Indole (BioDeep_00000002913)

 

Secondary id: BioDeep_00000400203, BioDeep_00000860852

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds natural product


代谢物信息卡片


2,3-Benzopyrrole

化学式: C8H7N (117.0578462)
中文名称: 吲哚
谱图信息: 最多检出来源 Viridiplantae(plant) 0.11%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Indole. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/indole (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000002913). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1(C=CC=C2)=C2NC=C1
InChI: InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

描述信息

Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine. Indole is a microbial metabolite and it can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, indole has a flowery smell and is a constituent of many flower scents (such as orange blossoms) and perfumes. As a volatile organic compound, indole has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230). Natural jasmine oil, used in the perfume industry, contains around 2.5\\\\\% of indole. Indole also occurs in coal tar. Indole has been found to be produced in a number of bacterial genera including Alcaligenes, Aspergillus, Escherichia, and Pseudomonas (PMID: 23194589, 2310183, 9680309). Indole plays a role in bacterial biofilm formation, bacterial motility, bacterial virulence, plasmid stability, and antibiotic resistance. It also functions as an intercellular signalling molecule (PMID: 26115989). Recently, it was determined that the bacterial membrane-bound histidine sensor kinase (HK) known as CpxA acts as a bacterial indole sensor to facilitate signalling (PMID: 31164470). It has been found that decreased indole concentrations in the gut promote bacterial pathogenesis, while increased levels of indole in the gut decrease bacterial virulence gene expression (PMID: 31164470). As a result, enteric pathogens sense a gradient of indole concentrations in the gut to migrate to different niches and successfully establish an infection.
Constituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs

Indole. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=120-72-9 (retrieved 2024-07-16) (CAS RN: 120-72-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Indole is an endogenous metabolite.
Indole is an endogenous metabolite.

同义名列表

11 个代谢物同义名

2,3-Benzopyrrole; Benzo[b]pyrrole; 1-Benzazole; 1-Azaindene; 1H-indole; Ketole; Indole; indol; Indole; Indole; Indole



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(6)

PlantCyc(2)

代谢反应

775 个相关的代谢反应过程信息。

Reactome(65)

BioCyc(98)

WikiPathways(0)

Plant Reactome(330)

INOH(0)

PlantCyc(278)

COVID-19 Disease Map(0)

PathBank(4)

PharmGKB(0)

178 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

  • Ying Cheng, Xilin Lyu, Chen Liu, Xiancheng Wang, Jing Cheng, Daizhou Zhang, Xiangjing Meng, Yujun Zhao. Synthesis and Biological Evaluation of Sclareolide-Indole Conjugates and Their Derivatives. Molecules (Basel, Switzerland). 2023 Feb; 28(4):. doi: 10.3390/molecules28041737. [PMID: 36838727]
  • Yubo Sun, Hao Wu, Wenning Zhou, Zhichun Yuan, Jianjun Hao, Xili Liu, Lirong Han. Effects of indole derivatives from Purpureocillium lilacinum in controlling tobacco mosaic virus. Pesticide biochemistry and physiology. 2022 May; 183(?):105077. doi: 10.1016/j.pestbp.2022.105077. [PMID: 35430069]
  • Sasikarn Seetasang, Takashi Kaneta. Dip-and-Read, Organic Solvent-Compatible, Paper-Based Analytical Devices Equipped with Chromatographic Separation for Indole Analysis in Shrimp. ACS sensors. 2022 04; 7(4):1194-1200. doi: 10.1021/acssensors.2c00300. [PMID: 35404587]
  • Yujia Wang, Yali Mu, Xiatong Hu, Caixia Zhang, Yanqing Gao, Zhiqing Ma, Juntao Feng, Xili Liu, Peng Lei. Indole/Tetrahydroquinoline as Renewable Natural Resource-Inspired Scaffolds in the Devising and Preparation of Potential Fungicide Candidates. Journal of agricultural and food chemistry. 2022 Apr; 70(15):4582-4590. doi: 10.1021/acs.jafc.1c07879. [PMID: 35385275]
  • Inês Delgado, Sofia Cussotto, Andrea Anesi, Sandra Dexpert, Agnès Aubert, Bruno Aouizerate, Cédric Beau, Damien Forestier, Patrick Ledaguenel, Eric Magne, Fulvio Mattivi, Lucile Capuron. Association between the indole pathway of tryptophan metabolism and subclinical depressive symptoms in obesity: a preliminary study. International journal of obesity (2005). 2022 04; 46(4):885-888. doi: 10.1038/s41366-021-01049-0. [PMID: 35001078]
  • Kun Fan, Cai-Feng Ding, Shi-Yu Deng, Wen Gao, Bang-Yin Tan, Hao Wu, Ying Guo, Jing-Feng Song, Lan-Chun Zhang, Rong-Ping Zhang, Hao-Fei Yu. Monoterpene indole N-oxide alkaloids from Tabernaemontana corymbosa and their antimicrobial activity. Fitoterapia. 2022 Apr; 158(?):105178. doi: 10.1016/j.fitote.2022.105178. [PMID: 35302006]
  • Ayako Kusakabe, Chen Wang, Ya-Ming Xu, István Molnár, S Patricia Stock. Selective Toxicity of Secondary Metabolites from the Entomopathogenic Bacterium Photorhabdus luminescens sonorensis against Selected Plant Parasitic Nematodes of the Tylenchina Suborder. Microbiology spectrum. 2022 02; 10(1):e0257721. doi: 10.1128/spectrum.02577-21. [PMID: 35138171]
  • Vladimír Skalický, Tereza Vojtková, Aleš Pěnčík, Jan Vrána, Katarzyna Juzoń, Veronika Koláčková, Michaela Sedlářová, Martin F Kubeš, Ondřej Novák. Auxin Metabolite Profiling in Isolated and Intact Plant Nuclei. International journal of molecular sciences. 2021 Nov; 22(22):. doi: 10.3390/ijms222212369. [PMID: 34830250]
  • Ángel Abellán, Raúl Domínguez-Perles, Cristina García-Viguera, Diego A Moreno. Evidence on the Bioaccessibility of Glucosinolates and Breakdown Products of Cruciferous Sprouts by Simulated In Vitro Gastrointestinal Digestion. International journal of molecular sciences. 2021 Oct; 22(20):. doi: 10.3390/ijms222011046. [PMID: 34681712]
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  • Zubeyir Elmazoglu, Marta Soltesova Prnova, Milan Stefek, Asli F Ceylan, Michael Aschner, Edgar Rangel-López, Abel Santamaria, Cimen Karasu. Protective Effects of Novel Substituted Triazinoindole Inhibitors of Aldose Reductase and Epalrestat in Neuron-like PC12 Cells and BV2 Rodent Microglial Cells Exposed to Toxic Models of Oxidative Stress: Comparison with the Pyridoindole Antioxidant Stobadine. Neurotoxicity research. 2021 Jun; 39(3):588-597. doi: 10.1007/s12640-021-00349-7. [PMID: 33713301]
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  • Liang Chang, Nathalie Fischer-Durand, Geoffrey Gontard, Benoît Bertrand, Serge Thorimbert, Luc Dechoux. A Solvent-free, Catalyst-free Formal [3+3] Cycloaddition Dearomatization Strategy: Towards New Fluorophores for Biomolecules Labelling. ChemSusChem. 2021 Apr; 14(8):1821-1824. doi: 10.1002/cssc.202100301. [PMID: 33651919]
  • Annett Richter, Adrian F Powell, Mahdieh Mirzaei, Lucy J Wang, Navid Movahed, Julia K Miller, Miguel A Piñeros, Georg Jander. Indole-3-glycerolphosphate synthase, a branchpoint for the biosynthesis of tryptophan, indole, and benzoxazinoids in maize. The Plant journal : for cell and molecular biology. 2021 04; 106(1):245-257. doi: 10.1111/tpj.15163. [PMID: 33458870]
  • Meng Ye, Miaomiao Liu, Matthias Erb, Gaétan Glauser, Jin Zhang, Xiwang Li, Xiaoling Sun. Indole primes defence signalling and increases herbivore resistance in tea plants. Plant, cell & environment. 2021 04; 44(4):1165-1177. doi: 10.1111/pce.13897. [PMID: 32996129]
  • Suhail Razak, Tayyaba Afsar, Nousheen Bibi, Mahmoud Abulmeaty, Wajhul Qamar, Ali Almajwal, Anam Inam, Dara Al Disi, Maria Shabbir, Mashooq Ahmad Bhat. Molecular docking, pharmacokinetic studies, and in vivo pharmacological study of indole derivative 2-(5-methoxy-2-methyl-1H-indole-3-yl)-N'-[(E)-(3-nitrophenyl) methylidene] acetohydrazide as a promising chemoprotective agent against cisplatin induced organ damage. Scientific reports. 2021 03; 11(1):6245. doi: 10.1038/s41598-021-84748-y. [PMID: 33737575]
  • Linda Jahn, Uta Hofmann, Jutta Ludwig-Müller. Indole-3-Acetic Acid Is Synthesized by the Endophyte Cyanodermella asteris via a Tryptophan-Dependent and -Independent Way and Mediates the Interaction with a Non-Host Plant. International journal of molecular sciences. 2021 Mar; 22(5):. doi: 10.3390/ijms22052651. [PMID: 33800748]
  • Chia-Shan Wu, Sai Deepak Venkata Muthyala, Cory Klemashevich, Arinzechukwu Uchenna Ufondu, Rani Menon, Zheng Chen, Sridevi Devaraj, Arul Jayaraman, Yuxiang Sun. Age-dependent remodeling of gut microbiome and host serum metabolome in mice. Aging. 2021 02; 13(5):6330-6345. doi: 10.18632/aging.202525. [PMID: 33612480]
  • Sascha K Manier, Christina Felske, Josef Zapp, Niels Eckstein, Markus R Meyer. Studies on the In Vitro and In Vivo Metabolic Fate of the New Psychoactive Substance N-Ethyl-N-Propyltryptamine for Analytical Purposes. Journal of analytical toxicology. 2021 Feb; 45(2):195-202. doi: 10.1093/jat/bkaa060. [PMID: 32507893]
  • Chih-Yu Yang, Ting-Wen Chen, Wan-Lun Lu, Shih-Shin Liang, Hsien-Da Huang, Ching-Ping Tseng, Der-Cherng Tarng. Synbiotics Alleviate the Gut Indole Load and Dysbiosis in Chronic Kidney Disease. Cells. 2021 01; 10(1):. doi: 10.3390/cells10010114. [PMID: 33435396]
  • Shintaro Inoue, Rihito Morita, Yoshiko Minami. An indigo-producing plant, Polygonum tinctorium, possesses a flavin-containing monooxygenase capable of oxidizing indole. Biochemical and biophysical research communications. 2021 01; 534(?):199-205. doi: 10.1016/j.bbrc.2020.11.112. [PMID: 33303189]
  • Harriet Wall. Welcome to volume 13 of Future Medicinal Chemistry. Future medicinal chemistry. 2021 01; 13(1):1-3. doi: 10.4155/fmc-2020-0338. [PMID: 33319591]
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  • Fangcong Dong, Fuhua Hao, Iain A Murray, Philip B Smith, Imhoi Koo, Alyssa M Tindall, Penny M Kris-Etherton, Krishne Gowda, Shantu G Amin, Andrew D Patterson, Gary H Perdew. Intestinal microbiota-derived tryptophan metabolites are predictive of Ah receptor activity. Gut microbes. 2020 11; 12(1):1-24. doi: 10.1080/19490976.2020.1788899. [PMID: 32783770]
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