Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:16 UTC
HMDB IDHMDB00763
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Hydroxyindoleacetic acid
Description5-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).
Structure
Thumb
Synonyms
  1. 5-HIAA
  2. 5-Hydroxy-1H-indole-3-acetate
  3. 5-Hydroxy-1H-indole-3-acetic acid
  4. 5-Hydroxy-3-indolylacetate
  5. 5-Hydroxy-IAA
  6. 5-Hydroxy-Indole-3-acetate
  7. 5-Hydroxy-Indole-3-acetic acid
  8. 5-Hydroxyheteroauxin
  9. 5-Hydroxyindol-3-ylacetate
  10. 5-Hydroxyindol-3-ylacetic acid
  11. 5-Hydroxyindole acetate
  12. 5-Hydroxyindole-3-acetate
  13. 5-Hydroxyindole-3-acetic acid
  14. 5-Hydroxyindoleacetate
  15. 5-Hydroxyindoleacetic acid
  16. 5-Oxyindoleacetate
  17. 5-Oxyindoleacetic acid
  18. 5HIAA
  19. Hydroxyindoleacetate
Chemical FormulaC10H9NO3
Average Molecular Weight191.1834
Monoisotopic Molecular Weight191.058243159
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetic acid
Traditional IUPAC Name(5-hydroxy-1H-indol-3-yl)acetic 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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassIndoles
Sub ClassIndolyl Carboxylic Acids and Derivatives
Other Descriptors
  • Indoles
  • indole-3-acetic acids(ChEBI)
Substituents
  • Carboxylic Acid
  • Phenol
  • Phenol Derivative
  • Pyrrole
Direct ParentIndole-3-acetic Acid Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
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 area73.32ChemAxon
rotatable bond count2ChemAxon
refractivity50.43ChemAxon
polarizability18.71ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Central Nervous System
  • Hippocampus
  • Hypothalamus
  • Liver
  • Nerve Cells
  • Platelet
  • Prostate
  • Spinal Cord
  • Spleen
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0516 +/- 0.0068 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.307 (0.152-0.462) uMInfant (0-1 year old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.428-1.122 uMChildren (1-13 year old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.119-0.608 uMChildren (1-13 year old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.07-0.14 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.109-0.214 uMChildren (1-13 year old)MaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.1-0.245 uMChildren (1-13 year old)MaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.61 +/- 0.06 uMChildren (1-13 year old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.4 +/- 0.07 uMAdult (>18 years old)MaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.47 (0.15-0.80) uMInfant (0-1 year old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.025 +/- 0.011 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.143 +/- 0.045 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
UrineDetected and Quantified3.0 (0.48-4.5) umol/mmol creatinineChildren (1-13 year old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified1.57 +/- 0.38 umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified4.75 +/- 5.38 umol/mmol creatinineInfant (0-1 year old)BothNormal
UrineDetected and Quantified1.18 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified11.0 (4.0-18.0) umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified1.5 (0-7.2) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified1.1 +/- 0.5 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified2.4 +/- 0.40 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified2.9 (0.4-5.8) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0475 +/- 0.0130 uMAdult (>18 years old)MaleSchizophrenia
BloodDetected and Quantified0.0449 +/- 0.0140 uMAdult (>18 years old)FemaleSchizophrenia
Cerebrospinal Fluid (CSF)Detected and Quantified0.0703 +/- 0.0254 uMAdult (>18 years old)Bothceliac disease
Cerebrospinal Fluid (CSF)Detected and Quantified0.22725 (0.117-0.519) uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.0045 (0.004-0.005) uMChildren (1-13 year old)Malesepiapterin reductase deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.0025 (0.0000-0.0050) uMInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.519 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.122 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.117 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.151 uMNewborn (0-30 days old)Not SpecifiedPNPO deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.071 +/- 0.0268 uMAdult (>18 years old)Not Specifiedceliac disease
Cerebrospinal Fluid (CSF)Detected and Quantified0.33 +/- 0.04 uMChildren (1-13 year old)BothEpilepsy
Cerebrospinal Fluid (CSF)Detected and Quantified0.1491 +/- 0.0591 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induce hypogonadism
Cerebrospinal Fluid (CSF)Detected and Quantified0.1373 +/- 0.0457 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment
Cerebrospinal Fluid (CSF)Detected and Quantified0.08 +/- 0.08 uMAdult (>18 years old)BothCommentMajor depression
Cerebrospinal Fluid (CSF)Detected and Quantified0.0887 +/- 0.0385 uMNot SpecifiedNot SpecifiedBipolar with childhood ADHD (attention-deficit hyperactivity disorder)
Cerebrospinal Fluid (CSF)Detected and Quantified0.116 +/- 0.0479 uMNot SpecifiedNot Specifiedpure bipolar
Cerebrospinal Fluid (CSF)Detected and Quantified0.126 +/- 0.0526 uMNot SpecifiedNot SpecifiedControl (men)
Cerebrospinal Fluid (CSF)Detected and Quantified0.096 +/- 0.0384 uMNot SpecifiedFemaleControl (women)
Cerebrospinal Fluid (CSF)Detected and Quantified0.112 +/- 0.0483 uMNot SpecifiedNot SpecifiedWith lithium treatment
Cerebrospinal Fluid (CSF)Detected and Quantified0.0983 +/- 0.0444 uMNot SpecifiedNot SpecifiedWithout lithium treatment
Cerebrospinal Fluid (CSF)Detected and Quantified0.0912 +/- 0.0387 uMNot SpecifiedNot SpecifiedWith antipsychotic treatment
Cerebrospinal Fluid (CSF)Detected and Quantified0.123 +/- 0.0505 uMNot SpecifiedNot SpecifiedWithout antipsychotic treatment
Cerebrospinal Fluid (CSF)Detected and Quantified0.116 +/- 0.053 uMNot SpecifiedNot SpecifiedWith episodes of interpersonal violence
Cerebrospinal Fluid (CSF)Detected and Quantified0.104 +/- 0.0386 uMNot SpecifiedNot SpecifiedWithout episodes of interpersonal violence
Cerebrospinal Fluid (CSF)Detected and Quantified0.1 +/- 0.01 uMAdult (>18 years old)BothFriedreich's ataxia
Cerebrospinal Fluid (CSF)Detected and Quantified0.11 +/- 0.01 uMAdult (>18 years old)BothOlivopontocerebellar atrophy (OPCA)
Cerebrospinal Fluid (CSF)Detected and Quantified0.1 +/- 0.02 uMAdult (>18 years old)BothSpastic Ataxia
Cerebrospinal Fluid (CSF)Detected and Quantified0.019 +/- 0.0094 uMAdult (>18 years old)BothSchizophrenia
UrineDetected and Quantified0.9 +/- 0.0 umol/mmol creatinineInfant (0-1 year old)MaleAromatic L-amino acid decarboxylase deficiency
UrineDetected and Quantified5.0 umol/mmol creatinineAdult (>18 years old)MaleCarcinoid tumors
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  • 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
Major depressive disorder
  • 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
Epilepsy
  • 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
Schizophrenia
  • 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
  • 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
Friedreich's ataxia
  • 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
  • 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
  • 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
Associated OMIM IDs
    608516 (Major depressive disorder)229300 (Friedreich's ataxia)182601 (Hereditary spastic paraplegia)181500 (Schizophrenia)107930 (Aromatic L-amino acid decarboxylase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001403
KNApSAcK IDC00000104
Chemspider ID1760
KEGG Compound IDC05635
BioCyc ID5-HYDROXYINDOLE_ACETATE
BiGG ID46167
Wikipedia Link5-Hydroxyindoleacetic acid
NuGOwiki LinkHMDB00763
Metagene LinkHMDB00763
METLIN ID2975
PubChem Compound1826
PDB IDHID
ChEBI ID27823
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. 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. Pubmed: 19212411
  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. 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
  5. 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
  6. Yamamoto M: Depression in Parkinson's disease: its prevalence, diagnosis, and neurochemical background. J Neurol. 2001 Sep;248 Suppl 3:III5-11. Pubmed: 11697689
  7. 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
  8. 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
  9. 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
  10. 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
  11. Feldman JM: Urinary serotonin in the diagnosis of carcinoid tumors. Clin Chem. 1986 May;32(5):840-4. Pubmed: 2421946
  12. 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
  13. 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
  14. Meltzer H: Serotonergic dysfunction in depression. Br J Psychiatry Suppl. 1989 Dec;(8):25-31. Pubmed: 2692637
  15. Csernansky JG, Sheline YI: Abnormalities of serotonin metabolism and nonpsychotic psychiatric disorders. Ann Clin Psychiatry. 1993 Dec;5(4):275-81. Pubmed: 8312985
  16. 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
  17. 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
  18. 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

Enzymes

Gene Name:
ASMT
Uniprot ID:
P46597
Reactions
S-Adenosylmethionine + 5-Hydroxyindoleacetic acid unknown S-Adenosylhomocysteine + 5-Methoxyindoleacetatedetails
Gene Name:
AOX1
Uniprot ID:
Q06278
Reactions
5-Hydroxyindoleacetaldehyde + Oxygen + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen peroxidedetails
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
ALDH2
Uniprot ID:
P05091
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water unknown 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails