Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:40:06 UTC
Update Date2024-04-30 19:32:55 UTC
Metabolite IDMMDBc0000540
Metabolite Identification
Common Name5-Hydroxyindoleacetic acid
Description5-Hydroxyindoleacetic acid, also known as 5-hydroxyindole-3-acetate or 5-HIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. In humans, 5-hydroxyindoleacetic acid is a breakdown product of serotonin that is excreted in the urine and it also participates in a number of enzymatic reactions. 5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde; which is catalyzed by the mitochondrial enzyme aldehyde dehydrogenase. In addition, 5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. 5-Hydroxyindoleacetic acid is also involved in the metabolism of tryptophan. 5-Hydroxyindoleacetic acid has been found to be associated with several human diseases such as brunner syndrome, friedreich's ataxia, schizophrenia, and olivopontocerebral atrophy; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder sepiapterin reductase deficiency. Elevated levels of 5-hydroxyindoleacetic acid in urine (>20 uM) are indicative of appendicitis and gastroenteritis (PMID: 11462886 ). Serotonin and 5-Hydroxyindoleacetic acid are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors (NCI). 5-Hydroxyindoleacetic acid has also been found to be a product of human gut microbiota.
Structure
Synonyms
ValueSource
5-HIAAChEBI
5-Hydroxy-1H-indole-3-acetic acidChEBI
5-Hydroxyindol-3-ylacetic acidChEBI
5-Hydroxyindole-3-acetic acidChEBI
5-Hydroxy-1H-indole-3-acetateGenerator
5-Hydroxyindol-3-ylacetateGenerator
5-Hydroxyindole-3-acetateGenerator
5-HydroxyindoleacetateGenerator
5-Hydroxy-3-indolylacetateHMDB
5-Hydroxy-iaaHMDB
5-Hydroxy-indole-3-acetateHMDB
5-Hydroxy-indole-3-acetic acidHMDB
5-HydroxyheteroauxinHMDB
5-Hydroxyindole acetateHMDB
5-OxyindoleacetateHMDB
5-Oxyindoleacetic acidHMDB
5HIAAHMDB
HydroxyindoleacetateHMDB
5-Hydroxyindolamine acetic acidMeSH, HMDB
Hydroxyindoleacetic acidMeSH, HMDB
5 Hydroxy 3 indoleacetic acidMeSH, HMDB
5 Hydroxyindolamine acetic acidMeSH, HMDB
5-Hydroxy-3-indoleacetic acidMeSH, HMDB
Acetic acid, 5-hydroxyindolamineMeSH, HMDB
Acid, hydroxyindoleaceticMeSH, HMDB
Acid, 5-hydroxy-3-indoleaceticMeSH, HMDB
Acid, 5-hydroxyindolamine aceticMeSH, HMDB
Molecular FormulaC10H9NO3
Average Mass191.1834
Monoisotopic Mass191.058243159
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetic acid
Traditional Namehydroxyindoleacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CNC2=C1C=C(O)C=C2
InChI Identifier
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)
InChI KeyDUUGKQCEGZLZNO-UHFFFAOYSA-N