Determine the necessary mass, volume, or concentration for preparing a solution.
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Moligand™, ≥97% Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Room temperature Ships Normal Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 36 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
| Pubchem Sid | 488181047 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488181047 |
| Sonrisas canónicas | CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C |
| IUPAC Name | (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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 |
| InChIKey | SMEROWZSTRWXGI-HVATVPOCSA-N |
| INCHI | 1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1 |
| Isómeros SMILES | C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C |
| WGK Alemania | 2 |
| RTECS | FZ2275000 |
| Peso molecular | 376.57 |
| Beilstein | 3217757 |
| Reaxy-Rn | 2818923 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2818923&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Clase | Steroids and steroid derivatives |
| Subclass | Bile acids, alcohols and derivatives |
| Intermediate Tree Nodes | Hydroxy bile acids, alcohols and derivatives |
| Direct Parent | Monohydroxy bile acids, alcohols and derivatives |
| Alternative Parents | 3-alpha-hydroxysteroids Secondary alcohols Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Substituents | Monohydroxy bile acid, alcohol, or derivatives - 3-hydroxysteroid - Hydroxysteroid - 3-alpha-hydroxysteroid - Cyclic alcohol - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Alcohol - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Aliphatic homopolycyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. |
| External Descriptors | C24 bile acids, alcohols, and derivatives |
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Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Fecha | Articulo |
|---|---|---|---|
| Certificate of Analysis | Nov 20, 2025 | L106779 | |
| Certificate of Analysis | Nov 20, 2025 | L106779 | |
| Certificate of Analysis | Nov 20, 2025 | L106779 | |
| Certificate of Analysis | Nov 20, 2025 | L106779 | |
| Certificate of Analysis | Jul 10, 2025 | L106779 | |
| Certificate of Analysis | Jul 10, 2025 | L106779 | |
| Certificate of Analysis | Jul 10, 2025 | L106779 | |
| Certificate of Analysis | Jul 22, 2024 | L106779 | |
| Certificate of Analysis | Jul 22, 2024 | L106779 | |
| Certificate of Analysis | Jul 22, 2024 | L106779 | |
| Certificate of Analysis | Jun 22, 2024 | L106779 | |
| Certificate of Analysis | Nov 09, 2023 | L106779 | |
| Certificate of Analysis | Nov 09, 2023 | L106779 | |
| Certificate of Analysis | Nov 09, 2023 | L106779 | |
| Certificate of Analysis | Nov 09, 2023 | L106779 | |
| Certificate of Analysis | Nov 09, 2023 | L106779 | |
| Certificate of Analysis | Nov 09, 2023 | L106779 | |
| Certificate of Analysis | Nov 09, 2023 | L106779 | |
| Certificate of Analysis | Nov 09, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 | |
| Certificate of Analysis | Mar 03, 2023 | L106779 |
| Rotación específica [α] | 35.5° |
|---|---|
| Punto de fusión (°C) | 183-188°C |
| Peso molecular | 376.600 g/mol |
| XLogP3 | 6.300 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Exact Mass | 376.298 Da |
| Monoisotopic Mass | 376.298 Da |
| Topological Polar Surface Area | 57.500 Ų |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Complexity | 574.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 9 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Yan Ma, Yang Cao, Xiaocui Song, Weichen Xu, Zichen Luo, Jinjun Shan, Jingjie Zhou. (2023) Integration of semi-empirical MS/MS library with characteristic features for the annotation of novel amino acid-conjugated bile acids. ANALYST, 148 (21): (5380-5389). [PMID:37743718] [10.1039/D3AN01237A] |
| 2. Qian Zhang, Wenchao Ye, Guojiao Li, Yanli Gong, Wenlang Liang, Yongxiang Leng. (2023) Nanotubular-aerogel/hydrogel hybrid for strain sensing applications. Journal of Materials Chemistry C, [PMID:] [10.1039/D3TC01866K] |
| 3. Xiong Xueru, Chen Yunhua, Wang Zhenxing, Liu Huan, Le Mengqi, Lin Caihong, Wu Gang, Wang Lin, Shi Xuetao, Jia Yong-Guang, Zhao Yanli. (2023) Polymerizable rotaxane hydrogels for three-dimensional printing fabrication of wearable sensors. Nature Communications, 14 (1): (1-12). [PMID:36898994] [10.1038/s41467-023-36920-3] |
| 4. Shuai Liu, Keming Zheng, Yilin Jiang, Susu Gai, Bohan Li, Dehai Li, Shuang Yang, Zhihua Lv. (2023) Biotransformation of Penindolone, an Influenza A Virus Inhibitor. MOLECULES, 28 (3): (1479). [PMID:36771146] [10.3390/molecules28031479] |
| 5. 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, [PMID:36345074] [10.1016/j.chroma.2022.463634] |
| 6. 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] |
| 7. 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] |
| 8. 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, [PMID:35447521] [10.1016/j.jchromb.2022.123249] |
| 9. Ding Shen, Wei Hu, Suqing Zhao, Chuanbin Mao. (2021) Rapid Naked-Eye Detection of a Liver Disease Biomarker by Discovering Its Monoclonal Antibody to Functionalize Engineered Red-Colored Bacteria Probes. ACS Omega, [PMID:34870023] [10.1021/acsomega.1c04779] |
| 10. Bo Wang, Yue Li, Liyan Han, Kun Liu, Bin Hao, Xiaoyu Wu. (2021) Soft-templated synthesis of core–shell heterostructured Ni3S2@polypyrrole nanotube aerogels as anode materials for high-performance lithium ion batteries. NEW JOURNAL OF CHEMISTRY, 45 (29): (13127-13136). [PMID:] [10.1039/D1NJ01841H] |
| 11. 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] |
| 12. Zhisheng Huang, Zhuoru He, Yu Kong, Zhongqiu Liu, Lingzhi Gong. (2020) Insight into osteoarthritis through integrative analysis of metabolomics and transcriptomics. CLINICA CHIMICA ACTA, [PMID:32653484] [10.1016/j.cca.2020.07.010] |
| 13. Zhuoru He, Qing Luo, Zhongqiu Liu, Lingzhi Gong. (2020) Extensive evaluation of sample preparation workflow for gas chromatography-mass spectrometry-based plasma metabolomics and its application in rheumatoid arthritis. ANALYTICA CHIMICA ACTA, [PMID:32928474] [10.1016/j.aca.2020.06.029] |
| 14. Chao Liu, Kaiyu Zhang, Qinxing Sun, Weina Li. (2020) Bile acid-terpyridine conjugates: Steroidal skeleton controlled AIE effect and metal-tunable fluorescence and supramolecular assembly properties. TETRAHEDRON, [PMID:] [10.1016/j.tet.2020.131283] |
| 15. 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, [PMID:32416340] [10.1016/j.jpba.2020.113317] |
| 16. Ke Zhou, Shao-Chun Chen, Fan Yang, Stijn van der Veen, Yue-Ping Yin. (2020) Impact of the gonococcal FC428 penA allele 60.001 on ceftriaxone resistance and biological fitness. Emerging Microbes & Infections, [PMID:32438866] [10.1080/22221751.2020.1773325] |
| 17. Xia Lu, Zhefeng Fan. (2019) Determination of cholic acid in body fluids by β‑cyclodextrin-modified N-doped carbon dot fluorescent probes. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:30921656] [10.1016/j.saa.2019.03.066] |
| 18. Sinan Wang, Wenxiao Dong, Li Liu, Mengque Xu, Yu Wang, Tianyu Liu, Yujie Zhang, Bangmao Wang, Hailong Cao. (2019) Interplay between bile acids and the gut microbiota promotes intestinal carcinogenesis. MOLECULAR CARCINOGENESIS, 58 (7): (1155-1167). [PMID:30828892] [10.1002/mc.22999] |
| 19. Gui-xin Zhang, Chen Zhan, Kai Wang, Jian Han, Dong Shang, Hai-long Chen. (2019) Qingyi Decoction amerliorates acute biliary pancreatitis by targeting Gpbar1/NF-kb pathway. Frontiers in Bioscience-Landmark, 24 (5): (833-848). [PMID:30844716] [10.2741/4754] |
| 20. Guolin Zhao, Muhanad Elhafiz, Jingwei Jiang, Debanjan Das, Zhijian Li, Wang Zhou, Sisi Fan, Changling Wang, Ziqiao Yuan, Dengqiu Xu, Zhenzhou Jiang, Luyong Zhang, Tao Wang. (2018) Adaptive homeostasis of the vitamin D–vitamin D nuclear receptor axis in 8-methoxypsoralen-induced hepatotoxicity. TOXICOLOGY AND APPLIED PHARMACOLOGY, [PMID:30419252] [10.1016/j.taap.2018.11.002] |
| 21. Dan Wang, Li Bie, Yanbin Su, Haoran Xu, Fengrong Zhang, Yanwen Su, Bo Zhang. (2018) Effect of lithocholic acid on biologically active α,β-unsaturated aldehydes induced by H2O2 in glioma mitochondria for use in glioma treatment. INTERNATIONAL JOURNAL OF MOLECULAR MEDICINE, 41 (6): (3195-3202). [PMID:29512691] [10.3892/ijmm.2018.3530] |
| 22. Xiaoguang Gao, Ting Fu, Changyuan Wang, Chenqing Ning, Yulong Kong, Zhihao Liu, Huijun Sun, Xiaodong Ma, Kexin Liu, Qiang Meng. (2017) Computational discovery and experimental verification of farnesoid X receptor agonist auraptene to protect against cholestatic liver injury. BIOCHEMICAL PHARMACOLOGY, [PMID:28987596] [10.1016/j.bcp.2017.09.016] |
| 23. 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, [PMID:27507206] [10.1016/S1875-5364(16)30065-6] |
| 24. Junyan Wang, Minmin Huang, Haihong Hu, Lushan Yu, Su Zeng. (2014) Pregnane X receptor-mediated transcriptional activation of UDP-glucuronosyltransferase 1A1 by natural constituents from foods and herbs. FOOD CHEMISTRY, [PMID:24996308] [10.1016/j.foodchem.2014.05.004] |
| 25. Liang Hang-fei, Yang Xiao, Li Hui-lin, Li Xuan, Tian Jia-ning, Su Hai-guo, Huang Min, Fang Jian-hong, Bi Hui-chang. (2024) Activation of pregnane X receptor protects against cholestatic liver injury by inhibiting hepatocyte pyroptosis. ACTA PHARMACOLOGICA SINICA, [PMID:39112769] [10.1038/s41401-024-01357-x] |
| 26. Zhiyuan Zhang, Guoqiang Guan, Zixuan Tang, Weimin Wan, Zhipeng Huang, Yuefeng Wang, Jianzhao Wu, Bo Li, Mingli Zhong, Kefeng Zhang, Lixian Nong, Ya Gao, Houkang Cao. (2024) Desmodium styracifolium (Osb.) Merr. extracts alleviate cholestatic liver disease by FXR pathway. JOURNAL OF ETHNOPHARMACOLOGY, [PMID:39454708] [10.1016/j.jep.2024.118972] |
| 27. Andong Zha, Ming Qi, Yuankun Deng, Hao Li, Nan Wang, Chengming Wang, Simeng Liao, Dan Wan, Xia Xiong, Peng Liao, Jing Wang, Yulong Yin, Bi'e Tan. (2024) Gut Bifidobacterium pseudocatenulatum protects against fat deposition by enhancing secondary bile acid biosynthesis. iMeta, 3 (6): (e261). [PMID:39742294] [10.1002/imt2.261] |
| 28. Qian Fang, Xiaoying Hou, Limei Fan, Yufei Deng, Xiaoxuan Li, Hongyun Zhang, Haiping Wang, Zhengqi Fu, Binlian Sun, Xiji Shu, Hongzhi Du, Yuchen Liu. (2025) Gut microbiota derived DCA enhances FOLFOX efficacy via Ugt1a6b mediated enterohepatic circulation in colon cancer. PHARMACOLOGICAL RESEARCH, [PMID:39894186] [10.1016/j.phrs.2025.107636] |
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