3-Indolepropionic acid (BioDeep_00000014962)

Main id: BioDeep_00000018442

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


Indole-3-propionic acid

化学式: C11H11NO2 (189.0789746)
中文名称: 3-吲哚丙酸(IPA)
谱图信息: 最多检出来源 Ailuropoda melanoleuca(feces) 0.93%

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=CN2)CCC(=O)O
InChI: InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)

描述信息

3-Indolepropionic acid is shown to be a powerful antioxidant and has potential in the treatment for Alzheimer’s disease.

同义名列表

3 个代谢物同义名

3-Indolepropionic acid; Indole-3-propionic acid; 3-IPA



数据库引用编号

19 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

10 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

  • Dingjiacheng Jia, Qiwen Wang, Yadong Qi, Yao Jiang, Jiamin He, Yifeng Lin, Yong Sun, Jilei Xu, Wenwen Chen, Lina Fan, Ruochen Yan, Wang Zhang, Guohong Ren, Chaochao Xu, Qiwei Ge, Lan Wang, Wei Liu, Fei Xu, Pin Wu, Yuhao Wang, Shujie Chen, Liangjing Wang. Microbial metabolite enhances immunotherapy efficacy by modulating T cell stemness in pan-cancer. Cell. 2024 Mar; 187(7):1651-1665.e21. doi: 10.1016/j.cell.2024.02.022. [PMID: 38490195]
  • Lianru Chen, Ya Chen, Bin Wang, Zhongcheng Yang, Zongyu Cai, Xuekun Wang, Lidan Sun, Zheng Li, Guangji Wang. Design, synthesis, and biological evaluation of deuterated indolepropionic acid derivatives as novel long-acting pan PPARα/γ/δ agonists. Bioorganic & medicinal chemistry. 2023 12; 96(?):117533. doi: 10.1016/j.bmc.2023.117533. [PMID: 37976807]
  • Lu Chen, Yuxuan Yang, Siyu Sun, Yuan Xie, Cailong Pan, Maining Li, Chen Li, Yu Liu, Zhipeng Xu, Wentao Liu, Minjun Ji. Indolepropionic acid reduces obesity-induced metabolic dysfunction through colonic barrier restoration mediated via tuft cell-derived IL-25. The FEBS journal. 2022 10; 289(19):5985-6004. doi: 10.1111/febs.16470. [PMID: 35509122]
  • Piotr Konopelski, Izabella Mogilnicka. Biological Effects of Indole-3-Propionic Acid, a Gut Microbiota-Derived Metabolite, and Its Precursor Tryptophan in Mammals' Health and Disease. International journal of molecular sciences. 2022 Jan; 23(3):. doi: 10.3390/ijms23031222. [PMID: 35163143]
  • Shan Li, Xiaoyong Zhao, Feihong Lin, Xuqing Ni, Xia Liu, Chang Kong, Xinyu Yao, Yunchang Mo, Qinxue Dai, Junlu Wang. Gut Flora Mediates the Rapid Tolerance of Electroacupuncture on Ischemic Stroke by Activating Melatonin Receptor through Regulating Indole-3-Propionic Acid. The American journal of Chinese medicine. 2022; 50(4):979-1006. doi: 10.1142/s0192415x22500409. [PMID: 35475976]
  • Solomon E Owumi, Moses T Otunla, Uche O Arunsi, Eseroghene S Najophe. 3-Indolepropionic acid upturned male reproductive function by reducing oxido-inflammatory responses and apoptosis along the hypothalamic-pituitary-gonadal axis of adult rats exposed to chlorpyrifos. Toxicology. 2021 11; 463(?):152996. doi: 10.1016/j.tox.2021.152996. [PMID: 34678318]
  • Cai-Jie Zhou, Bai-Ling Xie, Hai-Yang Han, Yin Wang, Yong-Hua Wang, Jing-Yi Hong, Yi-Xia Wei, Zhi-Gang Liu, Yan Feng, Gui Yang, Ping-Chang Yang. Short-Chain Fatty Acids Promote Immunotherapy by Modulating Immune Regulatory Property in B Cells. Journal of immunology research. 2021; 2021(?):2684361. doi: 10.1155/2021/2684361. [PMID: 34926702]
  • Hui-Wen Xiao, Ming Cui, Yuan Li, Jia-Li Dong, Shu-Qin Zhang, Chang-Chun Zhu, Mian Jiang, Tong Zhu, Bin Wang, Hai-Chao Wang, Sai-Jun Fan. Gut microbiota-derived indole 3-propionic acid protects against radiation toxicity via retaining acyl-CoA-binding protein. Microbiome. 2020 05; 8(1):69. doi: 10.1186/s40168-020-00845-6. [PMID: 32434586]
  • Vivek Krishna Pulakazhi Venu, Mahmoud Saifeddine, Koichiro Mihara, Yi-Cheng Tsai, Kristoff Nieves, Laurie Alston, Sridhar Mani, Kathy D McCoy, Morley D Hollenberg, Simon A Hirota. The pregnane X receptor and its microbiota-derived ligand indole 3-propionic acid regulate endothelium-dependent vasodilation. American journal of physiology. Endocrinology and metabolism. 2019 08; 317(2):E350-E361. doi: 10.1152/ajpendo.00572.2018. [PMID: 31211619]
  • Yen Chin Koay, Jibran A Wali, Alison W S Luk, Laurence Macia, Victoria C Cogger, Tamara J Pulpitel, Devin Wahl, Samantha M Solon-Biet, Andrew Holmes, Stephen J Simpson, John F O'Sullivan. Ingestion of resistant starch by mice markedly increases microbiome-derived metabolites. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2019 07; 33(7):8033-8042. doi: 10.1096/fj.201900177r. [PMID: 30925066]
  • Cristina Menni, Marisa Matey Hernandez, Marius Vital, Robert P Mohney, Tim D Spector, Ana M Valdes. Circulating levels of the anti-oxidant indoleproprionic acid are associated with higher gut microbiome diversity. Gut microbes. 2019; 10(6):688-695. doi: 10.1080/19490976.2019.1586038. [PMID: 31030641]
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  • Vanessa D de Mello, Jussi Paananen, Jaana Lindström, Maria A Lankinen, Lin Shi, Johanna Kuusisto, Jussi Pihlajamäki, Seppo Auriola, Marko Lehtonen, Olov Rolandsson, Ingvar A Bergdahl, Elise Nordin, Pirjo Ilanne-Parikka, Sirkka Keinänen-Kiukaanniemi, Rikard Landberg, Johan G Eriksson, Jaakko Tuomilehto, Kati Hanhineva, Matti Uusitupa. Indolepropionic acid and novel lipid metabolites are associated with a lower risk of type 2 diabetes in the Finnish Diabetes Prevention Study. Scientific reports. 2017 04; 7(?):46337. doi: 10.1038/srep46337. [PMID: 28397877]
  • Veit Rothhammer, Ivan D Mascanfroni, Lukas Bunse, Maisa C Takenaka, Jessica E Kenison, Lior Mayo, Chun-Cheih Chao, Bonny Patel, Raymond Yan, Manon Blain, Jorge I Alvarez, Hania Kébir, Niroshana Anandasabapathy, Guillermo Izquierdo, Steffen Jung, Nikolaus Obholzer, Nathalie Pochet, Clary B Clish, Marco Prinz, Alexandre Prat, Jack Antel, Francisco J Quintana. Type I interferons and microbial metabolites of tryptophan modulate astrocyte activity and central nervous system inflammation via the aryl hydrocarbon receptor. Nature medicine. 2016 06; 22(6):586-97. doi: 10.1038/nm.4106. [PMID: 27158906]
  • Sartaj Tabassum, Mehvash Zaki, Musheer Ahmad, Mohd Afzal, Saurabh Srivastav, Saripella Srikrishna, Farukh Arjmand. Synthesis and crystal structure determination of copper(II)-complex: In vitro DNA and HSA binding, pBR322 plasmid cleavage, cell imaging and cytotoxic studies. European journal of medicinal chemistry. 2014 Aug; 83(?):141-54. doi: 10.1016/j.ejmech.2014.06.018. [PMID: 24953031]
  • Grolamys Castillo, Alejandro Torrecillas, Clara Nogueiras, Georgina Michelena, José Sánchez-Bravo, Manuel Acosta. Simultaneous quantification of phytohormones in fermentation extracts of Botryodiplodia theobromae by liquid chromatography-electrospray tandem mass spectrometry. World journal of microbiology & biotechnology. 2014 Jul; 30(7):1937-46. doi: 10.1007/s11274-014-1612-5. [PMID: 24510403]
  • Hongyuan Yan, Fang Wang, Dandan Han, Gengliang Yang. Simultaneous determination of four plant hormones in bananas by molecularly imprinted solid-phase extraction coupled with high performance liquid chromatography. The Analyst. 2012 Jun; 137(12):2884-90. doi: 10.1039/c2an35362h. [PMID: 22553770]
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  • Qing Huang, Yi-Hong Lu, Guang-Ji Wang, Xin-Wen Wang, Nan Meng, Jie Gao, Di Lu, Xin Yan, Ying Zhang, Lin-Sheng Liu, Gang Hao, Bei Yan, Sheng-Hua Gu, Ji-Ye A. [Metabonomic profiling of plasma metabolites in Wistar rats to study the effect of aging by means of GC/TOFMS-based techniques]. Yao xue xue bao = Acta pharmaceutica Sinica. 2009 Oct; 44(10):1095-101. doi: NULL. [PMID: 20055130]
  • Bojana Savić, Sanja Tomić, Volker Magnus, Kristina Gruden, Katja Barle, Renata Grenković, Jutta Ludwig-Müller, Branka Salopek-Sondi. Auxin amidohydrolases from Brassica rapa cleave the alanine conjugate of indolepropionic acid as a preferable substrate: a biochemical and modeling approach. Plant & cell physiology. 2009 Sep; 50(9):1587-99. doi: 10.1093/pcp/pcp101. [PMID: 19602499]
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  • Mandi L Conrad, Annette C Moser, David S Hage. Evaluation of indole-based probes for high-throughput screening of drug binding to human serum albumin: Analysis by high-performance affinity chromatography. Journal of separation science. 2009 Apr; 32(8):1145-55. doi: 10.1002/jssc.200800567. [PMID: 19296478]
  • Magdalena Stasiak, Andrzej Lewiński, Małgorzata Karbownik-Lewińska. [Relationship between toxic effects of potassium bromate and endocrine glands]. Endokrynologia Polska. 2009 Jan; 60(1):40-50. doi: ". [PMID: 19224504]
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  • Ana Tomasić, Branimir Bertosa, Sanja Tomić, Milan Soskić, Volker Magnus. Binding behavior of amino acid conjugates of indole-3-acetic acid to immobilized human serum albumin. Journal of chromatography. A. 2007 Jun; 1154(1-2):240-9. doi: 10.1016/j.chroma.2007.03.095. [PMID: 17459401]
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  • Małgorzata Karbownik, Magdalena Stasiak, Arkadiusz Zygmunt, Krzysztof Zasada, Andrzej Lewiński. Protective effects of melatonin and indole-3-propionic acid against lipid peroxidation, caused by potassium bromate in the rat kidney. Cell biochemistry and function. 2006 Nov; 24(6):483-9. doi: 10.1002/cbf.1321. [PMID: 16397908]
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