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The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at The data is made available under the Creative Commons License (CC BY 3.0, For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:(5-hydroxyindol-3-yl)acetic acid
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Accession:CHEBI:27823 term browser browse the term
Definition:A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.
Synonyms:exact_synonym: (5-hydroxy-1H-indol-3-yl)acetic acid
 related_synonym: 5-HIAA;   5-Hydroxy-1H-indole-3-acetic acid;   5-Hydroxyindol-3-ylacetic acid;   5-Hydroxyindole-3-acetic acid;   5-Hydroxyindoleacetic acid;   Formula=C10H9NO3;   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);   InChIKey=DUUGKQCEGZLZNO-UHFFFAOYSA-N;   SMILES=OC(=O)Cc1c[nH]c2ccc(O)cc12
 alt_id: CHEBI:20585;   CHEBI:2071
 xref: Beilstein:168797;   CAS:54-16-0;   HMDB:HMDB0000763;   KEGG:C05635;   KNApSAcK:C00000104
 xref_mesh: MESH:D006897
 xref: MetaCyc:5-HYDROXYINDOLE_ACETATE;   PMID:11063613;   PMID:11113939;   PMID:22770225;   Reaxys:168797;   Wikipedia:5-Hydroxyindoleacetic_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:62622

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(5-hydroxyindol-3-yl)acetic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Adrb2 adrenoceptor beta 2 multiple interactions EXP [Albuterol binds to and results in increased activity of ADRB2 protein] which results in increased abundance of Hydroxyindoleacetic Acid CTD PMID:2463453 NCBI chr18:57,513,792...57,515,834
Ensembl chr18:57,513,793...57,515,834
JBrowse link
G Maoa monoamine oxidase A multiple interactions EXP [MAOA protein results in increased hydroxylation of Serotonin] which results in increased chemical synthesis of Hydroxyindoleacetic Acid CTD PMID:32243540 NCBI chr  X:6,554,698...6,620,722
Ensembl chr  X:6,554,698...6,620,722
JBrowse link
G Otc ornithine transcarbamylase affects abundance
multiple interactions
ISO OTC gene mutant form affects the abundance of Hydroxyindoleacetic Acid
Sodium Benzoate affects the reaction [OTC gene mutant form affects the abundance of Hydroxyindoleacetic Acid]
CTD PMID:3374991 NCBI chr  X:13,524,804...13,601,074
Ensembl chr  X:13,524,607...13,601,069
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      application 19426
        food additive 14725
          food acidity regulator 11682
            acetic acid 10814
              indole-3-acetic acids 3171
                (5-hydroxyindol-3-yl)acetic acid 3
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic molecule 19522
                              organic cyclic compound 19320
                                organic heterocyclic compound 18432
                                  organic heteropolycyclic compound 17844
                                    organic heterobicyclic compound 16765
                                      benzopyrrole 9530
                                        indoles 9198
                                          indolyl carboxylic acid 3173
                                            indol-3-yl carboxylic acid 3172
                                              indole-3-acetic acids 3171
                                                (5-hydroxyindol-3-yl)acetic acid 3
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.