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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:28 UTC
HMDB IDHMDB0000763
Secondary Accession Numbers
  • HMDB00763
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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 5-hydroxyindoleacetic acid participates in a number of enzymatic reactions. In particular, 5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde through the action of the enzyme aldehyde dehydrogenase, mitochondrial. In addition, 5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine; which is catalyzed by the enzyme acetylserotonin O-methyltransferase. In humans, 5-hydroxyindoleacetic acid is involved in tryptophan metabolism. In chemical analysis of urine samples, 5-HIAA is used to determine serotonin levels in the body.5-HIAA is tested by 24-hour urine samples combined with an acidic additive to maintain pH below 3. Midgut carcinoids are most apt to produce the carcinoid syndrome with 5-HIAA elevation. Outside of the human body, 5-hydroxyindoleacetic acid has been detected, but not quantified in, several different foods, such as black raspberries, pak choy, chinese chestnuts, black mulberries, and lemon balms. This could make 5-hydroxyindoleacetic acid a potential biomarker for the consumption of these foods. 5-Hydroxyindoleacetic acid has been found to be associated with several diseases such as epilepsy, hereditary spastic paraplegia, perillyl alcohol administration for cancer treatment, and crohn's disease; also 5-hydroxyindoleacetic acid has been linked to the inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency. Low levels of 5-HIAA in the cerebrospinal fluid have been associated with aggressive behavior and suicide by violent means, correlating with diminished serotonin levels. Carcinoid tumors may cause increased excretion of tryptophan, 5-hydroxytryptophan and histamine as well as serotonin. Serotonin, and consequently 5-HIAA, are produced in excess by most carcinoid tumors, especially those producing the carcinoid syndrome of flushing, hepatomegaly (enlarged liver), diarrhea, bronchospasm, and heart disease.
Structure
Data?1563860668
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
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-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
Chemical FormulaC10H9NO3
Average Molecular Weight191.1834
Monoisotopic Molecular Weight191.058243159
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetic acid
Traditional Namehydroxyindoleacetic acid
CAS Registry Number54-16-0
SMILES
OC(=O)CC1=CNC2=CC=C(O)C=C12
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
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
Substituents
  • 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 - 163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility24 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.8 g/LALOGPS
logP1.28ALOGPS
logP1.41ChemAxon
logS-2ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-0390100000-f473f1a32542afd5d101JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-1490100000-a72832b1524478059ef7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-0191000000-660345027702653fc000JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0293000000-66850e233e11ec787808JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0191200000-99e904e0c2698a9ec34dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0390100000-f473f1a32542afd5d101JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-1490100000-a72832b1524478059ef7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0191000000-660345027702653fc000JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0390100000-77c9d80e625d0da33fcfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0691000000-ad9e4829206c93db526aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-0900000000-4aceed1a9f20cfdd5d35JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0229-5093000000-805b9af9a37ffd246f4cJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-931e6e7603f58232f0e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0900000000-ec9ed3a4a7ed491064e7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-8900000000-b4144894cf8f60daf9faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-e3daf51d70668c08950dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-052b-0900000000-88af3a616d054b8917e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0900000000-cefb365d8f0aad3d766dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-12e9d882014f1a7bfd4dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-0900000000-7890fc93271437e3d2d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-1900000000-6c0974626895f2a0c437JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-003r-1900000000-9aa2c699af3e125036f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-3900000000-42fd55964480ac872c0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000x-6900000000-61fc171a48c42517d25fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9400000000-0fd99ccea1ed33b42bfaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-5f8ae429e297482d98b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-0900000000-759a3410e0268ce0d589JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-0900000000-0f6f5a0c9905b0c5883dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-4bf1424d8b0a831cae16JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-3e62c4d79b28ba65eab6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007p-2900000000-d626b2b22dd1b2bc9517JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-5f8ae429e297482d98b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-0900000000-759a3410e0268ce0d589JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-0900000000-0f6f5a0c9905b0c5883dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-4bf1424d8b0a831cae16JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-3e62c4d79b28ba65eab6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007p-2900000000-d626b2b22dd1b2bc9517JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Central Nervous System
  • Hippocampus
  • Hypothalamus
  • Liver
  • Nerve Cells
  • Platelet
  • Prostate
  • Spinal Cord
  • Spleen
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0516 +/- 0.0068 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.080 +/- 0.023 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.307 (0.152-0.462) uMInfant (0-1 year old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.143 +/- 0.0450 uMNot SpecifiedNot SpecifiedNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.428-1.122 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.119-0.608 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.07-0.14 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.109-0.214 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1-0.245 uMChildren (1-13 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.61 +/- 0.06 uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.4 +/- 0.07 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.47 (0.15-0.80) uMInfant (0-1 year old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.025 +/- 0.011 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.120-0.400 uMChildren (1-13 years old)Female
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.143 +/- 0.045 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.3-5.1 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.0 (0.48-4.5) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified1.57 +/- 0.38 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified4.75 +/- 5.38 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.5-2.0 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified1.18 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified11.0 (4.0-18.0) umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified54.058 +/- 23.536 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.583 +/- 5.31 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified1.5 (0-7.2) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.1 +/- 0.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.4-1.7 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified<21.85 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified2.4 +/- 0.40 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.9 (0.4-5.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.900-17.700 umol/mmol creatinineChildren (1-13 years old)Female
Normal
details
UrineDetected and Quantified0-0.0314 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0475 +/- 0.0130 uMAdult (>18 years old)MaleSchizophrenia details
BloodDetected and Quantified0.0449 +/- 0.0140 uMAdult (>18 years old)FemaleSchizophrenia details
BloodDetected but not Quantified Adult (>18 years old)Female
Breast cancer
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0703 +/- 0.0254 uMAdult (>18 years old)Bothceliac disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.22725 (0.117-0.519) uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0045 (0.004-0.005) uMChildren (1-13 years old)Malesepiapterin reductase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.056 +/- 0.022 uMAdult (>18 years old)BothSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0025 (0.0000-0.0050) uMInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.519 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.122 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.117 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.151 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.071 +/- 0.0268 uMAdult (>18 years old)Not Specifiedceliac disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.33 +/- 0.04 uMChildren (1-13 years old)BothEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1491 +/- 0.0591 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1373 +/- 0.0457 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment details
Cerebrospinal Fluid (CSF)Detected and Quantified0.08 +/- 0.08 uMAdult (>18 years old)Both
Major depression
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0887 +/- 0.0385 uMNot SpecifiedNot SpecifiedBipolar with childhood ADHD (attention-deficit hyperactivity disorder) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.116 +/- 0.0479 uMNot SpecifiedNot SpecifiedBipolar disorder details
Cerebrospinal Fluid (CSF)Detected and Quantified0.126 +/- 0.0526 uMNot SpecifiedNot SpecifiedControl (men) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.096 +/- 0.0384 uMNot SpecifiedFemaleControl (women) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.112 +/- 0.0483 uMNot SpecifiedNot Specified
Bipolar disorder
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0983 +/- 0.0444 uMNot SpecifiedNot Specified
Bipolar disorder
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0912 +/- 0.0387 uMNot SpecifiedNot Specified
Bipolar disorder
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.123 +/- 0.0505 uMNot SpecifiedNot Specified
Bipolar disorder
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.116 +/- 0.053 uMNot SpecifiedNot Specified
Bipolar disorder
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.104 +/- 0.0386 uMNot SpecifiedNot Specified
Bipolar disorder
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1 +/- 0.01 uMAdult (>18 years old)BothFriedreich's ataxia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.11 +/- 0.01 uMAdult (>18 years old)BothOlivopontocerebellar atrophy (OPCA) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1 +/- 0.02 uMAdult (>18 years old)BothAutosomal recessive spastic ataxia of Charlevoix-Saguena details
Cerebrospinal Fluid (CSF)Detected and Quantified0.019 +/- 0.0094 uMAdult (>18 years old)BothSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.027 uMInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0120-0.0220 uMChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency
details
Cerebrospinal Fluid (CSF)Detected but not Quantified Adult (>18 years old)Female
Breast cancer
details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not Quantified Children (6 - 18 years old)Bothenthesitis-related arthritis details
UrineDetected and Quantified0.8-1.4 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
UrineDetected but not Quantified Adult (>18 years old)Both
Metabolic syndrome
details
UrineDetected and Quantified0.9 +/- 0.0 umol/mmol creatinineInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency details
UrineDetected and Quantified69.452 +/- 34.984 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified87.711 +/- 36.841 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified5.004 +/- 1.463 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified5.0 umol/mmol creatinineAdult (>18 years old)MaleCarcinoid tumors details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
UrineDetected and Quantified0.0921 umol/mmol creatinineAdolescent (13-18 years old)FemaleDopamine-serotonin Vesicular Transport Defect details
UrineDetected and Quantified0.2 umol/mmol creatinineChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency
details
UrineDetected and Quantified2.2 umol/mmol creatinineInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency
details
UrineDetected but not Quantified Adult (>18 years old)Female
Breast cancer
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. [PubMed:2480613 ]
  2. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
  3. Gattaz WF, Waldmeier P, Beckmann H: CSF monoamine metabolites in schizophrenic patients. Acta Psychiatr Scand. 1982 Nov;66(5):350-60. [PubMed:6184954 ]
Epilepsy
  1. Shaywitz BA, Cohen DJ, Bowers MB: Reduced cerebrospinal fluid 5-hydroxyindoleacetic acid and homovanillic acid in children with epilepsy. Neurology. 1975 Jan;25(1):72-9. [PubMed:803305 ]
Major depressive disorder
  1. Sheline Y, Bardgett ME, Csernansky JG: Correlated reductions in cerebrospinal fluid 5-HIAA and MHPG concentrations after treatment with selective serotonin reuptake inhibitors. J Clin Psychopharmacol. 1997 Feb;17(1):11-4. [PubMed:9004051 ]
Friedreich's ataxia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Olivopontocerebral atrophy
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Hereditary spastic paraplegia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Aromatic L-amino acid decarboxylase deficiency
  1. Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [PubMed:16288991 ]
  2. Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Celiac disease
  1. Hallert C, Astrom J, Sedvall G: Psychic disturbances in adult coeliac disease. III. Reduced central monoamine metabolism and signs of depression. Scand J Gastroenterol. 1982 Jan;17(1):25-8. [PubMed:6182605 ]
  2. Hallert C, Allenmark S, Larsson-Cohn U, Sedvall G: High level of pyridoxal 5'-phosphate in the cerebrospinal fluid of adult celiac patients. Am J Clin Nutr. 1982 Nov;36(5):851-4. [PubMed:6182788 ]
Pyridoxamine 5-prime-phosphate oxidase deficiency
  1. Ormazabal A, Oppenheim M, Serrano M, Garcia-Cazorla A, Campistol J, Ribes A, Ruiz A, Moreno J, Hyland K, Clayton P, Heales S, Artuch R: Pyridoxal 5'-phosphate values in cerebrospinal fluid: reference values and diagnosis of PNPO deficiency in paediatric patients. Mol Genet Metab. 2008 Jun;94(2):173-7. doi: 10.1016/j.ymgme.2008.01.004. Epub 2008 Feb 21. [PubMed:18294893 ]
Sepiapterin reductase deficiency
  1. Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Bipolar disorder
  1. Ryden E, Johansson C, Blennow K, Landen M: Lower CSF HVA and 5-HIAA in bipolar disorder type 1 with a history of childhood ADHD. J Neural Transm (Vienna). 2009 Dec;116(12):1667-74. doi: 10.1007/s00702-009-0300-3. Epub 2009 Sep 12. [PubMed:19756368 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Carbamoyl Phosphate Synthetase Deficiency
  1. Ishida J, Iizuka R, Yamaguchi M: High-performance liquid chromatographic determination of 5-hydroxyindoles by post-column fluorescence derivatization. Analyst. 1993 Feb;118(2):165-9. [PubMed:7680187 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Perillyl alcohol administration for cancer treatment
  1. Nam H, Chung BC, Kim Y, Lee K, Lee D: Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification. Bioinformatics. 2009 Dec 1;25(23):3151-7. doi: 10.1093/bioinformatics/btp558. Epub 2009 Sep 25. [PubMed:19783829 ]
Metabolic syndrome
  1. Tulipani S, Llorach R, Jauregui O, Lopez-Uriarte P, Garcia-Aloy M, Bullo M, Salas-Salvado J, Andres-Lacueva C: Metabolomics unveils urinary changes in subjects with metabolic syndrome following 12-week nut consumption. J Proteome Res. 2011 Nov 4;10(11):5047-58. doi: 10.1021/pr200514h. Epub 2011 Sep 29. [PubMed:21905751 ]
Dopamine-serotonin Vesicular Transport Defect
  1. Rilstone JJ, Alkhater RA, Minassian BA: Brain dopamine-serotonin vesicular transport disease and its treatment. N Engl J Med. 2013 Feb 7;368(6):543-50. doi: 10.1056/NEJMoa1207281. Epub 2013 Jan 30. [PubMed:23363473 ]
Brunner Syndrome
  1. Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]
Associated OMIM IDs
  • 181500 (Schizophrenia)
  • 608516 (Major depressive disorder)
  • 229300 (Friedreich's ataxia)
  • 182601 (Hereditary spastic paraplegia)
  • 608643 (Aromatic L-amino acid decarboxylase deficiency)
  • 212750 (Celiac disease)
  • 610090 (Pyridoxamine 5-prime-phosphate oxidase deficiency)
  • 182125 (Sepiapterin reductase deficiency)
  • 125480 (Bipolar disorder)
  • 266600 (Crohn's disease)
  • 237300 (Carbamoyl Phosphate Synthetase Deficiency)
  • 610247 (Eosinophilic esophagitis)
  • 605552 (Metabolic syndrome)
  • 300615 (Brunner Syndrome)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001403
KNApSAcK IDC00000104
Chemspider ID1760
KEGG Compound IDC05635
BioCyc ID5-HYDROXYINDOLE_ACETATE
BiGG ID46167
Wikipedia Link5-Hydroxyindoleacetic_acid
METLIN ID2975
PubChem Compound1826
PDB IDNot Available
ChEBI ID27823
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis Reference Asero, B.; Colo, V. A.; Vercellone, A. Preparation of 5-hydroxy-3-indoleacetic acid. Farmaco, Edizione Scientifica (1956), 11 219-20.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Csernansky JG, Sheline YI: Abnormalities of serotonin metabolism and nonpsychotic psychiatric disorders. Ann Clin Psychiatry. 1993 Dec;5(4):275-81. [PubMed:8312985 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Meltzer H: Serotonergic dysfunction in depression. Br J Psychiatry Suppl. 1989 Dec;(8):25-31. [PubMed:2692637 ]
  10. Yamamoto M: Depression in Parkinson's disease: its prevalence, diagnosis, and neurochemical background. J Neurol. 2001 Sep;248 Suppl 3:III5-11. [PubMed:11697689 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. Feldman JM: Urinary serotonin in the diagnosis of carcinoid tumors. Clin Chem. 1986 May;32(5):840-4. [PubMed:2421946 ]
  17. 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 ]
  18. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  19. 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 ]

Enzymes

General function:
Involved in O-methyltransferase activity
Specific function:
Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:
ASMT
Uniprot ID:
P46597
Molecular weight:
41660.34
Reactions
S-Adenosylmethionine + 5-Hydroxyindoleacetic acid → S-Adenosylhomocysteine + 5-Methoxyindoleacetatedetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
5-Hydroxyindoleacetaldehyde + Oxygen + Water → 5-Hydroxyindoleacetic acid + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails