Reverse-triiodthyronine (BioDeep_00000006558)

 

Secondary id: BioDeep_00000415895

human metabolite


代谢物信息卡片


2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid

化学式: C15H12I3NO4 (650.7900602)
中文名称: 3,3,5-三碘- L -甲状腺氨酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)I)OC2=CC(=C(C(=C2)I)O)I
InChI: InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)

描述信息

This compound belongs to the family of Phenylpropanoic Acids. These are compounds whose structure contain a benzene ring conjugated to a propanoic acid.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

13 个代谢物同义名

2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid; 4-(4-Hydroxy-3,5-diiodophenoxy)-3-iodophenylalanine; O-(4-Hydroxy-3,5-diiodophenyl)-3-iodotyrosine; Reverse triiodothyronine (rT3); Reverse T3 thyroid hormone; 3,3,5-Triiodo-L-thyronine; Triiodothyronine, reverse; DL-3,3,5-Triiodothyronine; Reverse triiodothyronine; Reverse-triiodthyronine; 3,3,5-triiodothyronine; 3,3,5-Triiodothyronine; 3,3,5 Triiodothyronine



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(7)

BioCyc(0)

PlantCyc(0)

代谢反应

101 个相关的代谢反应过程信息。

Reactome(101)

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

  • Davide Corinti, Barbara Chiavarino, Mattia Spano, Aura Tintaru, Simonetta Fornarini, Maria Elisa Crestoni. Molecular Basis for the Remarkably Different Gas-Phase Behavior of Deprotonated Thyroid Hormones Triiodothyronine (T3) and Reverse Triiodothyronine (rT3): A Clue for Their Discrimination?. Analytical chemistry. 2021 11; 93(44):14869-14877. doi: 10.1021/acs.analchem.1c03892. [PMID: 34714056]
  • David J Halsall, Susan Oddy. Clinical and laboratory aspects of 3,3',5'-triiodothyronine (reverse T3). Annals of clinical biochemistry. 2021 01; 58(1):29-37. doi: 10.1177/0004563220969150. [PMID: 33040575]
  • Eleonore Fröhlich, Richard Wahl. Physiological Role and Use of Thyroid Hormone Metabolites - Potential Utility in COVID-19 Patients. Frontiers in endocrinology. 2021; 12(?):587518. doi: 10.3389/fendo.2021.587518. [PMID: 33981284]
  • Liam McKeever, Sarah J Peterson, Omar Lateef, Sally Freels, Tatiana L Fonseca, Barbara M L C Bocco, Gustavo W Fernandes, Kelly Roehl, Kristen Nowak, Marisa Mozer, Antonio C Bianco, Carol A Braunschweig. Higher Caloric Exposure in Critically Ill Patients Transiently Accelerates Thyroid Hormone Activation. The Journal of clinical endocrinology and metabolism. 2020 02; 105(2):. doi: 10.1210/clinem/dgz077. [PMID: 31581295]
  • Hung-Yun Lin, Heng-Yuan Tang, Matthew Leinung, Shaker A Mousa, Aleck Hercbergs, Paul J Davis. Action of Reverse T3 on Cancer Cells. Endocrine research. 2019 Nov; 44(4):148-152. doi: 10.1080/07435800.2019.1600536. [PMID: 30943372]
  • Giuseppe Bello, Giorgia Spinazzola, Valentina Giammatteo, Luca Montini, Gennaro De Pascale, Alessandra Bisanti, Maria G Annetta, Eliana Troiani, Antonio Bianchi, Alfredo Pontecorvi, Mariano A Pennisi, Giorgio Conti, Massimo Antonelli. Effects of Thyroid Hormone Treatment on Diaphragmatic Efficiency in Mechanically Ventilated Subjects With Nonthyroidal Illness Syndrome. Respiratory care. 2019 Oct; 64(10):1199-1207. doi: 10.4187/respcare.06770. [PMID: 31015389]
  • Haruki Fujisawa, Julie Gagné, Alexandra M Dumitrescu, Samuel Refetoff. Very Severe Resistance to Thyroid Hormone β in One of Three Affected Members of a Family with a Novel Mutation in the THRB Gene. Thyroid : official journal of the American Thyroid Association. 2019 10; 29(10):1518-1520. doi: 10.1089/thy.2019.0095. [PMID: 31432759]
  • Jianrong Li, Ines Donangelo, Kiyomi Abe, Oscar Scremin, Sujie Ke, Feng Li, Anna Milanesi, Yan-Yun Liu, Gregory A Brent. Thyroid hormone treatment activates protective pathways in both in vivo and in vitro models of neuronal injury. Molecular and cellular endocrinology. 2017 09; 452(?):120-130. doi: 10.1016/j.mce.2017.05.023. [PMID: 28549992]
  • Qing Chang, Yue'e Peng, Lifen Yun, Qingxin Zhu, Shenghong Hu, Qin Shuai. Rapid Identification of Unknown Organic Iodine in Small-Volume Complex Biological Samples Based on Nanospray Mass Spectrometry Coupled with in-Tube Solid Phase Microextraction. Analytical chemistry. 2017 04; 89(7):4147-4152. doi: 10.1021/acs.analchem.7b00037. [PMID: 28287711]
  • Simon H S Pearce, Salman Razvi, Mohammad E Yadegarfar, Carmen Martin-Ruiz, Andrew Kingston, Joanna Collerton, Theo J Visser, Tom B Kirkwood, Carol Jagger. Serum Thyroid Function, Mortality and Disability in Advanced Old Age: The Newcastle 85+ Study. The Journal of clinical endocrinology and metabolism. 2016 11; 101(11):4385-4394. doi: 10.1210/jc.2016-1935. [PMID: 27552542]
  • Arnaldo Moura Neto, Maria Candida Ribeiro Parisi, Sarah Monte Alegre, Elizabeth Joao Pavin, Marcos Antonio Tambascia, Denise Engelbrecht Zantut-Wittmann. Relation of thyroid hormone abnormalities with subclinical inflammatory activity in patients with type 1 and type 2 diabetes mellitus. Endocrine. 2016 Jan; 51(1):63-71. doi: 10.1007/s12020-015-0651-5. [PMID: 26049370]
  • S Kahl, T H Elsasser, R P Rhoads, R J Collier, L H Baumgard. Environmental heat stress modulates thyroid status and its response to repeated endotoxin challenge in steers. Domestic animal endocrinology. 2015 Jul; 52(?):43-50. doi: 10.1016/j.domaniend.2015.02.001. [PMID: 25804834]
  • Andreas Jurik, Barbara Zdrazil, Marion Holy, Thomas Stockner, Harald H Sitte, Gerhard F Ecker. A binding mode hypothesis of tiagabine confirms liothyronine effect on γ-aminobutyric acid transporter 1 (GAT1). Journal of medicinal chemistry. 2015 Mar; 58(5):2149-58. doi: 10.1021/jm5015428. [PMID: 25679268]
  • Hiroyuki Sakai, Hidenori Nagao, Mamoru Sakurai, Takako Okumura, Yoshiyuki Nagai, Junpei Shikuma, Rokuro Ito, Tetsuya Imazu, Takashi Miwa, Masato Odawara. Correlation between Serum Levels of 3,3',5'-Triiodothyronine and Thyroid Hormones Measured by Liquid Chromatography-Tandem Mass Spectrometry and Immunoassay. PloS one. 2015; 10(10):e0138864. doi: 10.1371/journal.pone.0138864. [PMID: 26426328]
  • Julie Anne Lucie Kiebooms, Jella Wauters, Julie Vanden Bussche, Lynn Vanhaecke. Validated ultra high performance liquid chromatography-tandem mass spectrometry method for quantitative analysis of total and free thyroid hormones in bovine serum. Journal of chromatography. A. 2014 Jun; 1345(?):164-73. doi: 10.1016/j.chroma.2014.04.032. [PMID: 24786658]
  • Solomon Maximo Greenberg, Alfonso Massimiliano Ferrara, Everton S Nicholas, Alexandra M Dumitrescu, Vivian Cody, Roy E Weiss, Samuel Refetoff. A novel mutation in the Albumin gene (R218S) causing familial dysalbuminemic hyperthyroxinemia in a family of Bangladeshi extraction. Thyroid : official journal of the American Thyroid Association. 2014 Jun; 24(6):945-50. doi: 10.1089/thy.2013.0540. [PMID: 24494774]
  • Rosalba Senese, Federica Cioffi, Pieter de Lange, Fernando Goglia, Antonia Lanni. Thyroid: biological actions of 'nonclassical' thyroid hormones. The Journal of endocrinology. 2014 May; 221(2):R1-12. doi: 10.1530/joe-13-0573. [PMID: 24464019]
  • Jiao Fu, Alexandra M Dumitrescu. Inherited defects in thyroid hormone cell-membrane transport and metabolism. Best practice & research. Clinical endocrinology & metabolism. 2014 Mar; 28(2):189-201. doi: 10.1016/j.beem.2013.05.014. [PMID: 24629861]
  • Denisa Lobotková, Daniela Staníková, Juraj Staník, Ol'ga Cervenová, Vladimír Bzdúch, L'ubica Tichá. Lack of association between peripheral activity of thyroid hormones and elevated TSH levels in childhood obesity. Journal of clinical research in pediatric endocrinology. 2014; 6(2):100-4. doi: 10.4274/jcrpe.1251. [PMID: 24932603]
  • Ana Paula Zanatta, Leila Zanatta, Renata Gonçalves, Ariane Zamoner, Fátima Regina Mena Barreto Silva. Rapid responses to reverse T₃ hormone in immature rat Sertoli cells: calcium uptake and exocytosis mediated by integrin. PloS one. 2013; 8(10):e77176. doi: 10.1371/journal.pone.0077176. [PMID: 24130850]
  • Gergo Tóth, Béla Noszál. [Thyroid hormones and their precursors I. Biochemical properties]. Acta pharmaceutica Hungarica. 2013; 83(2):35-45. doi: . [PMID: 23926648]
  • A Sibilio, R Ambrosio, C Bonelli, M A De Stefano, V Torre, M Dentice, D Salvatore. Deiodination in cancer growth: the role of type III deiodinase. Minerva endocrinologica. 2012 Dec; 37(4):315-27. doi: NULL. [PMID: 23235188]
  • Annemieke J Lem, Yolanda B de Rijke, Hans van Toor, Maria A J de Ridder, Theo J Visser, Anita C S Hokken-Koelega. Serum thyroid hormone levels in healthy children from birth to adulthood and in short children born small for gestational age. The Journal of clinical endocrinology and metabolism. 2012 Sep; 97(9):3170-8. doi: 10.1210/jc.2012-1759. [PMID: 22736771]
  • Davide Gnocchi, Silvia Leoni, Sandra Incerpi, Giovannella Bruscalupi. 3,5,3'-triiodothyronine (T3) stimulates cell proliferation through the activation of the PI3K/Akt pathway and reactive oxygen species (ROS) production in chick embryo hepatocytes. Steroids. 2012 May; 77(6):589-95. doi: 10.1016/j.steroids.2012.01.022. [PMID: 22366194]
  • Peter H M Klaren, Edwin J W Geven, Anika Nagelkerke, Gert Flik. Kinetics and thiol requirements of iodothyronine 5'-deiodination are tissue-specific in common carp (Cyprinus carpio L.). Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2012 Mar; 161(3):275-82. doi: 10.1016/j.cbpb.2011.12.005. [PMID: 22198122]
  • Tatsuya Kunisue, Akifumi Eguchi, Hisato Iwata, Shinsuke Tanabe, Kurunthachalam Kannan. Analysis of thyroid hormones in serum of Baikal seals and humans by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and immunoassay methods: application of the LC-MS/MS method to wildlife tissues. Environmental science & technology. 2011 Dec; 45(23):10140-7. doi: 10.1021/es203002a. [PMID: 22035339]
  • Alessandro Marsili, Dan Tang, John W Harney, Prabhat Singh, Ann Marie Zavacki, Monica Dentice, Domenico Salvatore, P Reed Larsen. Type II iodothyronine deiodinase provides intracellular 3,5,3'-triiodothyronine to normal and regenerating mouse skeletal muscle. American journal of physiology. Endocrinology and metabolism. 2011 Nov; 301(5):E818-24. doi: 10.1152/ajpendo.00292.2011. [PMID: 21771965]
  • Alessandro Marsili, Edith Sanchez, Praful Singru, John W Harney, Ann Marie Zavacki, Ronald M Lechan, P R Larsen. Thyroxine-induced expression of pyroglutamyl peptidase II and inhibition of TSH release precedes suppression of TRH mRNA and requires type 2 deiodinase. The Journal of endocrinology. 2011 Oct; 211(1):73-8. doi: 10.1530/joe-11-0248. [PMID: 21788297]
  • Anita Kinne, Ralf Schülein, Gerd Krause. Primary and secondary thyroid hormone transporters. Thyroid research. 2011 Aug; 4 Suppl 1(?):S7. doi: 10.1186/1756-6614-4-s1-s7. [PMID: 21835054]
  • Tatsuya Kunisue, Jeffrey W Fisher, Kurunthachalam Kannan. Modulation of thyroid hormone concentrations in serum of rats coadministered with perchlorate and iodide-deficient diet. Archives of environmental contamination and toxicology. 2011 Jul; 61(1):151-8. doi: 10.1007/s00244-011-9677-8. [PMID: 21573761]
  • Hidenori Nagao, Tetsuya Imazu, Hiroyuki Hayashi, Kenjo Takahashi, Kouichi Minato. Influence of thyroidectomy on thyroxine metabolism and turnover rate in rats. The Journal of endocrinology. 2011 Jul; 210(1):117-23. doi: 10.1530/joe-10-0484. [PMID: 21478227]
  • Elena Grasselli, Adriana Voci, Laura Canesi, Fernando Goglia, Silvia Ravera, Isabella Panfoli, Gabriella Gallo, Laura Vergani. Non-receptor-mediated actions are responsible for the lipid-lowering effects of iodothyronines in FaO rat hepatoma cells. The Journal of endocrinology. 2011 Jul; 210(1):59-69. doi: 10.1530/joe-11-0074. [PMID: 21508094]
  • Joanna Boguslawska, Anna Wojcicka, Agnieszka Piekielko-Witkowska, Adam Master, Alicja Nauman. MiR-224 targets the 3'UTR of type 1 5'-iodothyronine deiodinase possibly contributing to tissue hypothyroidism in renal cancer. PloS one. 2011; 6(9):e24541. doi: 10.1371/journal.pone.0024541. [PMID: 21912701]
  • Helen Karga, Irene Giagourta, Garyphallia Papaioannou, Paraskevi Katsichti, Argyris Pardalakis, Georgia Kassi, Apostolia Zagoreou, Maria Triantaphyllopoulou, Cherry Zerva. Transient changes in thyroid functions tests after zoledronic acid infusion. Endocrine journal. 2011; 58(11):969-77. doi: 10.1507/endocrj.ej11-0039. [PMID: 21891972]
  • Jesper Svanfelt, Johan Eriksson, Leif Kronberg. Analysis of thyroid hormones in raw and treated waste water. Journal of chromatography. A. 2010 Oct; 1217(42):6469-74. doi: 10.1016/j.chroma.2010.08.032. [PMID: 20850122]
  • Anita Kinne, Gunnar Kleinau, Carolin S Hoefig, Annette Grüters, Josef Köhrle, Gerd Krause, Ulrich Schweizer. Essential molecular determinants for thyroid hormone transport and first structural implications for monocarboxylate transporter 8. The Journal of biological chemistry. 2010 Sep; 285(36):28054-63. doi: 10.1074/jbc.m110.129577. [PMID: 20628049]
  • Dongli Wang, Heather M Stapleton. Analysis of thyroid hormones in serum by liquid chromatography-tandem mass spectrometry. Analytical and bioanalytical chemistry. 2010 Jul; 397(5):1831-9. doi: 10.1007/s00216-010-3705-9. [PMID: 20437035]
  • Bernt Rønning, Anne S Mortensen, Børge Moe, Olivier Chastel, Augustine Arukwe, Claus Bech. Food restriction in young Japanese quails: effects on growth, metabolism, plasma thyroid hormones and mRNA species in the thyroid hormone signalling pathway. The Journal of experimental biology. 2009 Oct; 212(19):3060-7. doi: 10.1242/jeb.029835. [PMID: 19749098]
  • E Forestier, S Vinzio, R Sapin, J L Schlienger, B Goichot. Increased reverse triiodothyronine is associated with shorter survival in independently-living elderly: the Alsanut study. European journal of endocrinology. 2009 Feb; 160(2):207-14. doi: 10.1530/eje-08-0519. [PMID: 19001060]
  • W Edward Visser, Jurgen Jansen, Edith C H Friesema, Monique H A Kester, Edna Mancilla, Johan Lundgren, Marjo S van der Knaap, Roelineke J Lunsing, Oebele F Brouwer, Theo J Visser. Novel pathogenic mechanism suggested by ex vivo analysis of MCT8 (SLC16A2) mutations. Human mutation. 2009 Jan; 30(1):29-38. doi: 10.1002/humu.20808. [PMID: 18636565]
  • Yves Debaveye, Björn Ellger, Liese Mebis, Theo J Visser, Veerle M Darras, Greet Van den Berghe. Effects of substitution and high-dose thyroid hormone therapy on deiodination, sulfoconjugation, and tissue thyroid hormone levels in prolonged critically ill rabbits. Endocrinology. 2008 Aug; 149(8):4218-28. doi: 10.1210/en.2007-1566. [PMID: 18450965]
  • Michelle Y Monette, Björn Thrandur Björnsson, Stephen D McCormick. Effects of short-term acid and aluminum exposure on the parr-smolt transformation in Atlantic salmon (Salmo salar): disruption of seawater tolerance and endocrine status. General and comparative endocrinology. 2008 Aug; 158(1):122-30. doi: 10.1016/j.ygcen.2008.05.014. [PMID: 18606407]
  • Paul J Davis, Jack L Leonard, Faith B Davis. Mechanisms of nongenomic actions of thyroid hormone. Frontiers in neuroendocrinology. 2008 May; 29(2):211-8. doi: 10.1016/j.yfrne.2007.09.003. [PMID: 17983645]
  • Sing-Yung Wu, Daniel H Polk, Wen-Sheng Huang, Eugene Ho, Jaffer M Kattan, Delbert A Fisher. 3'-monoiodothyronine sulfate and Triac sulfate are thyroid hormone metabolites in developing sheep. Pediatric research. 2008 Feb; 63(2):149-53. doi: 10.1203/pdr.0b013e31815f6551. [PMID: 18091342]
  • Maria Moreno, Pieter de Lange, Assunta Lombardi, Elena Silvestri, Antonia Lanni, Fernando Goglia. Metabolic effects of thyroid hormone derivatives. Thyroid : official journal of the American Thyroid Association. 2008 Feb; 18(2):239-53. doi: 10.1089/thy.2007.0248. [PMID: 18279024]
  • María Clemente, Pilar Ruiz-Cuevas, Antonio Carrascosa, Neus Potau, Jordi Almar, Salvador Salcedo, Diego Yeste. Thyroid function in preterm infants 27-29 weeks of gestational age during the first four months of life: results from a prospective study comprising 80 preterm infants. Journal of pediatric endocrinology & metabolism : JPEM. 2007 Dec; 20(12):1269-80. doi: 10.1515/jpem.2007.20.12.1269. [PMID: 18341087]
  • I Cassar-Malek, B Picard, S Kahl, J F Hocquette. Relationships between thyroid status, tissue oxidative metabolism, and muscle differentiation in bovine fetuses. Domestic animal endocrinology. 2007 Jul; 33(1):91-106. doi: 10.1016/j.domaniend.2006.04.011. [PMID: 16797912]
  • Peter H M Klaren, José M Guzmán, Sjoerd J Reutelingsperger, Juan M Mancera, Gert Flik. Low salinity acclimation and thyroid hormone metabolizing enzymes in gilthead seabream (Sparus auratus). General and comparative endocrinology. 2007 Jun; 152(2-3):215-22. doi: 10.1016/j.ygcen.2007.02.010. [PMID: 17382943]
  • Robin P Peeters, Wendy M van der Deure, Annewieke W van den Beld, Hans van Toor, Steven W J Lamberts, Joop A M J L Janssen, André G Uitterlinden, Theo J Visser. The Asp727Glu polymorphism in the TSH receptor is associated with insulin resistance in healthy elderly men. Clinical endocrinology. 2007 Jun; 66(6):808-15. doi: 10.1111/j.1365-2265.2007.02817.x. [PMID: 17408423]
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  • M P C Siroen, M A E van Bokhorst-de van der Schueren, M C Richir, H P Sauerwein, C R Leemans, J J Quak, P A M van Leeuwen. The prognostic value of severe malnutrition in the development of nonthyroidal illness in head and neck cancer patients. JPEN. Journal of parenteral and enteral nutrition. 2006 Sep; 30(5):415-20. doi: 10.1177/0148607106030005415. [PMID: 16931610]
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  • Mohammad Hassan Eftekhari, Seyed Ali Keshavarz, Mahmood Jalali, Eric Elguero, Mohammad R Eshraghian, Kirsten B Simondon. The relationship between iron status and thyroid hormone concentration in iron-deficient adolescent Iranian girls. Asia Pacific journal of clinical nutrition. 2006; 15(1):50-5. doi: NULL. [PMID: 16500878]
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  • Robin P Peeters, Serge van der Geyten, Pieter J Wouters, Veerle M Darras, Hans van Toor, Ellen Kaptein, Theo J Visser, Greet Van den Berghe. Tissue thyroid hormone levels in critical illness. The Journal of clinical endocrinology and metabolism. 2005 Dec; 90(12):6498-507. doi: 10.1210/jc.2005-1013. [PMID: 16174716]
  • Peter H M Klaren, Remco Haasdijk, Juriaan R Metz, Lisette M C Nitsch, Veerle M Darras, Serge Van der Geyten, Gert Flik. Characterization of an iodothyronine 5'-deiodinase in gilthead seabream (Sparus auratus) that is inhibited by dithiothreitol. Endocrinology. 2005 Dec; 146(12):5621-30. doi: 10.1210/en.2005-0050. [PMID: 16166227]
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