Taurodeoxycholic acid (BioDeep_00000003498)

 

Secondary id: BioDeep_00000229651, BioDeep_00000405394, BioDeep_00000408601, BioDeep_00001871104

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Bile acids PANOMIX LipidSearch


代谢物信息卡片


2-[[(4R)-4-[(3R,5R,9S,10S,12S,13R,14S,17R)-3,12-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]pentanoyl]amino]ethanesulfonic acid

化学式: C26H45NO6S (499.29674300000005)
中文名称: 牛磺脱氧氯酸, 牛磺去氧胆酸
谱图信息: 最多检出来源 Homo sapiens(feces) 10.9%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Taurodeoxycholic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/taurodeoxycholic_acid (retrieved 2024-11-25) (BioDeep RN: BioDeep_00000003498). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
InChI: InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1

描述信息

Taurodeoxycholic acid is a bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID:11316487, 16037564, 12576301, 11907135). Taurodeoxycholic acid can be found in Escherichia (PMID:30736766).
Taurodeoxycholic acid is a bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB]
D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics
D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts
D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
D013501 - Surface-Active Agents > D003902 - Detergents
Taurodeoxycholic acid, a bile acid, stabilizes the mitochondrial membrane, decreases free radical formation. Taurodeoxycholic acid inhibits apoptosis by blocking a calcium-mediated apoptotic pathway as well as caspase-12 activation. Taurodeoxycholic acid exhibits neuroprotective effect in 3-nitropropionic acid induced mouse model or genetic mouse model of Huntington's disease (HD)[1][2][3][4].
Taurodeoxycholic acid, a bile acid, stabilizes the mitochondrial membrane, decreases free radical formation. Taurodeoxycholic acid inhibits apoptosis by blocking a calcium-mediated apoptotic pathway as well as caspase-12 activation. Taurodeoxycholic acid exhibits neuroprotective effect in 3-nitropropionic acid induced mouse model or genetic mouse model of Huntington's disease (HD)[1][2][3][4].

同义名列表

23 个代谢物同义名

2-[[(4R)-4-[(3R,5R,9S,10S,12S,13R,14S,17R)-3,12-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]pentanoyl]amino]ethanesulfonic acid; 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid; 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid; 2-[(3α,12α-dihydroxy-24-oxo-5β-cholan-24-yl)amino]ethanesulfonic acid; N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-taurine; Taurodeoxycholic acid sodium salt hydrate; Taurodeoxycholate;Deoxycholyltaurine; Taurodeoxycholic acid sodium salt; Taurodeoxycholate, sodium; Sodium Taurodeoxycholate; Taurodesoxycholic acid; Acid, taurodeoxycholic; Deoxytaurocholic acid; taurodeoxycholic acid; Deoxycholate, taurine; Sodium taurodeoxylate; Taurine deoxycholate; Deoxycholyltaurine; Taurodesoxycholate; Taurodeoxycholate; Deoxytaurocholate; Tudcabil; Taurodeoxycholic acid (TDCA)



数据库引用编号

23 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)

5 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

  • Da-Xin Chen, Jian-Feng Chu, Shan Lin, Ling Zhang, Hong-Wei Chen, Zhi-Wei Sun, Jian-Feng Xu, Qiao-Yan Cai, Li-Li Wang, Jun Peng. Therapeutic Effects of Different Animal Bile Powders on Lipid Metabolism Disorders and Their Composition Analysis. Chinese journal of integrative medicine. 2022 Oct; 28(10):918-923. doi: 10.1007/s11655-021-3441-3. [PMID: 33609233]
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  • Yue Li, Dongming Yan, Jingyi Jin, Bo Tan, Xi Chen, Bin Zou, Guochao Song, Fengyi Weng, Chenghai Liu, Furong Qiu. Clarify the potential cholestatic hepatotoxicity components from Chinese Herb Medicine and metabolism's role via hBSEP vesicles and S9/hBSEP vesicles. Toxicology in vitro : an international journal published in association with BIBRA. 2022 Apr; 80(?):105324. doi: 10.1016/j.tiv.2022.105324. [PMID: 35101544]
  • Suzhen Lei, Lu Liu, Linyu Ding, Yi Zhang, Hongliang Zeng. Lotus seed resistant starch affects the conversion of sodium taurocholate by regulating the intestinal microbiota. International journal of biological macromolecules. 2021 Sep; 186(?):227-236. doi: 10.1016/j.ijbiomac.2021.07.031. [PMID: 34245735]
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  • Abir Ben Bacha, Ikram Jemel, Ramesa Shafi Bhat, Mona Awad Onizi. Inhibitory effects of various solvent extracts from Rhamnus frangula leaves on some inflammatory and metabolic enzymes. Cellular and molecular biology (Noisy-le-Grand, France). 2018 Oct; 64(13):55-62. doi: 10.14715/cmb/2018.64.13.11. [PMID: 30403596]
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  • Aline A Figueiredo, Ana P M Santana, Lucas A D Nicolau, Francisco J Batista-Lima, Deysi V T Wong, Larisse T Lucetti, Gabriela L P Batista, Natália A Caminha, Jand V R Medeiros, Durcilene A Silva, José R S A Leite, Armênio A Santos, Pedro M G Soares, Daniel Sifrim, Marcellus H L P Souza. Topical protection of mice laryngeal mucosa using the natural product cashew gum. The Laryngoscope. 2018 05; 128(5):1157-1162. doi: 10.1002/lary.26958. [PMID: 29076531]
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  • Barbara Renga, Andrea Mencarelli, Claudio D'Amore, Sabrina Cipriani, Maria Valeria D'Auria, Valentina Sepe, Maria Giovanna Chini, Maria Chiara Monti, Giuseppe Bifulco, Angela Zampella, Stefano Fiorucci. Discovery that theonellasterol a marine sponge sterol is a highly selective FXR antagonist that protects against liver injury in cholestasis. PloS one. 2012; 7(1):e30443. doi: 10.1371/journal.pone.0030443. [PMID: 22291955]
  • Renate Schreiber, Ulrike Taschler, Karina Preiss-Landl, Nuttaporn Wongsiriroj, Robert Zimmermann, Achim Lass. Retinyl ester hydrolases and their roles in vitamin A homeostasis. Biochimica et biophysica acta. 2012 Jan; 1821(1):113-23. doi: 10.1016/j.bbalip.2011.05.001. [PMID: 21586336]
  • Manoj Kumar, Ravinder Nagpal, Rajesh Kumar, R Hemalatha, Vinod Verma, Ashok Kumar, Chaitali Chakraborty, Birbal Singh, Francesco Marotta, Shalini Jain, Hariom Yadav. Cholesterol-lowering probiotics as potential biotherapeutics for metabolic diseases. Experimental diabetes research. 2012; 2012(?):902917. doi: 10.1155/2012/902917. [PMID: 22611376]
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  • Youcai Zhang, Iván L Csanaky, Lois D Lehman-McKeeman, Curtis D Klaassen. Loss of organic anion transporting polypeptide 1a1 increases deoxycholic acid absorption in mice by increasing intestinal permeability. Toxicological sciences : an official journal of the Society of Toxicology. 2011 Dec; 124(2):251-60. doi: 10.1093/toxsci/kfr236. [PMID: 21914718]
  • Jiao He, Jinru Liang, Sha Zhu, Wenna Zhao, Yongmin Zhang, Wenji Sun. Protective effect of taurohyodeoxycholic acid from Pulvis Fellis Suis on trinitrobenzene sulfonic acid induced ulcerative colitis in mice. European journal of pharmacology. 2011 Nov; 670(1):229-35. doi: 10.1016/j.ejphar.2011.08.036. [PMID: 21925164]
  • Jessica L Reiner, Karen W Phinney, Jennifer M Keller. Determination of perfluorinated compounds in human plasma and serum Standard Reference Materials using independent analytical methods. Analytical and bioanalytical chemistry. 2011 Nov; 401(9):2899-907. doi: 10.1007/s00216-011-5380-x. [PMID: 21912833]
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  • Sathaporn Ngamukote, Kittana Mäkynen, Thavaree Thilawech, Sirichai Adisakwattana. Cholesterol-lowering activity of the major polyphenols in grape seed. Molecules (Basel, Switzerland). 2011 Jun; 16(6):5054-61. doi: 10.3390/molecules16065054. [PMID: 21694670]
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  • Hai-Tao Jin, Teemu Lämsä, Panu H Nordback, Mervi T Hyvönen, Nikolay Grigorenko, Alex R Khomutov, Isto Nordback, Sari Räty, Ilkka Pörsti, Leena Alhonen, Juhani Sand. Association between remote organ injury and tissue polyamine homeostasis in acute experimental pancreatitis - treatment with a polyamine analogue bismethylspermine. Pharmacological reports : PR. 2011; 63(4):999-1008. doi: 10.1016/s1734-1140(11)70616-8. [PMID: 22001988]
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