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Compound Detail

CHEMBL318457

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CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc(/C=C/c2cccc(C(=O)O)c2)c(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL318457
Phase Preclinical
Structure Type MOL
InChI Key BYTNEISLBIENSA-MDZDMXLPSA-N
6
Targets
70
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

542.9
MW (Da)
8.87
ALogP
4
HBA
1
HBD
72.6
PSA (Ų)
0.23
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H22Cl3NO4
MW 542.85
Aromatic Rings 4
Heavy Atoms 36
NP-Likeness -0.64

Activity Summary

EC50 63 meas. best 7.92
IC50 7 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bile acid receptor
CHEMBL2047
 EC50 7.92 7.0898 12.0 60
Bile acid receptor
CHEMBL2047
 IC50 7.7 6.855 19.8 4
Unchecked
CHEMBL612545
 EC50 6.53 6.53 296.0 1
Bile acid receptor
CHEMBL5343
 EC50 5.7 5.7 2000.0 1
SW-620
CHEMBL612262
 IC50 5.12 5.12 7600.0 1
HT-29
CHEMBL384
 IC50 4.86 4.86 13800.0 1
Fatty acid-binding protein, liver
CHEMBL5421
 IC50 4.82 4.82 15300.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3136.0 ng.hr.mL-1 Mus musculus
AUC 3162.0 ng.hr.mL-1 Mus musculus
AUC 85226.0 ng.hr.mL-1 Mus musculus
AUC 85283.0 ng.hr.mL-1 Mus musculus
CL 36.0 mL.min-1.kg-1 Rattus norvegicus
CL 56.0 mL.min-1.g-1 Mus musculus
CL 26.33 mL.min-1.kg-1 Mus musculus
Cmax 8818.27 nM Mus musculus
F 10.0 % Rattus norvegicus
F 42.81 % Mus musculus
T1/2 3.5 hr Rattus norvegicus
T1/2 0.6833 hr Mus musculus
T1/2 1.53 hr Mus musculus
Tmax 0.5 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bile acid receptor EC50 = 12.0 nM 7.92 Agonist activity at human FXR expressed in HEK293 cells measured after 18 hrs by... 32991173
Bile acid receptor EC50 = 13.2 nM 7.88 Agonist activity at human FXR expressed in human HuH7 cells by luciferase report... 32616182
Bile acid receptor EC50 = 15.0 nM 7.82 Ligand dependent recruitment of SRC1(676-700) peptide to human Farnesoid X-activ... 10956205
Bile acid receptor EC50 = 15.0 nM 7.82 Agonist activity at FXR 23040732
Bile acid receptor EC50 = 15.0 nM 7.82 Agonist activity at FXR (unknown origin) by coactivator recruitment assay 24685112
Bile acid receptor EC50 = 15.0 nM 7.82 Agonist activity at FXR (unknown origin) 31930920
Bile acid receptor EC50 = 19.0 nM 7.72 Agonist activity at recombinant human GST-tagged FXR ligand binding domain (193 ... 29148806
Bile acid receptor EC50 = 20.0 nM 7.7 Agonist activity at GST-tagged FXR LBD (187 to 472 residues) (unknown origin) as... 27268696
Bile acid receptor EC50 = 20.0 nM 7.7 Agonist activity at human GST-fused FXR LBD assessed as cofactor peptide interac... 20638278
Bile acid receptor IC50 = 19.8 nM 7.7 Antagonist activity at human GST-tagged FXR after 20 mins by TR-FRET assay 24775917
Bile acid receptor EC50 = 20.0 nM 7.7 Transactivation of human FXR (unknown origin) expressed in HepG2 cells co-expres... 30996771
Bile acid receptor EC50 = 22.3 nM 7.65 Agonist activity at human FXR expressed in human Huh-7 cells co-transfected with... 34256254
Bile acid receptor EC50 = 26.0 nM 7.58 Agonist activity at human FXR expressed in HEK293 cells by luciferase reporter g... 25305688
Bile acid receptor EC50 = 26.73 nM 7.57 Agonist activity at FXR-LBD (unknown origin) assessed as induction of coactivato... 34998040
Bile acid receptor EC50 = 30.0 nM 7.52 Binding affinity for human Farnesoid X receptor in FRET assay 15317466
Bile acid receptor EC50 = 30.0 nM 7.52 Agonist activity at human full length FXR transfected in HEK293 cells coexpressi... 20638278
Bile acid receptor EC50 = 35.0 nM 7.46 Agonist activity at human GST-fused FXR LBD expressed in HEK293 cells coexpressi... 20638278
Bile acid receptor EC50 = 35.0 nM 7.46 Agonist activity at C-terminal Gal4-tagged human FXR (187 to 472 residues) expre... 27268696
Bile acid receptor EC50 = 37.0 nM 7.43 Agonist activity at FXR (unknown origin) 32339855
Bile acid receptor EC50 = 37.0 nM 7.43 Effective concentration against Farnesoid X receptor (FXR) 12166927

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4689842 Fibroblast 9
36130662 10.1016/j.bmcl.2022.128993 ADMET 9
27372840 10.1016/j.bmc.2016.06.039 Bile acid receptor 7
- 10.6019/CHEMBL4689842 U2OS 7
20638278 10.1016/j.bmcl.2010.06.084 Bile acid receptor 6
19328688 10.1016/j.bmcl.2009.03.008 Bile acid receptor 5
32616182 10.1016/j.bmc.2020.115512 Bile acid receptor 5
28845983 10.1021/acs.jmedchem.7b00398 Bile acid receptor 5
21256005 10.1016/j.bmcl.2010.12.089 Bile acid receptor 5
34998040 10.1016/j.ejmech.2021.114089 Bile acid receptor 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
23688559 10.1016/j.bmc.2013.04.069 Bile acid receptor 4
19410460 10.1016/j.bmcl.2009.04.047 Bile acid receptor 4
30996771 10.1021/acsmedchemlett.8b00423 Bile acid receptor 4
- 10.6019/CHEMBL5724696 TERT-RPE1 4
21890356 10.1016/j.bmcl.2011.08.034 Bile acid receptor 4
30996771 10.1021/acsmedchemlett.8b00423 ADMET 3
25255039 10.1021/jm500937v Bile acid receptor 3
24685112 10.1016/j.bmc.2014.02.053 Bile acid receptor 3

Data from ChEMBL 36 via Core Engine