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459789-99-2 | Obetichloic acid
CAS No: 459789-99-2 Catalog No: AG00368R MDL No:MFCD16621104
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 |
| Farnesoid X receptor agonist for the treatment of liver and metabolic disorders: focus on 6-ethyl-CDCA. | Mini reviews in medicinal chemistry 20110801 |
| 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 |
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