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Obetichloic acid

CAS No.:
459789-99-2
Catalog Number:
AG00368R
Molecular Formula:
C26H44O4
Molecular Weight:
420.6252
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%(HPLC)powder
In Stock USA
United States
$61
- +
10mg
98%(HPLC)powder
In Stock USA
United States
$87
- +
25mg
98%(HPLC)powder
In Stock USA
United States
$140
- +
50mg
98%(HPLC)powder
In Stock USA
United States
$228
- +
100mg
98%(HPLC)powder
In Stock USA
United States
$422
- +
Product Description
Catalog Number:
AG00368R
Chemical Name:
Obetichloic acid
CAS Number:
459789-99-2
Molecular Formula:
C26H44O4
Molecular Weight:
420.6252
MDL Number:
MFCD16621104
IUPAC Name:
(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
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
InChI Key:
ZXERDUOLZKYMJM-ZWECCWDJSA-N
SMILES:
CC[C@H]1[C@@H](O)[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@H]1C[C@H](O)CC2)C)[C@@H](CCC(=O)O)C
UNII:
0462Z4S4OZ
Properties
Complexity:
649  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
11  
Defined Bond Stereocenter Count:
0
Exact Mass:
420.324g/mol
Formal Charge:
0
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
420.634g/mol
Monoisotopic Mass:
420.324g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
77.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.7  
Literature
Title Journal
Yangonin protects against cholestasis and hepatotoxity via activation of farnesoid X receptor in vivo and in vitro. Toxicology and applied pharmacology 20180601
Steviol, an aglycone of steviol glycoside sweeteners, interacts with the pregnane X (PXR) and aryl hydrocarbon (AHR) receptors in detoxification regulation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20171101
Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicology in vitro : an international journal published in association with BIBRA 20170301
Dihydroartemisinin protects against alcoholic liver injury through alleviating hepatocyte steatosis in a farnesoid X receptor-dependent manner. Toxicology and applied pharmacology 20170115
Acetylated deoxycholic (DCA) and cholic (CA) acids are potent ligands of pregnane X (PXR) receptor. Toxicology letters 20170104
Obeticholic acid protects against carbon tetrachloride-induced acute liver injury and inflammation. Toxicology and applied pharmacology 20170101
Pyrazinamide Induced Rat Cholestatic Liver Injury through Inhibition of FXR Regulatory Effect on Bile Acid Synthesis and Transport. Toxicological sciences : an official journal of the Society of Toxicology 20160801
Obeticholic Acid: First Global Approval. Drugs 20160801
Farnesoid X Receptor Protects against Kidney Injury in Uninephrectomized Obese Mice. The Journal of biological chemistry 20160129
Synthetic farnesoid X receptor agonists induce high-density lipoprotein-mediated transhepatic cholesterol efflux in mice and monkeys and prevent atherosclerosis in cholesteryl ester transfer protein transgenic low-density lipoprotein receptor (-/-) mice. The Journal of pharmacology and experimental therapeutics 20121201
An improved synthesis of 6α-ethylchenodeoxycholic acid (6ECDCA), a potent and selective agonist for the Farnesoid X Receptor (FXR). Steroids 20121101
Testosterone and farnesoid X receptor agonist INT-747 counteract high fat diet-induced bladder alterations in a rabbit model of metabolic syndrome. The Journal of steroid biochemistry and molecular biology 20121001
Glucocorticoid receptor mediates the gluconeogenic activity of the farnesoid X receptor in the fasting condition. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20120701
Conicasterol E, a small heterodimer partner sparing farnesoid X receptor modulator endowed with a pregnane X receptor agonistic activity, from the marine sponge Theonella swinhoei. Journal of medicinal chemistry 20120112
Testosterone protects from metabolic syndrome-associated prostate inflammation: an experimental study in rabbit. The Journal of endocrinology 20120101
FXR protects lung from lipopolysaccharide-induced acute injury. Molecular endocrinology (Baltimore, Md.) 20120101
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Farnesoid X receptor agonists for primary biliary cirrhosis. Current opinion in gastroenterology 20110501
Farnesoid X receptor activation inhibits inflammation and preserves the intestinal barrier in inflammatory bowel disease. Gut 20110401
Synthesis and pharmacological validation of a novel series of non-steroidal FXR agonists. Bioorganic & medicinal chemistry letters 20100815
Farnesoid X receptor activation prevents the development of vascular calcification in ApoE-/- mice with chronic kidney disease. Circulation research 20100625
Pharmacotherapy of cholestatic liver diseases. Journal of digestive diseases 20100601
FXR activation reverses insulin resistance and lipid abnormalities and protects against liver steatosis in Zucker (fa/fa) obese rats. Journal of lipid research 20100401
Discovery of 6alpha-ethyl-23(S)-methylcholic acid (S-EMCA, INT-777) as a potent and selective agonist for the TGR5 receptor, a novel target for diabesity. Journal of medicinal chemistry 20091224
The farnesoid X receptor modulates renal lipid metabolism and diet-induced renal inflammation, fibrosis, and proteinuria. American journal of physiology. Renal physiology 20091201
Farnesoid x receptor ligands inhibit vascular smooth muscle cell inflammation and migration. Arteriosclerosis, thrombosis, and vascular biology 20071201
Nongenomic actions of bile acids. Synthesis and preliminary characterization of 23- and 6,23-alkyl-substituted bile acid derivatives as selective modulators for the G-protein coupled receptor TGR5. Journal of medicinal chemistry 20070906
The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution. American journal of physiology. Regulatory, integrative and comparative physiology 20070901
The farnesoid X receptor promotes adipocyte differentiation and regulates adipose cell function in vivo. Molecular pharmacology 20061001
Back door modulation of the farnesoid X receptor: design, synthesis, and biological evaluation of a series of side chain modified chenodeoxycholic acid derivatives. Journal of medicinal chemistry 20060713
Nuclear receptors, bile-acid detoxification, and cholestasis. Lancet (London, England) 20060211
Cross-talk between farnesoid-X-receptor (FXR) and peroxisome proliferator-activated receptor gamma contributes to the antifibrotic activity of FXR ligands in rodent models of liver cirrhosis. The Journal of pharmacology and experimental therapeutics 20051001
A farnesoid x receptor-small heterodimer partner regulatory cascade modulates tissue metalloproteinase inhibitor-1 and matrix metalloprotease expression in hepatic stellate cells and promotes resolution of liver fibrosis. The Journal of pharmacology and experimental therapeutics 20050801
The methyl transferase PRMT1 functions as co-activator of farnesoid X receptor (FXR)/9-cis retinoid X receptor and regulates transcription of FXR responsive genes. Molecular pharmacology 20050801
Protective effects of 6-ethyl chenodeoxycholic acid, a farnesoid X receptor ligand, in estrogen-induced cholestasis. The Journal of pharmacology and experimental therapeutics 20050501
The nuclear receptor SHP mediates inhibition of hepatic stellate cells by FXR and protects against liver fibrosis. Gastroenterology 20041101
The farnesoid X receptor: a novel drug target? Expert opinion on investigational drugs 20040901
Bile acid derivatives as ligands of the farnesoid X receptor. Synthesis, evaluation, and structure-activity relationship of a series of body and side chain modified analogues of chenodeoxycholic acid. Journal of medicinal chemistry 20040826
Binding mode of 6ECDCA, a potent bile acid agonist of the farnesoid X receptor (FXR). Bioorganic & medicinal chemistry letters 20030602
6alpha-ethyl-chenodeoxycholic acid (6-ECDCA), a potent and selective FXR agonist endowed with anticholestatic activity. Journal of medicinal chemistry 20020815
Nuclear receptors and lipid physiology: opening the X-files. Science (New York, N.Y.) 20011130
Identification of a nuclear receptor for bile acids. Science (New York, N.Y.) 19990521
Properties