CHENODIOL

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Search structure


Trade Names	CHENIX CHENODIOL
Synonyms	Anthropodeoxycholic acid Anthropodesoxycholic acid Anthropododesoxycholic acid Chendol Chendol 125 Chendol 250 Chenic acid Chenix Chenocedon Chenocol Chenodeoxycholate Chenodeoxycholic acid Chenodesoxycholic acid Chenodiol Chenofalk Chenossil Cholanorm Combidol Fluibil Gallodesoxycholic acid Lithofalk NSC-657949 NSC-757798 Xenbilox
Status
Molecule Category	UNKNOWN
UNII	0GEI24LG0J
EPA CompTox	DTXSID2020260


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	RUDATBOHQWOJDD-BSWAIDMHSA-N
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](O)CC[C@]4(C)[C@H]3CC[C@]12C
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

Bioactivity

Mechanism of Action	Action	Reference
Bile acid receptor FXR agonist	AGONIST	PubMed DailyMed


Protein: Bile acid receptor FXR Description: Bile acid receptor Organism : Homo sapiens Q96RI1 ENSG00000012504

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	6100-33000	-	-	-	-
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	3400-30000	-	-	-	-
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 1	16800	-	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	38
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	10600	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	37.88 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	71.62 %
Cytotoxicity against human WI38 cells assessed as inhibition of cell growth at 100 ug/ml by MTT assay	Homo sapiens	94.0 %
Cytotoxicity against human WI38 cells assessed as inhibition of cell growth at 20 ug/ml by MTT assay	Homo sapiens	27.0 %
Antitrypanosomal activity against Trypanosoma brucei brucei Lister 427 bloodstream forms assessed as inhibition of parasite growth at 100 ug/ml by microtiter plate based assay	Trypanosoma brucei brucei	100.0 %
Antitrypanosomal activity against Trypanosoma brucei brucei Lister 427 bloodstream forms assessed as inhibition of parasite growth at 20 ug/ml by microtiter plate based assay	Trypanosoma brucei brucei	11.0 %
Antiplasmodial activity against Plasmodium falciparum 3D7 assessed as inhibition of parasite viability at 100 ug/ml by parasite lactate dehydrogenase assay	Plasmodium falciparum 3D7	98.0 %
Antiplasmodial activity against Plasmodium falciparum 3D7 assessed as inhibition of parasite viability at 20 ug/ml by parasite lactate dehydrogenase assay	Plasmodium falciparum 3D7	77.0 %
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	17.86 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	4.842 %
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	0.05 %		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	0.05 %

Related Entries

Cross References

Resources	Reference
ChEBI	16755
ChEMBL	CHEMBL240597
DrugBank	DB06777
DrugCentral	4361
FDA SRS	0GEI24LG0J
Human Metabolome Database	HMDB0000518
Guide to Pharmacology	608
KEGG	C02528
PDB	JN3
PharmGKB	PA165958403
PubChem	10133
SureChEMBL	SCHEMBL25055
ZINC	ZINC000003914808

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).