5-Hydroxytryptophol (BioCAD00000019977)

blood cerebrospinal fluid (csf) urine plant natural products

Metabolite Card

Formula: C10H11NO2 (177.079)
SMILES: OCCC1=CNC2=CC=C(O)C=C12

Synonyms [en]

5-Hydroxytryptophol; Hydroxytryptophol; 5-Hydroxy-1H-indole-3-ethanol; 5-Hydroxyindole-3-ethanol; 5-HTOL; 5-hydroxyindoacetic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

5-Hydroxytryptophol. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000019977). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 154-02-9
  • PubChem: 9061
  • ChEBI: ChEBI:89825
  • HMDB: HMDB0001855
  • BioCyc: CPD-11671
  • NCBI MeSH: Hydroxytryptophol
  • RefMet: RM0006649
  • MoNA: HMDB0001855_ms_ms_1720
  • MoNA: HMDB0001855_ms_ms_1721
  • MoNA: HMDB0001855_ms_ms_1722
  • Coconut NaturalProduct: CNP0153274.0

Class / Ontology

Metabolic Network
ID EC Number Name
BioCyc:RXN-10784 2.4.1.17 5-hydroxytryptophol UDP-glucuronosyltransferase
BioCyc:RXN-10781 1.1.1.1 5-hydroxytryptophol dehydrogenase
BioCyc:RXN-10782 2.8.2.1 CPD-11671 + PAPS --> 3-5-ADP + PROTON + CPD-11674
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Organism Source

Taxonomy Source

  1. Citrullus lanatus [ncbi taxid: 3654]
  2. Homo sapiens [ncbi taxid: 9606]
  3. Hyrtios erectus [ncbi taxid: 279628]

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY66-401 superpathway of tryptophan utilization
BioCyc:META_PWY-6313 serotonin degradation
BioCyc:HUMAN_PWY-6313 serotonin degradation
BioCyc:THAPS_PWY-6313 serotonin degradation
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