FComEx: 5-Hydroxytryptophol (PC000515)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:07 UTC

Update date

2017-01-19 02:36:26 UTC

FoodComEx ID

PC000515

FoodDB Record

FDB022711

Chemical Information

Name

5-Hydroxytryptophol

Description

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.

CAS Number

154-02-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
5-HTOL	hmdb
5-Hydroxy-1H-indole-3-ethanol	hmdb
5-Hydroxy-1H-Indole-3-ethanol(9CI)	hmdb
5-hydroxy-3-indole	hmdb
5-hydroxy-indole-acetic acid	hmdb
5-hydroxyindoacetic acid	hmdb
5-hydroxyindol	hmdb
5-hydroxyindolacetate	hmdb
5-hydroxyindolacetate acid	hmdb
5-Hydroxyindole-3-ethanol	hmdb
5-hydroxyindole-acetic acid	hmdb
5-Hydroxytryptophol	hmdb
Hydroxytryptophol	hmdb

Chemical Formula

C10H11NO2

IUPAC name

3-(2-hydroxyethyl)-1H-indol-5-ol

InChI Identifier

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

InChI Key

KQROHCSYOGBQGJ-UHFFFAOYSA-N

Isomeric SMILES

OCCC1=CNC2=CC=C(O)C=C12

Average Molecular Weight

177.1998

Monoisotopic Molecular Weight

177.078978601

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents