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Record Information
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-16 18:04:09 UTC
NP-MRD IDNP0000098
Secondary Accession NumbersNone
Natural Product 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.
5-Hydroxy-1H-indole-3-acetic acidChEBI
5-Hydroxyindol-3-ylacetic acidChEBI
5-Hydroxyindole-3-acetic acidChEBI
Acid, 5-hydroxyindolamine aceticHMDB
Acid, hydroxyindoleaceticHMDB
5 Hydroxy 3 indoleacetic acidHMDB
5-Hydroxy-3-indoleacetic acidHMDB
Acetic acid, 5-hydroxyindolamineHMDB
5 Hydroxyindolamine acetic acidHMDB
5-Hydroxyindolamine acetic acidHMDB
Acid, 5-hydroxy-3-indoleaceticHMDB
Hydroxyindoleacetic acidHMDB
5-Hydroxy-indole-3-acetic acidHMDB
5-Hydroxyindole acetateHMDB
5-Oxyindoleacetic acidHMDB
Chemical FormulaC10H9NO3
Average Mass191.1834 Da
Monoisotopic Mass191.05824 Da
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetic acid
Traditional Namehydroxyindoleacetic acid
CAS Registry Number54-16-0
InChI Identifier
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species of Origin
  • Animalia
  • Chemical Taxonomy
    Description 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.
    KingdomOrganic compounds
    Super ClassOrganoheterocyclic compounds
    ClassIndoles and derivatives
    Sub ClassIndolyl carboxylic acids and derivatives
    Direct ParentIndole-3-acetic acid derivatives
    Alternative Parents
    • Indole-3-acetic acid derivative
    • 3-alkylindole
    • Hydroxyindole
    • Indole
    • 1-hydroxy-2-unsubstituted benzenoid
    • Substituted pyrrole
    • Benzenoid
    • Pyrrole
    • Heteroaromatic compound
    • Carboxylic acid derivative
    • Carboxylic acid
    • Monocarboxylic acid or derivatives
    • Azacycle
    • Organooxygen compound
    • Organonitrogen compound
    • Organopnictogen compound
    • Organic oxide
    • Organic nitrogen compound
    • Carbonyl group
    • Hydrocarbon derivative
    • Organic oxygen compound
    • Aromatic heteropolycyclic compound
    Molecular FrameworkAromatic heteropolycyclic compounds
    External Descriptors
    Physical Properties
    Experimental Properties
    Melting Point161 - 163 °CNot Available
    Boiling PointNot AvailableNot Available
    Water Solubility24 mg/mLNot Available
    LogPNot AvailableNot Available
    Predicted Properties
    Water Solubility1.8 g/LALOGPS
    pKa (Strongest Acidic)4.22ChemAxon
    pKa (Strongest Basic)-5.5ChemAxon
    Physiological Charge-1ChemAxon
    Hydrogen Acceptor Count3ChemAxon
    Hydrogen Donor Count3ChemAxon
    Polar Surface Area73.32 ŲChemAxon
    Rotatable Bond Count2ChemAxon
    Refractivity50.43 m³·mol⁻¹ChemAxon
    Polarizability18.71 ųChemAxon
    Number of Rings2ChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterYesChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0000763
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB001403
    KNApSAcK IDC00000104
    Chemspider ID1760
    KEGG Compound IDC05635
    BiGG ID46167
    Wikipedia Link5-Hydroxyindoleacetic_acid
    METLIN ID2975
    PubChem Compound1826
    PDB IDNot Available
    ChEBI ID27823
    Good Scents IDNot Available
    General References
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    2. Carpenter LL, Anderson GM, Siniscalchi JM, Chappell PB, Price LH: Acute changes in cerebrospinal fluid 5-HIAA following oral paroxetine challenge in healthy humans. Neuropsychopharmacology. 2003 Feb;28(2):339-47. [PubMed:12589387 ]
    3. Owens MJ, Nemeroff CB: Role of serotonin in the pathophysiology of depression: focus on the serotonin transporter. Clin Chem. 1994 Feb;40(2):288-95. [PubMed:7508830 ]
    4. Ilkhanizadeh B, Owji AA, Tavangar SM, Vasei M, Tabei SM: Spot urine 5-hydroxy indole acetic acid and acute appendicitis. Hepatogastroenterology. 2001 May-Jun;48(39):609-13. [PubMed:11462886 ]
    5. Rotondo A, Schuebel K, Bergen A, Aragon R, Virkkunen M, Linnoila M, Goldman D, Nielsen D: Identification of four variants in the tryptophan hydroxylase promoter and association to behavior. Mol Psychiatry. 1999 Jul;4(4):360-8. [PubMed:10483053 ]
    6. Walendzik H, Zimmer G, Skopp G: [Serotonin, 5-hydroxyindolylacetic acid and cholesterol content in blood, cerebrospinal fluid and brain areas for differentiation of suicidal from non-suicidal cause of death]. Arch Kriminol. 2000 May-Jun;205(5-6):131-44. [PubMed:10923167 ]
    7. Yamamoto M: Depression in Parkinson's disease: its prevalence, diagnosis, and neurochemical background. J Neurol. 2001 Sep;248 Suppl 3:III5-11. [PubMed:11697689 ]
    8. Mann JJ, McBride PA, Brown RP, Linnoila M, Leon AC, DeMeo M, Mieczkowski T, Myers JE, Stanley M: Relationship between central and peripheral serotonin indexes in depressed and suicidal psychiatric inpatients. Arch Gen Psychiatry. 1992 Jun;49(6):442-6. [PubMed:1376106 ]
    9. Christofides J, Bridel M, Egerton M, Mackay GM, Forrest CM, Stoy N, Darlington LG, Stone TW: Blood 5-hydroxytryptamine, 5-hydroxyindoleacetic acid and melatonin levels in patients with either Huntington's disease or chronic brain injury. J Neurochem. 2006 May;97(4):1078-88. Epub 2006 Mar 29. [PubMed:16573644 ]
    10. Celada P, Sarrias MJ, Artigas F: Serotonin and 5-hydroxyindoleacetic acid in plasma. Potential use as peripheral measures of MAO-A activity. J Neural Transm Suppl. 1990;32:149-54. [PubMed:1708403 ]
    11. Borg S, Kvande H, Liljeberg P, Mossberg D, Valverius P: 5-Hydroxyindoleacetic acid in cerebrospinal fluid in alcoholic patients under different clinical conditions. Alcohol. 1985 May-Jun;2(3):415-8. [PubMed:2411275 ]
    12. Feldman JM: Urinary serotonin in the diagnosis of carcinoid tumors. Clin Chem. 1986 May;32(5):840-4. [PubMed:2421946 ]
    13. Korpi ER, Kleinman JE, Goodman SI, Phillips I, DeLisi LE, Linnoila M, Wyatt RJ: Serotonin and 5-hydroxyindoleacetic acid in brains of suicide victims. Comparison in chronic schizophrenic patients with suicide as cause of death. Arch Gen Psychiatry. 1986 Jun;43(6):594-600. [PubMed:2423050 ]
    14. Fukuda H, Nakamura S, Hara K, Udaka F, Kameyama M: [Study on the concentration of 5-hydroxyindoleacetic acid (5-HIAA) in the lumbar cerebrospinal fluid (CSF) in neurological diseases]. Rinsho Shinkeigaku. 1989 Sep;29(9):1192-4. [PubMed:2480863 ]
    15. Meltzer H: Serotonergic dysfunction in depression. Br J Psychiatry Suppl. 1989 Dec;(8):25-31. [PubMed:2692637 ]
    16. Csernansky JG, Sheline YI: Abnormalities of serotonin metabolism and nonpsychotic psychiatric disorders. Ann Clin Psychiatry. 1993 Dec;5(4):275-81. [PubMed:8312985 ]
    17. Li JM, Kong LD, Wang YM, Cheng CH, Zhang WY, Tan WZ: Behavioral and biochemical studies on chronic mild stress models in rats treated with a Chinese traditional prescription Banxia-houpu decoction. Life Sci. 2003 Nov 21;74(1):55-73. [PubMed:14575813 ]
    18. Castejon AM, Paez X, Hernandez L, Cubeddu LX: Use of intravenous microdialysis to monitor changes in serotonin release and metabolism induced by cisplatin in cancer patients: comparative effects of granisetron and ondansetron. J Pharmacol Exp Ther. 1999 Dec;291(3):960-6. [PubMed:10565811 ]
    19. Lambert GW, Kaye DM, Cox HS, Vaz M, Turner AG, Jennings GL, Esler MD: Regional 5-hydroxyindoleacetic acid production in humans. Life Sci. 1995;57(3):255-67. [PubMed:7541101 ]