OBETICHOLIC ACID

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC A05AA04
UNII 0462Z4S4OZ
EPA CompTox DTXSID20196671

Structure

InChI Key ZXERDUOLZKYMJM-ZWECCWDJSA-N
Smiles CC[C@H]1[C@@H](O)[C@@H]2[C@H](CC[C@]3(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@@H]23)[C@@]2(C)CC[C@@H](O)C[C@@H]12
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

Bioactivity

Mechanism of Action Action Reference
Bile acid receptor FXR agonist AGONIST PubMed Other
Protein: Bile acid receptor FXR
Description: Bile acid receptor
Organism : Homo sapiens
Q96RI1 ENSG00000012504
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 - - - -
Assay Description Organism Bioactivity Reference
Binding affinity for Farnesoid X Receptor (FXR) Homo sapiens 99.0 nM
Effective concentration against Farnesoid X receptor (FXR) Homo sapiens 99.0 nM
Activation of human farnesoid X receptor Homo sapiens 99.0 nM
Binding affinity for human Farnesoid X receptor in FRET assay Homo sapiens 90.0 nM
Binding affinity to FXR assessed as ligand-dependent SRC1 recruitment by FRET based co-activator assay Homo sapiens 98.0 nM
Agonist activity at human TGR5 expressed in CHO cells after 5 hrs by CRE-driven luciferase reporter gene assay Homo sapiens 755.0 nM
Agonist activity at human FXR expressed in COS1 cells after 5 hrs by CRE-driven luciferase reporter gene assay Homo sapiens 361.0 nM
Agonist activity at FXR expressed in COS1 cells by cell-based bioluminescence assay None 99.0 nM
Agonist activity at human GST-fused FXR LBD assessed as coactivator interaction with receptor ligand binding domain by Alphascreen assay Homo sapiens 200.0 nM
Agonist activity at wild type TGR5 (unknown origin) Homo sapiens 100.0 nM
Agonist activity at FXR (unknown origin) by reporter gene assay Homo sapiens 85.0 nM
Agonist activity at human FXR expressed in human HeLa cells assessed as receptor activation by BSEP promoter-driven firefly luciferase reporter gene assay Homo sapiens 160.0 nM
Agonist activity at human full length FXR expressed in HeLa cells cotransfected with pSG5-human RXR after 24 hrs by Dual-Glo luciferase reporter gene assay Homo sapiens 160.0 nM
Agonist activity at FXR (unknown origin) assessed as recruitment of SRC1 peptide to FXR by FRET assay Homo sapiens 100.0 nM
Inhibition of sEH in human HepG2 cells assessed as NF-kappaB mRNA expression at 1 uM after 8 to 16 hrs by SYBR green based qRT-PCR analysis relative to DMSO control Homo sapiens 29.0 %
Agonist activity at recombinant human GST-tagged FXR ligand binding domain (193 to 472 residues) expressed in baculovirus infected insect cells assessed as induction of interaction with biotin labelled SRC-1 after 1 hr by HTRF assay Homo sapiens 10.0 nM
Agonist activity at human FXR expressed in HEK293T cells assessed as BSEP promoter driven cellular transcriptional activity after 24 hrs by luciferase reporter gene assay Homo sapiens 42.0 nM
Agonist activity at human TGR5 Homo sapiens 918.0 nM
Agonist activity at recombinant human GST-tagged FXR LBD (193 to 472 residues) expressed in baculovirus-infected insect cells assessed as recruitment of biotinylated SRC1 peptide measured after 1 hr by Alphascreen assay Homo sapiens 180.0 nM
Agonist activity at human TGR5 expressed in HEK293 cells assessed as increase in intracellular cAMP level after 1 hr by TR-FRET assay Homo sapiens 840.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -8.9 %
Agonist activity at FXR (unknown origin) Homo sapiens 99.0 nM
Agonist activity at FXR (unknown origin) by cell based assay Homo sapiens 85.0 nM
Transactivation of human FXR (unknown origin) expressed in HepG2 cells co-expressing pSG5RXR/pGL4.70 after 24 hrs post transfection by luciferase reporter gene assay Homo sapiens 500.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 10.87 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.996 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.1 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.1 %
Agonist activity at glutathione transferase-tagged human FXR-LBD using biotinylated Src-1 peptide incubated for 30 mins by recruitment coactivator assay Homo sapiens 150.0 nM
Agonist activity at GST-tagged human FXR LBD assessed as induction of biotinylated coactivator SRC-1 peptide recruitment measured after 2 hrs by streptavidin-conjugated AlphaScreen assay Homo sapiens 290.0 nM
Agonist activity at human FXR expressed in HEK293 cells measured after 18 hrs by steady-glo luciferase reporter gene assay Homo sapiens 710.0 nM
Agonist activity at human TGR5 expressed in HEK293 cells measured after 30 mins by cAMP substrate based assay Homo sapiens 23.7 nM

Related Entries

Cross References

Resources Reference
ChEBI 43602
ChEMBL CHEMBL566315
DrugBank DB05990
DrugCentral 5155
FDA SRS 0462Z4S4OZ
Guide to Pharmacology 3435
KEGG C15636
PDB CHC
PubChem 447715
SureChEMBL SCHEMBL715823
ZINC ZINC000014164617
CONTENTS