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Human Metabolome Database Version 3.5

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Showing metabocard for 5-Hydroxytryptophol (HMDB01855)

Record Information
Version 3.5
Creation Date 2006-02-21 01:10:09 -0700
Update Date 2013-02-08 17:10:52 -0700
HMDB ID HMDB01855
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Hydroxytryptophol
Description 5-Hydroxytryptophol is a relatively minor metabolite of serotonin that is excreted primarily as the glucuronide conjugate in human urine. 5-Hydroxytryptophol becomes more important quantitatively during alcohol intoxication, when a shift in the metabolism of serotonin occurs from 5-hydroxyindole acetic acid toward increased (15-fold higher) formation of 5-hydroxytryptophol due to the inhibition of aldehyde dehydrogenase by ethanol-derived acetaldehyde. Urinary excretion of 5-hydroxytryptophol has also been shown to be markedly increased for several hours following intake of foods rich in serotonin, such as bananas. Wide interspecies variation has been reported in the metabolism serotonin to 5-hydroxytryptophol; 5-Hydroxytryptophol makes up 35% of the excreted serotonin metabolites in the rat on average and 10 to 20% in several other species. Human UDP-glucuronosyltransferase 1A6 (UGT1A6) plays a predominant role in the glucuronidation of 5-hydroxytryptophol by human liver microsomes. (PMID 15258112 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5-HTOL
  2. 5-Hydroxy-1H-indole-3-ethanol
  3. 5-Hydroxy-1H-Indole-3-ethanol(9CI)
  4. 5-Hydroxy-3-indole
  5. 5-Hydroxy-3-indoleacetic acid
  6. 5-Hydroxy-indole-acetic acid
  7. 5-Hydroxyindoacetic acid
  8. 5-Hydroxyindol
  9. 5-Hydroxyindolacetate
  10. 5-Hydroxyindolacetate acid
  11. 5-Hydroxyindole-3-ethanol
  12. 5-Hydroxyindole-acetic acid
  13. 5-Hydroxytryptophol
  14. Hydroxyindoleacetic acid
  15. Hydroxytryptophol
Chemical Formula C10H11NO2
Average Molecular Weight 177.1998
Monoisotopic Molecular Weight 177.078978601
IUPAC Name 3-(2-hydroxyethyl)-1H-indol-5-ol
Traditional IUPAC Name 3-(2-hydroxyethyl)-1H-indol-5-ol
CAS Registry Number 154-02-9
SMILES OCCC1=CNC2=CC=C(O)C=C12
InChI Identifier InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2
InChI Key KQROHCSYOGBQGJ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class N/A
Other Descriptors
  • a small molecule(Cyc)
Substituents
  • Phenol
  • Phenol Derivative
  • Primary Alcohol
  • Pyrrole
Direct Parent Indoles
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.18 g/L ALOGPS
LogP 0.91 ALOGPS
LogP 1.29 ChemAxon
LogS -1.91 ALOGPS
pKa (strongest acidic) 9.56 ChemAxon
pKa (strongest basic) -2.4 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 56.25 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 50.7 ChemAxon
Polarizability 18.86 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
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
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.0009 +/- 0.0003 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.004 +/- 0.22 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.107 +/- 0.019 uM Not Specified Not Specified Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.11 +/- 0.013 uM Adult (>18 years old) Female Schizophrenia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.12 +/- 0.09 uM Children (1-13 year old) Not Specified Leukemia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.009 +/- 0.01 uM Not Specified Not Specified Neurological disorders (2 - 18 years old) Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.0846 +/- 0.0179 uM Adult (>18 years old) Not Specified Parkinson disease Not Available
Associated Disorders and Diseases
Disease References
Leukemia
  • Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. Pubmed: 1184685 Link_out
    Schizophrenia
    • Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4. Pubmed: 115032 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022711
      KNApSAcK ID Not Available
      Chemspider ID 8708 Link_out
      KEGG Compound ID Not Available
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB01855 Link_out
      Metagene Link HMDB01855 Link_out
      METLIN ID 5730 Link_out
      PubChem Compound 9061 Link_out
      PDB ID Not Available
      ChEBI ID Not Available
      References
      Synthesis Reference Da Prada, M.; Bartholini, G.; Pletscher, A. Formation of 5-hydroxytryptophol by blood platelets after thrombin and reserpine. Experientia (1965), 21(3), 135-6.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. Pubmed: 1184685 Link_out