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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL566315
CHEMBL566315
Compound Name OBETICHOLIC ACID
ChEMBL Synonyms OBETICHOLIC ACID | INT-747 | DSP-1747
Max Phase 4 (Approved)
Trade Names
Molecular Formula C26H44O4

Additional synonyms for CHEMBL566315 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC[C@H]1[C@@H](O)[C@H]2[C@@H]3CC[C@H]([C@H](C)CCC(=O)O)[C@@] ...
Download SMILES
Standard InChI InChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13 ...
Download InChI
Standard InChI Key ZXERDUOLZKYMJM-ZWECCWDJSA-N

Sources

  • Clinical Candidates
  • Manually Added Drugs
  • Orange Book
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL566315

Molecule Features

CHEMBL566315 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 Other PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
HEPATITIS, ALCOHOLICD006519EFO:1001345HEPATITIS, ALCOHOLIC2ClinicalTrials
LIVER DISEASESD008107EFO:0001421LIVER DISEASE1ClinicalTrials
OBESITYD009765EFO:0001073OBESITY1ClinicalTrials
NON-ALCOHOLIC FATTY LIVER DISEASED065626EFO:0003095NON-ALCOHOLIC FATTY LIVER DISEASE3ClinicalTrials
LIVER CIRRHOSIS, BILIARYD008105EFO:0004267BILIARY LIVER CIRRHOSIS4FDA

Clinical Data

ClinicalTrials.gov OBETICHOLIC ACID
The Cochrane Collaboration OBETICHOLIC ACID

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 CHEMBL566315. 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
CHEMBL5409 G-protein coupled bile acid receptor 1 Homo sapiens 1.000
CHEMBL1977 Vitamin D receptor Homo sapiens 1.000
CHEMBL1856 Steroid 5-alpha-reductase 2 Homo sapiens 1.000
CHEMBL1787 Steroid 5-alpha-reductase 1 Homo sapiens 1.000
CHEMBL281 Carbonic anhydrase IV Bos taurus 1.000
CHEMBL3150 Vitamin D receptor Rattus norvegicus 1.000
CHEMBL3305 Testis-specific androgen-binding protein Homo sapiens 1.000
CHEMBL2047 Bile acid receptor FXR Homo sapiens 1.000
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.991
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.892
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 0.863
CHEMBL3056 Androgen Receptor Mus musculus 0.738
CHEMBL1871 Androgen Receptor Homo sapiens 0.640
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.337
CHEMBL3072 Androgen Receptor Rattus norvegicus 0.216
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.207
CHEMBL3368 Glucocorticoid receptor Rattus norvegicus 0.206



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2027 Niemann-Pick C1-like protein 1 Homo sapiens 1.000
CHEMBL5409 G-protein coupled bile acid receptor 1 Homo sapiens 1.000
CHEMBL1856 Steroid 5-alpha-reductase 2 Homo sapiens 1.000
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 1.000
CHEMBL2047 Bile acid receptor FXR Homo sapiens 1.000
CHEMBL1787 Steroid 5-alpha-reductase 1 Homo sapiens 1.000
CHEMBL1977 Vitamin D receptor Homo sapiens 1.000
CHEMBL281 Carbonic anhydrase IV Bos taurus 1.000
CHEMBL3150 Vitamin D receptor Rattus norvegicus 1.000
CHEMBL3305 Testis-specific androgen-binding protein Homo sapiens 1.000
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 1.000
CHEMBL1697668 Solute carrier organic anion transporter family member 1B1 Homo sapiens 1.000
CHEMBL1743121 Solute carrier organic anion transporter family member 1B3 Homo sapiens 0.996
CHEMBL4370 UDP-glucuronosyltransferase 2B7 Homo sapiens 0.971
CHEMBL1828 DNA polymerase alpha subunit Homo sapiens 0.956
CHEMBL1871 Androgen Receptor Homo sapiens 0.945
CHEMBL3522 Cytochrome P450 17A1 Homo sapiens 0.915
CHEMBL3072 Androgen Receptor Rattus norvegicus 0.912
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.910
CHEMBL5868 Nuclear receptor ROR-alpha Homo sapiens 0.739

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
420.6 420.324 4.79 5 77.76 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 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 - 5.81 3.2 0 30 0.6

Structural Alerts

There are no structural alerts for CHEMBL566315

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A05 - BILE AND LIVER THERAPY
A05A - BILE THERAPY
A05AA - Bile acid preparations
A05AA04 - obeticholic acid

ChemSpider ChemSpider:ZXERDUOLZKYMJM-ZWECCWDJSA-N
DailyMed obeticholic acid

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL566315



ACToR 865244-30-0 459789-99-2
BindingDB 21675
ChEBI 43602
DrugBank DB05990
DrugCentral 5155
EPA CompTox Dashboard DTXSID20196671
FDA SRS 0462Z4S4OZ
Guide to Pharmacology 3435
KEGG Ligand C15636
MolPort MolPort-035-682-579
Nikkaji J2.007.345D
PDBe CHC
PubChem 447715
PubChem: Drugs of the Future 123055342
PubChem: Thomson Pharma 16101459 14880306
SureChEMBL SCHEMBL715823
ZINC ZINC000014164617

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