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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1551
CHEMBL1551
Compound Name URSODIOL
ChEMBL Synonyms URSODIOL | URSO 250 | URSOFALK | URSO FORTE | ACTIGALL | URSODEOXYCHOLIC ACID | URSODESOXYCHOLIC ACID | URDOX | CHOLURSO | URSO | URSOGAL | DESTOLIT
Max Phase 4 (Approved)
Trade Names URSODIOL | URSOFALK | ACTIGALL | CHOLURSO | URDOX | DESTOLIT | URSOGAL | URSO FORTE | URSO | URSO 250
Molecular Formula C24H40O4

Additional synonyms for CHEMBL1551 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H] ...
Download SMILES
Standard InChI InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24 ...
Download InChI
Standard InChI Key RUDATBOHQWOJDD-UZVSRGJWSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1551

Molecule Features

CHEMBL1551 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bile acid receptor FXR agonist Bile acid receptor FXR PubMed PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
ObesityD009765EFO:0001073obesity1ClinicalTrials
Glucose IntoleranceD018149HP:0000833Glucose intolerance1ClinicalTrials
Cholangitis, SclerosingD015209EFO:0004268sclerosing cholangitis2ClinicalTrials
Liver CirrhosisD008103EFO:0001422cirrhosis of liver1ClinicalTrials
PregnancyD011247EFO:0002950pregnancy3ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus2ClinicalTrials
Heart FailureD006333EFO:0000373congestive heart failure2ClinicalTrials
Hepatitis C, ChronicD019698EFO:0004220Chronic Hepatitis C infection3ClinicalTrials
InflammationD007249MP:0001845inflammation2ClinicalTrials
Jaundice, ObstructiveD041781EFO:1001068obstructive jaundice2ClinicalTrials
Liver DiseasesD008107EFO:0001421liver disease3ClinicalTrials
Non-alcoholic Fatty Liver DiseaseD065626EFO:0003095non-alcoholic fatty liver disease2ClinicalTrials
Huntington DiseaseD006816Orphanet:399Huntington disease1ClinicalTrials
Liver Cirrhosis, BiliaryD008105EFO:1001486primary biliary cirrhosis3ClinicalTrials
Parkinson DiseaseD010300EFO:0002508Parkinson's disease1ClinicalTrials
CholelithiasisD002769EFO:0004799cholelithiasis3ClinicalTrials
Adenomatous Polyposis ColiD011125Orphanet:733Familial adenomatous polyposis2ClinicalTrials

Clinical Data

ClinicalTrials.gov URSODIOL
The Cochrane Collaboration URSODIOL

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1551. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL281 Carbonic anhydrase IV Bos taurus 1.000
CHEMBL5409 G-protein coupled bile acid receptor 1 Homo sapiens 1.000
CHEMBL1856 Steroid 5-alpha-reductase 2 Homo sapiens 1.000
CHEMBL1787 Steroid 5-alpha-reductase 1 Homo sapiens 1.000
CHEMBL205 Carbonic anhydrase II Homo sapiens 1.000
CHEMBL1977 Vitamin D receptor Homo sapiens 1.000
CHEMBL261 Carbonic anhydrase I Homo sapiens 1.000
CHEMBL1871 Androgen Receptor Homo sapiens 1.000
CHEMBL3150 Vitamin D receptor Rattus norvegicus 1.000
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.990
CHEMBL3522 Cytochrome P450 17A1 Homo sapiens 0.986
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 0.977
CHEMBL2047 Bile acid receptor FXR Homo sapiens 0.968
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.956
CHEMBL3072 Androgen Receptor Rattus norvegicus 0.946
CHEMBL3368 Glucocorticoid receptor Rattus norvegicus 0.904
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.900
CHEMBL3056 Androgen Receptor Mus musculus 0.899
CHEMBL1987 Prostanoid FP receptor Homo sapiens 0.505
CHEMBL237 Kappa opioid receptor Homo sapiens 0.251



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5409 G-protein coupled bile acid receptor 1 Homo sapiens 1.000
CHEMBL2027 Niemann-Pick C1-like protein 1 Homo sapiens 1.000
CHEMBL281 Carbonic anhydrase IV Bos taurus 1.000
CHEMBL1856 Steroid 5-alpha-reductase 2 Homo sapiens 1.000
CHEMBL2047 Bile acid receptor FXR Homo sapiens 1.000
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 1.000
CHEMBL1787 Steroid 5-alpha-reductase 1 Homo sapiens 1.000
CHEMBL1977 Vitamin D receptor Homo sapiens 1.000
CHEMBL1697668 Solute carrier organic anion transporter family member 1B1 Homo sapiens 1.000
CHEMBL205 Carbonic anhydrase II Homo sapiens 1.000
CHEMBL261 Carbonic anhydrase I Homo sapiens 1.000
CHEMBL1743121 Solute carrier organic anion transporter family member 1B3 Homo sapiens 1.000
CHEMBL1871 Androgen Receptor Homo sapiens 1.000
CHEMBL3150 Vitamin D receptor Rattus norvegicus 1.000
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 1.000
CHEMBL3522 Cytochrome P450 17A1 Homo sapiens 0.999
CHEMBL1828 DNA polymerase alpha subunit Homo sapiens 0.998
CHEMBL1987 Prostanoid FP receptor Homo sapiens 0.996
CHEMBL4370 UDP-glucuronosyltransferase 2B7 Homo sapiens 0.995
CHEMBL2778 Ileal bile acid transporter Homo sapiens 0.985

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
392.6 392.2927 4.48 4 77.76 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 3 0 4 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.76 - 4.76 2.15 0 28 0.66

Structural Alerts

There are no structural alerts for CHEMBL1551

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A05 - BILE AND LIVER THERAPY
A05A - BILE THERAPY
A05AA - Bile acids and derivatives
A05AA02 - ursodeoxycholic acid

ChemSpider ChemSpider:RUDATBOHQWOJDD-UZVSRGJWSA-N
DailyMed ursodiol
PubChem SID: 11532904
Wikipedia Ursodiol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1551



ACToR 128-13-2
BindingDB 53721
Brenda 2673 36312 23149 74685 4288
ChEBI 9907
ChemicalBook CB1285736
DrugBank DB01586
DrugCentral 2797
eMolecules 32456315 29541168 533157
EPA CompTox Dashboard DTXSID6023731
FDA SRS 724L30Y2QR
Guide to Pharmacology 7104
Human Metabolome Database HMDB0000946
IBM Patent System B9245081C5895FB8D5C20C7935E77A5A
KEGG Ligand C07880
LINCS LSM-6555
LipidMaps LMST04010033
Mcule MCULE-4374611501
Metabolights MTBLC9907
MolPort MolPort-001-794-630
NIH Clinical Collection SAM002264653
Nikkaji J2.520H
PharmGKB PA451837
PubChem 31401
PubChem: Drugs of the Future 99431529
PubChem: Thomson Pharma 14780856 14756614
Selleck Ursodiol(Actigal)
SureChEMBL SCHEMBL27200
ZINC ZINC000003914809

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/RUDATBOHQWOJDD-UZVSRGJWSA-N spacer
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