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Record Information
Version3.6
Creation Date2006-02-21 08:10:09 UTC
Update Date2016-02-11 01:05:02 UTC
HMDB IDHMDB01855
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Hydroxytryptophol
Description5-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 ).
Structure
Thumb
Synonyms
ValueSource
HydroxytryptopholMetaCyc
5-Hydroxyindole-3-ethanolMetaCyc
5-Hydroxy-1H-indole-3-ethanolMetaCyc
5-HTOLHMDB
5-Hydroxy-1H-indole-3-ethanol(9ci)HMDB
5-Hydroxy-3-indoleHMDB
5-Hydroxy-3-indoleacetic acidHMDB
5-Hydroxy-indole-acetic acidHMDB
5-Hydroxyindoacetic acidHMDB
5-HydroxyindolHMDB
5-HydroxyindolacetateHMDB
5-Hydroxyindolacetic acidHMDB
5-Hydroxyindole-acetic acidHMDB
Hydroxyindoleacetic acidHMDB
Chemical FormulaC10H11NO2
Average Molecular Weight177.1998
Monoisotopic Molecular Weight177.078978601
IUPAC Name3-(2-hydroxyethyl)-1H-indol-5-ol
Traditional Namehydroxytryptophol
CAS Registry Number154-02-9
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 KeyInChIKey=KQROHCSYOGBQGJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • Hydroxyindole
  • Indole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.18 mg/mLALOGPS
logP0.91ALOGPS
logP1.29ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area56.25 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.7 m3·mol-1ChemAxon
Polarizability18.86 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01t9-0900000000-438566644fd2e8ec412eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-8baec8b2c7b82d489fc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-07vi-0900000000-c7bb9d840b92b2e189efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0900000000-db5db754e226df916966View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-dd31d267f7f54ef4d1c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ai-1900000000-784614cb940ba83ab52eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-2e8fd5660c103ab7f3cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0900000000-2ce11ad613dbaf000b6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-39a645eb4fa1a2571f5cView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0009 +/- 0.0003 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.22 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.107 +/- 0.019 uMNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.11 +/- 0.013 uMAdult (>18 years old)FemaleSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.12 +/- 0.09 uMChildren (1-13 years old)Not SpecifiedLeukemia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.009 +/- 0.01 uMNot SpecifiedNot SpecifiedNeurological disorders (2 - 18 years old) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0846 +/- 0.0179 uMAdult (>18 years old)Not SpecifiedParkinson's Disease details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. 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. [115032 ]
Leukemia
  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. [1184685 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022711
KNApSAcK IDNot Available
Chemspider ID8708
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01855
Metagene LinkHMDB01855
METLIN ID5730
PubChem Compound9061
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceDa 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. [1184685 ]
  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. [15258112 ]