Details of Metabolite

General Information of MET (ID: META00319)
Name 5-Hydroxyindoleacetic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
5 Hydroxy 3 indoleacetic acid; 5 Hydroxyindolamine acetic acid; 5-HIAA; 5-Hydroxy-1H-indole-3-acetate; 5-Hydroxy-1H-indole-3-acetic acid; 5-Hydroxy-3-indoleacetic acid; 5-Hydroxy-3-indolylacetate; 5-Hydroxy-iaa; 5-Hydroxy-indole-3-acetate; 5-Hydroxy-indole-3-acetic acid; 5-Hydroxyheteroauxin; 5-Hydroxyindol-3-ylacetate; 5-Hydroxyindol-3-ylacetic acid; 5-Hydroxyindolamine acetic acid; 5-Hydroxyindole acetate; 5-Hydroxyindole-3-acetate; 5-Hydroxyindole-3-acetic acid; 5-Hydroxyindoleacetate; 5-Oxyindoleacetate; 5-Oxyindoleacetic acid; 5HIAA; Acetic acid, 5-hydroxyindolamine; Acid, 5-hydroxy-3-indoleacetic; Acid, 5-hydroxyindolamine acetic; Acid, hydroxyindoleacetic; Hydroxyindoleacetate; Hydroxyindoleacetic acid
Source Endogenous;Food
Structure Type   Indolyl carboxylic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Indoles and derivatives
Indolyl carboxylic acids and derivatives
PubChem CID
1826
HMDB ID
HMDB0000763
Formula
C10H9NO3
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=1826"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C05635
ChEBI ID
27823
FooDB ID
FDB001403
ChemSpider ID
1760
METLIN ID
2975
Physicochemical Properties Molecular Weight 191.18 Topological Polar Surface Area 73.3
XlogP 1.1 Complexity 231
Heavy Atom Count 14 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Function
5-Hydroxyindoleacetic acid (5HIAA) is a breakdown product of serotonin that is excreted in the urine. Serotonin is a hormone found at high levels in many body tissues. Serotonin and 5HIAA 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 is found to be associated with aromatic L-amino acid decarboxylase deficiency, celiac disease, and sepiapterin reductase deficiency, which are inborn errors of metabolism. 5HIAA has been found to be a product of human gut microbiota. An elevated levels >20 uM in urine are indicative of appendicitis and gastroenteritis.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Alpha-N-acetylglucosaminidase (NAGLU) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Naglu
                      Induced Change 5-Hydroxyindoleacetic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lysosomal storage diseases [ICD-11: 5C56]
                      Details It is reported that knockout of Naglu leads to the decrease of 5-hydroxyindoleacetic acid levels compared with control group.
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Overexpression of AN2
                      Induced Change 5-Hydroxyindoleacetic acid concentration: decrease (FC = 0.49)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of 5-hydroxyindoleacetic acid levels compared with control group.
References
1 Near-Complete Correction of Profound Metabolomic Impairments Corresponding to Functional Benefit in MPS IIIB Mice after IV rAAV9-hNAGLU Gene Delivery. Mol Ther. 2017 Mar 1;25(3):792-802.
2 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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