| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:09:16 -0700 |
| HMDB ID |
HMDB00763 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
5-Hydroxyindoleacetic acid |
| Description |
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). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 5-HIAA
- 5-Hydroxy-1H-indole-3-acetate
- 5-Hydroxy-1H-indole-3-acetic 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-Hydroxyindole acetate
- 5-Hydroxyindole-3-acetate
- 5-Hydroxyindole-3-acetic acid
- 5-Hydroxyindoleacetate
- 5-Hydroxyindoleacetic acid
- 5-Oxyindoleacetate
- 5-Oxyindoleacetic acid
- 5HIAA
- Hydroxyindoleacetate
|
| Chemical Formula |
C10H9NO3 |
| Average Molecular Weight |
191.1834 |
| Monoisotopic Molecular Weight |
191.058243159 |
| IUPAC Name |
2-(5-hydroxy-1H-indol-3-yl)acetic acid |
| Traditional IUPAC Name |
(5-hydroxy-1H-indol-3-yl)acetic acid |
| CAS Registry Number |
54-16-0 |
| 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 Key |
DUUGKQCEGZLZNO-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteropolycyclic Compounds |
| Class |
Indoles |
| Sub Class |
Indolyl Carboxylic Acids and Derivatives |
| Other Descriptors |
- Indoles
- indole-3-acetic acids(ChEBI)
|
| Substituents |
- Carboxylic Acid
- Phenol
- Phenol Derivative
- Pyrrole
|
| Direct Parent |
Indole-3-acetic Acid Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
161 - 163 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
24 mg/mL |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|
| Gas-MS Spectrum |
| 1H NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50 |
| MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies ) |
| MS/MS Spectrum GC-MS |
| [1H,13C] 2D NMR Spectrum |
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
- Testes
- Liver
- Brain
- Prostate
- Nerve Cells
- Platelet
- Spleen
- Hippocampus
- Central Nervous System
- Spinal Cord
- Hypothalamus
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.0516 +/- 0.0068 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.307 (0.152-0.462) uM |
Infant (0-1 year old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.428-1.122 uM |
Children (1-13 year old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.119-0.608 uM |
Children (1-13 year old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.07-0.14 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.109-0.214 uM |
Children (1-13 year old) |
Male |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.1-0.245 uM |
Children (1-13 year old) |
Male |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.61 +/- 0.06 uM |
Children (1-13 year old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.4 +/- 0.07 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.47 (0.15-0.80) uM |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.025 +/- 0.011 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.143 +/- 0.045 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
3.0 (0.48-4.5) umol/mmol creatinine |
Children (1-13 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
1.57 +/- 0.38 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
4.75 +/- 5.38 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
1.18 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
11.0 (4.0-18.0) umol/mmol creatinine |
Infant (0-1 year old) |
Not Specified |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Urine compound detected by GC-MS
|
| Urine |
Detected and Quantified |
|
1.5 (0-7.2) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
1.1 +/- 0.5 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
2.4 +/- 0.40 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
2.9(0.4-5.8) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by GC-MS
|
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.0475 +/- 0.0130 uM |
Adult (>18 years old) |
Male |
Schizophrenia |
Not Available |
| Blood |
Detected and Quantified |
|
0.0449 +/- 0.0140 uM |
Adult (>18 years old) |
Female |
Schizophrenia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0703 +/- 0.0254 uM |
Adult (>18 years old) |
Both |
celiac disease |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.22725 (0.117-0.519) uM |
Newborn (0-30 days old) |
Not Specified |
PNPO deficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0045 (0.004-0.005) uM |
Children (1-13 year old) |
Male |
sepiapterin reductase deficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0025 (0.0000-0.0050) uM |
Infant (0-1 year old) |
Male |
Aromatic L-amino acid decarboxylase deficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.519 uM |
Newborn (0-30 days old) |
Not Specified |
PNPO deficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.122 uM |
Newborn (0-30 days old) |
Not Specified |
PNPO deficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.117 uM |
Newborn (0-30 days old) |
Not Specified |
PNPO deficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.151 uM |
Newborn (0-30 days old) |
Not Specified |
PNPO deficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.071 +/- 0.0268 uM |
Adult (>18 years old) |
Not Specified |
celiac disease |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.33 +/- 0.04 uM |
Children (1-13 year old) |
Both |
Epilepsy |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.1491 +/- 0.0591 uM |
Adult (>18 years old) |
Not Specified |
Leuprolide acetate-induce hypogonadism |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.1373 +/- 0.0457 uM |
Adult (>18 years old) |
Not Specified |
Leuprolide acetate-induced hypogonadism with testosterone replacment |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.08 +/- 0.08 uM |
Adult (>18 years old) |
Both |
Major depression |
Also known as major depressive disorder,...
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0887 +/- 0.0385 uM |
Not Specified |
Not Specified |
Bipolar with childhood ADHD (attention-deficit hyperactivity disorder) |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.116 +/- 0.0479 uM |
Not Specified |
Not Specified |
pure bipolar |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.126 +/- 0.0526 uM |
Not Specified |
Not Specified |
Control (men) |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.096 +/- 0.0384 uM |
Not Specified |
Female |
Control (women) |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.112 +/- 0.0483 uM |
Not Specified |
Not Specified |
With lithium treatment |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0983 +/- 0.0444 uM |
Not Specified |
Not Specified |
Without lithium treatment |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0912 +/- 0.0387 uM |
Not Specified |
Not Specified |
With antipsychotic treatment |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.123 +/- 0.0505 uM |
Not Specified |
Not Specified |
Without antipsychotic treatment |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.116 +/- 0.053 uM |
Not Specified |
Not Specified |
With episodes of interpersonal violence |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.104 +/- 0.0386 uM |
Not Specified |
Not Specified |
Without episodes of interpersonal violence |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.1 +/- 0.01 uM |
Adult (>18 years old) |
Both |
Friedreich's ataxia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.11 +/- 0.01 uM |
Adult (>18 years old) |
Both |
Olivopontocerebellar atrophy (OPCA) |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.1 +/- 0.02 uM |
Adult (>18 years old) |
Both |
Spastic Ataxia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.019 +/- 0.0094 uM |
Adult (>18 years old) |
Both |
Schizophrenia |
Not Available |
| Urine |
Detected and Quantified |
|
0.9 +/- 0.0 umol/mmol creatinine |
Infant (0-1 year old) |
Male |
Aromatic L-amino acid decarboxylase deficiency |
Not Available |
| Urine |
Detected and Quantified |
|
5.0 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Carcinoid tumors |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| 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
|
| 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
|
| 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
|
| 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
|
| 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
|
|
| Associated OMIM IDs |
- 107930
(Aromatic L-amino acid decarboxylase deficiency)
- 608516
(Major depressive disorder)
- 181500
(Schizophrenia)
- 229300
(Friedreich's ataxia)
- 182601
(Hereditary spastic paraplegia)
|
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB001403 |
| KNApSAcK ID |
C00000104  |
| Chemspider ID |
1760  |
| KEGG Compound ID |
C05635  |
| BioCyc ID |
5-HYDROXYINDOLE_ACETATE  |
| BiGG ID |
46167  |
| Wikipedia Link |
5-Hydroxyindoleacetic acid  |
| NuGOwiki Link |
HMDB00763  |
| Metagene Link |
HMDB00763  |
| METLIN ID |
2975  |
| PubChem Compound |
1826  |
| PDB ID |
HID  |
| ChEBI ID |
27823  |
| 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 |
- 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
- 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
- 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
- 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
- Csernansky JG, Sheline YI: Abnormalities of serotonin metabolism and nonpsychotic psychiatric disorders. Ann Clin Psychiatry. 1993 Dec;5(4):275-81.
Pubmed: 8312985
- 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
- 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
- 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
- Meltzer H: Serotonergic dysfunction in depression. Br J Psychiatry Suppl. 1989 Dec;(8):25-31.
Pubmed: 2692637
- Yamamoto M: Depression in Parkinson's disease: its prevalence, diagnosis, and neurochemical background. J Neurol. 2001 Sep;248 Suppl 3:III5-11.
Pubmed: 11697689
- 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
- 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
- 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
- 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
- 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
- Feldman JM: Urinary serotonin in the diagnosis of carcinoid tumors. Clin Chem. 1986 May;32(5):840-4.
Pubmed: 2421946
- 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
- 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
|