Record Information
Version1.0
Creation date2011-09-21 00:18:19 UTC
Update date2019-11-26 03:21:06 UTC
Primary IDFDB022711
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]. 5-Hydroxytryptophol is found in many foods, some of which are climbing bean, macadamia nut (m. tetraphylla), pepper (c. frutescens), and scarlet bean.
CAS Number154-02-9
Structure
Thumb
Synonyms
SynonymSource
5-HTOLHMDB
5-Hydroxy-1H-indole-3-ethanolHMDB
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-3-ethanolHMDB
5-Hydroxyindole-acetic acidHMDB
Hydroxyindoleacetic acidHMDB
HydroxytryptopholHMDB, MeSH
5-Hydroxy-1H-Indole-3-ethanol(9CI)hmdb
5-hydroxy-3-indolehmdb
5-hydroxy-indole-acetic acidhmdb
5-hydroxyindoacetic acidhmdb
5-hydroxyindolhmdb
5-hydroxyindolacetatehmdb
5-hydroxyindolacetate acidhmdb
5-hydroxyindole-acetic acidhmdb
5-Hydroxytryptopholhmdb
Predicted Properties
PropertyValueSource
Water Solubility2.18 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.7 m³·mol⁻¹ChemAxon
Polarizability18.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H11NO2
IUPAC name3-(2-hydroxyethyl)-1H-indol-5-ol
InChI IdentifierInChI=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 KeyKQROHCSYOGBQGJ-UHFFFAOYSA-N
Isomeric SMILESOCCC1=CNC2=CC=C(O)C=C12
Average Molecular Weight177.1998
Monoisotopic Molecular Weight177.078978601
Classification
Description 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
  • 3-alkylindole
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-Hydroxytryptophol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0900000000-9d105acbf4bc808f485dSpectrum
Predicted GC-MS5-Hydroxytryptophol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fs-4094000000-d1307c11143d51fcfef0Spectrum
Predicted GC-MS5-Hydroxytryptophol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01t9-0900000000-438566644fd2e8ec412e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-8baec8b2c7b82d489fc82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-07vi-0900000000-c7bb9d840b92b2e189ef2012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0900000000-db5db754e226df9169662015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-dd31d267f7f54ef4d1c62015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ai-1900000000-784614cb940ba83ab52e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-2e8fd5660c103ab7f3cb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0900000000-2ce11ad613dbaf000b6a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-39a645eb4fa1a2571f5c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ef6ae59e91e658cf298a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-0900000000-079cf44c5cb8c0abc83a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-988823631fda3bc6aced2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0900000000-c77361097a5dfc6286b32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r2-0900000000-ed0c8a92fe9e18ba8ebc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2900000000-f8bdbcda86acdd866a002021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID8708
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9061
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01855
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference