5-Hydroxyindoleacetic acid

5-Hydroxyindoleacetic acid
Names
Preferred IUPAC name
(5-Hydroxy-1H-indol-3-yl)acetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.179 Edit this at Wikidata
KEGG
MeSH Hydroxyindoleacetic+Acid
UNII
  • InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14) checkY
    Key: DUUGKQCEGZLZNO-UHFFFAOYSA-N checkY
  • InChI=1/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)
    Key: DUUGKQCEGZLZNO-UHFFFAOYAY
  • c1cc2c(cc1O)c(c[nH]2)CC(=O)O
Properties
C10H9NO3
Molar mass 191.186 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin. The metabolic intermediate 5-hydroxyindoleacetaldehyde (5-HIAL) is formed from serotonin by monoamine oxidase (MAO) and then 5-HIAA is formed from 5-HIAL via aldehyde dehydrogenase (ALDH). In chemical analysis of urine samples, 5-HIAA is used to determine serotonin levels in the body.