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), 5-羟色氨酸
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

18 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; 5-Hydroxytryptophol



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)

3 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]
  • Napoleon Waszkiewicz, Regina Popławska, Beata Konarzewska, Sławomir Dariusz Szajda, Beata Galińska, Piotr Rutkowski, Radosław Leśniak, Agata Szulc. [Biomarkers of alcohol abuse. Part II. New biomarkers and their interpretation]. Psychiatria polska. 2010 Jan; 44(1):137-46. doi: . [PMID: 20449987]
  • Gudrun Høiseth, Jean Paul Bernard, Nicolai Stephanson, Per T Normann, Asbjørg S Christophersen, Jørg Mørland, Anders Helander. Comparison between the urinary alcohol markers EtG, EtS, and GTOL/5-HIAA in a controlled drinking experiment. Alcohol and alcoholism (Oxford, Oxfordshire). 2008 Mar; 43(2):187-91. doi: 10.1093/alcalc/agm175. [PMID: 18230699]
  • Kornélia Tekes. HPLC determination of serotonin and its metabolites from human platelet-rich plasma; shift to 5-hydroxytryptophol formation following alcohol consumption. Journal of chromatographic science. 2008 Feb; 46(2):169-73. doi: 10.1093/chromsci/46.2.169. [PMID: 18366879]
  • S K Das, L Dhanya, D M Vasudevan. Biomarkers of alcoholism: an updated review. Scandinavian journal of clinical and laboratory investigation. 2008; 68(2):81-92. doi: 10.1080/00365510701532662. [PMID: 17852805]
  • Peter P Singer, Graham R Jones, Russell Lewis, Robert Johnson. Loss of ethanol from vitreous humor in drowning death. Journal of analytical toxicology. 2007 Oct; 31(8):522-5. doi: 10.1093/jat/31.8.522. [PMID: 17988467]
  • Nikolai Stephanson, Anders Helander, Olof Beck. Alcohol biomarker analysis: simultaneous determination of 5-hydroxytryptophol glucuronide and 5-hydroxyindoleacetic acid by direct injection of urine using ultra-performance liquid chromatography-tandem mass spectrometry. Journal of mass spectrometry : JMS. 2007 Jul; 42(7):940-9. doi: 10.1002/jms.1231. [PMID: 17565712]
  • Olof Beck, Nikolai Stephanson, Michael Böttcher, Norbert Dahmen, Christoph Fehr, Anders Helander. Biomarkers to disclose recent intake of alcohol: potential of 5-hydroxytryptophol glucuronide testing using new direct UPLC-tandem MS and ELISA methods. Alcohol and alcoholism (Oxford, Oxfordshire). 2007 Jul; 42(4):321-5. doi: 10.1093/alcalc/agm039. [PMID: 17533162]
  • M Stenbacka, O Beck, A Leifman, A Romelsjö, A Helander. Problem drinking in relation to treatment outcome among opiate addicts in methadone maintenance treatment. Drug and alcohol review. 2007 Jan; 26(1):55-63. doi: 10.1080/09595230601036994. [PMID: 17364837]
  • Adam Bisaga, Michael Laposata, Shan Xie, Suzette M Evans. Comparison of serum fatty acid ethyl esters and urinary 5-hydroxytryptophol as biochemical markers of recent ethanol consumption. Alcohol and alcoholism (Oxford, Oxfordshire). 2005 May; 40(3):214-8. doi: 10.1093/alcalc/agh154. [PMID: 15797884]
  • Robert D Johnson, Russell J Lewis, Dennis V Canfield, Kurt M Dubowski, C Leroy Blank. Utilizing the urinary 5-HTOL/5-HIAA ratio to determine ethanol origin in civil aviation accident victims. Journal of forensic sciences. 2005 May; 50(3):670-5. doi: NULL. [PMID: 15932105]
  • K Borucki, R Schreiner, J Dierkes, K Jachau, D Krause, S Westphal, F M Wurst, C Luley, H Schmidt-Gayk. Detection of recent ethanol intake with new markers: comparison of fatty acid ethyl esters in serum and of ethyl glucuronide and the ratio of 5-hydroxytryptophol to 5-hydroxyindole acetic acid in urine. Alcoholism, clinical and experimental research. 2005 May; 29(5):781-7. doi: 10.1097/01.alc.0000164372.67018.ea. [PMID: 15897723]
  • Nikolai Stephanson, Helen Dahl, Anders Helander, Olof Beck. Determination of urinary 5-hydroxytryptophol glucuronide by liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Feb; 816(1-2):107-12. doi: 10.1016/j.jchromb.2004.11.026. [PMID: 15664340]
  • Pia Nerfeldt, Peter Graf, Stefan Borg, Danielle Friberg. Prevalence of high alcohol and benzodiazepine consumption in sleep apnea patients studied with blood and urine tests. Acta oto-laryngologica. 2004 Dec; 124(10):1187-90. doi: 10.1080/00016480410017729. [PMID: 15768816]
  • Satyanarayana Sreemantula, Krishna M Boini, Srinivas Nammi. Reserpine methonitrate, a novel quaternary analogue of reserpine augments urinary excretion of VMA and 5-HIAA without affecting HVA in rats. BMC pharmacology. 2004 Nov; 4(?):30. doi: 10.1186/1471-2210-4-30. [PMID: 15546495]
  • R D Johnson, R J Lewis, D V Canfield, C L Blank. Accurate assignment of ethanol origin in postmortem urine: liquid chromatographic-mass spectrometric determination of serotonin metabolites. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Jun; 805(2):223-34. doi: 10.1016/j.jchromb.2004.02.042. [PMID: 15135094]
  • Olof Beck, Anders Helander. 5-hydroxytryptophol as a marker for recent alcohol intake. Addiction (Abingdon, England). 2003 Dec; 98 Suppl 2(?):63-72. doi: 10.1046/j.1359-6357.2003.00583.x. [PMID: 14984243]
  • Taisto Sarkola, Helen Dahl, C J Peter Eriksson, Anders Helander. Urinary ethyl glucuronide and 5-hydroxytryptophol levels during repeated ethanol ingestion in healthy human subjects. Alcohol and alcoholism (Oxford, Oxfordshire). 2003 Jul; 38(4):347-51. doi: 10.1093/alcalc/agg083. [PMID: 12814902]
  • A Helander. Biological markers in alcoholism. Journal of neural transmission. Supplementum. 2003; ?(66):15-32. doi: 10.1007/978-3-7091-0541-2_2. [PMID: 14582801]
  • Margareta Some, Anders Helander. Urinary excretion patterns of 5-hydroxyindole-3-acetic acid and 5-hydroxytryptophol in various animal species: implications for studies on serotonin metabolism and turnover rate. Life sciences. 2002 Oct; 71(20):2341-9. doi: 10.1016/s0024-3205(02)02043-x. [PMID: 12231396]
  • Anders Helander, A Wayne Jones. [5-HTOL--a new biochemical alcohol marker with forensic applications]. Lakartidningen. 2002 Oct; 99(40):3950-4. doi: NULL. [PMID: 12422751]
  • Anders Helander, C J Peter Eriksson. Laboratory tests for acute alcohol consumption: results of the WHO/ISBRA Study on State and Trait Markers of Alcohol Use and Dependence. Alcoholism, clinical and experimental research. 2002 Jul; 26(7):1070-7. doi: 10.1111/j.1530-0277.2002.tb02641.x. [PMID: 12170117]
  • 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]
  • F Schellenberg, B Nalpas. [Peripheral markers, future perspectives]. Pathologie-biologie. 2001 Nov; 49(9):775-80. doi: 10.1016/s0369-8114(01)00240-1. [PMID: 11762142]
  • H X Wang, F Liu, T B Ng. Examination of pineal indoles and 6-methoxy-2-benzoxazolinone for antioxidant and antimicrobial effects. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2001 Nov; 130(3):379-88. doi: 10.1016/s1532-0456(01)00264-2. [PMID: 11701394]
  • P C Sharpe. Biochemical detection and monitoring of alcohol abuse and abstinence. Annals of clinical biochemistry. 2001 Nov; 38(Pt 6):652-64. doi: 10.1258/0004563011901064. [PMID: 11732647]
  • T A Reader, C Hébert, A R Ase, N Le Marec. Distribution of serotonin, its metabolites and 5-HT transporters in the neostriatum of Lurcher and weaver mutant mice. Neurochemistry international. 2001 Sep; 39(3):169-77. doi: 10.1016/s0197-0186(01)00031-6. [PMID: 11434974]
  • A Helander, M Some. Dietary serotonin and alcohol combined may provoke adverse physiological symptoms due to 5-hydroxytryptophol. Life sciences. 2000 Jul; 67(7):799-806. doi: 10.1016/s0024-3205(00)00674-3. [PMID: 10968409]
  • W M Keung, L Kunze, D J Li, O Lazo. Volitional ethanol consumption affects overall serotonin metabolism in Syrian golden hamsters (Mesocricetus auratus). Biochemical and biophysical research communications. 2000 May; 271(3):823-30. doi: 10.1006/bbrc.2000.2718. [PMID: 10814546]
  • 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]
  • A Helander, J von Wachenfeldt, A Hiltunen, O Beck, P Liljeberg, S Borg. Comparison of urinary 5-hydroxytryptophol, breath ethanol, and self-report for detection of recent alcohol use during outpatient treatment: a study on methadone patients. Drug and alcohol dependence. 1999 Aug; 56(1):33-8. doi: 10.1016/s0376-8716(99)00007-1. [PMID: 10462090]
  • 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]
  • P Bendtsen, A W Jones, A Helander. Urinary excretion of methanol and 5-hydroxytryptophol as biochemical markers of recent drinking in the hangover state. Alcohol and alcoholism (Oxford, Oxfordshire). 1998 Jul; 33(4):431-8. doi: 10.1093/oxfordjournals.alcalc.a008415. [PMID: 9719404]
  • A W Jones, A Helander. Changes in the concentrations of ethanol, methanol and metabolites of serotonin in two successive urinary voids from drinking drivers. Forensic science international. 1998 May; 93(2-3):127-34. doi: 10.1016/s0379-0738(98)00038-3. [PMID: 9717263]
  • A Helander. Monitoring relapse drinking during disulfiram therapy by assay of urinary 5-hydroxytryptophol. Alcoholism, clinical and experimental research. 1998 Feb; 22(1):111-4. doi: 10.1111/j.1530-0277.1998.tb03623.x. [PMID: 9514292]
  • 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]
  • R L Hagan, A Helander. Urinary 5-hydroxytryptophol following acute ethanol consumption: clinical evaluation and potential aviation applications. Aviation, space, and environmental medicine. 1997 Jan; 68(1):30-4. doi: NULL. [PMID: 9006879]
  • A J Hiltunen, U M Koechling, A Voltaire-Carlsson, S Borg. Sub-populations of alcohol-dependent patients: differences in psychological functioning between high- and low-frequency alcohol consumers. Alcohol and alcoholism (Oxford, Oxfordshire). 1996 Jul; 31(4):429-38. doi: 10.1093/oxfordjournals.alcalc.a008173. [PMID: 8879293]
  • A Helander, O Beck, A W Jones. Laboratory testing for recent alcohol consumption: comparison of ethanol, methanol, and 5-hydroxytryptophol. Clinical chemistry. 1996 Apr; 42(4):618-24. doi: 10.1093/clinchem/42.4.618. [PMID: 8605681]
  • A W Jones, A Helander. Disclosing recent drinking after alcohol has been cleared from the body. Journal of analytical toxicology. 1996 Mar; 20(2):141-2. doi: 10.1093/jat/20.2.141. [PMID: 8868409]
  • S Borg, A Helander, A Voltaire Carlsson, A M Högström Brandt. Detection of relapses in alcohol-dependent patients using carbohydrate-deficient transferrin: improvement with individualized reference levels during long-term monitoring. Alcoholism, clinical and experimental research. 1995 Aug; 19(4):961-3. doi: 10.1111/j.1530-0277.1995.tb00974.x. [PMID: 7485846]
  • A Helander, C Löwenmo, O Beck. Determination of 5-hydroxytryptophol in urine by high-performance liquid chromatography: application of a new post-column derivatization method with fluorometric detection. Journal of pharmaceutical and biomedical analysis. 1995 Apr; 13(4-5):651-4. doi: 10.1016/0731-7085(95)01287-u. [PMID: 9696582]
  • A Helander, O Beck, L Boysen. 5-Hydroxytryptophol conjugation in man: influence of alcohol consumption and altered serotonin turnover. Life sciences. 1995; 56(18):1529-34. doi: 10.1016/0024-3205(95)00115-m. [PMID: 7752817]
  • A Helander, O Beck, A W Jones. Distinguishing ingested ethanol from microbial formation by analysis of urinary 5-hydroxytryptophol and 5-hydroxyindoleacetic acid. Journal of forensic sciences. 1995 Jan; 40(1):95-8. doi: NULL. [PMID: 7533206]
  • A Helander, O Beck, S Borg. The use of 5-hydroxytryptophol as an alcohol intake marker. Alcohol and alcoholism (Oxford, Oxfordshire). Supplement. 1994; 2(?):497-502. doi: NULL. [PMID: 8974374]
  • 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]
  • A Helander, O Beck, G Jacobsson, C Löwenmo, T Wikström. Time course of ethanol-induced changes in serotonin metabolism. Life sciences. 1993; 53(10):847-55. doi: 10.1016/0024-3205(93)90507-y. [PMID: 7689134]
  • K F Tipton, M C Harrington, N P Kennedy. Biochemical markers for the effects of ethanol. Alcohol and alcoholism (Oxford, Oxfordshire). Supplement. 1993; 2(?):87-90. doi: NULL. [PMID: 7538303]
  • A Helander, O Beck, A W Jones. Urinary 5HTOL/5HIAA as biochemical marker of postmortem ethanol synthesis. Lancet (London, England). 1992 Nov; 340(8828):1159. doi: 10.1016/0140-6736(92)93184-o. [PMID: 1279333]
  • A Helander, O Beck, S Borg. Determination of urinary 5-hydroxytryptophol by high-performance liquid chromatography with electrochemical detection. Journal of chromatography. 1992 Sep; 579(2):340-5. doi: 10.1016/0378-4347(92)80401-b. [PMID: 1429982]
  • A Voltaire, O Beck, S Borg. Urinary 5-hydroxytryptophol: a possible marker of recent alcohol consumption. Alcoholism, clinical and experimental research. 1992 Apr; 16(2):281-5. doi: 10.1111/j.1530-0277.1992.tb01377.x. [PMID: 1375446]
  • A Helander, T Wikström, C Löwenmo, G Jacobsson, O Beck. Urinary excretion of 5-hydroxyindole-3-acetic acid and 5-hydroxytryptophol after oral loading with serotonin. Life sciences. 1992; 50(17):1207-13. doi: 10.1016/0024-3205(92)90320-o. [PMID: 1373788]
  • T Shimizu, K Kouketsu. Metabolism of platelet 5-hydroxytryptamine in acidified platelet concentrates. Japanese journal of pharmacology. 1988 Feb; 46(2):147-53. doi: 10.1254/jjp.46.147. [PMID: 3379825]
  • J A McNulty, M M Prechel, T K Audhya, D Taylor, L Fox, T A Dombrowski, W H Simmons. Pineal ultrastructure and indole profiles spanning the summer rise in arginine vasotocin immunoactivity. Endocrinology. 1985 Sep; 117(3):1035-42. doi: 10.1210/endo-117-3-1035. [PMID: 2410234]
  • O Beck, S Borg, G Jonsson, A Lundman, P Valverius. Measurement of 5-hydroxytryptophol and 5-hydroxyindoleacetic acid in human and rat brain and plasma. Journal of neural transmission. 1984; 59(1):57-67. doi: 10.1007/bf01249878. [PMID: 6201590]
  • O Beck, S Borg, L Eriksson, A Lundman. 5-hydroxytryptophol in the cerebrospinal fluid and urine of alcoholics and healthy subjects. Naunyn-Schmiedeberg's archives of pharmacology. 1982 Dec; 321(4):293-7. doi: 10.1007/bf00498516. [PMID: 7167204]
  • I Nir, N Hirschmann, M Puder, J Petrank. Changes in rodent thyroid hormones and cyclic-AMP following treatment with pineal indolic compounds. Archives internationales de physiologie et de biochimie. 1978 May; 86(2):353-62. doi: 10.3109/13813457809069910. [PMID: 80990]
  • C M Banki, M Vojnik. Differential changes of blood and urinary indoleamines following intravenous ethanol administration in alcoholic and non-drinker women. Journal of neural transmission. 1978; 43(1):19-25. doi: 10.1007/bf02029016. [PMID: 690632]
  • J R Berstad. Total 5-hydroxyindoles in blood related to migraine attacks. Acta neurologica Scandinavica. 1976 Oct; 54(4):293-300. doi: 10.1111/j.1600-0404.1976.tb04360.x. [PMID: 973551]
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