Hyodeoxycholic_acid (BioDeep_00000230814)

 

Secondary id: BioDeep_00000016568, BioDeep_00000405352

PANOMIX_OTCML-2023 Bile acids


代谢物信息卡片


(4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-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]pentanoicacid

化学式: C24H40O4 (392.29264400000005)
中文名称: 猪去氧胆酸, 猪脱氧胆酸
谱图信息: 最多检出来源 Viridiplantae(plant) 5.88%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Hyodeoxycholic_acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/hyodeoxycholic_acid (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000230814). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](C[C@@H]2O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CCC(=O)O)C)C)C)O
InChI: InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20+,21+,23-,24-/m1/s1

描述信息

Hyodeoxycholic acid is a member of the class of 5beta-cholanic acids that is (5beta)-cholan-24-oic acid substituted by alpha-hydroxy groups at positions 3 and 6. It has a role as a human metabolite and a mouse metabolite. It is a bile acid, a member of 5beta-cholanic acids, a 6alpha,20xi-murideoxycholic acid and a C24-steroid. It is functionally related to a cholic acid. It is a conjugate acid of a hyodeoxycholate.
Hyodeoxycholic Acid has been used in trials studying the treatment of Hypercholesterolemia.
A member of the class of 5beta-cholanic acids that is (5beta)-cholan-24-oic acid substituted by alpha-hydroxy groups at positions 3 and 6.
D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts
D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
Hyodeoxycholic acid is a secondary bile acid formed in the small intestine by the gut flora, and acts as a TGR5 (GPCR19) agonist, with an EC50 of 31.6 μM in CHO cells.
Hyodeoxycholic acid is a secondary bile acid formed in the small intestine by the gut flora, and acts as a TGR5 (GPCR19) agonist, with an EC50 of 31.6 μM in CHO cells.
Hyodeoxycholic acid is a secondary bile acid formed in the small intestine by the gut flora, and acts as a TGR5 (GPCR19) agonist, with an EC50 of 31.6 μM in CHO cells.

同义名列表

61 个代谢物同义名

(4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-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]pentanoicacid; (R)-4-((3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid; Cholan-24-oic acid, 3,6-dihydroxy-, (3.alpha.,5.beta.,6.alpha.)-; 3,6-Dihydroxy-5.beta.-cholan-24-oic acid, (3.alpha.,6.alpha.)-; (3.ALPHA.,5.BETA.,6.ALPHA.)-3,6-DIHYDROXYCHOLAN-24-OIC ACID; Cholan-24-oic acid, 3,6-dihydroxy-, (3alpha,5beta,6alpha)-; 3-.alpha.,6-.alpha.-Dihydroxy-5-.beta.-cholan-24-oic acid; 5.beta.-Cholan-24-oic acid, 3.alpha.,6.alpha.-dihydroxy-; 5-Methyl-[1,3,4]oxadiazol-2-ylmethylaminehydrochloride; (3alpha,5beta,6alpha)-3,6-Dihydroxycholan-24-oic acid; 5-beta-Cholan-24-oic acid, 3-alpha,6-alpha-dihydroxy-; 3-alpha,6-alpha-Dihydroxy-5-beta-cholan-24-oic acid; 5beta-Cholan-24-oic acid, 3alpha,6alpha-dihydroxy-; 3.alpha.,6.alpha.-Dihydroxy-5.beta.-cholanoic acid; 3.alpha.,6.alpha.-Dihydroxy-5.beta.-cholanic acid; 3alpha,6alpha-Dihydroxy-5beta-cholan-24-oic acid; hyodeoxycholic acid, (3alpha,5beta,6beta)-isomer; Cholan-24-oic acid, 3,6-dihydroxy-, (3a,5b,6a)-; 5-.beta.-Cholanic acid-3-.alpha.,6-.alpha.-diol; 3alpha,6alpha-Dihydroxy-5beta-cholan-24-saeure; 3alpha,6alpha-Dihydroxy-5beta-cholanoic acid; 4-10-00-01600 (Beilstein Handbook Reference); 3alpha,6alpha-Dihydroxy-5beta-cholanic acid; hyodeoxycholic acid, (3alpha,6beta)-isomer; 5-beta-Cholanic acid-3-alpha,6-alpha-diol; 3.alpha.,6.alpha.-Dihydroxycholanic acid; 5beta-Cholanic acid-3alpha,6alpha-diol; 6|A-Dihydroxy-5|A-cholan-24-oic acid; 3alpha,6alpha-Dihydroxycholanic acid; 3,6-dihydroxy-5alpha-cholanoic acid; 6-.alpha.-Hydroxylithocholic acid; hyodeoxycholic acid, sodium salt; 6-alpha-Hydroxylithocholic acid; HYODEOXYCHOLIC ACID [WHO-DD]; Hyodeoxycholic acid, >=98\\%; .alpha.-Hyodeoxycholic acid; 6alpha-Hydroxylithocholate; Hyodeoxycholic acid (HDCA); alpha-Hyodeoxycholic acid; HYODEOXYCHOLIC ACID [MI]; sodium hyodeoxycholate; a-Hyodeoxycholic acid; 7-Deoxyhyocholic acid; murideoxycholic acid; hyodesoxycholic acid; hyodeoxycholic-acid; HYODEOXYCHOLIC_ACID; Hyodesoxycholsaeure; Hyodeoxycholic acid; hyodeoxycholicacid; Hyodesoxycholsaure; Iodeoxycholic acid; Hyodeoxycholate; UNII-7A33Y6EHYK; Hyodeoxycholic; NaHDC compound; SMP1_000164; ST 24:1;O4; 7A33Y6EHYK; HDCA; 3|A



数据库引用编号

16 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)

0 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

  • Jing Zhong, Xiaofang He, Xinxin Gao, Qiaohong Liu, Yu Zhao, Ying Hong, Weize Zhu, Juan Yan, Yifan Li, Yan Li, Ningning Zheng, Yiyang Bao, Hao Wang, Junli Ma, Wenjin Huang, Zekun Liu, Yuanzhi Lyu, Xisong Ke, Wei Jia, Cen Xie, Yiyang Hu, Lili Sheng, Houkai Li. Hyodeoxycholic acid ameliorates nonalcoholic fatty liver disease by inhibiting RAN-mediated PPARα nucleus-cytoplasm shuttling. Nature communications. 2023 09; 14(1):5451. doi: 10.1038/s41467-023-41061-8. [PMID: 37673856]
  • Junliang Kuang, Jieyi Wang, Yitao Li, Mengci Li, Mingliang Zhao, Kun Ge, Dan Zheng, Kenneth C P Cheung, Boya Liao, Shouli Wang, Tianlu Chen, Yinan Zhang, Congrong Wang, Guang Ji, Peng Chen, Hongwei Zhou, Cen Xie, Aihua Zhao, Weiping Jia, Xiaojiao Zheng, Wei Jia. Hyodeoxycholic acid alleviates non-alcoholic fatty liver disease through modulating the gut-liver axis. Cell metabolism. 2023 Aug; ?(?):. doi: 10.1016/j.cmet.2023.07.011. [PMID: 37591244]
  • Minghao Hu, Tingting Gou, Yuchen Chen, Min Xu, Rong Chen, Tao Zhou, Junjing Liu, Cheng Peng, Qiang Ye. A Novel Drug Delivery System: Hyodeoxycholic Acid-Modified Metformin Liposomes for Type 2 Diabetes Treatment. Molecules (Basel, Switzerland). 2023 Mar; 28(6):. doi: 10.3390/molecules28062471. [PMID: 36985444]
  • Han Zhu, Yuyan Bai, Gaorui Wang, Yousong Su, Yanlin Tao, Lupeng Wang, Liu Yang, Hui Wu, Fei Huang, Hailian Shi, Xiaojun Wu. Hyodeoxycholic acid inhibits lipopolysaccharide-induced microglia inflammatory responses through regulating TGR5/AKT/NF-κB signaling pathway. Journal of psychopharmacology (Oxford, England). 2022 07; 36(7):849-859. doi: 10.1177/02698811221089041. [PMID: 35475391]
  • 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]
  • Nitza Soto, Karoll Ferrer, Katy Díaz, César González, Lautaro Taborga, Andrés F Olea, Héctor Carrasco, Luis Espinoza. Synthesis and Biological Activity of New Brassinosteroid Analogs of Type 24-Nor-5β-Cholane and 23-Benzoate Function in the Side Chain. International journal of molecular sciences. 2021 May; 22(9):. doi: 10.3390/ijms22094808. [PMID: 34062717]
  • Iván L Csanaky, Andrew J Lickteig, Youcai Zhang, Curtis D Klaassen. Effects of patent ductus venosus on bile acid homeostasis in aryl hydrocarbon receptor (AhR)-null mice. Toxicology and applied pharmacology. 2020 09; 403(?):115136. doi: 10.1016/j.taap.2020.115136. [PMID: 32679164]
  • Min Song, Qiang Yang, Fenglin Zhang, Lin Chen, Han Su, Xiaohua Yang, Haiwen He, Fangfang Liu, Jisong Zheng, Mingfa Ling, Xumin Lai, Xiaotong Zhu, Lina Wang, Ping Gao, Gang Shu, Qingyan Jiang, Songbo Wang. Hyodeoxycholic acid (HDCA) suppresses intestinal epithelial cell proliferation through FXR-PI3K/AKT pathway, accompanied by alteration of bile acids metabolism profiles induced by gut bacteria. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2020 05; 34(5):7103-7117. doi: 10.1096/fj.201903244r. [PMID: 32246800]
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  • Jiayu Zhang, Shifeng Wang, Lulu Xu, Qiao Zhang, Zhanpeng Shang, Yanling Zhang, Qinghua Wu, Shiyou Li, Yanjiang Qiao. Multiple perspectives of qingkailing injection-fraction-single compound in revealing the hepatotoxicity of baicalin and hyodeoxycholic acid. Journal of ethnopharmacology. 2018 Apr; 215(?):147-155. doi: 10.1016/j.jep.2017.11.035. [PMID: 29222033]
  • María Isabel Duran, Cesar González, Alison Acosta, Andrés F Olea, Katy Díaz, Luis Espinoza. Synthesis of Five Known Brassinosteroid Analogs from Hyodeoxycholic Acid and Their Activities as Plant-Growth Regulators. International journal of molecular sciences. 2017 Mar; 18(3):. doi: 10.3390/ijms18030516. [PMID: 28282853]
  • Simona De Marino, Adriana Carino, Dario Masullo, Claudia Finamore, Silvia Marchianò, Sabrina Cipriani, Francesco Saverio Di Leva, Bruno Catalanotti, Ettore Novellino, Vittorio Limongelli, Stefano Fiorucci, Angela Zampella. Hyodeoxycholic acid derivatives as liver X receptor α and G-protein-coupled bile acid receptor agonists. Scientific reports. 2017 02; 7(?):43290. doi: 10.1038/srep43290. [PMID: 28233865]
  • Shiro Watanabe, Kyosuke Fujita. Dietary hyodeoxycholic acid exerts hypolipidemic effects by reducing farnesoid X receptor antagonist bile acids in mouse enterohepatic tissues. Lipids. 2014 Oct; 49(10):963-73. doi: 10.1007/s11745-014-3947-y. [PMID: 25189147]
  • Carlos A Penno, Stuart A Morgan, Adam J Rose, Stephan Herzig, Gareth G Lavery, Alex Odermatt. 11β-Hydroxysteroid dehydrogenase-1 is involved in bile acid homeostasis by modulating fatty acid transport protein-5 in the liver of mice. Molecular metabolism. 2014 Aug; 3(5):554-64. doi: 10.1016/j.molmet.2014.04.008. [PMID: 25061560]
  • 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]
  • Diana M Shih, Zory Shaposhnik, Yonghong Meng, Melenie Rosales, Xuping Wang, Judy Wu, Boris Ratiner, Filiberto Zadini, Giorgio Zadini, Aldons J Lusis. Hyodeoxycholic acid improves HDL function and inhibits atherosclerotic lesion formation in LDLR-knockout mice. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2013 Sep; 27(9):3805-17. doi: 10.1096/fj.12-223008. [PMID: 23752203]
  • Martin Perreault, Andrzej Białek, Jocelyn Trottier, Mélanie Verreault, Patrick Caron, Piotr Milkiewicz, Olivier Barbier. Role of glucuronidation for hepatic detoxification and urinary elimination of toxic bile acids during biliary obstruction. PloS one. 2013; 8(11):e80994. doi: 10.1371/journal.pone.0080994. [PMID: 24244729]
  • Xiaoqiang Xiang, Janne T Backman, Pertti J Neuvonen, Mikko Niemi. Gender, but not CYP7A1 or SLCO1B1 polymorphism, affects the fasting plasma concentrations of bile acids in human beings. Basic & clinical pharmacology & toxicology. 2012 Mar; 110(3):245-52. doi: 10.1111/j.1742-7843.2011.00792.x. [PMID: 21902813]
  • Fafeng Cheng, Xueqian Wang, Yi Lu, Xianggen Zhong, Yan Zhao, Qingguo Wang. Chinese medicine injection qingkailing for treatment of acute ischemia stroke: a systematic review of randomized controlled trials. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):213172. doi: 10.1155/2012/213172. [PMID: 22675376]
  • Zidong Donna Fu, Iván L Csanaky, Curtis D Klaassen. Gender-divergent profile of bile acid homeostasis during aging of mice. PloS one. 2012; 7(3):e32551. doi: 10.1371/journal.pone.0032551. [PMID: 22403674]
  • 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]
  • M F Yueh, P L Mellon, R H Tukey. Inhibition of human UGT2B7 gene expression in transgenic mice by the constitutive androstane receptor. Molecular pharmacology. 2011 Jun; 79(6):1053-60. doi: 10.1124/mol.110.070649. [PMID: 21415305]
  • Yu-Kun Jennifer Zhang, Grace L Guo, Curtis D Klaassen. Diurnal variations of mouse plasma and hepatic bile acid concentrations as well as expression of biosynthetic enzymes and transporters. PloS one. 2011 Feb; 6(2):e16683. doi: 10.1371/journal.pone.0016683. [PMID: 21346810]
  • Xue Qiao, Min Ye, De-lin Pan, Wen-juan Miao, Cheng Xiang, Jian Han, De-an Guo. Differentiation of various traditional Chinese medicines derived from animal bile and gallstone: simultaneous determination of bile acids by liquid chromatography coupled with triple quadrupole mass spectrometry. Journal of chromatography. A. 2011 Jan; 1218(1):107-17. doi: 10.1016/j.chroma.2010.10.116. [PMID: 21111425]
  • Jocelyn Trottier, Andrzej Białek, Patrick Caron, Robert J Straka, Piotr Milkiewicz, Olivier Barbier. Profiling circulating and urinary bile acids in patients with biliary obstruction before and after biliary stenting. PloS one. 2011; 6(7):e22094. doi: 10.1371/journal.pone.0022094. [PMID: 21760958]
  • Masahito Hagio, Megumi Matsumoto, Takaji Yajima, Hiroshi Hara, Satoshi Ishizuka. Voluntary wheel running exercise and dietary lactose concomitantly reduce proportion of secondary bile acids in rat feces. Journal of applied physiology (Bethesda, Md. : 1985). 2010 Sep; 109(3):663-8. doi: 10.1152/japplphysiol.00777.2009. [PMID: 20616226]
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  • Wei Yan, Tongxin Zhang, Jun Cheng, Xiangdong Zhou, Xiaolong Qu, Houyuan Hu. Liver X receptor agonist methyl-3β-hydroxy-5α,6α-epoxycholanate attenuates atherosclerosis in apolipoprotein E knockout mice without increasing plasma triglyceride. Pharmacology. 2010; 86(5-6):306-12. doi: 10.1159/000321320. [PMID: 21071998]
  • Yunkyung Han, Tomoaki Haraguchi, Sumie Iwanaga, Hiroyuki Tomotake, Yukako Okazaki, Shigeru Mineo, Akiho Moriyama, Junji Inoue, Norihisa Kato. Consumption of some polyphenols reduces fecal deoxycholic acid and lithocholic acid, the secondary bile acids of risk factors of colon cancer. Journal of agricultural and food chemistry. 2009 Sep; 57(18):8587-90. doi: 10.1021/jf900393k. [PMID: 19711910]
  • Carsten Gnewuch, Gerhard Liebisch, Thomas Langmann, Benjamin Dieplinger, Thomas Mueller, Meinhard Haltmayer, Hans Dieplinger, Alexandra Zahn, Wolfgang Stremmel, Gerhard Rogler, Gerd Schmitz. Serum bile acid profiling reflects enterohepatic detoxification state and intestinal barrier function in inflammatory bowel disease. World journal of gastroenterology. 2009 Jul; 15(25):3134-41. doi: 10.3748/wjg.15.3134. [PMID: 19575493]
  • Yibin Feng, Kayu Siu, Ning Wang, Kwan-Ming Ng, Sai-Wah Tsao, Tadashi Nagamatsu, Yao Tong. Bear bile: dilemma of traditional medicinal use and animal protection. Journal of ethnobiology and ethnomedicine. 2009 Jan; 5(?):2. doi: 10.1186/1746-4269-5-2. [PMID: 19138420]
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