L-Thyronine (BioDeep_00000026907)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid

化学式: C15H15NO4 (273.100103)
中文名称: L-甲状腺原氨酸, 甲状腺原氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.1%

分子结构信息

SMILES: C1=CC(=CC=C1CC(C(=O)O)N)OC2=CC=C(C=C2)O
InChI: InChI=1S/C15H15NO4/c16-14(15(18)19)9-10-1-5-12(6-2-10)20-13-7-3-11(17)4-8-13/h1-8,14,17H,9,16H2,(H,18,19)/t14-/m0/s1

描述信息

Thyronine (T0) is a de-iodinated form of thyroxine. Thyronine are a group of metabolites derived from thyroxine and triiodothyronine via the peripheral enzymatic removal of iodines from the thyroxine nucleus. Thyronine is the thyroxine nucleus devoid of its four iodine atoms. Thyronine (T0) has been identified in human urine. In 22 normal individuals urinary thyronine concentrations were found to range between 8-25 nmol‚ÅÑ24h (PMID: 479355). Thyronine is thought to be a byproduct of thyroxine metabolism and arises through the action of thyroxine deiodinases.
Iodide is actively absorbed from the bloodstream and concentrated in the thyroid follicles. (If there is a deficiency of dietary iodine, the thyroid enlarges in an attempt to trap more iodine, resulting in goitre.) Via a reaction with the enzyme thyroperoxidase, iodine is covalently bound to tyrosine residues in the thyroglobulin molecules, forming monoiodotyrosine (MIT) and diiodotyrosine (DIT). Linking two moieties of DIT produces thyroxine. Combining one particle of MIT and one particle of DIT produces triiodothyronine.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

12 个代谢物同义名

(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid; beta-(p-Hydroxyphenoxy)phenylalanine; 4-(4-Hydroxyphenoxy)-L-phenylalanine; b-(p-Hydroxyphenoxy)phenylalanine; O-(4-Hydroxyphenyl)-L-tyrosine; O-(4-Hydroxyphenyl)tyrosine; Desiodothyroxine; DL-THYRONINE; L-Thyronine; Thyronines; thyronine; Thyronine



数据库引用编号

9 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

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

  • Tian-Ci Yan, Hong-Hua Zhang, Jun Cao, Li-Hong Ye. Analysis of iodinated amino acids by microemulsion electrokinetic chromatography using aliphatic amine as a cosurfactant. Journal of chromatography. A. 2022 Dec; 1685(?):463644. doi: 10.1016/j.chroma.2022.463644. [PMID: 36403518]
  • Zhong-Min Li, Manuel Miller, Sogol Gachkar, Jens Mittag, Sonja C Schriever, Paul T Pfluger, Karl-Werner Schramm, Meri De Angelis. Determination of 3-iodothyronamine (3-T1AM) in mouse liver using liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Feb; 1165(?):122553. doi: 10.1016/j.jchromb.2021.122553. [PMID: 33503577]
  • Carla Moran, Christoph Seger, Kevin Taylor, Susan Oddy, Keith Burling, Odelia Rajanayagam, Louise Fairall, Anne McGowan, Greta Lyons, David Halsall, Mark Gurnell, John Schwabe, Krishna Chatterjee, Christopher Strey. Hyperthyroxinemia and Hypercortisolemia due to Familial Dysalbuminemia. Thyroid : official journal of the American Thyroid Association. 2020 11; 30(11):1681-1684. doi: 10.1089/thy.2020.0315. [PMID: 32669045]
  • Riccardo Zucchi. Thyroid Hormone Analogues: An Update. Thyroid : official journal of the American Thyroid Association. 2020 08; 30(8):1099-1105. doi: 10.1089/thy.2020.0071. [PMID: 32098589]
  • M Kim, K Park, I Choi. The metabolic suppressor 3-iodothyronamine enhances lipolysis in 3T3-L1 adipocytes via activation of the adenosine monophosphate-activated protein kinase/forkhead box O1 signaling pathway. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2020 Jun; 71(3):. doi: 10.26402/jpp.2020.3.12. [PMID: 33077693]
  • Haiyan Zhou, Bailong Hu, Xingde Liu. Thyroid Hormone Metabolite 3-Iodothyronamine (T1AM) Alleviates Hypoxia/Reoxygenation-Induced Cardiac Myocyte Apoptosis via Akt/FoxO1 Pathway. Medical science monitor : international medical journal of experimental and clinical research. 2020 Mar; 26(?):e923195. doi: 10.12659/msm.923195. [PMID: 32162616]
  • Lorenza Bellusci, Massimiliano Runfola, Vittoria Carnicelli, Simona Sestito, Federica Fulceri, Filippo Santucci, Paola Lenzi, Francesco Fornai, Simona Rapposelli, Nicola Origlia, Riccardo Zucchi, Grazia Chiellini. Endogenous 3-Iodothyronamine (T1AM) and Synthetic Thyronamine-like Analog SG-2 Act as Novel Pleiotropic Neuroprotective Agents Through the Modulation of SIRT6. Molecules (Basel, Switzerland). 2020 Feb; 25(5):. doi: 10.3390/molecules25051054. [PMID: 32110992]
  • Zhou Haiyan, Hu Bailong, Zhang Bei, Wang Yiming, Liu Xingde. Comparative Transcriptome Analysis Reveals the Potential Cardiovascular Protective Targets of the Thyroid Hormone Metabolite 3-Iodothyronamine (3-T1AM). BioMed research international. 2020; 2020(?):1302453. doi: 10.1155/2020/1302453. [PMID: 32685439]
  • Michael Rogowski, Lorenza Bellusci, Martina Sabatini, Simona Rapposelli, Shaikh M Rahman, Grazia Chiellini, Fariba M Assadi-Porter. Lipolytic Effects of 3-Iodothyronamine (T1AM) and a Novel Thyronamine-Like Analog SG-2 through the AMPK Pathway. International journal of molecular sciences. 2019 Aug; 20(16):. doi: 10.3390/ijms20164054. [PMID: 31434215]
  • Keith H Richards, Ray Monk, Kostja Renko, Daniel Rathmann, Eddy Rijntjes, Josef Köhrle. A combined LC-MS/MS and LC-MS3 multi-method for the quantification of iodothyronines in human blood serum. Analytical and bioanalytical chemistry. 2019 Aug; 411(21):5605-5616. doi: 10.1007/s00216-019-01941-9. [PMID: 31201460]
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  • Jeppe Lerche la Cour, Heidi M Christensen, Josef Köhrle, Ina Lehmphul, Caroline Kistorp, Birte Nygaard, Jens Faber. Association Between 3-Iodothyronamine (T1am) Concentrations and Left Ventricular Function in Chronic Heart Failure. The Journal of clinical endocrinology and metabolism. 2019 04; 104(4):1232-1238. doi: 10.1210/jc.2018-01466. [PMID: 30383216]
  • Salvatore Benvenga, Fabrizio Guarneri. Thyroid hormone binding motifs and iodination pattern of thyroglobulin. Frontiers in bioscience (Landmark edition). 2019 01; 24(2):212-230. doi: 10.2741/4714. [PMID: 30468652]
  • Fariba M Assadi-Porter, Hannah Reiland, Martina Sabatini, Leonardo Lorenzini, Vittoria Carnicelli, Micheal Rogowski, Ebru S Selen Alpergin, Marco Tonelli, Sandra Ghelardoni, Alessandro Saba, Riccardo Zucchi, Grazia Chiellini. Metabolic Reprogramming by 3-Iodothyronamine (T1AM): A New Perspective to Reverse Obesity through Co-Regulation of Sirtuin 4 and 6 Expression. International journal of molecular sciences. 2018 May; 19(5):. doi: 10.3390/ijms19051535. [PMID: 29786646]
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  • Ina Lehmphul, Carolin S Hoefig, Josef Köhrle. 3-Iodothyronamine reduces insulin secretion in vitro via a mitochondrial mechanism. Molecular and cellular endocrinology. 2018 01; 460(?):219-228. doi: 10.1016/j.mce.2017.07.026. [PMID: 28754352]
  • Josef Köhrle. Thyroid Hormones and Derivatives: Endogenous Thyroid Hormones and Their Targets. Methods in molecular biology (Clifton, N.J.). 2018; 1801(?):85-104. doi: 10.1007/978-1-4939-7902-8_9. [PMID: 29892819]
  • Susanne T Janssen, Onno E Janssen. Directional thyroid hormone distribution via the blood stream to target sites. Molecular and cellular endocrinology. 2017 Dec; 458(?):16-21. doi: 10.1016/j.mce.2017.02.037. [PMID: 28257828]
  • Leonardo Lorenzini, Sandra Ghelardoni, Alessandro Saba, Ginevra Sacripanti, Grazia Chiellini, Riccardo Zucchi. Recovery of 3-Iodothyronamine and Derivatives in Biological Matrixes: Problems and Pitfalls. Thyroid : official journal of the American Thyroid Association. 2017 10; 27(10):1323-1331. doi: 10.1089/thy.2017.0111. [PMID: 28859548]
  • Ebru S Selen Alpergin, Zeinab Bolandnazar, Martina Sabatini, Michael Rogowski, Grazia Chiellini, Riccardo Zucchi, Fariba M Assadi-Porter. Metabolic profiling reveals reprogramming of lipid metabolic pathways in treatment of polycystic ovary syndrome with 3-iodothyronamine. Physiological reports. 2017 Jan; 5(1):. doi: 10.14814/phy2.13097. [PMID: 28082426]
  • Nancy Schanze, Simon Friedrich Jacobi, Eddy Rijntjes, Stefan Mergler, Marta Del Olmo, Carolin Stephanie Hoefig, Noushafarin Khajavi, Ina Lehmphul, Heike Biebermann, Jens Mittag, Josef Köhrle. 3-Iodothyronamine Decreases Expression of Genes Involved in Iodide Metabolism in Mouse Thyroids and Inhibits Iodide Uptake in PCCL3 Thyrocytes. Thyroid : official journal of the American Thyroid Association. 2017 01; 27(1):11-22. doi: 10.1089/thy.2016.0182. [PMID: 27788620]
  • Carolin Stephanie Hoefig, Riccardo Zucchi, Josef Köhrle. Thyronamines and Derivatives: Physiological Relevance, Pharmacological Actions, and Future Research Directions. Thyroid : official journal of the American Thyroid Association. 2016 12; 26(12):1656-1673. doi: 10.1089/thy.2016.0178. [PMID: 27650974]
  • Lies Langouche, Ina Lehmphul, Sarah Vander Perre, Josef Köhrle, Greet Van den Berghe. Circulating 3-T1AM and 3,5-T2 in Critically Ill Patients: A Cross-Sectional Observational Study. Thyroid : official journal of the American Thyroid Association. 2016 12; 26(12):1674-1680. doi: 10.1089/thy.2016.0214. [PMID: 27676423]
  • 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]
  • Xiuju Li, Aruna Augustine, Difei Sun, Liang Li, Larry Fliegel. Activation of the Na+/H+ exchanger in isolated cardiomyocytes through β-Raf dependent pathways. Role of Thr653 of the cytosolic tail. Journal of molecular and cellular cardiology. 2016 Oct; 99(?):65-75. doi: 10.1016/j.yjmcc.2016.08.014. [PMID: 27555478]
  • Carolin S Hoefig, Simon F Jacobi, Amy Warner, Lisbeth Harder, Nancy Schanze, Björn Vennström, Jens Mittag. 3-Iodothyroacetic acid lacks thermoregulatory and cardiovascular effects in vivo. British journal of pharmacology. 2015 Jul; 172(13):3426-33. doi: 10.1111/bph.13131. [PMID: 25765843]
  • H Ju, H Shin, C Son, K Park, I Choi. 3-Iodothyronamine-mediated metabolic suppression increases the phosphorylation of AMPK and induces fuel choice toward lipid mobilization. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2015 Jul; 47(8):605-10. doi: 10.1055/s-0034-1394380. [PMID: 25372779]
  • Svetlana S Efimova, Ludmila V Schagina, Olga S Ostroumova. The influence of halogen derivatives of thyronine and fluorescein on the dipole potential of phospholipid membranes. The Journal of membrane biology. 2014 Aug; 247(8):739-45. doi: 10.1007/s00232-014-9703-7. [PMID: 25024118]
  • Claudia Musilli, Gaetano De Siena, Maria Elena Manni, Andrea Logli, Elisa Landucci, Riccardo Zucchi, Alessandro Saba, Riccardo Donzelli, Maria Beatrice Passani, Gustavo Provensi, Laura Raimondi. Histamine mediates behavioural and metabolic effects of 3-iodothyroacetic acid, an endogenous end product of thyroid hormone metabolism. British journal of pharmacology. 2014 Jul; 171(14):3476-84. doi: 10.1111/bph.12697. [PMID: 24641572]
  • 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]
  • Zahra Ghanian, Sepideh Maleki, Hannah Reiland, Daniel E Bütz, Grazia Chiellini, Fariba M Assadi-Porter, Fariba-Assadi Porter, Mahsa Ranji. Optical imaging of mitochondrial redox state in rodent models with 3-iodothyronamine. Experimental biology and medicine (Maywood, N.J.). 2014 Feb; 239(2):151-8. doi: 10.1177/1535370213510252. [PMID: 24302559]
  • Fleur van der Valk, Carlijne Hassing, Maartje Visser, Purav Thakkar, Anookh Mohanan, Kaushal Pathak, Chaitanya Dutt, Vijay Chauthaiwale, Mariette Ackermans, Aart Nederveen, Mireille Serlie, Max Nieuwdorp, Erik Stroes. The effect of a diiodothyronine mimetic on insulin sensitivity in male cardiometabolic patients: a double-blind randomized controlled trial. PloS one. 2014; 9(2):e86890. doi: 10.1371/journal.pone.0086890. [PMID: 24586256]
  • G Lakshmi Kumari, Sachin Kumar, Satish Gupta, Anuradha Saini, Sudesh K Sharma, Navneet Kaur. Influence of iodothyronine conjugates of bovine serum albumin and horseradish peroxidase on enzyme immunosorbent assay of thyroid hormones. Journal of immunoassay & immunochemistry. 2014; 35(2):139-56. doi: 10.1080/15321819.2013.824899. [PMID: 24295178]
  • Veronica Mariotti, Erika Melissari, Caterina Iofrida, Marco Righi, Manuela Di Russo, Riccardo Donzelli, Alessandro Saba, Sabina Frascarelli, Grazia Chiellini, Riccardo Zucchi, Silvia Pellegrini. Modulation of gene expression by 3-iodothyronamine: genetic evidence for a lipolytic pattern. PloS one. 2014; 9(11):e106923. doi: 10.1371/journal.pone.0106923. [PMID: 25379707]
  • J A Haviland, H Reiland, D E Butz, M Tonelli, W P Porter, R Zucchi, T S Scanlan, G Chiellini, F M Assadi-Porter. NMR-based metabolomics and breath studies show lipid and protein catabolism during low dose chronic T(1)AM treatment. Obesity (Silver Spring, Md.). 2013 Dec; 21(12):2538-44. doi: 10.1002/oby.20391. [PMID: 23512955]
  • Ariel A Petruk, Marcelo C Sosa Morales, Rosa M S Álvarez. Iodothyronine-phospholipid interactions in the lipid gel phase probed by Raman spectral markers. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2013 Aug; 112(?):403-9. doi: 10.1016/j.saa.2013.04.094. [PMID: 23694898]
  • Ke-fan Miao, Wei Duan, Yan Qian, Da-qing Chen. [Analysis of influencing factors of transient hypothyroxinemia and low T3 syndrome in premature infants]. Zhonghua er ke za zhi = Chinese journal of pediatrics. 2013 Aug; 51(8):607-11. doi: NULL. [PMID: 24225293]
  • Maria Elena Manni, Gaetano De Siena, Alessandro Saba, Maja Marchini, Elisa Landucci, Elisabetta Gerace, Marina Zazzeri, Claudia Musilli, Domenico Pellegrini-Giampietro, Rosanna Matucci, Riccardo Zucchi, Laura Raimondi. Pharmacological effects of 3-iodothyronamine (T1AM) in mice include facilitation of memory acquisition and retention and reduction of pain threshold. British journal of pharmacology. 2013 Jan; 168(2):354-62. doi: 10.1111/j.1476-5381.2012.02137.x. [PMID: 22889145]
  • Sarah A Hackenmueller, Thomas S Scanlan. Identification and quantification of 3-iodothyronamine metabolites in mouse serum using liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2012 Sep; 1256(?):89-97. doi: 10.1016/j.chroma.2012.07.052. [PMID: 22885046]
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