OBETICHOLIC ACID

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Trade Names:
Synonyms:
Status: Approved (2016)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: A05AA04
UNII: 0462Z4S4OZ

Structure
InChI Key ZXERDUOLZKYMJM-ZWECCWDJSA-N
Smile CC[C@@H]1[C@@H]2C[C@H](O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@@H]3[C@H](C)CCC(=O)O)[C@@H]2[C@@H]1O
InChI
InChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H44O4
Molecular Weight 420.63
AlogP 5.11
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 77.76
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 30.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Bile acid receptor FXR agonist PubMed Other
Primary Target
Farnesoid X receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Serine protease Serine protease SC clan Serine protease S33 family
- - - - 29
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
24-20000 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group H Nuclear hormone receptor subfamily 1 group H member 4
10-99000 - - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Liver Cirrhosis, Biliary 4 D008105 ClinicalTrials
Liver Cirrhosis, Biliary 4 D008105 FDA
Non-alcoholic Fatty Liver Disease 3 D065626 ClinicalTrials
Non-alcoholic Fatty Liver Disease 3 D065626 ClinicalTrials
Diarrhea 2 D003967 ClinicalTrials
Hepatitis, Alcoholic 2 D006519 ClinicalTrials
Lipodystrophy, Familial Partial 2 D052496 ClinicalTrials
Cholangitis, Sclerosing 2 D015209 ClinicalTrials
Barrett Esophagus 2 D001471 ClinicalTrials
Obesity 1 D009765 ClinicalTrials
Liver Diseases 1 D008107 ClinicalTrials
Cholestasis 1 D002779 ClinicalTrials

Related Entries

MCS

Scaffolds

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Skin and subcutaneous tissue disorders
19.86
General disorders and administration site conditions
12.24
Gastrointestinal disorders
9.87
Investigations
7.31
Nervous system disorders
6.65
Vascular disorders
5.09
Hepatobiliary disorders
4.84
Cardiac disorders
4.12
Injury, poisoning and procedural complications
4.03
Musculoskeletal and connective tissue disorders
4.0
Respiratory, thoracic and mediastinal disorders
3.34
Psychiatric disorders
3.18
Metabolism and nutrition disorders
2.84
Infections and infestations
2.4

Cross References

Resources Reference
CAS NUMBER 459789-99-2
ChEBI 43602
ChEMBL CHEMBL566315
DrugBank DB05990
DrugCentral 5155
EPA CompTox DTXSID20196671
FDA SRS 0462Z4S4OZ
Guide to Pharmacology 3435
KEGG C15636
PDB CHC
PubChem 447715
SureChEMBL SCHEMBL715823
ZINC ZINC000014164617
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