beta-muricholic acid (BioDeep_00001868944)

Main id: BioDeep_00000638108

 

PANOMIX_OTCML-2023 Bile acids Volatile Flavor Compounds


代谢物信息卡片


beta-muricholic acid

化学式: C24H40O5 (408.28755900000004)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(C(C4C3(CCC(C4)O)C)O)O)C
InChI: InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1

描述信息

D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts
D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
β-Muricholic acid is a potent and orally active biliary cholesterol-desaturating agent. β-Muricholic acid prevents cholesterol gallstones. β-Muricholic acid inhibits lipid accumulation. β-Muricholic acid has the potential for the research of nonalcoholic fatty liver disease (NAFLD)[1][2].

同义名列表

3 个代谢物同义名

beta-muricholic acid; β-Muricholic acid; beta-Muricholate



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Zeping Zhang, Boyan Zhang, Xianzhe Jiang, Yue Yu, Yimeng Cui, Hailing Luo, Bing Wang. Hyocholic acid retards renal fibrosis by regulating lipid metabolism and inflammatory response in a sheep model. International immunopharmacology. 2023 Jul; 122(?):110670. doi: 10.1016/j.intimp.2023.110670. [PMID: 37481851]
  • Yang Xie, Feng Shen, Yafang He, Canjie Guo, Ruixu Yang, Haixia Cao, Qin Pan, Jiangao Fan. Gamma-Muricholic Acid Inhibits Nonalcoholic Steatohepatitis: Abolishment of Steatosis-Dependent Peroxidative Impairment by FXR/SHP/LXRα/FASN Signaling. Nutrients. 2023 Mar; 15(5):. doi: 10.3390/nu15051255. [PMID: 36904254]
  • Jie Jiang, Yuandi Ma, Yameng Liu, Dasheng Lu, Xiaoxia Gao, Kristopher W Krausz, Dhimant Desai, Shantu G Amin, Andrew D Patterson, Frank J Gonzalez, Cen Xie. Glycine-β-muricholic acid antagonizes the intestinal farnesoid X receptor-ceramide axis and ameliorates NASH in mice. Hepatology communications. 2022 12; 6(12):3363-3378. doi: 10.1002/hep4.2099. [PMID: 36196594]
  • Antwi-Boasiako Oteng, Sei Higuchi, Alexander S Banks, Rebecca A Haeusler. Cyp2c-deficiency depletes muricholic acids and protects against high-fat diet-induced obesity in male mice but promotes liver damage. Molecular metabolism. 2021 11; 53(?):101326. doi: 10.1016/j.molmet.2021.101326. [PMID: 34438105]
  • Dany Gaillard, David Masson, Erwan Garo, Maamar Souidi, Jean-Paul Pais de Barros, Kristina Schoonjans, Jacques Grober, Philippe Besnard, Charles Thomas. Muricholic Acids Promote Resistance to Hypercholesterolemia in Cholesterol-Fed Mice. International journal of molecular sciences. 2021 Jul; 22(13):. doi: 10.3390/ijms22137163. [PMID: 34281217]
  • Anders Ø Petersen, Hanna Julienne, Tuulia Hyötyläinen, Partho Sen, Yong Fan, Helle Krogh Pedersen, Sirkku Jäntti, Tue H Hansen, Trine Nielsen, Torben Jørgensen, Torben Hansen, Pernille Neve Myers, H Bjørn Nielsen, S Dusko Ehrlich, Matej Orešič, Oluf Pedersen. Conjugated C-6 hydroxylated bile acids in serum relate to human metabolic health and gut Clostridia species. Scientific reports. 2021 06; 11(1):13252. doi: 10.1038/s41598-021-91482-y. [PMID: 34168163]
  • Xiaojiao Zheng, Tianlu Chen, Runqiu Jiang, Aihua Zhao, Qing Wu, Junliang Kuang, Dongnan Sun, Zhenxing Ren, Mengci Li, Mingliang Zhao, Shouli Wang, Yuqian Bao, Huating Li, Cheng Hu, Bing Dong, Defa Li, Jiayu Wu, Jialin Xia, Xuemei Wang, Ke Lan, Cynthia Rajani, Guoxiang Xie, Aiping Lu, Weiping Jia, Changtao Jiang, Wei Jia. Hyocholic acid species improve glucose homeostasis through a distinct TGR5 and FXR signaling mechanism. Cell metabolism. 2021 04; 33(4):791-803.e7. doi: 10.1016/j.cmet.2020.11.017. [PMID: 33338411]
  • Xiaojiao Zheng, Tianlu Chen, Aihua Zhao, Zhangchi Ning, Junliang Kuang, Shouli Wang, Yijun You, Yuqian Bao, Xiaojing Ma, Haoyong Yu, Jian Zhou, Miao Jiang, Mengci Li, Jieyi Wang, Xiaohui Ma, Shuiping Zhou, Yitao Li, Kun Ge, Cynthia Rajani, Guoxiang Xie, Cheng Hu, Yike Guo, Aiping Lu, Weiping Jia, Wei Jia. Hyocholic acid species as novel biomarkers for metabolic disorders. Nature communications. 2021 03; 12(1):1487. doi: 10.1038/s41467-021-21744-w. [PMID: 33674561]
  • Sayuri Takada, Tsutomu Matsubara, Hideki Fujii, Misako Sato-Matsubara, Atsuko Daikoku, Naoshi Odagiri, Yuga Amano-Teranishi, Norifumi Kawada, Kazuo Ikeda. Stress can attenuate hepatic lipid accumulation via elevation of hepatic β-muricholic acid levels in mice with nonalcoholic steatohepatitis. Laboratory investigation; a journal of technical methods and pathology. 2021 02; 101(2):193-203. doi: 10.1038/s41374-020-00509-x. [PMID: 33303970]
  • Jan Freark de Boer, Hilde D de Vries, Anna Palmiotti, Rumei Li, Marwah Doestzada, Joanne A Hoogerland, Jingyuan Fu, Anouk M La Rose, Marit Westerterp, Niels L Mulder, Milaine V Hovingh, Martijn Koehorst, Niels J Kloosterhuis, Justina C Wolters, Vincent W Bloks, Joel T Haas, David Dombrowicz, Bart Staels, Bart van de Sluis, Folkert Kuipers. Cholangiopathy and Biliary Fibrosis in Cyp2c70-Deficient Mice Are Fully Reversed by Ursodeoxycholic Acid. Cellular and molecular gastroenterology and hepatology. 2021; 11(4):1045-1069. doi: 10.1016/j.jcmgh.2020.12.004. [PMID: 33309945]
  • Yunhuan Liu, Kefei Chen, Fengyuan Li, Zelin Gu, Qi Liu, Liqing He, Tuo Shao, Qing Song, Fenxia Zhu, Lihua Zhang, Mengwei Jiang, Yun Zhou, Shirish Barve, Xiang Zhang, Craig J McClain, Wenke Feng. Probiotic Lactobacillus rhamnosus GG Prevents Liver Fibrosis Through Inhibiting Hepatic Bile Acid Synthesis and Enhancing Bile Acid Excretion in Mice. Hepatology (Baltimore, Md.). 2020 06; 71(6):2050-2066. doi: 10.1002/hep.30975. [PMID: 31571251]
  • Sara Straniero, Amit Laskar, Christina Savva, Jennifer Härdfeldt, Bo Angelin, Mats Rudling. Of mice and men: murine bile acids explain species differences in the regulation of bile acid and cholesterol metabolism. Journal of lipid research. 2020 04; 61(4):480-491. doi: 10.1194/jlr.ra119000307. [PMID: 32086245]
  • Jin Chen, Minghua Zheng, Jun Liu, Yan Luo, Wenjun Yang, Jing Yang, Juan Liu, Jingxing Zhou, Chengfu Xu, Faling Zhao, Mingming Su, Shufei Zang, Junping Shi. Ratio of Conjugated Chenodeoxycholic to Muricholic Acids is Associated with Severity of Nonalcoholic Steatohepatitis. Obesity (Silver Spring, Md.). 2019 12; 27(12):2055-2066. doi: 10.1002/oby.22627. [PMID: 31657148]
  • Marine Coué, Angela Tesse, Juliette Falewée, Audrey Aguesse, Mikaël Croyal, Lionel Fizanne, Julien Chaigneau, Jérôme Boursier, Khadija Ouguerram. Spirulina Liquid Extract Protects against Fibrosis Related to Non-Alcoholic Steatohepatitis and Increases Ursodeoxycholic Acid. Nutrients. 2019 Jan; 11(1):. doi: 10.3390/nu11010194. [PMID: 30669332]
  • Sandra von Hardenberg, Carsten Gnewuch, Gerd Schmitz, Jürgen Borlak. ApoE is a major determinant of hepatic bile acid homeostasis in mice. The Journal of nutritional biochemistry. 2018 02; 52(?):82-91. doi: 10.1016/j.jnutbio.2017.09.008. [PMID: 29175670]
  • Tammy L Kindel, Crystal Krause, Melissa C Helm, Corrigan L McBride, Dmitry Oleynikov, Rhishikesh Thakare, Jawaher Alamoudi, Vishal Kothari, Yazen Alnouti, Rohit Kohli. Increased glycine-amidated hyocholic acid correlates to improved early weight loss after sleeve gastrectomy. Surgical endoscopy. 2018 02; 32(2):805-812. doi: 10.1007/s00464-017-5747-y. [PMID: 28779240]
  • Jia Liu, Guan Lian, Ting Wang, Yuanheng Ma, Junto Zhou, Changtao Jiang, Yuxin Yin. An HPLC-MS/MS method for quantitation of Gly-MCA in mouse plasma: Application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2017 Nov; 146(?):53-58. doi: 10.1016/j.jpba.2017.07.020. [PMID: 28854403]
  • Kyosuke Fujita, Yusuke Iguchi, Mizuho Une, Shiro Watanabe. Ursodeoxycholic Acid Suppresses Lipogenesis in Mouse Liver: Possible Role of the Decrease in β-Muricholic Acid, a Farnesoid X Receptor Antagonist. Lipids. 2017 04; 52(4):335-344. doi: 10.1007/s11745-017-4242-5. [PMID: 28315136]
  • Shogo Takahashi, Tatsuki Fukami, Yusuke Masuo, Chad N Brocker, Cen Xie, Kristopher W Krausz, C Roland Wolf, Colin J Henderson, Frank J Gonzalez. Cyp2c70 is responsible for the species difference in bile acid metabolism between mice and humans. Journal of lipid research. 2016 12; 57(12):2130-2137. doi: 10.1194/jlr.m071183. [PMID: 27638959]
  • Mats Rudling. Understanding mouse bile acid formation: Is it time to unwind why mice and rats make unique bile acids?. Journal of lipid research. 2016 12; 57(12):2097-2098. doi: 10.1194/jlr.c072876. [PMID: 27777318]
  • Ylva Bonde, Gösta Eggertsen, Mats Rudling. Mice Abundant in Muricholic Bile Acids Show Resistance to Dietary Induced Steatosis, Weight Gain, and to Impaired Glucose Metabolism. PloS one. 2016; 11(1):e0147772. doi: 10.1371/journal.pone.0147772. [PMID: 26824238]
  • Changtao Jiang, Cen Xie, Ying Lv, Jing Li, Kristopher W Krausz, Jingmin Shi, Chad N Brocker, Dhimant Desai, Shantu G Amin, William H Bisson, Yulan Liu, Oksana Gavrilova, Andrew D Patterson, Frank J Gonzalez. Intestine-selective farnesoid X receptor inhibition improves obesity-related metabolic dysfunction. Nature communications. 2015 Dec; 6(?):10166. doi: 10.1038/ncomms10166. [PMID: 26670557]
  • Zidong Donna Fu, Curtis D Klaassen. Increased bile acids in enterohepatic circulation by short-term calorie restriction in male mice. Toxicology and applied pharmacology. 2013 Dec; 273(3):680-90. doi: 10.1016/j.taap.2013.10.020. [PMID: 24183703]
  • Martin Perreault, Louis Gauthier-Landry, Jocelyn Trottier, Mélanie Verreault, Patrick Caron, Moshe Finel, Olivier Barbier. The Human UDP-glucuronosyltransferase UGT2A1 and UGT2A2 enzymes are highly active in bile acid glucuronidation. Drug metabolism and disposition: the biological fate of chemicals. 2013 Sep; 41(9):1616-20. doi: 10.1124/dmd.113.052613. [PMID: 23756265]
  • Tatsuki Mizuochi, Akihiko Kimura, Atsushi Tanaka, Akina Muto, Hiroshi Nittono, Yoshitaka Seki, Tomoyuki Takahashi, Takao Kurosawa, Masayoshi Kage, Hajime Takikawa, Toyojiro Matsuishi. Characterization of urinary bile acids in a pediatric BRIC-1 patient: effect of rifampicin treatment. Clinica chimica acta; international journal of clinical chemistry. 2012 Aug; 413(15-16):1301-4. doi: 10.1016/j.cca.2012.04.011. [PMID: 22525741]
  • Charles Desmarchelier, Christoph Dahlhoff, Sylvia Keller, Manuela Sailer, Gerhard Jahreis, Hannelore Daniel. C57Bl/6 N mice on a western diet display reduced intestinal and hepatic cholesterol levels despite a plasma hypercholesterolemia. BMC genomics. 2012 Mar; 13(?):84. doi: 10.1186/1471-2164-13-84. [PMID: 22394543]
  • Youcai Zhang, Pallavi B Limaye, Lois D Lehman-McKeeman, Curtis D Klaassen. Dysfunction of organic anion transporting polypeptide 1a1 alters intestinal bacteria and bile acid metabolism in mice. PloS one. 2012; 7(4):e34522. doi: 10.1371/journal.pone.0034522. [PMID: 22496825]
  • Ai-Luen Wu, Sally Coulter, Christopher Liddle, Anne Wong, Jeffrey Eastham-Anderson, Dorothy M French, Andrew S Peterson, Junichiro Sonoda. FGF19 regulates cell proliferation, glucose and bile acid metabolism via FGFR4-dependent and independent pathways. PloS one. 2011 Mar; 6(3):e17868. doi: 10.1371/journal.pone.0017868. [PMID: 21437243]
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  • Masahito Hagio, Megumi Matsumoto, Michihiro Fukushima, Hiroshi Hara, Satoshi Ishizuka. Improved analysis of bile acids in tissues and intestinal contents of rats using LC/ESI-MS. Journal of lipid research. 2009 Jan; 50(1):173-80. doi: 10.1194/jlr.d800041-jlr200. [PMID: 18772484]
  • Yazen Alnouti, Iván L Csanaky, Curtis D Klaassen. Quantitative-profiling of bile acids and their conjugates in mouse liver, bile, plasma, and urine using LC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Oct; 873(2):209-17. doi: 10.1016/j.jchromb.2008.08.018. [PMID: 18801708]
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