Human Metabolome Database Version 3.5

Showing metabocard for 5-Hydroxytryptophol (HMDB01855)

Record Information
Version 3.5
Creation Date 2006-02-21 01:10:09 -0700
Update Date 2013-05-29 13:32:30 -0600
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 | PDB | 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-Hydroxyindolacetic 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
Sorry, spectra are temporarily unavailable.
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 Reference
Blood Detected and Quantified
0.0009 +/- 0.0003 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.004 +/- 0.22 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.107 +/- 0.019 uM Not Specified Not Specified Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 0.11 +/- 0.013 uM Adult (>18 years old) Female Schizophrenia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.12 +/- 0.09 uM Children (1-13 year old) Not Specified Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.009 +/- 0.01 uM Not Specified Not Specified Neurological disorders (2 - 18 years old)
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0846 +/- 0.0179 uM Adult (>18 years old) Not Specified Parkinson disease
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
          DrugBank Metabolite 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
          2. Krishnaswamy S, Hao Q, Von Moltke LL, Greenblatt DJ, Court MH: Evaluation of 5-hydroxytryptophol and other endogenous serotonin (5-hydroxytryptamine) analogs as substrates for UDP-glucuronosyltransferase 1A6. Drug Metab Dispos. 2004 Aug;32(8):862-9. Pubmed: 15258112 Link_out