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Compound Detail

CHEMBL205596

CHOLIC ACID
💊 Approved Drug
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💊 Approved Drug
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C

Basic Information

ChEMBL ID CHEMBL205596
Name CHOLIC ACID
Phase Approved
Structure Type MOL
InChI Key BHQCQFFYRZLCQQ-OELDTZBJSA-N
Therapeutic ✓ Yes

Known Names

Cholalic acid Cholbam Cholic acid E1000 Kolbam NSC-6135 Orphacol
5
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
7
Known Names
6
Indications
1
Mechanisms

Molecular Properties

408.6
MW (Da)
3.45
ALogP
4
HBA
4
HBD
98.0
PSA (Ų)
0.57
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Year 2014

Extended Properties

Molecular Formula C24H40O5
MW 408.58
Aromatic Rings 0
Heavy Atoms 29
NP-Likeness 2.78

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Indications

Digestive System Diseases Liver Diseases Metabolism, Inborn Errors Peroxisomal Disorders Fatty Liver Smith-Lemli-Opitz Syndrome

ATC Classification

A05AA03
cholic acid
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: BILE AND LIVER THERAPY

Activity Summary

EC50 10 meas. best 5.11
IC50 6 meas. best 5.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
G-protein coupled bile acid receptor 1
CHEMBL1255150
IC50 5.28 5.28 5300.0 1
G-protein coupled bile acid receptor 1
CHEMBL5409
IC50 5.22 5.22 6000.0 1
G-protein coupled bile acid receptor 1
CHEMBL5409
EC50 5.11 4.76 7720.0 8
Bile acid receptor
CHEMBL2047
EC50 4.35 4.245 45000.0 2
MCF7
CHEMBL387
IC50 4.3 4.3 50000.0 1
Oryctolagus cuniculus
CHEMBL374
IC50 4.08 4.08 83000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
G-protein coupled bile acid receptor 1 IC50 = 5300.0 nM 5.28 Agonist activity at mouse TGR5 receptor expressed in HEK293 cells assessed as in... 20801037
G-protein coupled bile acid receptor 1 IC50 = 6000.0 nM 5.22 Agonist activity at human TGR5 receptor expressed in HEK293 cells assessed as in... 20801037
G-protein coupled bile acid receptor 1 EC50 = 7720.0 nM 5.11 Agonist activity at human TGR5 38691888
G-protein coupled bile acid receptor 1 EC50 = 13600.0 nM 4.87 Agonist activity at human TGR5 expressed in CHO cells after 5 hrs by CRE-driven ... 17685603
G-protein coupled bile acid receptor 1 EC50 = 13600.0 nM 4.87 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
G-protein coupled bile acid receptor 1 EC50 = 13600.0 nM 4.87 Agonist activity at human TGR5 expressed in CHO cells assessed as increase in CR... 20014870
G-protein coupled bile acid receptor 1 EC50 = 13600.0 nM 4.87 Agonist activity at TGR5 expressed in NCI-H716 cells assessed as cAMP level afte... 24900463
G-protein coupled bile acid receptor 1 EC50 = 19830.0 nM 4.7 Agonist activity at wild type TGR5 (unknown origin) 24900622
G-protein coupled bile acid receptor 1 EC50 = 38700.0 nM 4.41 Positive allosteric modulator activity at human TGR5 expressed in HEK293T cells ... 37536263
G-protein coupled bile acid receptor 1 EC50 = 41500.0 nM 4.38 Agonist activity at TGR5 in human NCI-H716 cells assessed as increase in cAMP le... 37813065
Bile acid receptor EC50 = 45000.0 nM 4.35 Agonist activity at GST-tagged FXR-LBD (unknown origin) assessed as biotin-label... 29275233
MCF7 IC50 = 50000.0 nM 4.3 Antiproliferative activity against human MCF7 cells by MTT assay 18805690
Bile acid receptor EC50 = 73000.0 nM 4.14 Activation of GST-tagged FXR LBD (unknown origin) using biotinylated Src-1 pepti... 37813065
Oryctolagus cuniculus IC50 = 83000.0 nM 4.08 Tested for inhibition of Na+ -dependent [3H]taurocholate uptake into rabbit ilea... 7932551
Oryctolagus cuniculus IC50 = 83000.0 nM 4.08 The compound was evaluated for the inhibition of Na+-dependent [3H]taurocholate ... 8151614

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
27652492 10.1021/acs.jmedchem.6b01126 ADMET 11
- 10.6019/CHEMBL5303304 Fibroblast 9
20014870 10.1021/jm901390p ADMET 6
17210767 10.1128/aac.01048-06 Escherichia coli 6
24900622 10.1021/ml400247k Unchecked 6
19102680 10.1021/np8004453 Phospholipase A2 5
- 10.6019/CHEMBL5303304 U2OS 5
24900622 10.1021/ml400247k G-protein coupled bile acid receptor 1 5
20038628 10.1128/aac.01126-09 Escherichia coli 5
20014870 10.1021/jm901390p Rattus norvegicus 4
26774929 10.1016/j.ejmech.2016.01.002 Vitamin D3 receptor 4
39149112 10.1039/d4md00007b Plasmodium falciparum 4
33949869 10.1021/acs.jmedchem.1c00562 Unchecked 4
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B4 3
30108740 10.1039/C7MD00475C HUVEC 3
20713311 10.1016/j.bmc.2010.07.030 ADMET 3
8151614 10.1021/jm00033a001 Oryctolagus cuniculus 3
26299346 10.1016/j.bmcl.2015.08.006 Mycobacterium tuberculosis 3
26063305 10.1016/j.ejmech.2015.05.044 Trypanosoma brucei brucei 3

Data from ChEMBL 36 via Core Engine