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Compound Detail

CHEMBL1551

URSODIOL
💊 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 CHEMBL1551
Name URSODIOL
Phase Approved
Structure Type MOL
InChI Key RUDATBOHQWOJDD-UZVSRGJWSA-N
Therapeutic ✓ Yes

Known Names

Acide ursodeoxycholique Acido ursodeoxicolico Actigall Cholurso Destolit NSC-683769 Urdox Urso Urso 250 Urso forte Ursodeoxycholate Ursodeoxycholic acid +5 more
7
Targets
17
Activities
3
Assay Types
5
PK Parameters
20
Publications
17
Known Names
20
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 1987
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1988

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

Liver Cirrhosis, Biliary Liver Cirrhosis, Biliary Cholelithiasis Cholestasis, Intrahepatic Diabetes Mellitus, Type 2 Diabetes, Gestational Hepatitis C, Chronic Liver Diseases Liver Diseases Adenomatous Polyposis Coli Arthritis, Rheumatoid Chemical and Drug Induced Liver Injury Cholangitis, Sclerosing Cholestasis Colorectal Neoplasms Diabetes Mellitus Heart Failure Hepatitis D Inflammation Jaundice, Obstructive

ATC Classification

A05AA02
ursodeoxycholic acid
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: BILE AND LIVER THERAPY

Activity Summary

EC50 10 meas. best 5.62
IC50 4 meas. best 5.58
Ki 3 meas. best 5.95

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
 Ki 5.95 5.95 1134.0 1
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 5.62 5.03 2390.0 2
Aminopeptidase N
CHEMBL4117
 IC50 5.58 5.58 2600.0 1
Unchecked
CHEMBL612545
 EC50 5.49 4.67 3270.0 7
Hepatic sodium/bile acid cotransporter
CHEMBL5287
 IC50 5.44 5.44 3600.0 1
Autotaxin
CHEMBL3691
 IC50 5.03 5.03 9260.0 1
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
 IC50 4.58 4.58 26540.0 1
Ileal sodium/bile acid cotransporter
CHEMBL2778
 Ki 4.12 4.12 75000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 2.0 hr Homo sapiens
Tmax 1.0 hr Rattus norvegicus
Tmax 0.75 hr Rattus norvegicus
Tmax 0.75 hr Rattus norvegicus
Tmax 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CDGSH iron-sulfur domain-containing protein 1 Ki = 1134.0 nM 5.95 Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M... 27687671
G-protein coupled bile acid receptor 1 EC50 = 2390.0 nM 5.62 Agonist activity at human GPBAR1 expressed in HEK293 cells assessed as increase ... 25735208
Aminopeptidase N IC50 = 2600.0 nM 5.58 PUBCHEM_BIOASSAY: Inhibitors of Plasmodium falciparum M1- Family Alanyl Aminopep... -
Unchecked EC50 = 3270.0 nM 5.49 Agonist activity at MRGPRX4 83S (unknown origin) expressed in CHO-K1 cells asses... 37967029
Hepatic sodium/bile acid cotransporter IC50 = 3600.0 nM 5.44 TP_TRANSPORTER: inhibition of Taurocholate uptake in NTCP-expressing HeLa cells 10565843
Unchecked EC50 = 4930.0 nM 5.31 Agonist activity at MRGPRX4 83L (unknown origin) expressed in HEK293 cells co-ex... 37967029
Autotaxin IC50 = 9260.0 nM 5.03 Inhibition of human ATX in using LPC as substrate by fluorescence based micropla... 38091892
CDGSH iron-sulfur domain-containing protein 1 IC50 = 26540.0 nM 4.58 Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M... 27687671
Unchecked EC50 = 33800.0 nM 4.47 Agonist activity at MRGPRX4 83L (unknown origin) expressed in CHO cells assessed... 37967029
G-protein coupled bile acid receptor 1 EC50 = 36400.0 nM 4.44 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
Unchecked EC50 = 41100.0 nM 4.39 Agonist activity at MRGPRX4 83L (unknown origin) expressed in human 1321N1 gliob... 37967029
Unchecked EC50 = 41100.0 nM 4.39 Agonist activity at MRGPRX4 83L expressed in human HEK293 cells co- expressing G... 37975421
Unchecked EC50 = 47500.0 nM 4.32 Agonist activity at MRGPRX4 83S in human LN229 glioblastoma cells assessed as ch... 37967029
Unchecked EC50 = 47500.0 nM 4.32 Agonist activity at MRGPRX4 83S expressed in human HEK293 cells co- expressing G... 37975421
Ileal sodium/bile acid cotransporter Ki = 75000.0 nM 4.12 TP_TRANSPORTER: inhibition of Taurocholate uptake in ASBT-expressing COS cells 9458785

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
8667370 10.1021/jm9508503 Rattus norvegicus 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
- 10.1007/s00044-011-9828-5 Mus musculus 11
27652492 10.1021/acs.jmedchem.6b01126 ADMET 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
27372840 10.1016/j.bmc.2016.06.039 Bile acid receptor 7
27729186 10.1016/j.bmcl.2016.06.059 Huh-7 6
6737415 10.1021/jm00372a007 Rattus norvegicus 6
21158453 10.1021/jm100860s Glucocorticoid receptor 6
18598019 10.1021/jm800167u HepG2 5
18598019 10.1021/jm800167u NON-PROTEIN TARGET 5
37967029 10.1021/acs.jmedchem.3c01013 Unchecked 5
26774929 10.1016/j.ejmech.2016.01.002 Vitamin D3 receptor 4
25162837 10.1021/jm500889f Mus musculus 4
27652492 10.1021/acs.jmedchem.6b01126 No relevant target 3
20014752 10.1021/tx900326k Hepatotoxicity 3
8667370 10.1021/jm9508503 ADMET 3
20713311 10.1016/j.bmc.2010.07.030 ADMET 3

Data from ChEMBL 36 via Core Engine