Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL272427

TAURURSODIOL
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
C[C@H](CCC(=O)NCCS(=O)(=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 CHEMBL272427
Name TAURURSODIOL
Phase Approved
Structure Type MOL
InChI Key BHTRKEVKTKCXOH-LBSADWJPSA-N
Therapeutic ✓ Yes

Known Names

Tauroursodeoxycholic acid Tauroursodesoxycholic acid Taurursodiol Taurursodiol component of relyvrio Ur-906 Ursodeoxy cholic acid Ursodeoxycholyltaurine Ursodoxicoltaurine
6
Targets
9
Activities
4
Assay Types
0
PK Parameters
20
Publications
8
Known Names
2
Indications
1
Mechanisms

Molecular Properties

499.7
MW (Da)
3.40
ALogP
5
HBA
4
HBD
123.9
PSA (Ų)
0.40
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2022
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Year 2020

Extended Properties

Molecular Formula C26H45NO6S
MW 499.71
Aromatic Rings 0
Heavy Atoms 34
NP-Likeness 1.77

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Amyotrophic Lateral Sclerosis Neurodegenerative Diseases

ATC Classification

A05AA05
ursodoxicoltaurine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: BILE AND LIVER THERAPY

Activity Summary

IC50 4 meas. best 5.52
EC50 3 meas. best 4.52
Kd 1 meas. best 5.0
Ki 1 meas. best 4.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis B virus
CHEMBL613497
 IC50 5.52 5.52 3000.0 1
Phospholipase A2
CHEMBL4426
 Kd 5.0 5.0 10000.0 1
Autotaxin
CHEMBL3691
 IC50 4.99 4.985 10300.0 2
Ileal sodium/bile acid cotransporter
CHEMBL2778
 Ki 4.55 4.55 28000.0 1
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 4.52 4.41 30000.0 2
Bile acid receptor
CHEMBL2047
 IC50 4.17 4.17 68220.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis B virus IC50 = 3000.0 nM 5.52 Antiviral activity against HBV infected in human HepG2-NTCP cells assessed as re... 33906348
Phospholipase A2 Kd = 10000.0 nM 5.0 Binding affinity to human pancreatic recombinant 1B PLA2 expressed in Escherichi... 19102680
Autotaxin IC50 = 10300.0 nM 4.99 Inhibition of human ATX expressed in HEK293 Flp-In cells assessed as decrease in... 28165241
Autotaxin IC50 = 10400.0 nM 4.98 Inhibition of ATX (unknown origin) 38091892
Ileal sodium/bile acid cotransporter Ki = 28000.0 nM 4.55 TP_TRANSPORTER: inhibition of Taurocholate uptake in ASBT-expressing COS cells 9458785
G-protein coupled bile acid receptor 1 EC50 = 30000.0 nM 4.52 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
G-protein coupled bile acid receptor 1 EC50 = 50500.0 nM 4.3 Agonist activity at wild type human TGR5 expressed in HEK293 cells assessed as r... 26435512
Bile acid receptor IC50 = 68220.0 nM 4.17 Antagonist activity against human FXR transfected in HEK293T cells co-transfecte... 38043493

Literature References

PubMed DOI Target Context # Activities
19102680 10.1021/np8004453 Phospholipase A2 8
27729186 10.1016/j.bmcl.2016.06.059 Huh-7 8
20713311 10.1016/j.bmc.2010.07.030 ADMET 4
26435512 10.1016/j.ejmech.2015.09.024 G-protein coupled bile acid receptor 1 3
7557095 10.1016/0016-5085(95)90588-x Solute carrier organic anion transporter family member 1A2 3
27729186 10.1016/j.bmcl.2016.06.059 NON-PROTEIN TARGET 3
28165241 10.1021/acs.jmedchem.6b01743 Autotaxin 2
38043493 10.1016/j.ejmech.2023.115992 Bile acid receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
11093941 10.1152/ajpgi.2000.279.6.g1188 Solute carrier organic anion transporter family member 1A5 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
33906348 10.1021/acs.jmedchem.1c00078 Hepatitis B virus 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19102680 10.1021/np8004453 Bile acid receptor 2
18307294 10.1021/jm7015864 G-protein coupled bile acid receptor 1 2
38091892 10.1016/j.ejmech.2023.116029 Autotaxin 1
9398014 10.1002/hep.510260641 Hepatic sodium/bile acid cotransporter 1
12883481 10.1053/jhep.2003.50331 ATP-binding cassette sub-family C member 4 1
12842829 10.1152/ajpgi.00352.2002 Solute carrier organic anion transporter family member 1A1 1
12404240 10.1053/gast.2002.36587 Bile salt export pump 1

Data from ChEMBL 36 via Core Engine