Tryptamine (BioDeep_00000000123)

 

Secondary id: BioDeep_00000399993, BioDeep_00000412404

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


代谢物信息卡片


2-(1H-indol-3-yl)ethan-1-amine

化学式: C10H12N2 (160.1000432)
中文名称: 色胺
谱图信息: 最多检出来源 Homo sapiens(blood) 0.01%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Tryptamine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/tryptamine (retrieved 2024-11-21) (BioDeep RN: BioDeep_00000000123). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=CN2)CCN
InChI: InChI=1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

描述信息

Tryptamine, also known as TrpN, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine (PMID: 30120222). Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods.
Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is an aminoalkylindole, an indole alkaloid, an aralkylamino compound and a member of tryptamines. It is a conjugate base of a tryptaminium.
Tryptamine is a natural product found in Mus musculus, Prosopis glandulosa, and other organisms with data available.
Occurs widely in plants, especies Lens esculenta (lentil) and the fungi Coprinus micaceus (glistening ink cap)
An aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position.
KEIO_ID T031

同义名列表

63 个代谢物同义名

InChI=1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H; 5-22-10-00045 (Beilstein Handbook Reference); (Amino-2 ethyl)-3 indole;3-Indoleethylamine; Tryptamine, Vetec(TM) reagent grade, 98\\%; 5E7B376B-5933-446C-9D88-661B5F480122; (Amino-2 ethyl)-3 indole [French]; Tryptamine, analytical standard; 2-(1H-Indol-3-Yl)Ethan-1-Amine; 2-(1H-indol-3-yl)-ethyl-amine; 2-(1H-Indol-3-yl)ethanamine #; 2-(1h-indol-3-yl) ethylamine; 2-(1H-INDOL-3-YL)-ETHYLAMINE; .beta.-(3-Indolyl)ethylamine; tryptamine monohydrochloride; 2-(1H-indol-3-yl)ethylamine; 2-(1H-Indol-3-yl)ethanamine; 3-(2-Aminoethyl)-1H-indole; beta-(3-Indolyl)ethylamine; 3-(beta-aminoethyl)-indole; Indole, 3-(2-aminoethyl)-; (Amino-2 ethyl)-3 indole; 2-(Indol-3-yl)ethylamine; 2-Indol-3-yl-aethylamin; 2-indol-3-yl-ethylamine; 3-(2-amino)ethyl indole; 2-(3-Indolyl)ethylamine; Β-(3-indolyl)ethylamine; 1H-Indole-3-ethanamine; 2-Indol-3-ylethylamine; 3-(2-aminoethyl)indole; 3-[2-Aminoethyl]indole; Tryptamine, free base; (3-Indolyl)ethylamine; 3-indolylethylamine; 3-Indoleethylamine; tryptamine sulfate; 3-Indoleethanamine; Indol-3-ethylamine; Spectrum5_001296; Spectrum2_000873; Tryptamine, 98\\%; Spectrum3_001890; Spectrum4_000850; TRYPTAMINE [MI]; Oprea1_870097; Lopac0_000061; DivK1c_000862; KBio2_000393; KBio2_002961; KBio1_000862; KBio3_002903; KBio2_005529; IDI1_000862; triptamine; Tryptamine; Tryptamin; TRPN; TSH; beta-3-Indolylethylamine hydrochloride; 3-(2-Aminoethyl)indole Hydrochloride; Tryptamine; Tryptamine; Tryptamine



数据库引用编号

35 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

473 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(464)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(7)

PharmGKB(0)

197 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

  • Lei-Qi Liu, Jing-Ze Chen, Wu-Sheng Fu, Cui-Ying Tang. [Determination of amanita peptide and tryptamine toxins in wild mushrooms by high performance liquid chromatography-tandem mass spectrometry]. Se pu = Chinese journal of chromatography. 2023 Nov; 41(11):976-985. doi: 10.3724/sp.j.1123.2023.07013. [PMID: 37968816]
  • Daijing Wei, Yun Yang, Ruiying Xi, Yunqing He, Ighodaro Igbe, Fei Wang, Guolin Zhang, Yinggang Luo. Hunteriasines A - D, tryptamine-derived alkaloids from Hunteria umbellata. Phytochemistry. 2023 Sep; 213(?):113752. doi: 10.1016/j.phytochem.2023.113752. [PMID: 37330032]
  • Lixiang Zhai, Haitao Xiao, Chengyuan Lin, Hoi Leong Xavier Wong, Yan Y Lam, Mengxue Gong, Guojun Wu, Ziwan Ning, Chunhua Huang, Yijing Zhang, Chao Yang, Jingyuan Luo, Lu Zhang, Ling Zhao, Chenhong Zhang, Johnson Yiu-Nam Lau, Aiping Lu, Lok-Ting Lau, Wei Jia, Liping Zhao, Zhao-Xiang Bian. Gut microbiota-derived tryptamine and phenethylamine impair insulin sensitivity in metabolic syndrome and irritable bowel syndrome. Nature communications. 2023 Aug; 14(1):4986. doi: 10.1038/s41467-023-40552-y. [PMID: 37591886]
  • Jie Chen, Yueqi Zhang, Huanran Yin, Wei Liu, Xin Hu, Dongqin Li, Caixia Lan, Lifeng Gao, Zhonghu He, Fa Cui, Alisdair R Fernie, Wei Chen. The pathway of melatonin biosynthesis in common wheat (Triticum aestivum). Journal of pineal research. 2023 Mar; 74(2):e12841. doi: 10.1111/jpi.12841. [PMID: 36396897]
  • Fateme Zohairi, Himanshu Khandelia, Ali Asghar Hakami Zanjani. Interaction of psychedelic tryptamine derivatives with a lipid bilayer. Chemistry and physics of lipids. 2023 Mar; 251(?):105279. doi: 10.1016/j.chemphyslip.2023.105279. [PMID: 36627076]
  • Marcus Daniel Brandbjerg Bohn Lorensen, Nanna Bjarnholt, Benoit St-Pierre, Vincent Courdavault, Sarah Heinicke, Sarah O'Connor, Christian Janfelt. Spatial localization of monoterpenoid indole alkaloids in Rauvolfia tetraphylla by high resolution mass spectrometry imaging. Phytochemistry. 2023 Feb; ?(?):113620. doi: 10.1016/j.phytochem.2023.113620. [PMID: 36863602]
  • Lea Wagmann, Sascha K Manier, Markus R Meyer. Can the Intake of a Synthetic Tryptamine be Detected Only by Blood Plasma Analysis? A Clinical Toxicology Case Involving 4-HO-MET. Journal of analytical toxicology. 2022 May; 46(5):567-572. doi: 10.1093/jat/bkab062. [PMID: 34100553]
  • Rajasree G Krishnan, Beena Saraswathyamma. Murexide-derived in vitro electrochemical sensor for the simultaneous determination of neurochemicals. Analytical and bioanalytical chemistry. 2021 Nov; 413(27):6803-6812. doi: 10.1007/s00216-021-03282-y. [PMID: 33774711]
  • Jiahui Shao, Yucong Li, Zunfeng Li, Zhihui Xu, Weibing Xun, Nan Zhang, Haichao Feng, Youzhi Miao, Qirong Shen, Ruifu Zhang. Participating mechanism of a major contributing gene ysnE for auxin biosynthesis in Bacillus amyloliquefaciens SQR9. Journal of basic microbiology. 2021 Jun; 61(6):569-575. doi: 10.1002/jobm.202100098. [PMID: 33914927]
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  • Hana Leontovyčová, Lucie Trdá, Petre Ivanov Dobrev, Vladimír Šašek, Elise Gay, Marie-Hélène Balesdent, Lenka Burketová. Auxin biosynthesis in the phytopathogenic fungus Leptosphaeria maculans is associated with enhanced transcription of indole-3-pyruvate decarboxylase LmIPDC2 and tryptophan aminotransferase LmTAM1. Research in microbiology. 2020 Jul; 171(5-6):174-184. doi: 10.1016/j.resmic.2020.05.001. [PMID: 32540203]
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  • Xiwen Tong, Yundan Wang, Pengcheng Yang, Chengshu Wang, Le Kang. Tryptamine accumulation caused by deletion of MrMao-1 in Metarhizium genome significantly enhances insecticidal virulence. PLoS genetics. 2020 04; 16(4):e1008675. doi: 10.1371/journal.pgen.1008675. [PMID: 32271756]
  • Brian G O'Flynn, Eric M Lewandowski, Karin Claire Prins, Gabriela Suarez, Angelica N McCaskey, Nasha M Rios-Guzman, Ryan L Anderson, Britney A Shepherd, Ioannis Gelis, James W Leahy, Yu Chen, David J Merkler. Characterization of Arylalkylamine N-Acyltransferase from Tribolium castaneum: An Investigation into a Potential Next-Generation Insecticide Target. ACS chemical biology. 2020 02; 15(2):513-523. doi: 10.1021/acschembio.9b00973. [PMID: 31967772]
  • Jakub Staroń, Rafał Kurczab, Dawid Warszycki, Grzegorz Satała, Martyna Krawczyk, Ryszard Bugno, Tomasz Lenda, Piotr Popik, Adam S Hogendorf, Agata Hogendorf, Krzysztof Dubiel, Mikołaj Matłoka, Rafał Moszczyński-Pętkowski, Jerzy Pieczykolan, Maciej Wieczorek, Paweł Zajdel, Andrzej J Bojarski. Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties. European journal of medicinal chemistry. 2020 Jan; 185(?):111857. doi: 10.1016/j.ejmech.2019.111857. [PMID: 31734022]
  • Yang Yu, Mei-Fen Bao, Jing Wu, Jing Chen, Yu-Rong Yang, Johann Schinnerl, Xiang-Hai Cai. Tabernabovines A-C: Three Monoterpenoid Indole Alkaloids from the Leaves of Tabernaemontana bovina. Organic letters. 2019 08; 21(15):5938-5942. doi: 10.1021/acs.orglett.9b02060. [PMID: 31294995]
  • Alma Vázquez-Luna, Fabio García-García, Diana I Caudillo Contreras, Eduardo Rivadeneyra-Domínguez, Rafael Díaz-Sobac. Effect of orange juice and tryptamine on the behavior and c-fos expression of Wistar rats. Metabolic brain disease. 2019 04; 34(2):519-525. doi: 10.1007/s11011-018-0365-5. [PMID: 30604026]
  • Mauro Commisso, Stefano Negri, Martino Bianconi, Sofia Gambini, Sara Avesani, Stefania Ceoldo, Linda Avesani, Flavia Guzzo. Untargeted and Targeted Metabolomics and Tryptophan Decarboxylase In Vivo Characterization Provide Novel Insight on the Development of Kiwifruits (Actinidia deliciosa). International journal of molecular sciences. 2019 Feb; 20(4):. doi: 10.3390/ijms20040897. [PMID: 30791398]
  • Tiantian Ye, Xiaoming Yin, Lei Yu, Shu-Jian Zheng, Wen-Jing Cai, Yan Wu, Yu-Qi Feng. Metabolic analysis of the melatonin biosynthesis pathway using chemical labeling coupled with liquid chromatography-mass spectrometry. Journal of pineal research. 2019 Jan; 66(1):e12531. doi: 10.1111/jpi.12531. [PMID: 30299556]
  • Brian Torres, James S Tyler, Kenneth A Satyshur, Arnold E Ruoho. Human indole(ethyl)amine-N-methyltransferase (hINMT) catalyzed methylation of tryptamine, dimethylsulfide and dimethylselenide is enhanced under reducing conditions - A comparison between 254C and 254F, two common hINMT variants. PloS one. 2019; 14(7):e0219664. doi: 10.1371/journal.pone.0219664. [PMID: 31310642]
  • Felix Blei, Janis Fricke, Jonas Wick, Jason C Slot, Dirk Hoffmeister. Iterative l-Tryptophan Methylation in Psilocybe Evolved by Subdomain Duplication. Chembiochem : a European journal of chemical biology. 2018 10; 19(20):2160-2166. doi: 10.1002/cbic.201800336. [PMID: 30098085]
  • Geofrey Sing'ombe Ombiro, Taku Sawai, Yoshiteru Noutoshi, Yuta Nishina, Hidenori Matsui, Mikihiro Yamamoto, Kazuhiro Toyoda, Yuki Ichinose. Specific growth inhibitors of Ralstonia solanacearum, Xanthomonas oryzae pv. oryzae, X. campestris pv. campestris, and Clavibacter michiganensis subsp. michiganensis. Microbiological research. 2018 Oct; 215(?):29-35. doi: 10.1016/j.micres.2018.06.005. [PMID: 30172306]
  • Desiree Pressnitz, Eva-Maria Fischereder, Jakob Pletz, Christina Kofler, Lucas Hammerer, Katharina Hiebler, Horst Lechner, Nina Richter, Elisabeth Eger, Wolfgang Kroutil. Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-ß-carbolines Catalyzed by Strictosidine Synthases. Angewandte Chemie (International ed. in English). 2018 08; 57(33):10683-10687. doi: 10.1002/anie.201803372. [PMID: 29852524]
  • Yang Yu, Yan Lv, Yana Shi, Tao Li, Yanchun Chen, Dake Zhao, Zhiwei Zhao. The Role of Phyto-Melatonin and Related Metabolites in Response to Stress. Molecules (Basel, Switzerland). 2018 Jul; 23(8):. doi: 10.3390/molecules23081887. [PMID: 30060559]
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