Indole-3-lactic acid (BioDeep_00000001357)

 

Secondary id: BioDeep_00000229616, BioDeep_00001868441

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(AlphaS)-alpha-hydroxy-1H-indole-3-propanoic acid

化学式: C11H11NO3 (205.0738896)
中文名称: DL-3-吲哚乳酸, 3-吲哚乙酸, 吲哚-3-乳酸, S-2-羟基-3-吲哚基丙酸
谱图信息: 最多检出来源 Homo sapiens(blood) 1.96%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Indole-3-lactic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/indole-3-lactic_acid (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000001357). 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)CC(C(=O)O)O
InChI: InChI=1S/C11H11NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12-13H,5H2,(H,14,15)

描述信息

Indolelactic acid (CAS: 1821-52-9) is a tryptophan metabolite found in human plasma, serum, and urine. Tryptophan is metabolized by two major pathways in humans, either through kynurenine or via a series of indoles, and some of its metabolites are known to be biologically active. Indolelactic acid is present in various amounts, significantly higher in umbilical fetal plasma than in maternal plasma in the protein-bound form (PMID 2361979, 1400722, 3597614, 11060358, 1400722). Indolelactic acid is also a microbial metabolite; urinary indole-3-lactate is produced by Clostridium sporogenes (PMID: 29168502).
Indolelactic acid is a tryptophan metabolite found in human plasma and serum and normal urine. Tryptophan is metabolized by two major pathways in humans, either through kynurenine or via a series of indoles, and some of its metabolites are known to be biologically active. Indolelactic acid is present in various amounts, significantly higher in umbilical foetal plasma than in maternal plasma in the protein-bound form. (PMID 2361979, 1400722, 3597614, 11060358, 1400722) [HMDB]
Indolelactic acid (Indole-3-lactic acid) is a tryptophan (Trp) catabolite in Azotobacter vinelandii cultures. Indolelactic acid has anti-inflammation and potential anti-viral activity[1][3][4].

同义名列表

56 个代谢物同义名

(AlphaS)-alpha-hydroxy-1H-indole-3-propanoic acid; (AlphaS)-alpha-hydroxy-1H-indole-3-propionic acid; (2S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid; (2S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acid; (S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid; DL-Indole-3-lactic acid (3-Indolelactic acid); (S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acid; (+)-alpha-hydroxy-1H-indole-3-propanoic acid; (+)-alpha-hydroxy-1H-indole-3-propionic acid; 2-Hydroxy-3-(1H-indol-3-yl)propanoic acid; (ΑS)-α-hydroxy-1H-indole-3-propanoic acid; (ΑS)-α-hydroxy-1H-indole-3-propionic acid; (S)-2-hydroxy-3-indol-3-yl-propionic acid; (+)-2-hydroxy-3-indol-3-yl-propionic acid; 2-Hydroxy-3-(1H-indol-3-yl)propionic acid; alpha-Hydroxy-1H-indole-3-propanoic acid; (+)-alpha-hydroxy-1H-indole-3-propionate; alpha-Hydroxy-1H-indole-3-propionic acid; (+)-alpha-hydroxy-1H-indole-3-propanoate; (+)-a-hydroxy-1H-indole-3-propionic acid; (+)-a-hydroxy-1H-indole-3-propanoic acid; (2S)-2-Hydroxy-3-indoylpropanoic acid; 3-(3-Indolyl)-2-hydroxypropanoic acid; 3-(3-Indolyl)-2-hydroxypropionic acid; 2-Hydroxy-3-indol-3-yl-propionic acid; 2-Hydroxy-3-(3-indolyl)propanoic acid; (+)-2-hydroxy-3-indol-3-yl-propionate; (S)-2-hydroxy-3-indol-3-yl-propionate; (2S)-2-Hydroxy-3-indoylpropionic acid; 2-Hydroxy-3-(3-indolyl)propionic acid; 2-Hydroxy-3-indol-3-yl-propionsaeure; Α-hydroxy-1H-indole-3-propanoic acid; (+)-a-hydroxy-1H-indole-3-propanoate; Α-hydroxy-1H-indole-3-propionic acid; (+)-a-hydroxy-1H-indole-3-propionate; 2-Hydroxy-3-indol-3-yl-propionate; 2-(1H-indol-3-yl)Acetaldehyde; 3-(3-Indolyl)-DL-lactic acid; beta-(3-Indolyl)lactic acid; L-3-(3-Indolyl)lactic acid; 3-(indol-3-yl) LACTic acid; Β-(3-indolyl)lactic acid; (S)-Indole-3-lactic acid; beta-Indolyllactic acid; DL-Indole-3-lactic acid; 3-(indol-3-yl) lactate; DL-3-indolelactic acid; Indole-3-L-lactic acid; L-Indole-3-lactic acid; 3-Indolyllactic acid; Β-indolyllactic acid; Indole-3-lactic Acid; DL-3-indolelactate; Indolelactic acid; Indolelactate; Indole-3-lactic Acid



数据库引用编号

21 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(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

  • Tryptophan Metabolism: Phosphoadenosine phosphosulfate + indolylmethyl-desulfoglucosinolate ⟶ Adenosine 3',5'-diphosphate + Glucobrassicin + Hydrogen Ion

PharmGKB(0)

11 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

  • Moeun Lee, Daun Kim, Ji Yoon Chang. Metabolites of Kimchi Lactic Acid Bacteria, Indole-3-Lactic Acid, Phenyllactic Acid, and Leucic Acid, Inhibit Obesity-Related Inflammation in Human Mesenchymal Stem Cells. Journal of microbiology and biotechnology. 2023 Oct; 34(3):1-8. doi: 10.4014/jmb.2308.08015. [PMID: 37940180]
  • Bethany M Henrick, Lucie Rodriguez, Tadepally Lakshmikanth, Christian Pou, Ewa Henckel, Aron Arzoomand, Axel Olin, Jun Wang, Jaromir Mikes, Ziyang Tan, Yang Chen, Amy M Ehrlich, Anna Karin Bernhardsson, Constantin Habimana Mugabo, Ylva Ambrosiani, Anna Gustafsson, Stephanie Chew, Heather K Brown, Johann Prambs, Kajsa Bohlin, Ryan D Mitchell, Mark A Underwood, Jennifer T Smilowitz, J Bruce German, Steven A Frese, Petter Brodin. Bifidobacteria-mediated immune system imprinting early in life. Cell. 2021 07; 184(15):3884-3898.e11. doi: 10.1016/j.cell.2021.05.030. [PMID: 34143954]
  • Takeshi Tanaka, Masahiko Mori, Motohiro Sekino, Ushio Higashijima, Masahiro Takaki, Yoshiro Yamashita, Satoshi Kakiuchi, Masato Tashiro, Konosuke Morimoto, Osamu Tasaki, Koichi Izumikawa. Impact of plasma 5-hydroxyindoleacetic acid, a serotonin metabolite, on clinical outcome in septic shock, and its effect on vascular permeability. Scientific reports. 2021 07; 11(1):14146. doi: 10.1038/s41598-021-93649-z. [PMID: 34238999]
  • Adam T Watson, Storm Hassell-Hart, John Spencer, Antony M Carr. Rice (Oryza sativa) TIR1 and 5'adamantyl-IAA Significantly Improve the Auxin-Inducible Degron System in Schizosaccharomyces pombe. Genes. 2021 06; 12(6):. doi: 10.3390/genes12060882. [PMID: 34201031]
  • 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]
  • 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]
  • Qilin Fan, Xiaojing Guan, Yuanlong Hou, Yali Liu, Wei Wei, Xiaoying Cai, Youying Zhang, Guangji Wang, Xiao Zheng, Haiping Hao. Paeoniflorin modulates gut microbial production of indole-3-lactate and epithelial autophagy to alleviate colitis in mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Dec; 79(?):153345. doi: 10.1016/j.phymed.2020.153345. [PMID: 33002829]
  • Amy M Ehrlich, Alline R Pacheco, Bethany M Henrick, Diana Taft, Gege Xu, M Nazmul Huda, Darya Mishchuk, Michael L Goodson, Carolyn Slupsky, Daniela Barile, Carlito B Lebrilla, Charles B Stephensen, David A Mills, Helen E Raybould. Indole-3-lactic acid associated with Bifidobacterium-dominated microbiota significantly decreases inflammation in intestinal epithelial cells. BMC microbiology. 2020 11; 20(1):357. doi: 10.1186/s12866-020-02023-y. [PMID: 33225894]
  • Yurong Cheng, Yong Li, Paula Benkowitz, Claudia Lamina, Anna Köttgen, Peggy Sekula. The relationship between blood metabolites of the tryptophan pathway and kidney function: a bidirectional Mendelian randomization analysis. Scientific reports. 2020 07; 10(1):12675. doi: 10.1038/s41598-020-69559-x. [PMID: 32728058]
  • Kyoungmi Kim, Josephine F Trott, Guimin Gao, Arlene Chapman, Robert H Weiss. Plasma metabolites and lipids associate with kidney function and kidney volume in hypertensive ADPKD patients early in the disease course. BMC nephrology. 2019 02; 20(1):66. doi: 10.1186/s12882-019-1249-6. [PMID: 30803434]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Mengsha Li, Rui Guo, Fei Yu, Xu Chen, Haiyan Zhao, Huixin Li, Jun Wu. Indole-3-Acetic Acid Biosynthesis Pathways in the Plant-Beneficial Bacterium Arthrobacter pascens ZZ21. International journal of molecular sciences. 2018 Feb; 19(2):. doi: 10.3390/ijms19020443. [PMID: 29389906]
  • Nicola Wilck, Mariana G Matus, Sean M Kearney, Scott W Olesen, Kristoffer Forslund, Hendrik Bartolomaeus, Stefanie Haase, Anja Mähler, András Balogh, Lajos Markó, Olga Vvedenskaya, Friedrich H Kleiner, Dmitry Tsvetkov, Lars Klug, Paul I Costea, Shinichi Sunagawa, Lisa Maier, Natalia Rakova, Valentin Schatz, Patrick Neubert, Christian Frätzer, Alexander Krannich, Maik Gollasch, Diana A Grohme, Beatriz F Côrte-Real, Roman G Gerlach, Marijana Basic, Athanasios Typas, Chuan Wu, Jens M Titze, Jonathan Jantsch, Michael Boschmann, Ralf Dechend, Markus Kleinewietfeld, Stefan Kempa, Peer Bork, Ralf A Linker, Eric J Alm, Dominik N Müller. Salt-responsive gut commensal modulates TH17 axis and disease. Nature. 2017 11; 551(7682):585-589. doi: 10.1038/nature24628. [PMID: 29143823]
  • Christian Ulrich von Linstow, Jonas Waider, Manuela Grebing, Athanasios Metaxas, Klaus Peter Lesch, Bente Finsen. Serotonin augmentation therapy by escitalopram has minimal effects on amyloid-β levels in early-stage Alzheimer's-like disease in mice. Alzheimer's research & therapy. 2017 Sep; 9(1):74. doi: 10.1186/s13195-017-0298-y. [PMID: 28899417]
  • Ling Zhao, Hai-Tao Xiao, Huai-Xue Mu, Tao Huang, Ze-Si Lin, Linda L D Zhong, Guang-Zhi Zeng, Bao-Min Fan, Cheng-Yuan Lin, Zhao-Xiang Bian. Magnolol, a Natural Polyphenol, Attenuates Dextran Sulfate Sodium-Induced Colitis in Mice. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071218. [PMID: 28726741]
  • Noera Kieviet, Vera van Keulen, Peter Marinus van de Ven, Koert Melchior Dolman, Martine Deckers, Adriaan Honig. Serotonin and poor neonatal adaptation after antidepressant exposure in utero. Acta neuropsychiatrica. 2017 Feb; 29(1):43-53. doi: 10.1017/neu.2016.30. [PMID: 27387606]
  • Roope Tikkanen, Tero Saukkonen, Malin Fex, Hedvig Bennet, Marja-Riitta Rautiainen, Tiina Paunio, Mika Koskinen, Rony Panarsky, Laura Bevilacqua, Rickard L Sjöberg, Jari Tiihonen, Matti Virkkunen. The effects of a HTR2B stop codon and testosterone on energy metabolism and beta cell function among antisocial Finnish males. Journal of psychiatric research. 2016 10; 81(?):79-86. doi: 10.1016/j.jpsychires.2016.06.019. [PMID: 27420381]
  • Leiv Otto Watne, Ane-Victoria Idland, Durk Fekkes, Johan Raeder, Frede Frihagen, Anette Hylen Ranhoff, Farrukh Abbas Chaudhry, Knut Engedal, Torgeir Bruun Wyller, Bjørnar Hassel. Increased CSF levels of aromatic amino acids in hip fracture patients with delirium suggests higher monoaminergic activity. BMC geriatrics. 2016 08; 16(?):149. doi: 10.1186/s12877-016-0324-0. [PMID: 27484129]
  • Michael T Nedelcovych, Robert W Gould, Xiaoyan Zhan, Michael Bubser, Xuewen Gong, Michael Grannan, Analisa T Thompson, Magnus Ivarsson, Craig W Lindsley, P Jeffrey Conn, Carrie K Jones. A rodent model of traumatic stress induces lasting sleep and quantitative electroencephalographic disturbances. ACS chemical neuroscience. 2015 Mar; 6(3):485-93. doi: 10.1021/cn500342u. [PMID: 25581551]
  • Soumen K Manna, Matthew D Thompson, Frank J Gonzalez. Application of mass spectrometry-based metabolomics in identification of early noninvasive biomarkers of alcohol-induced liver disease using mouse model. Advances in experimental medicine and biology. 2015; 815(?):217-38. doi: 10.1007/978-3-319-09614-8_13. [PMID: 25427910]
  • Huawei Zhang, Peng Fu, Beilei Ke, Shuping Wang, Min Li, Lin Han, Chengcheng Peng, Weidong Zhang, Runhui Liu. Metabolomic analysis of biochemical changes in the plasma and urine of collagen-induced arthritis in rats after treatment with Huang-Lian-Jie-Du-Tang. Journal of ethnopharmacology. 2014 May; 154(1):55-64. doi: 10.1016/j.jep.2014.03.007. [PMID: 24709313]
  • Helen G Gika, Ian D Wilson. Global metabolic profiling for the study of alcohol-related disorders. Bioanalysis. 2014 Jan; 6(1):59-77. doi: 10.4155/bio.13.301. [PMID: 24341495]
  • Magdalena Hilbert, Lars M Voll, Yi Ding, Jörg Hofmann, Monica Sharma, Alga Zuccaro. Indole derivative production by the root endophyte Piriformospora indica is not required for growth promotion but for biotrophic colonization of barley roots. The New phytologist. 2012 Oct; 196(2):520-534. doi: 10.1111/j.1469-8137.2012.04275.x. [PMID: 22924530]
  • Doris M Jacobs, Jens C Fuhrmann, Ferdinand A van Dorsten, Dietrich Rein, Sonja Peters, Ewoud J J van Velzen, Boudewijn Hollebrands, Richard Draijer, John van Duynhoven, Ursula Garczarek. Impact of short-term intake of red wine and grape polyphenol extract on the human metabolome. Journal of agricultural and food chemistry. 2012 Mar; 60(12):3078-85. doi: 10.1021/jf2044247. [PMID: 22372405]
  • Kristina Gruden, Matjaž Hren, Ana Herman, Andrej Blejec, Tanja Albrecht, Joachim Selbig, Chris Bauer, Johannes Schuchardt, Michal Or-Guil, Klemen Zupančič, Urban Svajger, Borut Stabuc, Alojz Ihan, Andreja Nataša Kopitar, Maja Ravnikar, Miomir Knežević, Primož Rožman, Matjaž Jeras. A 'crossomics' study analysing variability of different components in peripheral blood of healthy caucasoid individuals. PloS one. 2012; 7(1):e28761. doi: 10.1371/journal.pone.0028761. [PMID: 22253695]
  • Rongli Sun, Juan Zhang, Mengzhen Xiong, Yue Chen, Lihong Yin, Yuepu Pu. Metabonomics biomarkers for subacute toxicity screening for benzene exposure in mice. Journal of toxicology and environmental health. Part A. 2012; 75(18):1163-73. doi: 10.1080/15287394.2012.699858. [PMID: 22891888]
  • Kun Hao, Ping Gong, Shi-Qing Sun, Hai-Ping Hao, Guang-Ji Wang, Yue Dai, Yuan-Cheng Chen, Yan Liang, Lin Xie, Fei-Yan Li, Hao-Ye Li. Mechanism-based pharmacokinetic-pharmacodynamic modeling of the estrogen-like effect of ginsenoside Rb1 on neural 5-HT in ovariectomized mice. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2011 Sep; 44(1-2):117-26. doi: 10.1016/j.ejps.2011.06.014. [PMID: 21740969]
  • Soumen K Manna, Andrew D Patterson, Qian Yang, Kristopher W Krausz, Jeffrey R Idle, Albert J Fornace, Frank J Gonzalez. UPLC-MS-based urine metabolomics reveals indole-3-lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. Journal of proteome research. 2011 Sep; 10(9):4120-33. doi: 10.1021/pr200310s. [PMID: 21749142]
  • Joanna R Zgoda-Pols, Swapan Chowdhury, Mark Wirth, Michael V Milburn, Danny C Alexander, Kevin B Alton. Metabolomics analysis reveals elevation of 3-indoxyl sulfate in plasma and brain during chemically-induced acute kidney injury in mice: investigation of nicotinic acid receptor agonists. Toxicology and applied pharmacology. 2011 Aug; 255(1):48-56. doi: 10.1016/j.taap.2011.05.015. [PMID: 21640743]
  • Oliver Fiehn, W Timothy Garvey, John W Newman, Kerry H Lok, Charles L Hoppel, Sean H Adams. Plasma metabolomic profiles reflective of glucose homeostasis in non-diabetic and type 2 diabetic obese African-American women. PloS one. 2010 Dec; 5(12):e15234. doi: 10.1371/journal.pone.0015234. [PMID: 21170321]
  • Pratibha Vyas, Robin Joshi, K C Sharma, Praveen Rahi, Ashu Gulati, Arvind Gulati. Cold-adapted and rhizosphere-competent strain of Rahnella sp. with broad-spectrum plant growth-promotion potential. Journal of microbiology and biotechnology. 2010 Dec; 20(12):1724-34. doi: . [PMID: 21193830]
  • Soumen K Manna, Andrew D Patterson, Qian Yang, Kristopher W Krausz, Henghong Li, Jeffrey R Idle, Albert J Fornace, Frank J Gonzalez. Identification of noninvasive biomarkers for alcohol-induced liver disease using urinary metabolomics and the Ppara-null mouse. Journal of proteome research. 2010 Aug; 9(8):4176-88. doi: 10.1021/pr100452b. [PMID: 20540569]
  • Francisco A Moreno, Damian Parkinson, Craig Palmer, Wm Lesley Castro, John Misiaszek, Aram El Khoury, Aleksander A Mathé, Ron Wright, Pedro L Delgado. CSF neurochemicals during tryptophan depletion in individuals with remitted depression and healthy controls. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. 2010 Jan; 20(1):18-24. doi: 10.1016/j.euroneuro.2009.10.003. [PMID: 19896342]
  • Abdulla A-B Badawy, Christopher J Morgan. Rapid Isocratic Liquid Chromatographic Separation and Quantification of Tryptophan and Six kynurenine Metabolites in Biological Samples with Ultraviolet and Fluorimetric Detection. International journal of tryptophan research : IJTR. 2010; 3(?):175-86. doi: 10.4137/ijtr.s6225. [PMID: 22084598]
  • S P Quigley, D O Kleemann, S K Walker, P A Speck, S R Rudiger, G S Nattrass, M J DeBlasio, J A Owens. Effect of variable long-term maternal feed allowance on the development of the ovine placenta and fetus. Placenta. 2008 Jun; 29(6):539-48. doi: 10.1016/j.placenta.2008.02.014. [PMID: 18417210]
  • Fili Fazzino, Carol Montes, Mary Urbina, Isabel Carreira, Lucimey Lima. Serotonin transporter is differentially localized in subpopulations of lymphocytes of major depression patients. Effect of fluoxetine on proliferation. Journal of neuroimmunology. 2008 May; 196(1-2):173-80. doi: 10.1016/j.jneuroim.2008.03.012. [PMID: 18462811]
  • Ivan Kosalec, Olivier Puel, Marcel Delaforge, Nevenka Kopjar, Roberto Antolovic, Dubravko Jelic, Biserka Matica, Pierre Galtier, Stjepan Pepeljnjak. Isolation and cytotoxicity of low-molecular-weight metabolites of Candida albicans. Frontiers in bioscience : a journal and virtual library. 2008 May; 13(?):6893-904. doi: 10.2741/3197. [PMID: 18508703]
  • Kuang Ren Chung, Turksen Shilts, Umran Ertürk, L W Timmer, Peter P Ueng. Indole derivatives produced by the fungus Colletotrichum acutatum causing lime anthracnose and postbloom fruit drop of citrus. FEMS microbiology letters. 2003 Sep; 226(1):23-30. doi: 10.1016/s0378-1097(03)00605-0. [PMID: 13129603]
  • Nobuhisa Ueda, Reiji Yoshimura, Koji Shinkai, Yumi Sakata, Jun Nakamura. Higher plasma 5-hydroxyindoleacetic acid levels are associated with SSRI-induced nausea. Neuropsychobiology. 2003; 48(1):31-4. doi: 10.1159/000071826. [PMID: 12886038]
  • X Liu, E Lam. Two binding sites for the plant transcription factor ASF-1 can respond to auxin treatments in transgenic tobacco. The Journal of biological chemistry. 1994 Jan; 269(1):668-75. doi: 10.1016/s0021-9258(17)42401-x. [PMID: 8276868]
  • H Körber, N Strizhov, D Staiger, J Feldwisch, O Olsson, G Sandberg, K Palme, J Schell, C Koncz. T-DNA gene 5 of Agrobacterium modulates auxin response by autoregulated synthesis of a growth hormone antagonist in plants. The EMBO journal. 1991 Dec; 10(13):3983-91. doi: 10.1002/j.1460-2075.1991.tb04973.x. [PMID: 1756712]
  • P P Chou, P K Jaynes. Determination of urinary 5-hydroxyindole-3-acetic acid using solid-phase extraction and reversed-phase high-performance liquid chromatography with electrochemical detection. Journal of chromatography. 1985 May; 341(1):167-71. doi: 10.1016/s0378-4347(00)84022-0. [PMID: 2410438]
  • K Ikeda, H Yoshitomi, T Nakayama, S Goto, T Kimura. Plasma protein binding of frusemide in renal failure rabbits: investigation of endogenous protein binding inhibitors. The Journal of pharmacy and pharmacology. 1984 Oct; 36(10):663-7. doi: 10.1111/j.2042-7158.1984.tb04839.x. [PMID: 6150082]
  • J E Hall, J R Seed. Increased urinary excretion of aromatic amino acid catabolites by Microtus montanus chronically infected with Trypanosoma brucei gambiense. Comparative biochemistry and physiology. B, Comparative biochemistry. 1984; 77(4):755-60. doi: 10.1016/0305-0491(84)90309-2. [PMID: 6375946]
  • W Snedden, C S Mellor, J R Martin. Hypertryptophanemia and indoleketonuria in two mentally subnormal siblings. The New England journal of medicine. 1982 Nov; 307(22):1405. doi: 10.1056/nejm198211253072219. [PMID: 7133092]