URSODIOL

Search structure
Trade Names:
Synonyms:
Status: Approved (1987)
Entry Type: Small molecule
Molecule Category: UNKNOWN
UNII: 724L30Y2QR

Structure
InChI Key RUDATBOHQWOJDD-UZVSRGJWSA-N
Smile 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@@]21C
InChI
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H40O4
Molecular Weight 392.58
AlogP 4.48
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 4.0
Polar Surface Area 77.76
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 28.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Bile acid receptor FXR agonist PubMed PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Steroid-like ligand receptor
2390-36400 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 150
Unclassified protein
- 26540 - 1134 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Liver Cirrhosis, Biliary 4 D008105 ClinicalTrials
Liver Diseases 3 D008107 ClinicalTrials
Liver Diseases 3 D008107 ClinicalTrials
Hepatitis C, Chronic 3 D019698 ClinicalTrials
Cholelithiasis 3 D002769 ClinicalTrials
Cholestasis, Intrahepatic 3 D002780 ClinicalTrials
Pregnancy 2 D011247 ClinicalTrials
Heart Failure 2 D006333 ClinicalTrials
Chemical and Drug Induced Liver Injury 2 D056486 ClinicalTrials
Cholangitis, Sclerosing 2 D015209 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Diabetes Mellitus, Type 2 2 D003924 ClinicalTrials
Jaundice, Obstructive 2 D041781 ClinicalTrials
Adenomatous Polyposis Coli 2 D011125 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Inflammation 2 D007249 ClinicalTrials
Cholestasis 2 D002779 ClinicalTrials
Obesity 1 D009765 ClinicalTrials
Liver Cirrhosis 1 D008103 ClinicalTrials
Glucose Intolerance 1 D018149 ClinicalTrials
Huntington Disease 1 D006816 ClinicalTrials

Related Entries

MCS

Scaffolds

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Hepatobiliary disorders
12.35
General disorders and administration site conditions
10.67
Injury, poisoning and procedural complications
10.35
Pregnancy, puerperium and perinatal conditions
8.08
Gastrointestinal disorders
7.63
Skin and subcutaneous tissue disorders
6.61
Investigations
4.72
Immune system disorders
4.29
Respiratory, thoracic and mediastinal disorders
4.27
Vascular disorders
3.95
Infections and infestations
3.49
Nervous system disorders
3.39
Musculoskeletal and connective tissue disorders
2.74
Blood and lymphatic system disorders
2.69
Psychiatric disorders
2.4
Cardiac disorders
2.18
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.13

Cross References

Resources Reference
CAS NUMBER 128-13-2
ChEBI 9907
ChEMBL CHEMBL1551
DrugBank DB01586
DrugCentral 2797
EPA CompTox DTXSID6023731
FDA SRS 724L30Y2QR
Human Metabolome Database HMDB0000946
Guide to Pharmacology 7104
KEGG C07880
PDB IU5
PharmGKB PA451837
PubChem 31401
SureChEMBL SCHEMBL27200
ZINC ZINC000003914809
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