Compound Detail

CHEMBL224867

TAUROCHOLIC ACID

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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]3C[C@H](O)[C@]12C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL224867
Name	TAUROCHOLIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	WBWWGRHZICKQGZ-HZAMXZRMSA-N

Known Names

Cholaic acid Cholic acid taurine conjugate N-Choloyltaurine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

515.7

MW (Da)

2.37

ALogP

HBA

HBD

144.2

PSA (Å²)

0.33

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C26H45NO7S
MW	515.71
Aromatic Rings	0
Heavy Atoms	35
NP-Likeness	2.08

Activity Summary

Ki 9 meas. best 4.97

IC50 6 meas. best 5.28

EC50 1 meas. best 5.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
G-protein coupled bile acid receptor 1 CHEMBL5409	EC50	5.3	5.3	4950.0	1
Hepatic sodium/bile acid cotransporter CHEMBL5287	IC50	5.28	5.28	5300.0	1
Hepatic sodium/bile acid cotransporter CHEMBL4847	IC50	5.22	5.22	6000.0	1
Solute carrier organic anion transporter family member 1A1 CHEMBL1781859	Ki	4.97	4.735	10800.0	2
Solute carrier organic anion transporter family member 1A4 CHEMBL1781860	Ki	4.41	4.41	39400.0	1
Multidrug resistance associated protein CHEMBL2073669	IC50	4.4	4.4	40000.0	1
Ileal sodium/bile acid cotransporter CHEMBL2778	Ki	4.38	4.38	41500.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	4.0	hr	-
T1/2	6.0	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
G-protein coupled bile acid receptor 1	EC50	=	4950.0	nM	5.3	Agonist activity at human TGR5 expressed in CHO cells by luciferase assay	18307294
Hepatic sodium/bile acid cotransporter	IC50	=	5300.0	nM	5.28	TP_TRANSPORTER: inhibition of Taurocholate uptake in NTCP-expressing HeLa cells	10565843
Hepatic sodium/bile acid cotransporter	IC50	=	6000.0	nM	5.22	Inhibition of [3H]taurocholate uptake in rat hepatocytes	15261266
Solute carrier organic anion transporter family member 1A1	Ki	=	10800.0	nM	4.97	TP_TRANSPORTER: inhibition of E217betaG uptake in Oatp1-expressing LLC-PK1 cells	11408557
Solute carrier organic anion transporter family member 1A1	Ki	=	32000.0	nM	4.5	TP_TRANSPORTER: inhibition of Enalapril uptake in Oatp1-expressing HeLa cells	9794920
Solute carrier organic anion transporter family member 1A4	Ki	=	39400.0	nM	4.41	TP_TRANSPORTER: inhibition of E217betaG uptake in Oatp2-expressing LLC-PK1 cells	11408557
Multidrug resistance associated protein	IC50	=	40000.0	nM	4.4	TP_TRANSPORTER: inhibition of E217betaG uptake (E217betaG: 0.4 uM) in membrane v...	12924948
Ileal sodium/bile acid cotransporter	Ki	=	41500.0	nM	4.38	TP_TRANSPORTER: inhibition of Taurocholate uptake in ASBT-expressing COS cells	9458785

Literature References

PubMed	DOI	Target Context	# Activities
10644759	10.1074/jbc.275.4.2905	ATP-binding cassette sub-family C member 3	8
12719432	10.1074/jbc.m301106200	Organic solute transporter subunit alpha	7
18725450	10.1128/aac.00245-08	Pasteurella multocida	7
23129211	10.1124/dmd.112.044891	Hepatocyte	6
17210767	10.1128/aac.01048-06	Escherichia coli	6
23255551	10.1124/dmd.112.047910	Solute carrier organic anion transporter family member	6
20038628	10.1128/aac.01126-09	Escherichia coli	5
7557095	10.1016/0016-5085(95)90588-x	Solute carrier organic anion transporter family member 1A2	5
31301948	10.1016/j.bmc.2019.07.012	Hepatic sodium/bile acid cotransporter	4
11093941	10.1152/ajpgi.2000.279.6.g1188	Solute carrier organic anion transporter family member 1A5	4
12518026	10.1194/jlr.m200220-jlr200	Bile salt export pump	4
8045503	10.1016/0270-9139(94)90194-5	Solute carrier organic anion transporter family member 1A1	4
12842829	10.1152/ajpgi.00352.2002	Solute carrier organic anion transporter family member 1A1	4
11306713	10.1124/mol.59.5.1277	Organic anion transporter 3	3
11438506	10.1053/gast.2001.25542	ATP-dependent translocase ABCB1	3
9458785	10.1152/ajpgi.1998.274.1.g157	Ileal sodium/bile acid cotransporter	3
20713311	10.1016/j.bmc.2010.07.030	ADMET	3
19102680	10.1021/np8004453	Phospholipase A2	3
11316767	10.1210/endo.142.5.8115	Solute carrier organic anion transporter family member 4A1	3
12842829	10.1152/ajpgi.00352.2002	Hepatic sodium/bile acid cotransporter	2

Data from ChEMBL 36 via Core Engine