Sobetirome (BioDeep_00000014884)
Secondary id: BioDeep_00000858956
human metabolite blood metabolite Volatile Flavor Compounds
代谢物信息卡片
2-(4-{[4-hydroxy-3-(propan-2-yl)phenyl]methyl}-3,5-dimethylphenoxy)acetic acid
化学式: C20H24O4 (328.1674504)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 1.15%
分子结构信息
SMILES: CC(C)C1=C(O)C=CC(CC2=C(C)C=C(OCC(O)=O)C=C2C)=C1
InChI: InChI=1S/C20H24O4/c1-12(2)17-9-15(5-6-19(17)21)10-18-13(3)7-16(8-14(18)4)24-11-20(22)23/h5-9,12,21H,10-11H2,1-4H3,(H,22,23)
描述信息
C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent
Same as: D09381
同义名列表
13 个代谢物同义名
2-(4-{[4-hydroxy-3-(propan-2-yl)phenyl]methyl}-3,5-dimethylphenoxy)acetic acid; 2-(4-{[4-hydroxy-3-(propan-2-yl)phenyl]methyl}-3,5-dimethylphenoxy)acetate; 4-[(4-hydroxy-3-isopropylphenyl)methyl]-3,5-dimethylphenoxyacetic acid; {4-[4-hydroxy-3-(1-methylethyl)benzyl]-3,5-dimethylphenoxy}acetate; (3,5-Dimethyl-4-(4-hydoxy-3-isopropylbenzyl)phenoxy)acetic acid; GC-1 Compound; GC 1 Compound; Sobetirome; GC-1 CPD; QRX 431; QRX-431; GC-1; Sobetirome
数据库引用编号
13 个数据库交叉引用编号
- ChEBI: CHEBI:79988
- KEGG: C15618
- PubChem: 9862248
- HMDB: HMDB0258355
- Metlin: METLIN70980
- DrugBank: DB07425
- ChEMBL: CHEMBL107400
- chemspider: 8037944
- CAS: 211110-63-3
- PubChem: 17396609
- PDB-CCD: B72
- NIKKAJI: J1.430.329D
- KNApSAcK: 79988
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)
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
- Wanqian Guo, Chenping Kang, Xiaoxia Wang, Haoran Zhang, Lilan Yuan, Xuetao Wei, Qianqian Xiao, Weidong Hao. Chlorocholine chloride exposure induced spermatogenic dysfunction via iron overload caused by AhR/PERK axis-dependent ferritinophagy activation.
Ecotoxicology and environmental safety.
2024 Apr; 274(?):116193. doi:
10.1016/j.ecoenv.2024.116193. [PMID: 38460407] - Xiaoxia Wang, Chenping Kang, Wanqian Guo, Lilan Yuan, Haoran Zhang, Qiong Zhang, Qianqian Xiao, Weidong Hao. Chlormequat chloride induced activation of calmodulin mediated PI3K/AKT signaling pathway led to impaired sperm quality in pubertal mice.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2024 Jan; 185(?):114475. doi:
10.1016/j.fct.2024.114475. [PMID: 38286265] - 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] - Meredith D Hartley, Mitra D Shokat, Margaret J DeBell, Tania Banerji, Lisa L Kirkemo, Thomas S Scanlan. Pharmacological Complementation Remedies an Inborn Error of Lipid Metabolism.
Cell chemical biology.
2020 05; 27(5):551-559.e4. doi:
10.1016/j.chembiol.2020.02.008. [PMID: 32169163] - Karis Kosar, Pamela Cornuet, Sucha Singh, Silvia Liu, Kari Nejak-Bowen. The Thyromimetic Sobetirome (GC-1) Alters Bile Acid Metabolism in a Mouse Model of Hepatic Cholestasis.
The American journal of pathology.
2020 05; 190(5):1006-1017. doi:
10.1016/j.ajpath.2020.01.015. [PMID: 32205094] - Rosalba Senese, Federica Cioffi, Giuseppe Petito, Fernando Goglia, Antonia Lanni. Thyroid hormone metabolites and analogues.
Endocrine.
2019 10; 66(1):105-114. doi:
10.1007/s12020-019-02025-5. [PMID: 31359245] - Mark Barahman, Wei Zhang, Hillary Yaffe Harris, Anita Aiyer, Rafi Kabarriti, Milan Kinkhabwala, Namita Roy-Chowdhury, Amanda P Beck, Thomas S Scanlan, Jayanta Roy-Chowdhury, Patrik Asp, Chandan Guha. Radiation-primed hepatocyte transplantation in murine monogeneic dyslipidemia normalizes cholesterol and prevents atherosclerosis.
Journal of hepatology.
2019 06; 70(6):1170-1179. doi:
10.1016/j.jhep.2019.01.010. [PMID: 30654068] - Soledad Bárez-López, Meredith D Hartley, Carmen Grijota-Martínez, Thomas S Scanlan, Ana Guadaño-Ferraz. Sobetirome and its Amide Prodrug Sob-AM2 Exert Thyromimetic Actions in Mct8-Deficient Brain.
Thyroid : official journal of the American Thyroid Association.
2018 09; 28(9):1211-1220. doi:
10.1089/thy.2018.0008. [PMID: 29845892] - Amedeo Columbano, Grazia Chiellini, Marta Anna Kowalik. GC-1: A Thyromimetic With Multiple Therapeutic Applications in Liver Disease.
Gene expression.
2017 11; 17(4):265-275. doi:
10.3727/105221617x14968563796227. [PMID: 28635586] - Carly S Filgueira, Andrea Ballerini, Eugenia Nicolov, Corrine Ying Xuan Chua, Priya Jain, Zachary W Smith, April L Gilbert, Francesco Scaglione, Alessandro Grattoni. A pharmacokinetic study of GC-1 delivery using a nanochannel membrane device.
Nanomedicine : nanotechnology, biology, and medicine.
2017 07; 13(5):1739-1744. doi:
10.1016/j.nano.2017.02.012. [PMID: 28259802] - C S Filgueira, E Nicolov, R L Hood, A Ballerini, J Garcia-Huidobro, J Z Lin, D Fraga, P Webb, O M Sabek, A O Gaber, K J Phillips, A Grattoni. Sustained zero-order delivery of GC-1 from a nanochannel membrane device alleviates metabolic syndrome.
International journal of obesity (2005).
2016 11; 40(11):1776-1783. doi:
10.1038/ijo.2016.129. [PMID: 27460601] - K Kannisto, S Rehnmark, K Slätis, P Webb, L Larsson, M Gåfvels, G Eggertsen, P Parini. The thyroid receptor β modulator GC-1 reduces atherosclerosis in ApoE deficient mice.
Atherosclerosis.
2014 Dec; 237(2):544-54. doi:
10.1016/j.atherosclerosis.2014.09.035. [PMID: 25463087] - Martha J Kelly, Sherrie Pietranico-Cole, J Douglas Larigan, Nancy-Ellen Haynes, Charles H Reynolds, Nathan Scott, John Vermeulen, Mark Dvorozniak, Karin Conde-Knape, Kuo-Sen Huang, Sung-Sau So, Kshitij Thakkar, Yimin Qian, Bruce Banner, Frank Mennona, Sara Danzi, Irwin Klein, Rebecca Taub, Jefferson Tilley. Discovery of 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yloxy)phenyl]-3,5-dioxo-2,3,4,5-tetrahydro[1,2,4]triazine-6-carbonitrile (MGL-3196), a Highly Selective Thyroid Hormone Receptor β agonist in clinical trials for the treatment of dyslipidemia.
Journal of medicinal chemistry.
2014 May; 57(10):3912-23. doi:
10.1021/jm4019299. [PMID: 24712661] - Naoki Takahashi, Yukiyasu Asano, Koji Maeda, Nobuhide Watanabe. In vivo evaluation of 1-benzyl-4-aminoindole-based thyroid hormone receptor β agonists: importance of liver selectivity in drug discovery.
Biological & pharmaceutical bulletin.
2014; 37(7):1103-8. doi:
10.1248/bpb.b13-00915. [PMID: 24989002] - Daniel F Vatner, Dirk Weismann, Sara A Beddow, Naoki Kumashiro, Derek M Erion, Xiao-Hui Liao, Gary J Grover, Paul Webb, Kevin J Phillips, Roy E Weiss, Jonathan S Bogan, John Baxter, Gerald I Shulman, Varman T Samuel. Thyroid hormone receptor-β agonists prevent hepatic steatosis in fat-fed rats but impair insulin sensitivity via discrete pathways.
American journal of physiology. Endocrinology and metabolism.
2013 Jul; 305(1):E89-100. doi:
10.1152/ajpendo.00573.2012. [PMID: 23651850] - Miles E Matsen, Joshua P Thaler, Brent E Wisse, Stephan J Guyenet, Thomas H Meek, Kayoko Ogimoto, Alex Cubelo, Jonathan D Fischer, Karl J Kaiyala, Michael W Schwartz, Gregory J Morton. In uncontrolled diabetes, thyroid hormone and sympathetic activators induce thermogenesis without increasing glucose uptake in brown adipose tissue.
American journal of physiology. Endocrinology and metabolism.
2013 Apr; 304(7):E734-46. doi:
10.1152/ajpendo.00488.2012. [PMID: 23384771] - Gergo Tóth, Béla Noszál. [Thyroid hormones and their precursors I. Biochemical properties].
Acta pharmaceutica Hungarica.
2013; 83(2):35-45. doi:
. [PMID: 23926648] - Jean Z Lin, Alexandro J Martagón, Willa A Hsueh, John D Baxter, Jan-Åke Gustafsson, Paul Webb, Kevin J Phillips. Thyroid hormone receptor agonists reduce serum cholesterol independent of the LDL receptor.
Endocrinology.
2012 Dec; 153(12):6136-44. doi:
10.1210/en.2011-2081. [PMID: 23087171] - Ivan Tancevski, Egon Demetz, Philipp Eller. Sobetirome: a selective thyromimetic for the treatment of dyslipidemia.
Recent patents on cardiovascular drug discovery.
2011 Jan; 6(1):16-9. doi:
10.2174/157489011794578473. [PMID: 21208155] - Federica Cioffi, Antonia Lanni, Fernando Goglia. Thyroid hormones, mitochondrial bioenergetics and lipid handling.
Current opinion in endocrinology, diabetes, and obesity.
2010 Oct; 17(5):402-7. doi:
10.1097/med.0b013e32833cf354. [PMID: 20625286] - P Venditti, G Chiellini, L Di Stefano, G Napolitano, R Zucchi, A Columbano, T S Scanlan, S Di Meo. The TRbeta-selective agonist, GC-1, stimulates mitochondrial oxidative processes to a lesser extent than triiodothyronine.
The Journal of endocrinology.
2010 Jun; 205(3):279-89. doi:
10.1677/joe-10-0036. [PMID: 20360308] - Ivan Tancevski, Philipp Eller, Josef R Patsch, Andreas Ritsch. The resurgence of thyromimetics as lipid-modifying agents.
Current opinion in investigational drugs (London, England : 2000).
2009 Sep; 10(9):912-8. doi:
NULL. [PMID: 19705333] - P Venditti, G Chiellini, A Bari, L Di Stefano, R Zucchi, A Columbano, T S Scanlan, S Di Meo. T3 and the thyroid hormone beta-receptor agonist GC-1 differentially affect metabolic capacity and oxidative damage in rat tissues.
The Journal of experimental biology.
2009 Apr; 212(Pt 7):986-93. doi:
10.1242/jeb.021808. [PMID: 19282495] - Edward E Cable, Patricia D Finn, Jeffrey W Stebbins, Jinzhao Hou, Bruce R Ito, Paul D van Poelje, David L Linemeyer, Mark D Erion. Reduction of hepatic steatosis in rats and mice after treatment with a liver-targeted thyroid hormone receptor agonist.
Hepatology (Baltimore, Md.).
2009 Feb; 49(2):407-17. doi:
10.1002/hep.22572. [PMID: 19072834] - Serge H Boyer, Hongjian Jiang, Jason D Jacintho, Mali Venkat Reddy, Haiqing Li, Wenyu Li, Jennifer L Godwin, William G Schulz, Edward E Cable, Jinzhao Hou, Rongrong Wu, James M Fujitaki, Scott J Hecker, Mark D Erion. Synthesis and biological evaluation of a series of liver-selective phosphonic acid thyroid hormone receptor agonists and their prodrugs.
Journal of medicinal chemistry.
2008 Nov; 51(22):7075-93. doi:
10.1021/jm800824d. [PMID: 18975928] - C Josseaume, Y Lorcy. [Thyroid hormone analogs: an important biological supply and new therapeutic possibilities].
Annales d'endocrinologie.
2008 Sep; 69 Suppl 1(?):S33-6. doi:
10.1016/s0003-4266(08)73966-0. [PMID: 18954857] - Andrea Perra, Gabriella Simbula, Michela Simbula, Monica Pibiri, Marta A Kowalik, Pia Sulas, Maria T Cocco, Giovanna M Ledda-Columbano, Amedeo Columbano. Thyroid hormone (T3) and TRbeta agonist GC-1 inhibit/reverse nonalcoholic fatty liver in rats.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2008 Aug; 22(8):2981-9. doi:
10.1096/fj.08-108464. [PMID: 18434432] - Jimena Manzano, Maria Cuadrado, Beatriz Morte, Juan Bernal. Influence of thyroid hormone and thyroid hormone receptors in the generation of cerebellar gamma-aminobutyric acid-ergic interneurons from precursor cells.
Endocrinology.
2007 Dec; 148(12):5746-51. doi:
10.1210/en.2007-0567. [PMID: 17761765] - Amedeo Columbano, Monica Pibiri, Manuela Deidda, Costanza Cossu, Thomas S Scanlan, Grazia Chiellini, Sandro Muntoni, Giovanna M Ledda-Columbano. The thyroid hormone receptor-beta agonist GC-1 induces cell proliferation in rat liver and pancreas.
Endocrinology.
2006 Jul; 147(7):3211-8. doi:
10.1210/en.2005-1561. [PMID: 16574785] - Shaker A Mousa, Laura J O'Connor, Joel J Bergh, Faith B Davis, Thomas S Scanlan, Paul J Davis. The proangiogenic action of thyroid hormone analogue GC-1 is initiated at an integrin.
Journal of cardiovascular pharmacology.
2005 Sep; 46(3):356-60. doi:
10.1097/01.fjc.0000175438.94906.a0. [PMID: 16116342] - Lisen Johansson, Mats Rudling, Thomas S Scanlan, Thomas Lundåsen, Paul Webb, John Baxter, Bo Angelin, Paolo Parini. Selective thyroid receptor modulation by GC-1 reduces serum lipids and stimulates steps of reverse cholesterol transport in euthyroid mice.
Proceedings of the National Academy of Sciences of the United States of America.
2005 Jul; 102(29):10297-302. doi:
10.1073/pnas.0504379102. [PMID: 16006512] - Fatima R S Freitas, Luciane P Capelo, Patrick J O'Shea, Vanda Jorgetti, Anselmo S Moriscot, Thomas S Scanlan, Graham R Williams, Telma M T Zorn, Cecilia H A Gouveia. The thyroid hormone receptor beta-specific agonist GC-1 selectively affects the bone development of hypothyroid rats.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research.
2005 Feb; 20(2):294-304. doi:
10.1359/jbmr.041116. [PMID: 15647824] - John D Baxter, Paul Webb, Gary Grover, Tom S Scanlan. Selective activation of thyroid hormone signaling pathways by GC-1: a new approach to controlling cholesterol and body weight.
Trends in endocrinology and metabolism: TEM.
2004 May; 15(4):154-7. doi:
10.1016/j.tem.2004.03.008. [PMID: 15109613] - Gary J Grover, Donald M Egan, Paul G Sleph, Blake C Beehler, Grazia Chiellini, Ngoc-Ha Nguyen, John D Baxter, Thomas S Scanlan. Effects of the thyroid hormone receptor agonist GC-1 on metabolic rate and cholesterol in rats and primates: selective actions relative to 3,5,3'-triiodo-L-thyronine.
Endocrinology.
2004 Apr; 145(4):1656-61. doi:
10.1210/en.2003-0973. [PMID: 14701670] - K Kinugawa, K Yonekura, R C Ribeiro, Y Eto, T Aoyagi, J D Baxter, S A Camacho, M R Bristow, C S Long, P C Simpson. Regulation of thyroid hormone receptor isoforms in physiological and pathological cardiac hypertrophy.
Circulation research.
2001 Sep; 89(7):591-8. doi:
10.1161/hh1901.096706. [PMID: 11577024] - S U Trost, E Swanson, B Gloss, D B Wang-Iverson, H Zhang, T Volodarsky, G J Grover, J D Baxter, G Chiellini, T S Scanlan, W H Dillmann. The thyroid hormone receptor-beta-selective agonist GC-1 differentially affects plasma lipids and cardiac activity.
Endocrinology.
2000 Sep; 141(9):3057-64. doi:
10.1210/endo.141.9.7681. [PMID: 10965874] - P A Schueler, H L Schwartz, K A Strait, C N Mariash, J H Oppenheimer. Binding of 3,5,3'-triiodothyronine (T3) and its analogs to the in vitro translational products of c-erbA protooncogenes: differences in the affinity of the alpha- and beta-forms for the acetic acid analog and failure of the human testis and kidney alpha-2 products to bind T3.
Molecular endocrinology (Baltimore, Md.).
1990 Feb; 4(2):227-34. doi:
10.1210/mend-4-2-227. [PMID: 2158622]