5-Hydroxytryptophol (BioDeep_00000022417)

 

Secondary id: BioDeep_00000405466

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


5-Hydroxy-3-(2-hydroxyethyl)-indole

化学式: C10H11NO2 (177.0789746)
中文名称: 5-羟基色醇(Hydroxytryptophol)
谱图信息: 最多检出来源 Homo sapiens(blood) 0.03%

分子结构信息

SMILES: C1=CC2=C(C=C1O)C(=CN2)CCO
InChI: InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2

描述信息

5-Hydroxytryptophol is a relatively minor metabolite of serotonin that is excreted primarily as the glucuronide conjugate in human urine. 5-Hydroxytryptophol becomes more important quantitatively during alcohol intoxication, when a shift in the metabolism of serotonin occurs from 5-hydroxyindole acetic acid toward increased (15-fold higher) formation of 5-hydroxytryptophol due to the inhibition of aldehyde dehydrogenase by ethanol-derived acetaldehyde. Urinary excretion of 5-hydroxytryptophol has also been shown to be markedly increased for several hours following intake of foods rich in serotonin, such as bananas. Wide interspecies variation has been reported in the metabolism serotonin to 5-hydroxytryptophol; 5-Hydroxytryptophol makes up 35\\\% of the excreted serotonin metabolites in the rat on average and 10 to 20\\\% in several other species. Human UDP-glucuronosyltransferase 1A6 (UGT1A6) plays a predominant role in the glucuronidation of 5-hydroxytryptophol by human liver microsomes. (PMID 15258112) [HMDB]. 5-Hydroxytryptophol is found in many foods, some of which are climbing bean, macadamia nut (m. tetraphylla), pepper (c. frutescens), and scarlet bean.
5-Hydroxytryptophol is a relatively minor metabolite of serotonin that is excreted primarily as the glucuronide conjugate in human urine. 5-Hydroxytryptophol becomes more important quantitatively during alcohol intoxication, when a shift in the metabolism of serotonin occurs from 5-hydroxyindole acetic acid toward increased (15-fold higher) formation of 5-hydroxytryptophol due to the inhibition of aldehyde dehydrogenase by ethanol-derived acetaldehyde. Urinary excretion of 5-hydroxytryptophol has also been shown to be markedly increased for several hours following intake of foods rich in serotonin, such as bananas. Wide interspecies variation has been reported in the metabolism serotonin to 5-hydroxytryptophol; 5-Hydroxytryptophol makes up 35\\\% of the excreted serotonin metabolites in the rat on average and 10 to 20\\\% in several other species. Human UDP-glucuronosyltransferase 1A6 (UGT1A6) plays a predominant role in the glucuronidation of 5-hydroxytryptophol by human liver microsomes. (PMID 15258112).
5-Hydroxytryptophol is a mammalian serotonin metabolite, acting as a marker of acute alcohol consumption.

同义名列表

17 个代谢物同义名

5-Hydroxy-3-(2-hydroxyethyl)-indole; 5-Hydroxy-1H-indole-3-ethanol(9ci); 3-(2-Hydroxyethyl)-1H-indol-5-ol; 5-Hydroxy-3-indoleacetic acid; 5-Hydroxy-1H-indole-3-ethanol; 5-Hydroxy-indole-acetic acid; 5-Hydroxyindole-acetic acid; 5-Hydroxyindole-3-ethanol; 5-Hydroxyindolacetic acid; 5-Hydroxyindoacetic acid; Hydroxyindoleacetic acid; 5-Hydroxyindolacetate; 5-Hydroxytryptophol; 5-Hydroxy-3-indole; Hydroxytryptophol; 5-Hydroxyindol; 5-HTOL



数据库引用编号

12 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

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(4)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

4 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

  • Tadashi Hayama, Yurika Yabuuchi, Tomomi Iwamatsu, Erina Tamashima, Yusuke Kawami, Miki Itoyama, Hideyuki Yoshida, Masatoshi Yamaguchi, Hitoshi Nohta. Concerted derivatization and concentration method with dispersive liquid-liquid microextraction for liquid chromatographic analysis of 5-hydroxyindoles in human serum. Talanta. 2013 Dec; 117(?):27-31. doi: 10.1016/j.talanta.2013.08.035. [PMID: 24209305]
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  • Friedrich Martin Wurst, Joerg Metzger. The ethanol conjugate ethyl glucuronide is a useful marker of recent alcohol consumption. Alcoholism, clinical and experimental research. 2002 Jul; 26(7):1114-9. doi: 10.1111/j.1530-0277.2002.tb02646.x. [PMID: 12170122]
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  • M Some, S Svensson, J O Höög, A Helander. Studies on the interaction between ethanol and serotonin metabolism in rat, using deuterated ethanol and 4-methylpyrazole. Biochemical pharmacology. 2000 Feb; 59(4):385-91. doi: 10.1016/s0006-2952(99)00336-6. [PMID: 10644046]
  • A W Jones, L Hylén, E Svensson, A Helander. Storage of specimens at 4 degrees C or addition of sodium fluoride (1\%) prevents formation of ethanol in urine inoculated with Candida albicans. Journal of analytical toxicology. 1999 Sep; 23(5):333-6. doi: 10.1093/jat/23.5.333. [PMID: 10488919]
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  • C D Spies, J Herpell, O Beck, C Müller, F Pragst, S Borg, A Helander. The urinary ratio of 5-hydroxytryptophol to 5-hydroxyindole-3-acetic acid in surgical patients with chronic alcohol misuse. Alcohol (Fayetteville, N.Y.). 1999 Jan; 17(1):19-27. doi: 10.1016/s0741-8329(98)00028-7. [PMID: 9895033]
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  • M Some, O Beck, A Helander. Acute interaction between ethanol and serotonin metabolism in the rat. Life sciences. 1997; 61(5):577-83. doi: 10.1016/s0024-3205(97)00417-7. [PMID: 9247327]
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  • A V Carlsson, A J Hiltunen, O Beck, H Stibler, S Borg. Detection of relapses in alcohol-dependent patients: comparison of carbohydrate-deficient transferrin in serum, 5-hydroxytryptophol in urine, and self-reports. Alcoholism, clinical and experimental research. 1993 Jun; 17(3):703-8. doi: 10.1111/j.1530-0277.1993.tb00823.x. [PMID: 7687417]
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