Skatole (BioDeep_00000406539)

Main id: BioDeep_00000001241

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


3-Methylindole

化学式: C9H9N (131.0734954)
中文名称: 3-甲基吲哚
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=1C=CC2=C(C1)NC=C2C
InChI: InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3

描述信息

A methylindole carrying a methyl substituent at position 3. It is produced during the anoxic metabolism of L-tryptophan in the mammalian digestive tract.
Skatole is produced by intestinal bacteria, regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38[1].
Skatole is produced by intestinal bacteria, regulates intestinal epithelial cellular functions through activating aryl hydrocarbon receptors and p38[1].

同义名列表

3 个代谢物同义名

3-Methylindole; Skatole; 3-Methyl-1H-indole



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

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)

16 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

  • Nannan Liu, Xuehua Yan, Bohan Lv, Yanxiang Wu, Xuehong Hu, Chunyan Zheng, Siyu Tao, Ruxue Deng, Jinfang Dou, Binfang Zeng, Guangjian Jiang. A study on the association between gut microbiota, inflammation, and type 2 diabetes. Applied microbiology and biotechnology. 2024 Feb; 108(1):213. doi: 10.1007/s00253-024-13041-5. [PMID: 38358546]
  • Sin-Hyoung Hong, Yeonhee Hong, Minji Lee, Byeong-Rak Keum, Gun-Hwa Kim. Natural Product Skatole Ameliorates Lipotoxicity-Induced Multiple Hepatic Damage under Hyperlipidemic Conditions in Hepatocytes. Nutrients. 2023 Mar; 15(6):. doi: 10.3390/nu15061490. [PMID: 36986221]
  • Petr Doležal, Kamila Pokorná, Jaroslav Čítek, Roman Stupka. Development of an analytical method for the determination of sterol compounds in boars' saliva. Analytical biochemistry. 2022 12; 658(?):114932. doi: 10.1016/j.ab.2022.114932. [PMID: 36191667]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • HyeonJi Kim, EunSeob Song, JaeHee Lee, Ravi Gautam, SoJung Shin, AhRang Cho, YeonGyeong Kim, SuJeong Yang, JiHun Jo, Manju Acharya, Anju Maharjan, ChangYul Kim, Yong Heo, HyoungAh Kim. Dysregulation of murine immune functions on inhalational exposure to ammonia, dimethyl disulfide, 3-methylindole, or propionic acid. Toxicology and industrial health. 2021 Apr; 37(4):219-228. doi: 10.1177/0748233721996559. [PMID: 33663293]
  • C Dugué, A Prunier, M J Mercat, M Monziols, B Blanchet, C Larzul. Genetic determinism of boar taint and relationship with growth traits, meat quality and lesions. Animal : an international journal of animal bioscience. 2020 Jul; 14(7):1333-1341. doi: 10.1017/s1751731120000105. [PMID: 32051054]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • D Rivaroli, A Prunier, K Meteau, I N do Prado, S Prache. Tannin-rich sainfoin pellet supplementation reduces fat volatile indoles content and delays digestive parasitism in lambs grazing alfalfa. Animal : an international journal of animal bioscience. 2019 Sep; 13(9):1883-1890. doi: 10.1017/s1751731118003543. [PMID: 30614428]
  • E Heyrman, E Kowalski, S Millet, F A M Tuyttens, B Ampe, S Janssens, N Buys, J Wauters, L Vanhaecke, M Aluwé. Monitoring of behavior, sex hormones and boar taint compounds during the vaccination program for immunocastration in three sire lines. Research in veterinary science. 2019 Jun; 124(?):293-302. doi: 10.1016/j.rvsc.2019.04.010. [PMID: 31026762]
  • Xingfa Han, Min Zhou, Xiaohan Cao, Xiaogang Du, Fengyan Meng, Guixian Bu, Fanli Kong, Anqi Huang, Xianyin Zeng. Mechanistic insight into the role of immunocastration on eliminating skatole in boars. Theriogenology. 2019 Jun; 131(?):32-40. doi: 10.1016/j.theriogenology.2019.03.017. [PMID: 30939354]
  • Xiaoqiong Li, Bent Borg Jensen, Nuria Canibe. The Mode of Action of Chicory Roots on Skatole Production in Entire Male Pigs Is neither via Reducing the Population of Skatole-Producing Bacteria nor via Increased Butyrate Production in the Hindgut. Applied and environmental microbiology. 2019 03; 85(6):. doi: 10.1128/aem.02327-18. [PMID: 30635386]
  • Tujuba Ayele Tesso, Aijuan Zheng, Huiyi Cai, Guohua Liu. Isolation and characterization of two Acinetobacter species able to degrade 3-methylindole. PloS one. 2019; 14(1):e0211275. doi: 10.1371/journal.pone.0211275. [PMID: 30689668]
  • C Visscher, A Kruse, S Sander, C Keller, J Mischok, R Tabeling, H Henne, R Deitmer, J Kamphues. Dietary approaches reducing boar taint-Importance of Lawsonia intracellularis colonisation for interpreting results. Journal of animal physiology and animal nutrition. 2018 Apr; 102 Suppl 1(?):3-15. doi: 10.1111/jpn.12860. [PMID: 29623688]
  • Kazutoshi Sakurai, Kenichi Tomiyama, Yukihiro Kawakami, Yoshihiro Yaguchi, Yoshinori Asakawa. Characteristic Scent from the Tahitian Liverwort, Cyathodium foetidissimum. Journal of oleo science. 2018; 67(10):1265-1269. doi: 10.5650/jos.ess18160. [PMID: 30305559]
  • Reynaldo Patiño, Rakib H Rashel, Amede Rubio, Scott Longing. Growth-suppressing and algicidal properties of an extract from Arundo donax, an invasive riparian plant, against Prymnesium parvum, an invasive harmful alga. Harmful algae. 2018 01; 71(?):1-9. doi: 10.1016/j.hal.2017.11.005. [PMID: 29306391]
  • Linlin Deng, Qianna Zhen, Jieying Gao, Mingchao Jin, Min Ding, Biao Xu. [Simultaneous determination of plasma indole and skatole in pregnant women with hepatitis B virus infection by high performance liquid chromatography]. Se pu = Chinese journal of chromatography. 2017 Jul; 35(7):735-740. doi: 10.3724/sp.j.1123.2017.03025. [PMID: 29048838]
  • Cristina C Jacob, Gaud Dervilly-Pinel, Yoann Deceuninck, Audrey Gicquiau, Patrick Chevillon, Michel Bonneau, Bruno Le Bizec. Urinary signature of pig carcasses with boar taint by liquid chromatography-high-resolution mass spectrometry. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2017 Feb; 34(2):218-227. doi: 10.1080/19440049.2016.1265152. [PMID: 27885948]
  • Sara Corral, Carmela Belloch, José Javier López-Díez, Ana Salvador, Mónica Flores. Yeast inoculation as a strategy to improve the physico-chemical and sensory properties of reduced salt fermented sausages produced with entire male fat. Meat science. 2017 Jan; 123(?):1-7. doi: 10.1016/j.meatsci.2016.08.007. [PMID: 27579788]
  • C Brunius, J K Vidanarachchi, J Tomankova, K Lundström, K Andersson, G Zamaratskaia. Skatole metabolites in urine as a biological marker of pigs with enhanced hepatic metabolism. Animal : an international journal of animal bioscience. 2016 Oct; 10(10):1734-40. doi: 10.1017/s1751731116000574. [PMID: 27080076]
  • Raffael Wesoly, Volker Stefanski, Ulrike Weiler. Influence of sampling procedure, sampling location and skin contamination on skatole and indole concentrations in adipose tissue of pigs. Meat science. 2016 Jan; 111(?):85-91. doi: 10.1016/j.meatsci.2015.08.015. [PMID: 26348413]
  • J Wauters, J Vanden Bussche, K Verplanken, K M Bekaert, M Aluwé, A Van den Broeke, A Coussé, N Buys, L Vanhaecke. Development of a quantitative method for the simultaneous analysis of the boar taint compounds androstenone, skatole and indole in porcine serum and plasma by means of ultra-high performance liquid chromatography coupled to high resolution mass spectrometry. Food chemistry. 2015 Nov; 187(?):120-9. doi: 10.1016/j.foodchem.2015.04.066. [PMID: 25977006]
  • A Van den Broeke, M Aluwé, S Janssens, J Wauters, L Vanhaecke, N Buys, S Millet, F A M Tuyttens. The effect of the MC4R gene on boar taint compounds, sexual maturity and behaviour in growing-finishing boars and gilts. Animal : an international journal of animal bioscience. 2015 Oct; 9(10):1688-97. doi: 10.1017/s1751731115001135. [PMID: 26155873]
  • R Thomsen, S A Edwards, B B Jensen, T Rousing, J T Sørensen. Effect of faecal soiling on skatole and androstenone occurrence in organic entire male pigs. Animal : an international journal of animal bioscience. 2015 Sep; 9(9):1587-96. doi: 10.1017/s1751731115000798. [PMID: 25990887]
  • S P Parois, A Prunier, M J Mercat, E Merlot, C Larzul. Genetic relationships between measures of sexual development, boar taint, health, and aggressiveness in pigs. Journal of animal science. 2015 Aug; 93(8):3749-58. doi: 10.2527/jas.2014-8290. [PMID: 26440153]
  • Xiaoqiong Li, Rikke Lassen Jensen, Ole Højberg, Nuria Canibe, Bent Borg Jensen. Olsenella scatoligenes sp. nov., a 3-methylindole- (skatole) and 4-methylphenol- (p-cresol) producing bacterium isolated from pig faeces. International journal of systematic and evolutionary microbiology. 2015 Apr; 65(Pt 4):1227-1233. doi: 10.1099/ijs.0.000083. [PMID: 25634945]
  • Raffael Wesoly, Ina Jungbluth, Volker Stefanski, Ulrike Weiler. Pre-slaughter conditions influence skatole and androstenone in adipose tissue of boars. Meat science. 2015 Jan; 99(?):60-7. doi: 10.1016/j.meatsci.2014.08.015. [PMID: 25282669]
  • Suzanne J Rowe, Burak Karacaören, Dirk-Jan de Koning, Boris Lukic, Nicola Hastings-Clark, Ingela Velander, Chris S Haley, Alan L Archibald. Analysis of the genetics of boar taint reveals both single SNPs and regional effects. BMC genomics. 2014 Jun; 15(?):424. doi: 10.1186/1471-2164-15-424. [PMID: 24894739]
  • Atsushi Usami, Ryota Motooka, Ayumi Takagi, Hiroshi Nakahashi, Yoshiharu Okuno, Mitsuo Miyazawa. Chemical composition, aroma evaluation, and oxygen radical absorbance capacity of volatile oil extracted from Brassica rapa cv. 'yukina' used in Japanese traditional food. Journal of oleo science. 2014; 63(7):723-30. doi: 10.5650/jos.ess14033. [PMID: 24919480]
  • A Prunier, A Brillouët, E Merlot, M C Meunier-Salaün, C Tallet. Influence of housing and season on pubertal development, boar taint compounds and skin lesions of male pigs. Animal : an international journal of animal bioscience. 2013 Dec; 7(12):2035-43. doi: 10.1017/s1751731113001596. [PMID: 24047862]
  • Nicholas Wicks, Spencer Crouch, Christopher A Pearl. Effects of Improvac and Bopriva on the testicular function of boars ten weeks after immunization. Animal reproduction science. 2013 Nov; 142(3-4):149-59. doi: 10.1016/j.anireprosci.2013.09.017. [PMID: 24139761]
  • Asep Gunawan, Sudeep Sahadevan, Christiane Neuhoff, Christine Große-Brinkhaus, Ahmed Gad, Luc Frieden, Dawit Tesfaye, Ernst Tholen, Christian Looft, Muhammad Jasim Uddin, Karl Schellander, Mehmet Ulas Cinar. RNA deep sequencing reveals novel candidate genes and polymorphisms in boar testis and liver tissues with divergent androstenone levels. PloS one. 2013; 8(5):e63259. doi: 10.1371/journal.pone.0063259. [PMID: 23696805]
  • Asep Gunawan, Sudeep Sahadevan, Mehmet Ulas Cinar, Christiane Neuhoff, Christine Große-Brinkhaus, Luc Frieden, Dawit Tesfaye, Ernst Tholen, Christian Looft, Dessie Salilew Wondim, Michael Hölker, Karl Schellander, Muhammad Jasim Uddin. Identification of the novel candidate genes and variants in boar liver tissues with divergent skatole levels using RNA deep sequencing. PloS one. 2013; 8(8):e72298. doi: 10.1371/journal.pone.0072298. [PMID: 23991084]
  • Martin Skrlep, Nina Batorek, Michel Bonneau, Gregor Fazarinc, Blaž Segula, Marjeta Candek-Potokar. Elevated fat skatole levels in immunocastrated, surgically castrated and entire male pigs with acute dysentery. Veterinary journal (London, England : 1997). 2012 Dec; 194(3):417-9. doi: 10.1016/j.tvjl.2012.04.013. [PMID: 22613221]
  • D Zammerini, J D Wood, F M Whittington, G R Nute, S I Hughes, M Hazzledine, K Matthews. Effect of dietary chicory on boar taint. Meat science. 2012 Aug; 91(4):396-401. doi: 10.1016/j.meatsci.2012.01.020. [PMID: 22353791]
  • P Wiercinska, Y Lou, E J Squires. The roles of different porcine cytochrome P450 enzymes and cytochrome b5A in skatole metabolism. Animal : an international journal of animal bioscience. 2012 May; 6(5):834-45. doi: 10.1017/s1751731111002175. [PMID: 22558931]
  • Joscelyn Sarsby, Mark W Towers, Chris Stain, Rainer Cramer, Olga A Koroleva. Mass spectrometry imaging of glucosinolates in Arabidopsis flowers and siliques. Phytochemistry. 2012 May; 77(?):110-8. doi: 10.1016/j.phytochem.2012.01.026. [PMID: 22386577]
  • Carl Brunius, Galia Zamaratskaia, Kristina Andersson, Gang Chen, Mattias Norrby, Andrzej Madej, Kerstin Lundström. Early immunocastration of male pigs with Improvac(®) - effect on boar taint, hormones and reproductive organs. Vaccine. 2011 Nov; 29(51):9514-20. doi: 10.1016/j.vaccine.2011.10.014. [PMID: 22008824]
  • M Eickermann, B Ulber, S Vidal. Resynthesized lines and cultivars of Brassica napus L. provide sources of resistance to the cabbage stem weevil ( Ceutorhynchus pallidactylus (Mrsh.)). Bulletin of entomological research. 2011 Jun; 101(3):287-94. doi: 10.1017/s0007485310000489. [PMID: 21092380]
  • Jasmine Leong, Patrick C H Morel, Roger W Purchas, Brian H P Wilkinson. Effects of dietary components including garlic on concentrations of skatole and indole in subcutaneous fat of female pigs. Meat science. 2011 May; 88(1):45-50. doi: 10.1016/j.meatsci.2010.12.001. [PMID: 21216539]
  • E Grindflek, T H E Meuwissen, T Aasmundstad, H Hamland, M H S Hansen, T Nome, M Kent, P Torjesen, S Lien. Revealing genetic relationships between compounds affecting boar taint and reproduction in pigs. Journal of animal science. 2011 Mar; 89(3):680-92. doi: 10.2527/jas.2010-3290. [PMID: 21346135]
  • M Aluwé, K M Bekaert, F A M Tuyttens, L Vanhaecke, S De Smet, H F De Brabander, D L De Brabander, S Millet. Influence of soiling on boar taint in boars. Meat science. 2011 Mar; 87(3):175-9. doi: 10.1016/j.meatsci.2010.10.005. [PMID: 21074948]
  • Valentina Vasta, Giuseppe Luciano, Corrado Dimauro, Florian Röhrle, Alessandro Priolo, Frank J Monahan, Aidan P Moloney. The volatile profile of longissimus dorsi muscle of heifers fed pasture, pasture silage or cereal concentrate: implication for dietary discrimination. Meat science. 2011 Mar; 87(3):282-9. doi: 10.1016/j.meatsci.2010.11.003. [PMID: 21126829]
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  • Frida R Svensson, Per Lincoln, Bengt Nordén, Elin K Esbjörner. Tryptophan orientations in membrane-bound gramicidin and melittin-a comparative linear dichroism study on transmembrane and surface-bound peptides. Biochimica et biophysica acta. 2011 Jan; 1808(1):219-28. doi: 10.1016/j.bbamem.2010.10.004. [PMID: 20951675]
  • Jing Fu, Shiping Wang. Insights into auxin signaling in plant-pathogen interactions. Frontiers in plant science. 2011; 2(?):74. doi: 10.3389/fpls.2011.00074. [PMID: 22639609]
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  • I C Oskam, S Lervik, H Tajet, E Dahl, E Ropstad, Ø Andresen. Differences in testosterone, androstenone, and skatole levels in plasma and fat between pubertal purebred Duroc and Landrace boars in response to human chorionic gonadotrophin stimulation. Theriogenology. 2010 Oct; 74(6):1088-98. doi: 10.1016/j.theriogenology.2010.05.006. [PMID: 20580070]
  • Hélène Zuber, Jean-Claude Davidian, Grégoire Aubert, Delphine Aimé, Maya Belghazi, Raphaël Lugan, Dimitri Heintz, Markus Wirtz, Rüdiger Hell, Richard Thompson, Karine Gallardo. The seed composition of Arabidopsis mutants for the group 3 sulfate transporters indicates a role in sulfate translocation within developing seeds. Plant physiology. 2010 Oct; 154(2):913-26. doi: 10.1104/pp.110.162123. [PMID: 20702726]
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  • Ross C Beier, Robin C Anderson, Nathan A Krueger, Thomas S Edrington, Todd R Callaway, David J Nisbet. Effect of nitroethane and nitroethanol on the production of indole and 3-methylindole (skatole) from bacteria in swine feces by gas chromatography. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2009 Aug; 44(6):613-20. doi: 10.1080/03601230903000701. [PMID: 20183070]
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