 nM 7.64 Agonist activity at doxycycline-promoter regulated overexpressed human TGR5 rece... 23337601
G-protein coupled bile acid receptor 1 EC50 = 24.0 nM 7.62 Agonist activity at human TGR5 expressed in deoxycycline-induced Flp-In-CHO-TO c... 24900564
Unchecked EC50 = 31.62 nM 7.5 Agonist activity at canine TGR5 expressed in melanophores assessed as melanosome... 19902954
G-protein coupled bile acid receptor 1 EC50 = 79.43 nM 7.1 Agonist activity at human TGR5 expressed in melanophores assessed as melanosome ... 19902954
G-protein coupled bile acid receptor 1 EC50 = 79.43 nM 7.1 Agonist activity at human TGR5 receptor expressed in human U2-OS cells assessed ... 20097073
G-protein coupled bile acid receptor 1 EC50 = 316.0 nM 6.5 Agonist activity at human TGR5 expressed in uninduced Flp-In-CHO-TO cells assess... 24900564
Cytochrome P450 2C19 IC50 = 316.23 nM 6.5 Inhibition of CYP2C19 19902954
Unchecked EC50 = 445.0 nM 6.35 Agonist activity at dog TGR5 expressed in uninduced Flp-In-CHO-TO cells assessed... 24900564
G-protein coupled bile acid receptor 1 EC50 = 457.0 nM 6.34 Agonist activity at human TGR5 receptor in CHO cells assessed as elevation of cA... 23337601
G-protein coupled bile acid receptor 1 EC50 = 501.19 nM 6.3 Agonist activity at TGR5 expressed in human U2-OS cells assessed as increase in ... 19902954
Homo sapiens EC50 = 600.0 nM 6.22 Ex vivo activation of TGR5 in human PBMC assessed as elevation of cAMP level by ... 23337601
G-protein coupled bile acid receptor 1 EC50 = 630.96 nM 6.2 Agonist activity at rat TGR5 expressed in melanophores assessed as melanosome di... 19902954
Cytochrome P450 3A4 IC50 = 1258.93 nM 5.9 Inhibition of CYP3A4 19902954
Melanophore EC50 = 31622.78 nM 4.5 Induction of melanosome dispersion in melanophores 19902954

Literature References

PubMed DOI Target Context # Activities
19902954 10.1021/jm901434t Canis familiaris 6
19902954 10.1021/jm901434t Rattus norvegicus 4
19902954 10.1021/jm901434t G-protein coupled bile acid receptor 1 3
23337601 10.1016/j.bmcl.2012.12.076 G-protein coupled bile acid receptor 1 2
24900564 10.1021/ml300277t G-protein coupled bile acid receptor 1 2
19902954 10.1021/jm901434t ADMET 2
19902954 10.1021/jm901434t Cytochrome P450 1A2 1
24900564 10.1021/ml300277t Liver microsomes 1
24900564 10.1021/ml300277t Unchecked 1
24900564 10.1021/ml300277t No relevant target 1
20097073 10.1016/j.bmcl.2010.01.003 G-protein coupled bile acid receptor 1 1
19902954 10.1021/jm901434t Voltage-gated inwardly rectifying potassium channel KCNH2 1
19902954 10.1021/jm901434t No relevant target 1
19902954 10.1021/jm901434t Cytochrome P450 2D6 1
19902954 10.1021/jm901434t Cytochrome P450 2C9 1
19902954 10.1021/jm901434t Cytochrome P450 3A4 1
19902954 10.1021/jm901434t Cytochrome P450 2C19 1
19902954 10.1021/jm901434t Hepatocyte 1
19902954 10.1021/jm901434t Melanophore 1
19902954 10.1021/jm901434t Unchecked 1

Data from ChEMBL 36 via Core Engine