5-Hydroxytryptophol

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

Formula: C10H11NO2 (177.079)
Chinese Name: 5-羟基色醇(Hydroxytryptophol), 5-羟色氨酸, 5-羟基色醇
BioDeep ID: BioDeep_00000022417 ( View LC/MS Profile)
SMILES: C1=CC2=C(C=C1O)C(=CN2)CCO



Found 3 Sample Hits

m/z Adducts Species Organ Scanning Sample
178.0839 [M+H]+
PPM:13.2
Vitis vinifera Fruit MALDI (DHB)
grape_dhb_91_1 - Grape Database
Resolution: 50μm, 120x114

Description

Grape berries fruit, condition: Ripe

178.0839 [M+H]+
PPM:13.2
Vitis vinifera Fruit MALDI (DHB)
grape_dhb_164_1 - Grape Database
Resolution: 17μm, 136x122

Description

Grape berries fruit, condition: Late

178.0838 [M+H]+
PPM:13.8
Vitis vinifera Fruit MALDI (DHB)
grape_dhb_163_1 - Grape Database
Resolution: 17μm, 132x115

Description

Grape berries fruit, condition: Late


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.