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Compound Detail

CHEMBL185878

TAUROCHENODEOXYCHOLATE
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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 CHEMBL185878
Name TAUROCHENODEOXYCHOLATE
Phase Preclinical
Structure Type MOL
InChI Key BHTRKEVKTKCXOH-BJLOMENOSA-N
6
Targets
9
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

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
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

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

Activity Summary

EC50 4 meas. best 5.72
IC50 3 meas. best 4.55
Ki 2 meas. best 5.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 5.72 5.2967 1920.0 3
Bile acid receptor
CHEMBL2047
 EC50 5.52 5.52 3000.0 1
Ileal sodium/bile acid cotransporter
CHEMBL2778
 Ki 5.21 5.21 6100.0 1
Oryctolagus cuniculus
CHEMBL374
 IC50 4.55 4.55 28000.0 2
Bile salt export pump
CHEMBL6020
 Ki 4.55 4.55 28000.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.26 4.26 55000.0 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 = 1920.0 nM 5.72 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
G-protein coupled bile acid receptor 1 EC50 = 2300.0 nM 5.64 Agonist activity at wild type human TGR5 expressed in HEK293 cells assessed as r... 26435512
Bile acid receptor EC50 = 3000.0 nM 5.52 Binding affinity for Farnesoid X Receptor (FXR) 12749886
Ileal sodium/bile acid cotransporter Ki = 6100.0 nM 5.21 TP_TRANSPORTER: inhibition of Taurocholate uptake in ASBT-expressing COS cells 9458785
Oryctolagus cuniculus IC50 = 28000.0 nM 4.55 Tested for inhibition of Na+ -dependent [3H]taurocholate uptake into rabbit ilea... 7932551
Oryctolagus cuniculus IC50 = 28000.0 nM 4.55 The compound was evaluated for the inhibition of Na+-dependent [3H]taurocholate ... 8151614
Bile salt export pump Ki = 28000.0 nM 4.55 TP_TRANSPORTER: competitive inhibition of Taurocholate uptake in membrane vesicl... 12404239
G-protein coupled bile acid receptor 1 EC50 = 29570.0 nM 4.53 Agonist activity at human TGR5 Y89A mutant expressed in HEK293 cells assessed as... 26435512
ATP-binding cassette sub-family C member 4 IC50 = 55000.0 nM 4.26 TP_TRANSPORTER: inhibition of E217betaG uptake in membrane vesicles from MRP4-ex... 12523936

Literature References

PubMed DOI Target Context # Activities
7932551 10.1021/jm00046a007 Oryctolagus cuniculus 3
8151614 10.1021/jm00033a001 Oryctolagus cuniculus 3
26435512 10.1016/j.ejmech.2015.09.024 G-protein coupled bile acid receptor 1 3
20713311 10.1016/j.bmc.2010.07.030 ADMET 3
8045503 10.1016/0270-9139(94)90194-5 Solute carrier organic anion transporter family member 1A1 2
11093941 10.1152/ajpgi.2000.279.6.g1188 Solute carrier organic anion transporter family member 1A5 2
12220224 10.1042/bj20021081 Multidrug resistance associated protein 2
7557095 10.1016/0016-5085(95)90588-x Solute carrier organic anion transporter family member 1A2 2
8938553 10.1016/s0168-8278(96)80246-7 Solute carrier organic anion transporter family member 1A2 2
18307294 10.1021/jm7015864 G-protein coupled bile acid receptor 1 2
9398014 10.1002/hep.510260641 Hepatic sodium/bile acid cotransporter 1
15297262 10.1152/ajpgi.00360.2003 Unchecked 1
12883481 10.1053/jhep.2003.50331 ATP-binding cassette sub-family C member 4 1
11093941 10.1152/ajpgi.2000.279.6.g1188 Ileal sodium/bile acid cotransporter 1
8132774 10.1172/jci117091 Hepatic sodium/bile acid cotransporter 1
10607905 10.1016/s0378-1119(99)00460-6 Bile salt export pump 1
7912687 10.1016/0270-9139(94)90150-3 Multidrug resistance protein 1a 1
10464146 10.1016/s0016-5085(99)70463-4 Solute carrier organic anion transporter family member 1A4 1
12842829 10.1152/ajpgi.00352.2002 Solute carrier organic anion transporter family member 1A1 1
15990295 10.1016/j.bmcl.2005.06.015 Cytochrome P450 3A4 1

Data from ChEMBL 36 via Core Engine