Cholylglycine (BioDeep_00000229687)

Main id: BioDeep_00000000126

 

human metabolite PANOMIX_OTCML-2023 Bile acids Antitumor activity BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


N-(3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholan-24-oyl)-glycine

化学式: C26H43NO6 (465.30902180000004)
中文名称: 甘氨胆酸, 甘氨胆酸水合物, 甘胆酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(C(C([H])(C4(C)1)CCC1([H])C(C(O)3)(C(CC(O)4)([H])C(C)(C([H])2C3)CCC(C2)O)[H])C)CC(=O)NCC(O)=O
InChI: InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1

描述信息

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
Glycocholic acid is a bile acid with anticancer activity, targeting against pump resistance-related and non-pump resistance-related pathways[1].
Glycocholic acid is a bile acid with anticancer activity, targeting against pump resistance-related and non-pump resistance-related pathways[1].

同义名列表

5 个代谢物同义名

N-(3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholan-24-oyl)-glycine; Glycocholic acid; Cholylglycine; ST 24:1;O5;G; Glycocholate



数据库引用编号

18 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)

2 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

  • Hamid Alghurabi, Huda Jassim Muhammad, Tatsuaki Tagami, Koki Ogawa, Tetsuya Ozeki. Optimization, cellular uptake, and in vivo evaluation of Eudragit S100-coated bile salt-containing liposomes for oral colonic delivery of 5-aminosalicylic acid. International journal of pharmaceutics. 2023 Dec; 648(?):123597. doi: 10.1016/j.ijpharm.2023.123597. [PMID: 37952559]
  • Yu Tang, Zhu Han, Han Zhang, Li Che, Genjie Liao, Jun Peng, Yu Lin, Yi Wang. Characterization of Calculus bovis by principal component analysis assisted qHNMR profiling to distinguish nefarious frauds. Journal of pharmaceutical and biomedical analysis. 2023 Mar; 228(?):115320. doi: 10.1016/j.jpba.2023.115320. [PMID: 36871364]
  • Shibin Yao, Shengjie Ren, Chunfang Cai, Xiamin Cao, Ye Shi, Ping Wu, Yuantu Ye. Glycocholic acid supplementation improved growth performance and alleviated tissue damage in the liver and intestine in Pelteobagrus fulvidraco fed a high-pectin diet. Fish physiology and biochemistry. 2022 Dec; ?(?):. doi: 10.1007/s10695-022-01148-3. [PMID: 36454392]
  • Xiaolu Zhou, Yaling Li, Ren Mu, Chuanming Wang, Yuyan Song, Caibi Zhou, Xin Mei. Duyun compound green tea extracts regulate bile acid metabolism on mice induced by high-fat diet. The British journal of nutrition. 2022 Oct; ?(?):1-9. doi: 10.1017/s0007114522003166. [PMID: 36210537]
  • Jian Wu, Yanping Xu, Yubao Cui, Mariza Bortolanza, Minjie Wang, Bin Jiang, Meina Yan, Wei Liang, Yiwen Yao, Qiaoling Pan, Jinfeng Yang, Jiong Yu, Dawei Wang, Hongcui Cao, Lanjuan Li. Dynamic changes of serum metabolites associated with infection and severity of patients with acute hepatitis E infection. Journal of medical virology. 2022 06; 94(6):2714-2726. doi: 10.1002/jmv.27669. [PMID: 35199373]
  • Feiyang Deng, You Han Bae. Lipid raft-mediated and upregulated coordination pathways assist transport of glycocholic acid-modified nanoparticle in a human breast cancer cell line of SK-BR-3. International journal of pharmaceutics. 2022 Apr; 617(?):121589. doi: 10.1016/j.ijpharm.2022.121589. [PMID: 35176336]
  • Hongxue Liu, Haidong Wang, Muling Zhang. Deep Learning Algorithm-Based Magnetic Resonance Imaging Feature-Guided Serum Bile Acid Profile and Perinatal Outcomes in Intrahepatic Cholestasis of Pregnancy. Computational and mathematical methods in medicine. 2022; 2022(?):8081673. doi: 10.1155/2022/8081673. [PMID: 35707042]
  • Michelle L Manni, Victoria A Heinrich, Gregory J Buchan, James P O'Brien, Crystal Uvalle, Veronika Cechova, Adolf Koudelka, Dharti Ukani, Mohamad Rawas-Qalaji, Tim D Oury, Renee Hart, Madeline Ellgass, Steven J Mullett, Merritt L Fajt, Sally E Wenzel, Fernando Holguin, Bruce A Freeman, Stacy G Wendell. Nitroalkene fatty acids modulate bile acid metabolism and lung function in obese asthma. Scientific reports. 2021 09; 11(1):17788. doi: 10.1038/s41598-021-96471-9. [PMID: 34493738]
  • Xiping Cui, Qiyi He, Huiyi Yang, Yingshan Chen, Ding Shen, Sergei A Eremin, Yunping Mu, Suqing Zhao. Development of enzyme-free single-step immunoassays for glycocholic acid based on palladium nanoparticle-mediated signal generation. Analytical and bioanalytical chemistry. 2021 Sep; 413(23):5733-5742. doi: 10.1007/s00216-021-03548-5. [PMID: 34476526]
  • Ying Han, Wei Liu, Liqing Chen, Xin Xin, Qiming Wang, Xintong Zhang, Mingji Jin, Zhonggao Gao, Wei Huang. Effective oral delivery of Exenatide-Zn2+ complex through distal ileum-targeted double layers nanocarriers modified with deoxycholic acid and glycocholic acid in diabetes therapy. Biomaterials. 2021 08; 275(?):120944. doi: 10.1016/j.biomaterials.2021.120944. [PMID: 34153783]
  • Hui Li, Yan Wang, Shizhao Ma, Chaoqun Zhang, Hua Liu, Dianxing Sun. Clinical significance of small molecule metabolites in the blood of patients with different types of liver injury. Scientific reports. 2021 06; 11(1):11642. doi: 10.1038/s41598-021-91164-9. [PMID: 34079030]
  • Rong Wang, Hongmin Jiang, Yongjun Wang, Yuanqing Yang. Serum TBA and GCA Levels Across Pregnancy and the Gestational Age-Specific Reference Intervals for Pregnant Chinese. Clinical laboratory. 2021 Jun; 67(6):. doi: 10.7754/clin.lab.2020.201043. [PMID: 34107618]
  • Qiyi He, Yanxiong Fang, Huiyi Yang, Ding Shen, Yingshan Chen, Yingying Zhong, Xiangguang Li, Sergei A Eremin, Xiping Cui, Suqing Zhao. Enhanced performance of a surface plasmon resonance-based immunosensor for the detection of glycocholic acid. Analytical methods : advancing methods and applications. 2021 04; 13(16):1919-1924. doi: 10.1039/d1ay00357g. [PMID: 33913980]
  • Guangzheng Zhang, Zhenyuan Lang, Qifan Yang, You Nie, Zhihan Wang, Ming Gao, Nan Zhang, Xia Xu. UPLC-Q-TOF/MS-based plasma metabolome to identify biomarkers and time of injury in traumatic brain injured rats. Neuroreport. 2021 04; 32(6):415-422. doi: 10.1097/wnr.0000000000001576. [PMID: 33788810]
  • Chong Fu, Yali Xu. Value of Serum Glycocholic Acid and Total Bile Acids in Predicting Maternal and Perinatal Outcomes in Intrahepatic Cholestasis of Pregnancy. Journal of healthcare engineering. 2021; 2021(?):3911998. doi: 10.1155/2021/3911998. [PMID: 34540186]
  • Ruirui Dong, Ningzhen Ye, Shaojie Zhao, Gaoying Wang, Yan Zhang, Tiejun Wang, Ping Zou, Jing Wang, Tingting Yao, Minjian Chen, Conghua Zhou, Ting Zhang, Liang Luo. Studies on Novel Diagnostic and Predictive Biomarkers of Intrahepatic Cholestasis of Pregnancy Through Metabolomics and Proteomics. Frontiers in immunology. 2021; 12(?):733225. doi: 10.3389/fimmu.2021.733225. [PMID: 34721396]
  • José Tadeu Stefano, Laura Vilar Guedes, Arthur Alencar Arrais de Souza, Denise Siqueira Vanni, Venâncio Avancini Ferreira Alves, Flair José Carrilho, Alvaro Largura, Marco Arrese, Claudia P Oliveira. Usefulness of collagen type IV in the detection of significant liver fibrosis in nonalcoholic fatty liver disease. Annals of hepatology. 2021 Jan; 20(?):100253. doi: 10.1016/j.aohep.2020.08.070. [PMID: 32949785]
  • Qiyi He, Huiyi Yang, Yingshan Chen, Ding Shen, Xiping Cui, Chunguo Zhang, Huanxin Xiao, Sergei A Eremin, Yanxiong Fang, Suqing Zhao. Prussian blue nanoparticles with peroxidase-mimicking properties in a dual immunoassays for glycocholic acid. Journal of pharmaceutical and biomedical analysis. 2020 Aug; 187(?):113317. doi: 10.1016/j.jpba.2020.113317. [PMID: 32416340]
  • Jiayao Liu, Wenjuan Xu, Anna Zhu, Haoxiang Kang, Yu Cao, Feng Long. Reusable optofluidic point-of-care testing platform with lyophilized specific antibody for fluorescence detection of cholylglycine in serum. Mikrochimica acta. 2020 07; 187(8):439. doi: 10.1007/s00604-020-04424-2. [PMID: 32653962]
  • Weiguo Sui, Qing Gan, Fuhua Liu, Minglin Ou, Bingguo Wang, Songbai Liao, Liusheng Lai, Huaizhou Chen, Ming Yang, Yong Dai. Dynamic Metabolomics Study of the Bile Acid Pathway During Perioperative Primary Hepatic Carcinoma Following Liver Transplantation. Annals of transplantation. 2020 Jun; 25(?):e921844. doi: 10.12659/aot.921844. [PMID: 32572018]
  • Erikka Loftfield, Joseph A Rothwell, Rashmi Sinha, Pekka Keski-Rahkonen, Nivonirina Robinot, Demetrius Albanes, Stephanie J Weinstein, Andriy Derkach, Joshua Sampson, Augustin Scalbert, Neal D Freedman. Prospective Investigation of Serum Metabolites, Coffee Drinking, Liver Cancer Incidence, and Liver Disease Mortality. Journal of the National Cancer Institute. 2020 03; 112(3):286-294. doi: 10.1093/jnci/djz122. [PMID: 31168595]
  • Kyoung Sub Kim, Yu Seok Youn, You Han Bae. Immune-triggered cancer treatment by intestinal lymphatic delivery of docetaxel-loaded nanoparticle. Journal of controlled release : official journal of the Controlled Release Society. 2019 10; 311-312(?):85-95. doi: 10.1016/j.jconrel.2019.08.027. [PMID: 31461664]
  • Patricia Mitry, Nina Wawro, Sapna Sharma, Jennifer Kriebel, Anna Artati, Jerzy Adamski, Margit Heier, Christa Meisinger, Barbara Thorand, Harald Grallert, Annette Peters, Jakob Linseisen. Associations between usual food intake and faecal sterols and bile acids: results from the Cooperative Health Research in the Augsburg Region (KORA FF4) study. The British journal of nutrition. 2019 08; 122(3):309-321. doi: 10.1017/s000711451900103x. [PMID: 31182174]
  • Issey Takehara, Nobuaki Watanabe, Daiki Mori, Osamu Ando, Hiroyuki Kusuhara. Effect of Rifampicin on the Plasma Concentrations of Bile Acid-O-Sulfates in Monkeys and Human Liver-Transplanted Chimeric Mice With or Without Bile Flow Diversion. Journal of pharmaceutical sciences. 2019 08; 108(8):2756-2764. doi: 10.1016/j.xphs.2019.03.021. [PMID: 30905707]
  • Alvaro Alonso, Bing Yu, Yan V Sun, Lin Y Chen, Laura R Loehr, Wesley T O'Neal, Elsayed Z Soliman, Eric Boerwinkle. Serum Metabolomics and Incidence of Atrial Fibrillation (from the Atherosclerosis Risk in Communities Study). The American journal of cardiology. 2019 06; 123(12):1955-1961. doi: 10.1016/j.amjcard.2019.03.017. [PMID: 30979411]
  • Qiangyuan Fan, Yongtai Zhang, Xuefeng Hou, Zhe Li, Kai Zhang, Qun Shao, Nianping Feng. Improved oral bioavailability of notoginsenoside R1 with sodium glycocholate-mediated liposomes: Preparation by supercritical fluid technology and evaluation in vitro and in vivo. International journal of pharmaceutics. 2018 Dec; 552(1-2):360-370. doi: 10.1016/j.ijpharm.2018.10.005. [PMID: 30292894]
  • Qiyi He, Xiping Cui, Ding Shen, Yingshan Chen, Zhengyun Jiang, Rui Lv, Sergei A Eremin, Suqing Zhao. Development of a simple, rapid and high-throughput fluorescence polarization immunoassay for glycocholic acid in human urine. Journal of pharmaceutical and biomedical analysis. 2018 Sep; 158(?):431-437. doi: 10.1016/j.jpba.2018.06.023. [PMID: 29945060]
  • Xiping Cui, Natalia Vasylieva, Ding Shen, Bogdan Barnych, Jun Yang, Qiyi He, Zhengyun Jiang, Suqing Zhao, Bruce D Hammock. Biotinylated single-chain variable fragment-based enzyme-linked immunosorbent assay for glycocholic acid. The Analyst. 2018 Apr; 143(9):2057-2065. doi: 10.1039/c7an02024d. [PMID: 29629470]
  • Cheng Guo, Cong Xie, Peili Ding, Guangming Qin, Weimin Mo, Xiaoji Cao, Shu Zheng. Quantification of glycocholic acid in human serum by stable isotope dilution ultra performance liquid chromatography electrospray ionization tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Jan; 1072(?):315-319. doi: 10.1016/j.jchromb.2017.11.037. [PMID: 29202363]
  • Xiping Cui, Natalia Vasylieva, Panpan Wu, Bogdan Barnych, Jun Yang, Ding Shen, Qiyi He, Shirley J Gee, Suqing Zhao, Bruce D Hammock. Development of an Indirect Competitive Enzyme-Linked Immunosorbent Assay for Glycocholic Acid Based on Chicken Single-Chain Variable Fragment Antibodies. Analytical chemistry. 2017 10; 89(20):11091-11097. doi: 10.1021/acs.analchem.7b03190. [PMID: 28942640]
  • Mariapina D'Onofrio, Carlo Giorgio Barracchia, Andrea Bortot, Francesca Munari, Serena Zanzoni, Michael Assfalg. Molecular differences between human liver fatty acid binding protein and its T94A variant in their unbound and lipid-bound states. Biochimica et biophysica acta. Proteins and proteomics. 2017 Sep; 1865(9):1152-1159. doi: 10.1016/j.bbapap.2017.06.025. [PMID: 28668637]
  • Veronika Thöni, Alexandra Pfister, Andreas Melmer, Barbara Enrich, Karin Salzmann, Susanne Kaser, Claudia Lamina, Christoph F Ebenbichler, Hubert Hackl, Herbert Tilg, Alexander R Moschen. Dynamics of Bile Acid Profiles, GLP-1, and FGF19 After Laparoscopic Gastric Banding. The Journal of clinical endocrinology and metabolism. 2017 08; 102(8):2974-2984. doi: 10.1210/jc.2017-00235. [PMID: 28591793]
  • Xiao-Hong Yu, Jing Sun, Yan Wang, Ya-Bin Zhou. Biomarkers of unstable angina pectoris and yangxin decoction intervention: An exploratory metabonomics study of blood plasma. Medicine. 2017 May; 96(21):e6998. doi: 10.1097/md.0000000000006998. [PMID: 28538412]
  • Hui Li, Su-Fang Fan, Yan Wang, Shi-Gang Shen, Dian-Xing Sun. Rapid Detection of Small Molecule Metabolites in Serum of Hepatocellular Carcinoma Patients Using Ultrafast Liquid Chromatography-Ion Trap-Time of Flight Tandem Mass Spectrometry. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2017; 33(5):573-578. doi: 10.2116/analsci.33.573. [PMID: 28496060]
  • Alessandra Maroni, Maria Dorly Del Curto, Stefano Salmaso, Lucia Zema, Alice Melocchi, Paolo Caliceti, Andrea Gazzaniga. In vitro and in vivo evaluation of an oral multiple-unit formulation for colonic delivery of insulin. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2016 Nov; 108(?):76-82. doi: 10.1016/j.ejpb.2016.08.002. [PMID: 27519826]
  • Quan-Fu Li, Yan-Mei Zhan, Yong-Gang Zhong, Bo Zhang, Chang-Qing Ge. Macromolecular Crowding Agents-Assisted Imprinted Polymers For Analysis Of Glycocholic Acid In Human Plasma And Urine. Biomedical chromatography : BMC. 2016 Nov; 30(11):1706-1713. doi: 10.1002/bmc.3737. [PMID: 27061917]
  • Hongmin Xu, Lei Zhang, Huan Kang, Jiandong Zhang, Jie Liu, Shuye Liu. Serum Metabonomics of Mild Acute Pancreatitis. Journal of clinical laboratory analysis. 2016 Nov; 30(6):990-998. doi: 10.1002/jcla.21969. [PMID: 27169745]
  • Monika Rau, Bruno Stieger, Maria J Monte, Johannes Schmitt, Daniel Jahn, Isabelle Frey-Wagner, Tina Raselli, Jose J G Marin, Beat Müllhaupt, Gerhard Rogler, Andreas Geier. Alterations in Enterohepatic Fgf15 Signaling and Changes in Bile Acid Composition Depend on Localization of Murine Intestinal Inflammation. Inflammatory bowel diseases. 2016 10; 22(10):2382-9. doi: 10.1097/mib.0000000000000879. [PMID: 27580383]
  • Shyamchand Mayengbam, James D House, Michel Aliani. Investigation of vitamin B₆ inadequacy, induced by exposure to the anti-B₆ factor 1-amino D-proline, on plasma lipophilic metabolites of rats: a metabolomics approach. European journal of nutrition. 2016 Apr; 55(3):1213-23. doi: 10.1007/s00394-015-0934-x. [PMID: 26009005]
  • Gergő Horváth, Ákos Bencsura, Ágnes Simon, Gregory P Tochtrop, Gregory T DeKoster, Douglas F Covey, David P Cistola, Orsolya Toke. Structural determinants of ligand binding in the ternary complex of human ileal bile acid binding protein with glycocholate and glycochenodeoxycholate obtained from solution NMR. The FEBS journal. 2016 Feb; 283(3):541-55. doi: 10.1111/febs.13610. [PMID: 26613247]
  • Guixia Ling, Tianhong Zhang, Peng Zhang, Jin Sun, Zhonggui He. Synergistic and complete reversal of the multidrug resistance of mitoxantrone hydrochloride by three-in-one multifunctional lipid-sodium glycocholate nanocarriers based on simultaneous BCRP and Bcl-2 inhibition. International journal of nanomedicine. 2016 ; 11(?):4077-91. doi: 10.2147/ijn.s95767. [PMID: 27601896]
  • James E Heubi, Kenneth D R Setchell, Pinky Jha, Donna Buckley, Wujuan Zhang, Philip Rosenthal, Carol Potter, Simon Horslen, David Suskind. Treatment of bile acid amidation defects with glycocholic acid. Hepatology (Baltimore, Md.). 2015 Jan; 61(1):268-74. doi: 10.1002/hep.27401. [PMID: 25163551]
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