Goitrin (BioDeep_00000229763)

Main id: BioDeep_00000004093

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(5R)-5-ethenyl-1,3-oxazolidine-2-thione

化学式: C5H7NOS (129.02483320000002)
中文名称: DL-甲状腺肿素, 表告依春, (R)-5-乙烯基-2-恶唑啉硫酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=CC1CN=C(S)O1
InChI: InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)

描述信息

5-ethenyl-1,3-oxazolidine-2-thione is a member of the class of oxazolidines that is 1,3-oxazolidine substituted by sulfanylidene and ethenyl groups at positions 2 and 5, respectively. It is a member of oxazolidines and an olefinic compound.
DL-Goitrin is a natural product found in Isatis tinctoria with data available.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D013956 - Antithyroid Agents
D000890 - Anti-Infective Agents > D023303 - Oxazolidinones
(R)-goitrin is a 5-ethenyl-1,3-oxazolidine-2-thione that has R-configuration. It is a constituent of a traditional Chinese herbal medicine, Radix isatidis. It has a role as an antiviral agent and a plant metabolite. It is an enantiomer of a (S)-goitrin.
Epigoitrin is a natural product found in Isatis tinctoria, Diplotaxis harra, and other organisms with data available.
A 5-ethenyl-1,3-oxazolidine-2-thione that has R-configuration. It is a constituent of a traditional Chinese herbal medicine, Radix isatidis.
DL-Goitrin, also called (R, S)- report by the spring, consists of the epigoitrin (reported by the R- Spring) and the spring (-S- reported by spring), and the two mutually isomers, and the mixture is the ingredient of cruciferous vegetables[1].
DL-Goitrin, also called (R, S)- report by the spring, consists of the epigoitrin (reported by the R- Spring) and the spring (-S- reported by spring), and the two mutually isomers, and the mixture is the ingredient of cruciferous vegetables[1].
Epigoitrin is a natural alkaloid from Isatis tinctoria, with antiviral activities. Epigoitrin reduces susceptibility to influenza virus via mitochondrial antiviral signaling[1][2].
Epigoitrin is a natural alkaloid from Isatis tinctoria, with antiviral activities. Epigoitrin reduces susceptibility to influenza virus via mitochondrial antiviral signaling[1][2].

同义名列表

58 个代谢物同义名

2-OXAZOLIDINETHIONE, 5-ETHENYL-, (5S)-; 2-Oxazolidinethione, 5-vinyl-, DL-; 5-ethenyl-1,3-oxazolidine-2-thione; 5-Vinyl-1,3-oxazolidine-2-thione #; 5-vinyl-4,5-dihydrooxazol-2-thiol; 2-Oxazolidinethione, 5-ethenyl-; 5-vinyl-2-oxazolidine-2-thione; 2-OXAZOLIDINETHIONE, 5-VINYL-; 5-Ethenyl-2-oxazolidinethione; 5-vinyl-oxazolidine-2-thione; 5-vinyl-2-thiooxazolidinone; 5-vinyloxazolidine-2-thione; UZQVYLOFLQICCT-UHFFFAOYSA-N; 5-Vinyl-2-oxazolidinethione; 5-Vinyloxazolidone-2-thione; 5-vinyloxazolidin-2-thione; 5-vinyl-2-thiooxazolidone; 5-vinyloxazolidinethione; 5-vinylthiooxazolidone; goitrin, (+-)-isomer; goitrin, (R)-isomer; goitrin, (S)-isomer; (plusmn)-goitrin; UNII-O8KVD7J2P5; GOITRIN, (+/-)-; (+/-)-goitrin; ( -)-Goitrin; GOITRIN, DL-; (+-)-Goitrin; O8KVD7J2P5; Epigoitrin; DL-Goitrin; goitrin; (5R)-5-ethenyl-1,3-oxazolidine-2-thione; 2-Oxazolidinethione, 5-ethenyl-, (5R)-; 2-Oxazolidinethione, 5-ethenyl-, (R)-; (5r)-5-vinyl-1,3-oxazolidine-2-thione; 2-Oxazolidinethione, 5-vinyl-, (R)-; (R)-5-Ethenyl-2-oxazolidinethione; (r)-5-vinyloxazolidine-2-thione; (+)-5-VINYL-2-OXAZOLIDINETHIONE; (r)-5-vinyl-2-oxazolidinethione; R-5-Vinyl-2-oxazolidinethione; Epigoitrin (optically pure); Ethyl-p-methoxycinnamate; UNII-2N815D740R; GOITRIN, (+)-; ba-51-090278; BA 51-090278; GOITRIN, D-; EPI-GOITRIN; (R)-Goitrin; 2N815D740R; Epigotrin; AI3-52770; D-Goitrin; Goitrine; C5H7NOS



数据库引用编号

20 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)

22 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

  • Deqing Ruan, Jingyi Yang, Qianfei Luo, Yanhong Shi, Lili Ding, Zhengtao Wang, Rui Wang, Li Yang. The Protective Effects of Goitrin on LPS-Induced Septic Shock in C57BL/6J Mice via Caspase-11 Non-Canonical Inflammasome Inhibition. Molecules (Basel, Switzerland). 2023 Mar; 28(7):. doi: 10.3390/molecules28072883. [PMID: 37049646]
  • Mingming Li, Yang Xiao, Lianggui Xiao, Yu Li, Mengting Jia, Yu Sun, Tingli Pan, Lei Zhou, Yixing Li. Epigoitrin alleviates lipid and glucose metabolic disorders induced by a high-fat diet. Food & function. 2022 Jul; 13(13):7260-7273. doi: 10.1039/d2fo00242f. [PMID: 35723416]
  • Ru Zhao, Xinyu Yang, Aoqi Zhang, Tieyang Zhou, Yunwei Zhou, Lei Yang. An efficient approach for simultaneously obtaining oil and epigoitrin from Orychophragmus violaceus seeds by microwave-mediated immiscible binary solvent extraction. Food chemistry. 2022 Mar; 372(?):131258. doi: 10.1016/j.foodchem.2021.131258. [PMID: 34627086]
  • Li-Xing Nie, Yan-Lin Wu, Zhong Dai, Shuang-Cheng Ma. Antiviral activity of Isatidis Radix derived glucosinolate isomers and their breakdown products against influenza A in vitro/ovo and mechanism of action. Journal of ethnopharmacology. 2020 Apr; 251(?):112550. doi: 10.1016/j.jep.2020.112550. [PMID: 31918015]
  • Jinhang Li, Yanhong Shi, Yan Xu, Li Yang, Zhengtao Wang, Han Han, Rui Wang. Metabolic profiles and pharmacokinetics of goitrin in rats through liquid chromatography combined with electrospray ionization-tandem mass spectrometry. Biomedical chromatography : BMC. 2019 Oct; 33(10):e4606. doi: 10.1002/bmc.4606. [PMID: 31132308]
  • Yanhong Shi, Cheng Zheng, Jinhang Li, Li Yang, Zhengtao Wang, Rui Wang. Separation and Quantification of Four Main Chiral Glucosinolates in Radix Isatidis and Its Granules Using High-Performance Liquid Chromatography/Diode Array Detector Coupled with Circular Dichroism Detection. Molecules (Basel, Switzerland). 2018 May; 23(6):. doi: 10.3390/molecules23061305. [PMID: 29844266]
  • L P Zhu, J P Wang, X M Ding, S P Bai, Q F Zeng, Z W Su, Y Xuan, K Y Zhang. The Deposition and Elimination of Glucosinolate Metabolites Derived from Rapeseed Meal in Eggs of Laying Hens. Journal of agricultural and food chemistry. 2018 Feb; 66(6):1560-1568. doi: 10.1021/acs.jafc.7b05782. [PMID: 29345135]
  • Meike Siebers, Thomas Rohr, Marina Ventura, Vadim Schütz, Stephan Thies, Filip Kovacic, Karl-Erich Jaeger, Martin Berg, Peter Dörmann, Margot Schulz. Disruption of microbial community composition and identification of plant growth promoting microorganisms after exposure of soil to rapeseed-derived glucosinolates. PloS one. 2018; 13(7):e0200160. doi: 10.1371/journal.pone.0200160. [PMID: 29969500]
  • Liwei He, Fangtian Fan, Xianbang Hou, Hongyan Wu, Juan Wang, Huiqin Xu, Yun Sun. 4(3H)-Quinazolone regulates innate immune signaling upon respiratory syncytial virus infection by moderately inhibiting the RIG-1 pathway in RAW264.7 cell. International immunopharmacology. 2017 Nov; 52(?):245-252. doi: 10.1016/j.intimp.2017.09.010. [PMID: 28957692]
  • Xiaowei Huo, Chenqi Liu, Li Gao, Xudong Xu, Nailiang Zhu, Li Cao. Hepatoprotective Effect of Aqueous Extract from the Seeds of Orychophragmus violaceus against Liver Injury in Mice and HepG2 Cells. International journal of molecular sciences. 2017 Jun; 18(6):. doi: 10.3390/ijms18061197. [PMID: 28617329]
  • Peter Felker, Ronald Bunch, Angela M Leung. Concentrations of thiocyanate and goitrin in human plasma, their precursor concentrations in brassica vegetables, and associated potential risk for hypothyroidism. Nutrition reviews. 2016 Apr; 74(4):248-58. doi: 10.1093/nutrit/nuv110. [PMID: 26946249]
  • Ming-Ming Tan, Yong Huang, Xiao-Fei Xu, Zhuo-Neng Zhang, Qiao-Hua Deng. [Influence of drying method on content of epigoitrin and uridine in isatidis radix]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Apr; 37(4):578-80. doi: ". [PMID: 25345127]
  • Li-Na Ma, Cong-En Zhang, Dan Yan, Man-Rong Tan, Han-Bing Li, Le-Le Zhang, Yin Xiong, Xiao-He Xiao. [Screening bioactive compounds inhibiting influenza virus from isatidis radix by ultrafiltration mass spectrometry]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Mar; 39(5):812-6. doi: . [PMID: 25204170]
  • Si-Hui Nian, Chun-Yun Liu, Li-Min Liu, Li-Fen Yang. [The extraction technology of epigoitri from isatidis radix by supercritical CO2 fluid]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Jul; 36(7):1163-6. doi: ". [PMID: 24417156]
  • Qian-Qian Liu, Kang-Cai Wang, Chun-Hong Luo, Li-Si Zou. [Accumulation law of epigoitrin in roots of Isatis indigotica of different breed types]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Feb; 36(2):199-201. doi: ". [PMID: 23901642]
  • Zhiyong Xie, Yanhong Shi, Zhengtao Wang, Rui Wang, Yiming Li. Biotransformation of glucosinolates epiprogoitrin and progoitrin to (R)- and (S)-Goitrin in Radix isatidis. Journal of agricultural and food chemistry. 2011 Dec; 59(23):12467-72. doi: 10.1021/jf203321u. [PMID: 22023255]
  • Ishita Ahuja, Birgit Hafeld Borgen, Magnor Hansen, Bjørn Ivar Honne, Caroline Müller, Jens Rohloff, John Trevor Rossiter, Atle Magnar Bones. Oilseed rape seeds with ablated defence cells of the glucosinolate-myrosinase system. Production and characteristics of double haploid MINELESS plants of Brassica napus L. Journal of experimental botany. 2011 Oct; 62(14):4975-93. doi: 10.1093/jxb/err195. [PMID: 21778185]
  • Xiaoming Cai, Yan Zhang, Long Yu, Zhimou Guo, Xiuli Zhang, Xinmiao Liang. [Detection of drug-human serum albumin binding ratios of two Chinese medicinal ingredients by high performance affinity chromatography]. Se pu = Chinese journal of chromatography. 2011 Apr; 29(4):358-61. doi: 10.3724/sp.j.1123.2011.00358. [PMID: 21770248]
  • Stephen Wooding, Howard Gunn, Purita Ramos, Sophie Thalmann, Chao Xing, Wolfgang Meyerhof. Genetics and bitter taste responses to goitrin, a plant toxin found in vegetables. Chemical senses. 2010 Oct; 35(8):685-92. doi: 10.1093/chemse/bjq061. [PMID: 20551074]
  • Birgit Hafeld Borgen, Ole Petter Thangstad, Ishita Ahuja, John Trevor Rossiter, Atle Magnar Bones. Removing the mustard oil bomb from seeds: transgenic ablation of myrosin cells in oilseed rape (Brassica napus) produces MINELESS seeds. Journal of experimental botany. 2010 Jun; 61(6):1683-97. doi: 10.1093/jxb/erq039. [PMID: 20219777]
  • Claudia Voelckel, Mehdi Mirzaei, Michael Reichelt, Zhiwei Luo, Dana Pascovici, Peter B Heenan, Silvia Schmidt, Bart Janssen, Paul A Haynes, Peter J Lockhart. Transcript and protein profiling identify candidate gene sets of potential adaptive significance in New Zealand Pachycladon. BMC evolutionary biology. 2010 May; 10(?):151. doi: 10.1186/1471-2148-10-151. [PMID: 20482888]
  • Chunmei Gu, Hongbin Pan, Zewei Sun, Guixin Qin. Effect of soybean variety on anti-nutritional factors content, and growth performance and nutrients metabolism in rat. International journal of molecular sciences. 2010 Mar; 11(3):1048-56. doi: 10.3390/ijms11031048. [PMID: 20479998]
  • Ralph Kissen, Tom W Pope, Murray Grant, John A Pickett, John T Rossiter, Glen Powell. Modifying the alkylglucosinolate profile in Arabidopsis thaliana alters the tritrophic interaction with the herbivore Brevicoryne brassicae and parasitoid Diaeretiella rapae. Journal of chemical ecology. 2009 Aug; 35(8):958-69. doi: 10.1007/s10886-009-9677-6. [PMID: 19701726]
  • I Mewis, Ch Ulrlchs. Plant wounding affects the oviposition of Hellula undalis(F.). The impact of leaf chemistry. Communications in agricultural and applied biological sciences. 2004; 69(3):311-21. doi: ". [PMID: 15759429]
  • Marja Tolonen, Marianne Taipale, Britta Viander, Juha-Matti Pihlava, Hannu Korhonen, Eeva-Liisa Ryhänen. Plant-derived biomolecules in fermented cabbage. Journal of agricultural and food chemistry. 2002 Nov; 50(23):6798-803. doi: 10.1021/jf0109017. [PMID: 12405778]
  • S Galletti, R Bernardi, O Leoni, P Rollin, S Palmieri. Preparation and biological activity of four epiprogoitrin myrosinase-derived products. Journal of agricultural and food chemistry. 2001 Jan; 49(1):471-6. doi: 10.1021/jf000736f. [PMID: 11170613]
  • I K Paik. Nutritional value of processed rapeseed meal. Advances in experimental medicine and biology. 1991; 289(?):403-14. doi: 10.1007/978-1-4899-2626-5_29. [PMID: 1716819]
  • H J Lewerenz, D W Bleyl, R Plass, H Przybilski, W Schnaak. [The subchronic toxicity of 5-vinyloxazolidine-2-thione in rats]. Die Nahrung. 1989; 33(10):965-73. doi: 10.1002/food.19890331014. [PMID: 2634245]
  • P Langer, O Földes, K Gschwendtová. In vivo effect of amiodarone, thiocyanate, perchlorate and goitrin on thyroxine deiodination in rat liver. Endocrinologia experimentalis. 1984 Sep; 18(3):177-82. doi: . [PMID: 6092032]
  • J Lüthy, B Carden, U Friederich, M Bachmann. Goitrin--a nitrosatable constitutent of plant foodstuffs. Experientia. 1984 May; 40(5):452-3. doi: 10.1007/bf01952381. [PMID: 6723906]
  • A W Pearson, N M Greenwood, E J Butler, G R Fenwick. Biochemical changes in layer and broiler chickens when fed on a high-glucosinolate rapeseed meal. British poultry science. 1983 Jul; 24(3):417-27. doi: 10.1080/00071668308416756. [PMID: 6193844]
  • H F de Brabander, R Verbeke. Determination of oxazolidine-2-thiones in biological fluids in the ppb range. Journal of chromatography. 1982 Dec; 252(?):225-39. doi: 10.1016/s0021-9673(01)88414-4. [PMID: 7182410]
  • K Nishie, E Daxenbichler. Hepatic effects of R-goitrin in Sprague-Dawley rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1982 Jun; 20(3):279-87. doi: 10.1016/s0278-6915(82)80294-9. [PMID: 6179840]
  • D Ballester, P Vera, J King, O Brunser, E Yánez. Comparative effects of semisynthetic D-5-vinyl-2-thiooxazolidone and water-extracted rapeseed meal in the rat. Annals of nutrition & metabolism. 1982; 26(5):301-7. doi: 10.1159/000176578. [PMID: 7137953]