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Compound Detail

CHEMBL408701

TAUROLITHOCHOLIC ACID
🧪 Phase III
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🧪 Phase III
C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL408701
Name TAUROLITHOCHOLIC ACID
Phase Phase III
Structure Type MOL
InChI Key QBYUNVOYXHFVKC-GBURMNQMSA-N

Known Names

Taurolithocholate Taurolithocholic acid
4
Targets
8
Activities
2
Assay Types
0
PK Parameters
20
Publications
2
Known Names
7
Indications

Molecular Properties

483.7
MW (Da)
4.43
ALogP
4
HBA
3
HBD
103.7
PSA (Ų)
0.46
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Unknown

Flags

Natural Product

Extended Properties

Molecular Formula C26H45NO5S
MW 483.72
Aromatic Rings 0
Heavy Atoms 33
NP-Likeness 1.66

Indications

Amyotrophic Lateral Sclerosis Liver Cirrhosis, Biliary Amyloid Neuropathies, Familial Diabetes Mellitus, Type 1 Asthma Multiple Sclerosis Liver Cirrhosis

Activity Summary

EC50 4 meas. best 6.54
IC50 4 meas. best 4.84

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 6.54 6.2725 290.0 4
Vitamin D3 receptor
CHEMBL1977
 IC50 4.84 4.84 14500.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.7 4.7 20000.0 1
Ephrin type-A receptor 2
CHEMBL4105859
 IC50 4.14 4.14 72000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
G-protein coupled bile acid receptor 1 EC50 = 290.0 nM 6.54 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
G-protein coupled bile acid receptor 1 EC50 = 330.0 nM 6.48 Agonist activity at recombinant human TGR5 expressed in CHO cells assessed as in... 31268316
G-protein coupled bile acid receptor 1 EC50 = 847.0 nM 6.07 Agonist activity at recombinant human TGR5 expressed in CHO cells assessed as in... 31268316
G-protein coupled bile acid receptor 1 EC50 = 1005.4 nM 6.0 Agonist activity at recombinant human TGR5 expressed in CHO cells assessed as in... 34046622
Vitamin D3 receptor IC50 = 14500.0 nM 4.84 Antagonist activity against VDR-LBD (unknown origin) expressed in Escherichia co... 26774929
ATP-binding cassette sub-family C member 4 IC50 = 20000.0 nM 4.7 TP_TRANSPORTER: inhibition of E217betaG uptake in membrane vesicles from MRP4-ex... 12523936
Ephrin type-A receptor 2 IC50 = 72000.0 nM 4.14 Displacement of biotinylated ephrin-A1-Fc from recombinant mouse EphA2 receptor ... 28005388

Literature References

PubMed DOI Target Context # Activities
26774929 10.1016/j.ejmech.2016.01.002 Vitamin D3 receptor 4
31268316 10.1021/acs.jmedchem.9b00770 G-protein coupled bile acid receptor 1 3
19102680 10.1021/np8004453 Phospholipase A2 2
19102680 10.1021/np8004453 Bile acid receptor 2
18307294 10.1021/jm7015864 G-protein coupled bile acid receptor 1 2
12739759 10.1023/a:1023278211849 Bile salt export pump 2
8132774 10.1172/jci117091 Hepatic sodium/bile acid cotransporter 1
34046622 10.1039/d0md00425a G-protein coupled bile acid receptor 1 1
22541068 10.1021/jm300212s Solute carrier organic anion transporter family member 1B1 1
22541068 10.1021/jm300212s Solute carrier organic anion transporter family member 1B3 1
22541068 10.1021/jm300212s Solute carrier organic anion transporter family member 2B1 1
12523936 10.1042/bj20021886 ATP-binding cassette sub-family C member 4 1
9188796 10.1016/s0005-2736(97)00003-5 Multidrug resistance-associated protein 1 1
7912687 10.1016/0270-9139(94)90150-3 ATP-dependent translocase ABCB1 1
12920197 10.1124/mol.64.3.610 Broad substrate specificity ATP-binding cassette transporter ABCG2 1
7912687 10.1016/0270-9139(94)90150-3 Multidrug resistance protein 1a 1
10869290 10.1053/jhep.2000.8263 Bile salt export pump 1
11897625 10.1152/ajpgi.00383.2001 ATP-binding cassette sub-family C member 2 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1

Data from ChEMBL 36 via Core Engine