5-hydroxytryptophol (PAMDB120397)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120397
Identification
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 ).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • hydroxytryptophol
  • 5-hydroxyindole-3-ethanol
  • 5-hydroxy-1H-indole-3-ethanol
  • 1H-indole-3-ethanol
  • 5-hydroxy-indole-3-ethanol
Chemical Formula: C10H11NO2
Average Molecular Weight: 177.202
Monoisotopic Molecular Weight: 177.07898
InChI Key: KQROHCSYOGBQGJ-UHFFFAOYSA-N
InChI: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
CAS number: 154-02-9
IUPAC Name:3-(2-hydroxyethyl)-1H-indol-5-ol
Traditional IUPAC Name: hydroxytryptophol
SMILES:C(O)CC1(=CNC2(=C1C=C(O)C=C2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct Parent Hydroxyindoles
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 Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
5-hydroxytryptophol + NAD+ → 5-hydroxyindole acetaldehyde + NADH + Hydrogen ion
Pathways: Not Available
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
References
References:
  • 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 ]
  • 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 ]
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)
External Links:
ResourceLink
HMDBHMDB01855
CHEMSPIDER8708
PUBCHEM9061