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Compound Detail

CHEMBL240597

CHENODIOL
💊 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]3CC[C@]12C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL240597
Name CHENODIOL
Phase Approved
Structure Type MOL
InChI Key RUDATBOHQWOJDD-BSWAIDMHSA-N
Therapeutic ✓ Yes

Known Names

Acide chenodesoxycholique Acido quenodeoxicolico Anthropodeoxycholic acid Anthropodesoxycholic acid Anthropododesoxycholic acid Chendol Chendol 125 Chendol 250 Chenic acid Chenix Chenocedon Chenocol +15 more
8
Targets
49
Activities
3
Assay Types
1
PK Parameters
20
Publications
27
Known Names
4
Indications
1
Mechanisms

Molecular Properties

392.6
MW (Da)
4.48
ALogP
3
HBA
3
HBD
77.8
PSA (Ų)
0.66
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1983
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1978

Extended Properties

Molecular Formula C24H40O4
MW 392.58
Aromatic Rings 0
Heavy Atoms 28
NP-Likeness 2.43

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bile acid receptor FXR agonist AGONIST Bile acid receptor ✓ ✓

Indications

Metabolism, Inborn Errors Xanthomatosis, Cerebrotendinous Irritable Bowel Syndrome Paraplegia

ATC Classification

A05AA01
chenodeoxycholic acid
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: BILE AND LIVER THERAPY

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States

Activity Summary

EC50 42 meas. best 5.47
IC50 5 meas. best 4.97
Ki 2 meas. best 5.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Ileal sodium/bile acid cotransporter
CHEMBL2778
 Ki 5.48 5.48 3300.0 1
Bile acid receptor
CHEMBL2047
 EC50 5.47 4.9407 3400.0 29
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 5.35 4.935 4430.0 10
Bile salt export pump
CHEMBL6020
 IC50 4.97 4.97 10600.0 1
Unchecked
CHEMBL612545
 EC50 4.9 4.9 12500.0 1
Bile acid receptor/Retinoic acid receptor RXR-alpha
CHEMBL3885529
 EC50 4.78 4.78 16800.0 1
Bile acid receptor
CHEMBL5343
 EC50 4.78 4.78 16800.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.72 4.72 18900.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 8000.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Ileal sodium/bile acid cotransporter Ki = 3300.0 nM 5.48 TP_TRANSPORTER: inhibition of Taurocholate uptake in ASBT-expressing COS cells 9458785
Bile acid receptor EC50 = 3400.0 nM 5.47 Ligand dependent recruitment of SRC1(676-700) peptide to human Farnesoid X-activ... 10956205
Bile acid receptor EC50 = 3500.0 nM 5.46 Effective concentration for recruitment of SRC-1 LxxLL-containing peptide to hum... 16107136
G-protein coupled bile acid receptor 1 EC50 = 4430.0 nM 5.35 Agonist activity at human TGR5 38691888
G-protein coupled bile acid receptor 1 EC50 = 6100.0 nM 5.21 Agonist activity at human GPBAR1 expressed in HEK293 cells assessed as increase ... 25735208
Bile acid receptor EC50 = 6310.0 nM 5.2 Agonist activity at FXR assessed as activation by cell based luciferase transact... 18815030
G-protein coupled bile acid receptor 1 EC50 = 6710.0 nM 5.17 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
G-protein coupled bile acid receptor 1 EC50 = 6710.0 nM 5.17 Agonist activity at human TGR5 expressed in CHO cells after 5 hrs by CRE-driven ... 17685603
G-protein coupled bile acid receptor 1 EC50 = 6700.0 nM 5.17 Agonist activity at TGR5 expressed in NCI-H716 cells assessed as cAMP level afte... 24900463
Bile acid receptor EC50 = 7010.0 nM 5.15 Transactivation of full-length FXR (unknown origin) expressed in HEK293 cells af... 30393515
Bile acid receptor EC50 = 8000.0 nM 5.1 Agonist activity at GST-tagged FXR-LBD (unknown origin) assessed as biotinylated... 31673308
Bile acid receptor EC50 = 8660.0 nM 5.06 Binding affinity for human Farnesoid X receptor in FRET assay 15317466
Bile acid receptor EC50 = 8660.0 nM 5.06 Binding affinity for Farnesoid X Receptor (FXR) 12749886
Bile acid receptor EC50 = 8660.0 nM 5.06 Agonist activity at FXR (unknown origin) 31930920
Bile acid receptor EC50 = 8660.0 nM 5.06 Binding affinity to FXR assessed as ligand-dependent SRC1 recruitment by FRET ba... 16821780
Bile acid receptor EC50 = 8660.0 nM 5.06 Effective concentration against Farnesoid X receptor (FXR) 12166927
Bile acid receptor EC50 = 8660.0 nM 5.06 Agonist activity at human FXR assessed as recruitment of SRC1 peptide by TR-FRET... 29259742
Bile acid receptor EC50 = 9000.0 nM 5.05 Agonist activity at FXR (unknown origin) assessed as recruitment of SRC1 peptide... 28252961
Bile acid receptor EC50 = 10000.0 nM 5.0 Agonist activity at FXR 22014750
Bile acid receptor EC50 = 10000.0 nM 5.0 Agonist activity at glutathione transferase-tagged human FXR-LBD using biotinyla... 27652492

Literature References

PubMed DOI Target Context # Activities
31494470 10.1016/j.ejmech.2019.111652 Bile acid receptor 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
30108740 10.1039/C7MD00475C HUVEC 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
21459580 10.1016/j.bmc.2011.03.004 Bile acid receptor 9
27652492 10.1021/acs.jmedchem.6b01126 ADMET 9
28845983 10.1021/acs.jmedchem.7b00398 Bile acid receptor 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
30108740 10.1039/C7MD00475C Danio rerio 7
22472691 10.1016/j.bmcl.2012.03.057 Bile acid receptor 7
25255039 10.1021/jm500937v Bile acid receptor 7
24900622 10.1021/ml400247k Unchecked 6
25934227 10.1016/j.bmc.2015.04.035 Bile acid receptor 6
24900622 10.1021/ml400247k G-protein coupled bile acid receptor 1 5
18768321 10.1016/j.bmc.2008.07.046 HCT-116 4
29275233 10.1016/j.ejmech.2017.12.034 No relevant target 4
20014870 10.1021/jm901390p Rattus norvegicus 4
25127166 10.1016/j.bmcl.2014.07.045 Bile acid receptor 4
22683342 10.1016/j.bmcl.2012.05.057 Bile acid receptor 4
18768321 10.1016/j.bmc.2008.07.046 GBM 4

Data from ChEMBL 36 via Core Engine