Determine the necessary mass, volume, or concentration for preparing a solution.
Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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SKU | Size | Availability | Price | Qty |
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U110696-20mg | 20mg | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $42.90 |
Synonyms | UDCS | 4-10-00-01604 (Beilstein Handbook Reference) | Lyeton | MFCD00003680 | URSODIOL [USP-RS] | UNII-724L30Y2QR | 3alpha,7beta-Dihydroxy-5beta-cholanic acid | Acido ursodeoxicolico [INN-Spanish] | URSODIOL [INCI] | Ursodiol [USAN] | 17-beta-(1-Methyl-3- |
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Specifications & Purity | Moligand™, analytical standard |
Storage Temp | Argon charged |
Shipped In | Normal |
Grade | analytical standard, Moligand™ |
Action Type | INHIBITOR |
Mechanism of action | Inhibitor of Sodium/bile acid and sulphated solute cotransporter 1 |
Product Description | Ursodeoxycholic acid is a bile acid with significant colon chemopreventive activity. |
ALogP | 4.9 |
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Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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IUPAC Name | (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-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 |
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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 |
InChi Key | RUDATBOHQWOJDD-UZVSRGJWSA-N |
Canonical SMILES | CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C |
Isomeric SMILES | C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C |
WGK Germany | 2 |
RTECS | FZ2000000 |
PubChem CID | 31401 |
Molecular Weight | 392.57 |
Beilstein | 3219888 |
DrugBank Ligand | DB01586 |
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PubChem CID | 31401 |
CAS Registry No. | 128-13-2 |
ChEMBL Ligand | CHEMBL1551 |
Wikipedia | Ursodeoxycholic acid |
ChEBI | CHEBI:9907 |
DrugCentral Ligand | 2797 |
Enter Lot Number to search for COA:
Solubility | Soluble in ethanol (79 mg/ml at 25 °C), alcohol (freely), chloroform (slightly), and DMSO (79 mg/ml at 25 °C). Insoluble in water. |
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Specific Rotation[α] | 60.5 ° (C=4, EtOH) |
Melt Point(°C) | 203°C |
Pictogram(s) | GHS07 |
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Signal | Warning |
Hazard Statements | H315:Causes skin irritation H319:Causes serious eye irritation |
Precautionary Statements | P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P264:Wash hands [and …] thoroughly after handling. P362+P364:Take off contaminated clothing and wash it before reuse. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. |
WGK Germany | 2 |
RTECS | FZ2000000 |
Merck Index | 9889 |
1. Mu-Qiang Wang, Zhi-Neng You, Bing-Yi Yang, Zi-Wei Xia, Qi Chen, Jiang Pan, Chun-Xiu Li, Jian-He Xu. (2023) Machine-Learning-Guided Engineering of an NADH-Dependent 7β-Hydroxysteroid Dehydrogenase for Economic Synthesis of Ursodeoxycholic Acid. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 71 (49): (19672–19681). [PMID:38016669] [10.1021/acs.jafc.3c06339] |
2. Yang Chang, Yafei Xia, Xiaojun Liu, Putian Yu, Furong Fan, Yangyang Shi, Shixin Yan, Shu Yan. (2023) Integrated 16 S rRNA gene sequencing and serum metabolomics approaches to decipher the mechanism of Qingre Lidan decoction in the treatment of cholestatic liver injury. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 234 (115535). [PMID:37390604] [10.1016/j.jpba.2023.115535] |
3. Si-xuan Zhou, Xiao-tong Lin, Jie Wang, Hai-xiang Wang, Gui-tang Chen. (2023) Novel hydrocortisone magnetic molecularly imprinted polymers: Preparation, characterization, and application. FOOD CHEMISTRY, 421 (136196). [PMID:37116443] [10.1016/j.foodchem.2023.136196] |
4. Bing-Yi Yang, Zhi-Neng You, Jiang-Tao Xue, Jiang Pan, Chun-Xiu Li, Jian-He Xu. (2023) Clean enzymatic production of ursodeoxycholic acid enabled by a newly identified NADH-dependent 7β-hydroxysteroid dehydrogenase. Molecular Catalysis, 537 (112946). [PMID:] [10.1016/j.mcat.2023.112946] |
5. Bin Huang, Kai Yang, Charles Amanze, Zhen Yan, Hongbo Zhou, Xueduan Liu, Guanzhou Qiu, Weimin Zeng. (2023) Sequence and structure-guided discovery of a novel NADH-dependent 7β-hydroxysteroid dehydrogenase for efficient biosynthesis of ursodeoxycholic acid. BIOORGANIC CHEMISTRY, 131 (106340). [PMID:36586301] [10.1016/j.bioorg.2022.106340] |
6. Yafei Xia, Shixin Yan, Yang Chang, Jiaoyang Yin, Hongyu Li, Shu Yan. (2022) Mechanism and Active Components of Qingre Lidan Tablets Alleviate Intrahepatic Cholestasis by Activating the Farnesoid X Receptor. Evidence-based Complementary and Alternative Medicine, 2022 (1589388). [PMID:36506808] [10.1155/2022/1589388] |
7. Wang Rulin, Yuan Tengteng, Sun Jing, Yang Menghuan, Chen Yunna, Wang Lei, Wang Yanyan, Chen Weidong, Peng Daiyin. (2022) Paeoniflorin alleviates 17α-ethinylestradiol-induced cholestasis via the farnesoid X receptor-mediated bile acid homeostasis signaling pathway in rats. Frontiers in Pharmacology, 13 [PMID:36479204] [10.3389/fphar.2022.1064653] |
8. Qing Yang, Xubo Wu, Zhiyu Pan, Ruifang Guan, Ping Yang, Ye Liu, Xiaolei Yang, Wandi Du, Jingru Liang, Jiarong Hu, Weimin Cai, Guo Ma. (2023) Integration of pharmacodynamics, network pharmacology and metabolomics to elucidate effect and mechanism of Artemisia capillaris Thunb. in the treatment of jaundice. JOURNAL OF ETHNOPHARMACOLOGY, 303 (115943). [PMID:36414211] [10.1016/j.jep.2022.115943] |
9. Jiating Zheng, Xiaoru Peng, Taifeng Zhu, Shuyao Huang, Chao Chen, Guosheng Chen, Shuqin Liu, Gangfeng Ouyang. (2022) Detection of bile acids in small volume human bile samples via an amino metal-organic framework composite based solid-phase microextraction probe. JOURNAL OF CHROMATOGRAPHY A, 1685 (463634). [PMID:36345074] [10.1016/j.chroma.2022.463634] |
10. Wei Xu, Yingying Kong, Tuo Zhang, Zhihua Gong, Wenjun Xiao. (2022) L-Theanine regulates lipid metabolism by modulating gut microbiota and bile acid metabolism. JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 103 (3): (1283-1293). [PMID:36087337] [10.1002/jsfa.12222] |
11. Meng Song, Zijun Chen, Ruian Qiu, Tingwei Zhi, Wenmin Xie, Yingya Zhou, Nachuan Luo, Fuqian Chen, Fang Liu, Chuangpeng Shen, Sheng Lin, Fengxue Zhang, Yong Gao, Changhui Liu. (2022) Inhibition of NLRP3-mediated crosstalk between hepatocytes and liver macrophages by geniposidic acid alleviates cholestatic liver inflammatory injury. Redox Biology, 55 (102404). [PMID:35868156] [10.1016/j.redox.2022.102404] |
12. Ma Wen, Yang Bingxin, Li Jun, Liu Mingxia, Li Xianjiang, Liu Huwei. (2022) Maltose-functional metal–organic framework assisted laser desorption/ionization mass spectrometry for small biomolecule determination. MICROCHIMICA ACTA, 189 (7): (1-8). [PMID:35689150] [10.1007/s00604-022-05338-x] |
13. Xiaoxu Cheng, Zifeng Pi, Zhong Zheng, Shu Liu, Fengrui Song, Zhiqiang Liu. (2022) Combined 16S rRNA gene sequencing and metabolomics to investigate the protective effects of Wu-tou decoction on rheumatoid arthritis in rats. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1199 (123249). [PMID:35447521] [10.1016/j.jchromb.2022.123249] |
14. Fangfang Xu, Jun Wang, Pan Wang, Tao Hou, Han Zhou, Yaopeng Zhao, Jixia Wang, Yanfang Liu, Xinmiao Liang. (2022) Ursodesoxycholic acid is an FFA4 agonist and reduces hepatic steatosis via FFA4 signaling. EUROPEAN JOURNAL OF PHARMACOLOGY, 917 (174760). [PMID:35033554] [10.1016/j.ejphar.2022.174760] |
15. Ya-Wen Zhang, Ling-Lan Tu, Yi Zhang, Jie-Chao Pan, Gao-Li Zheng, Li-Na Yin. (2021) Liver-targeted delivery of asiatic acid nanostructured lipid carrier for the treatment of liver fibrosis. DRUG DELIVERY, 28 (1): (2534-2547). [PMID:34854788] [10.1080/10717544.2021.2008054] |
16. Chuang Zhang, Suolin Li, Chi Sun, Lin Liu, Yanbin Fang, Xiaofeng Yang, Xingxin Pan, Ben Zhang. (2021) Vitexin ameliorates glycochenodeoxycholate-induced hepatocyte injury through SIRT6 and JAK2/STAT3 pathways. Iranian Journal of Basic Medical Sciences, 24 (12): ( 1717–1725). [PMID:35432812] [10.22038/IJBMS.2021.59424.13196] |
17. Xinyue Li, Yaqi Yao, Meiling Chen, Haoran Ding, Chenrui Liang, Ling Lv, Huan Zhao, Guanru Zhou, Zhanglong Luo, Yubo Li, Han Zhang. (2022) Comprehensive evaluation integrating omics strategy and machine learning algorithms for consistency of calculus bovis from different sources. TALANTA, 237 (122873). [PMID:34736706] [10.1016/j.talanta.2021.122873] |
18. Cui Xiping, He Qiyi, Yang Huiyi, Chen Yingshan, Shen Ding, Eremin Sergei A., Mu Yunping, Zhao Suqing. (2021) Development of enzyme-free single-step immunoassays for glycocholic acid based on palladium nanoparticle-mediated signal generation. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 413 (23): (5733-5742). [PMID:34476526] [10.1007/s00216-021-03548-5] |
19. Qiyi He, Yanxiong Fang, Huiyi Yang, Ding Shen, Yingshan Chen, Yingying Zhong, Xiangguang Li, Sergei A. Eremin, Xiping Cui, Suqing Zhao. (2021) Enhanced performance of a surface plasmon resonance-based immunosensor for the detection of glycocholic acid. Analytical Methods, 13 (16): (1919-1924). [PMID:33913980] [10.1039/D1AY00357G] |
20. Min Wen, Yubei Liu, Ruiying Chen, Ping He, Feihua Wu, Rui Li, Yining Lin. (2021) Geniposide suppresses liver injury in a mouse model of DDC-induced sclerosing cholangitis. PHYTOTHERAPY RESEARCH, 35 (7): (3799-3811). [PMID:33763888] [10.1002/ptr.7086] |
21. Yufei Sun, Zhiqiang Liu, Zifeng Pi, Fengrui Song, Jianlin Wu, Shu Liu. (2021) Poria cocos could ameliorate cognitive dysfunction in APP/PS1 mice by restoring imbalance of Aβ production and clearance and gut microbiota dysbiosis. PHYTOTHERAPY RESEARCH, 35 (5): (2678-2690). [PMID:33432644] [10.1002/ptr.7014] |
22. Xiaofen Zhang, Ziyao Yang, Ziyu Shi, Zijia Zhu, Cai Li, Zhicheng Du, Yiding Zhang, Zipeng Wang, Zhenrui Jiao, Xin Tian, Ji Zhang, Wenlong Zhai, Quancheng Kan. (2021) Analysis of bile acid profile in plasma to differentiate cholangiocarcinoma from benign biliary diseases and healthy controls. JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 205 (105775). [PMID:33130021] [10.1016/j.jsbmb.2020.105775] |
23. Qiyi He, Huiyi Yang, Yingshan Chen, Ding Shen, Xiping Cui, Chunguo Zhang, Huanxin Xiao, Sergei A. Eremin, Yanxiong Fang, Suqing Zhao. (2020) Prussian blue nanoparticles with peroxidase-mimicking properties in a dual immunoassays for glycocholic acid. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 187 (113317). [PMID:32416340] [10.1016/j.jpba.2020.113317] |
24. Meijing Liu, Guohui Zhang, Shuangcheng Wu, Meng Song, Jueyu Wang, Weibin Cai, Suiqing Mi, Changhui Liu. (2020) Schaftoside alleviates HFD-induced hepatic lipid accumulation in mice via upregulating farnesoid X receptor. JOURNAL OF ETHNOPHARMACOLOGY, 255 (112776). [PMID:32205261] [10.1016/j.jep.2020.112776] |
25. Meijing Liu, Changhui Liu, Hao Chen, Xiaotao Huang, Xiaohui Zeng, Juncheng Zhou, Suiqing Mi. (2017) Prevention of cholesterol gallstone disease by schaftoside in lithogenic diet-induced C57BL/6 mouse model. EUROPEAN JOURNAL OF PHARMACOLOGY, 815 (1). [PMID:28993159] [10.1016/j.ejphar.2017.10.003] |
26. Zhuo-Wei SHEN, Meng-Yue LUO, Hai-Hong HU, Hui ZHOU, Hui-Di JIANG, Lu-Shan YU, Su ZENG. (2016) Screening and verifying potential NTCP inhibitors from herbal medicinal ingredients using the LLC-PK1 cell model stably expressing human NTCP. Chinese Journal of Natural Medicines, 14 (549). [PMID:27507206] [10.1016/S1875-5364(16)30065-6] |
27. Xing Zhou, Yang Zhao, Siyu Chen, Songling Han, Xiaoqiu Xu, Jiawei Guo, Mengyu Liu, Ling Che, Xiaohui Li, Jianxiang Zhang. (2016) Self-Assembly of pH-Responsive Microspheres for Intestinal Delivery of Diverse Lipophilic Therapeutics. BIOMACROMOLECULES, 17 (8): (2540–2554). [PMID:27398635] [10.1021/acs.biomac.6b00512] |
28. Pan Chen, Jingjie Li, Xiaomei Fan, Hang Zeng, Rongrong Deng, Dongshun Li, Min Huang, Huichang Bi. (2015) Oleanolic acid attenuates obstructive cholestasis in bile duct-ligated mice, possibly via activation of NRF2-MRPs and FXR antagonism. EUROPEAN JOURNAL OF PHARMACOLOGY, 765 (131). [PMID:26297978] [10.1016/j.ejphar.2015.08.029] |
29. Huang Xiaomei, Cao Xuejun. (2015) Preparation of ursodeoxycholic acid from 7-ketone lithocholic acid by stereoselective electroreduction. Bioresources and Bioprocessing, 2 (1): (1-9). [PMID:] [10.1186/s40643-015-0058-4] |
30. Ma Xiaolei, Cao Xuejun. (2014) Separation of ursodeoxycholic acid by silylation crystallization. Bioresources and Bioprocessing, 1 (1): (1-8). [PMID:] [10.1186/s40643-014-0005-9] |
31. Yuan Xiangxi, Ma Xiaolei, Cao Xuejun. (2014) Preparation of ursodeoxycholic acid by direct electro-reduction of 7-ketolithocholic acid. KOREAN JOURNAL OF CHEMICAL ENGINEERING, 31 (7): (1276-1280). [PMID:] [10.1007/s11814-013-0245-y] |
32. Shuai Xue,Jianli Yin,Jiawei Shao,Yuanhuan Yu,Linfeng Yang,Yidan Wang,Mingqi Xie,Martin Fussenegger,Haifeng Ye. (2017-02-06) A Synthetic-Biology-Inspired Therapeutic Strategy for Targeting and Treating Hepatogenous Diabetes.. Molecular therapy : the journal of the American Society of Gene Therapy, 25 ((2)): (443-455). [PMID:28153094] |
1. Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J. (2007) Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: a population-based cohort study.. Hepatology, 46 (4): (1131-7). [PMID:17685473] [10.1021/op500134e] |
2. Sun L, Cai J, Gonzalez FJ. (2021) The role of farnesoid X receptor in metabolic diseases, and gastrointestinal and liver cancer.. Nat Rev Gastroenterol Hepatol, 18 (5): (335-347). [PMID:33568795] [10.1021/op500134e] |
3. Brevini T, Maes M, Webb GJ, John BV, Fuchs CD, Buescher G, Wang L, Griffiths C, Brown ML, Scott 3rd WE et al.. (2022) FXR inhibition may protect from SARS-CoV-2 infection by reducing ACE2.. Nature, 71 (13): (1755-70). [PMID:36470304] [10.1038/s41586-022-05594-0] |
4. Hagey LR, Crombie DL, Espinosa E, Carey MC, Igimi H, Hofmann AF. (1993) Ursodeoxycholic acid in the Ursidae: biliary bile acids of bears, pandas, and related carnivores.. J Lipid Res, 34 (11): (1911-7). [PMID:8263415] [10.1021/op500134e] |
5. Mu-Qiang Wang, Zhi-Neng You, Bing-Yi Yang, Zi-Wei Xia, Qi Chen, Jiang Pan, Chun-Xiu Li, Jian-He Xu. (2023) Machine-Learning-Guided Engineering of an NADH-Dependent 7β-Hydroxysteroid Dehydrogenase for Economic Synthesis of Ursodeoxycholic Acid. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 71 (49): (19672–19681). [PMID:38016669] [10.1021/acs.jafc.3c06339] |
6. Yang Chang, Yafei Xia, Xiaojun Liu, Putian Yu, Furong Fan, Yangyang Shi, Shixin Yan, Shu Yan. (2023) Integrated 16 S rRNA gene sequencing and serum metabolomics approaches to decipher the mechanism of Qingre Lidan decoction in the treatment of cholestatic liver injury. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 234 (115535). [PMID:37390604] [10.1016/j.jpba.2023.115535] |
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