3-Methylsulfinylpropyl isothiocyanate (BioDeep_00000017407)

 

Secondary id: BioDeep_00000604298

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Antitumor activity Volatile Flavor Compounds


代谢物信息卡片


ISOTHIOCYANIC ACID, 3-(METHYLSULFINYL)PROPYL ESTER

化学式: C5H9NOS2 (163.0125544)
中文名称: 3-甲基亚磺酰丙基异硫氰酸酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.78%

分子结构信息

SMILES: CS(=O)CCCN=C=S
InChI: InChI=1S/C5H9NOS2/c1-9(7)4-2-3-6-5-8/h2-4H2,1H3

描述信息

Consumption of broccoli sprouts has shown to be effective at inhibiting Helicobacter pylori growth with sulforaphane being at least one of the active agents. Sulforaphane is an anticancer and antimicrobial compound which can be obtained by eating cruciferous vegetables such as brussel sprouts, broccoli, cauliflower, bok choy, kale, collards, arugula, broccoli sprouts, chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, watercress and cabbage. The enzyme myrosinase transforms glucoraphanin (a glucosinolate) into sulforaphane upon damage to the plant (such as from chewing). The young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin.
Iberin is an isothiocyanate that is 1-isothiocyanatopropane in which a hydrogen at position 3 has been replaced by a methylsulfinyl group. A glucosinolate hydrolysis product found in many members of the Brassicaceae family, it is a quorum-sensing inhibitor (QSI) of the bacterial pathogen Pseudomonas aeruginosa. It has a role as a quorum sensing inhibitor, a plant metabolite and an apoptosis inducer. It is a sulfoxide and an isothiocyanate.
Iberin is a natural product found in Arabidopsis thaliana, Brassica, and Brassica oleracea with data available.
An isothiocyanate that is 1-isothiocyanatopropane in which a hydrogen at position 3 has been replaced by a methylsulfinyl group. A glucosinolate hydrolysis product found in many members of the Brassicaceae family, it is a quorum-sensing inhibitor (QSI) of the bacterial pathogen Pseudomonas aeruginosa.

同义名列表

23 个代谢物同义名

ISOTHIOCYANIC ACID, 3-(METHYLSULFINYL)PROPYL ESTER; (R)-1-Isothiocyanato-3-(methylsulphinyl)propane; Propane, 1-isothiocyanato-3-(methylsulfinyl)-; 1-Isothiocyanato-3-(methylsulfinyl)propane #; 1-isothiocyanato-3-(methylsulphinyl)propane; 1-isothiocyanato-3-(methylsulfinyl)propane; 3-Methylsulphinylpropyl isothiocyanic acid; 1-isothiocyanato-3-methanesulfinylpropane; 3-Methylsulfinylpropyl isothiocyanic acid; 3-Isothiocyanatopropyl methyl sulphoxide; 1-isothiocyanato-3-methylsulfinylpropane; 3-isothiocyanatopropyl methyl sulfoxide; Methylsulphinylpropylisothiocyanic acid; Methylsulfinylpropylisothiocyanic acid; 3-Methylsulphinylpropyl isothiocyanate; 3-Methylsulfinylpropyl isothiocyanate; 3-Methylsulphinylpropylisothiocyanate; Methylsulphinylpropylisothiocyanate; METHYLSULFINYLPROPYLISOTHIOCYANATE; LELAOEBVZLPXAZ-UHFFFAOYSA-N; Iberin; IMSP; Iberin



数据库引用编号

14 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

  • John A Bouranis, Laura M Beaver, Jaewoo Choi, Carmen P Wong, Duo Jiang, Thomas J Sharpton, Jan F Stevens, Emily Ho. Composition of the Gut Microbiome Influences Production of Sulforaphane-Nitrile and Iberin-Nitrile from Glucosinolates in Broccoli Sprouts. Nutrients. 2021 Aug; 13(9):. doi: 10.3390/nu13093013. [PMID: 34578891]
  • Teresa Oliviero, Simone Lamers, Edoardo Capuano, Matthijs Dekker, Ruud Verkerk. Bioavailability of Isothiocyanates From Broccoli Sprouts in Protein, Lipid, and Fiber Gels. Molecular nutrition & food research. 2018 09; 62(18):e1700837. doi: 10.1002/mnfr.201700837. [PMID: 29532635]
  • Nan Wang, Wei Wang, Caiqin Liu, Jianchang Jin, Bo Shao, Lianqing Shen. Inhibition of growth and induction of apoptosis in A549 cells by compounds from oxheart cabbage extract. Journal of the science of food and agriculture. 2016 Aug; 96(11):3813-20. doi: 10.1002/jsfa.7575. [PMID: 26679410]
  • Takahiro Shibata, Fumie Nakashima, Kazuya Honda, Yu-Jhang Lu, Tatsuhiko Kondo, Yusuke Ushida, Koichi Aizawa, Hiroyuki Suganuma, Sho Oe, Hiroshi Tanaka, Takashi Takahashi, Koji Uchida. Toll-like receptors as a target of food-derived anti-inflammatory compounds. The Journal of biological chemistry. 2014 Nov; 289(47):32757-72. doi: 10.1074/jbc.m114.585901. [PMID: 25294874]
  • Sean Yang-Yi Tan, Yang Liu, Song Lin Chua, Rebecca Munk Vejborg, Tim Holm Jakobsen, Su Chuen Chew, Yingying Li, Thomas E Nielsen, Tim Tolker-Nielsen, Liang Yang, Michael Givskov. Comparative systems biology analysis to study the mode of action of the isothiocyanate compound Iberin on Pseudomonas aeruginosa. Antimicrobial agents and chemotherapy. 2014 Nov; 58(11):6648-59. doi: 10.1128/aac.02620-13. [PMID: 25155599]
  • Teresa Oliviero, Ruud Verkerk, Martijn Vermeulen, Matthijs Dekker. In vivo formation and bioavailability of isothiocyanates from glucosinolates in broccoli as affected by processing conditions. Molecular nutrition & food research. 2014 Jul; 58(7):1447-56. doi: 10.1002/mnfr.201300894. [PMID: 24687744]
  • Lawrence N Barrera, Ian T Johnson, Yongping Bao, Aedin Cassidy, Nigel J Belshaw. Colorectal cancer cells Caco-2 and HCT116 resist epigenetic effects of isothiocyanates and selenium in vitro. European journal of nutrition. 2013 Jun; 52(4):1327-41. doi: 10.1007/s00394-012-0442-1. [PMID: 22923034]
  • Tim Holm Jakobsen, Steinn Kristinn Bragason, Richard Kerry Phipps, Louise Dahl Christensen, Maria van Gennip, Morten Alhede, Mette Skindersoe, Thomas Ostenfeld Larsen, Niels Høiby, Thomas Bjarnsholt, Michael Givskov. Food as a source for quorum sensing inhibitors: iberin from horseradish revealed as a quorum sensing inhibitor of Pseudomonas aeruginosa. Applied and environmental microbiology. 2012 Apr; 78(7):2410-21. doi: 10.1128/aem.05992-11. [PMID: 22286987]
  • 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]
  • Karen F Chambers, James R Bacon, E Katherine Kemsley, Robert D Mills, Richard Y Ball, Richard F Mithen, Maria H Traka. Gene expression profile of primary prostate epithelial and stromal cells in response to sulforaphane or iberin exposure. The Prostate. 2009 Sep; 69(13):1411-21. doi: 10.1002/pros.20986. [PMID: 19489030]
  • Unmesh Jadhav, Ravesanker Ezhilarasan, Steven F Vaughn, Mark A Berhow, Sanjeeva Mohanam. Iberin induces cell cycle arrest and apoptosis in human neuroblastoma cells. International journal of molecular medicine. 2007 Mar; 19(3):353-61. doi: 10.3892/ijmm.19.3.353. [PMID: 17273780]
  • Ahmed A Al Janobi, Richard F Mithen, Amy V Gasper, P Nicholas Shaw, Richard J Middleton, Catharine A Ortori, David A Barrett. Quantitative measurement of sulforaphane, iberin and their mercapturic acid pathway metabolites in human plasma and urine using liquid chromatography-tandem electrospray ionisation mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Dec; 844(2):223-34. doi: 10.1016/j.jchromb.2006.07.007. [PMID: 16931178]
  • J Jakubikova, Y Bao, J Bodo, J Sedlak. Isothiocyanate iberin modulates phase II enzymes, posttranslational modification of histones and inhibits growth of Caco-2 cells by inducing apoptosis. Neoplasma. 2006; 53(6):463-70. doi: ". [PMID: 17167713]
  • M A Wallig, S Kingston, R Staack, E H Jefferey. Induction of rat pancreatic glutathione S-transferase and quinone reductase activities by a mixture of glucosinolate breakdown derivatives found in Brussels sprouts. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1998 May; 36(5):365-73. doi: 10.1016/s0278-6915(97)00156-7. [PMID: 9662411]
  • A M Kore, E H Jeffery, M A Wallig. Effects of 1-isothiocyanato-3-(methylsulfinyl)-propane on xenobiotic metabolizing enzymes in rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1993 Oct; 31(10):723-9. doi: 10.1016/0278-6915(93)90143-m. [PMID: 8225130]
  • A M Kore, M A Wallig. Histological and serum biochemical effects of 1-isothiocyanato-3- (methylsulphinyl)-propane in the F344 rat. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1993 Aug; 31(8):549-59. doi: 10.1016/0278-6915(93)90204-c. [PMID: 8349200]
  • M Sano. Subcellular localizations of guanylate cyclase and 3',5'-cyclic nucleotide phosphodiesterase in sea urchin sperm. Biochimica et biophysica acta. 1976 Apr; 428(2):525-31. doi: 10.1016/0304-4165(76)90061-1. [PMID: 6049]