You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 21:10:36 UTC
Update Date2019-03-20 17:19:16 UTC
HMDB IDHMDB0003447
Secondary Accession Numbers
  • HMDB03447
Metabolite Identification
Common NameTryptophanol
DescriptionTryptophanol, also called indole-3-ethanol, is a dietary indole present in cruciferous vegetables that has been shown to influence estradiol metabolism in humans and may provide a new chemopreventive approach to estrogen-dependent diseases. (PMID 2342128 ). Tryptophanol has been identified as the hypnotic agent in trypanosomal sleeping sickness, and because it is formed in vivo after ethanol or disulfiram treatment, is also associated with the study of alcoholism. (PMID 7241135 ). Tryptophanol is also a microbial metabolite, urinary Tryptophanol is produced by Clostrida sp. (PMID: 30120222 ).
Structure
Data?1547234255
Synonyms
ValueSource
1H-Indole-3-ethanolChEBI
1H-Indolyl-3-ethanolChEBI
2-(indol-3-yl)EthanolChEBI
3-(2-Hydroxyethyl)indoleChEBI
Indole-3-ethanolChEBI
TryptopholKegg
2-(1H-indol-3-yl)EthanolHMDB
2-(3-Indolyl)ethanolHMDB
2-(3-IndolylethanolHMDB
3-(b-Hydroxyethyl)indoleHMDB
3-(beta-Hydroxyethyl)indoleHMDB
3-IndoleethanolHMDB
3-IndolylethanolHMDB
b-(3-Indole)ethanolHMDB
beta-(3-Indole)ethanolHMDB
beta-indol-3-YlethanolHMDB
DL-TryptophanolHMDB
IEAHMDB
Indole ethanolHMDB
IndoleethanolHMDB
TryptophanolChEBI
Chemical FormulaC10H11NO
Average Molecular Weight161.2004
Monoisotopic Molecular Weight161.084063979
IUPAC Name2-(1H-indol-3-yl)ethan-1-ol
Traditional Nametryptophol
CAS Registry Number526-55-6
SMILES
OCCC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2
InChI KeyMBBOMCVGYCRMEA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point59 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP1.82ALOGPS
logP1.59ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)15.8ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.72 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1591000000-5b173cc0ac0dc2b874a9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1591000000-5b173cc0ac0dc2b874a9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0490000000-15708d306e1f75b1e76fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0900000000-d2769447ff27a79be367JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00yi-5690000000-765b6a566d2067c199b0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-593c6fbb6f64e16e7f05JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03e9-0900000000-54f7b6548b8a00c91c3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-003u-0900000000-fb2793cd76eefaaf45c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-016r-0900000000-a97ae0f4c1633b83c415JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-0900000000-d00c24bc728f46156c60JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-593c6fbb6f64e16e7f05JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03e9-0900000000-54f7b6548b8a00c91c3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-003u-0900000000-fb2793cd76eefaaf45c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-016r-0900000000-78c3b34c10c43b6a9317JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-d00c24bc728f46156c60JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-0900000000-d41cd8e81a55b3e00538JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0900000000-5fb5f5b5efe809cbe9adJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-0900000000-44158c348db109504af4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-6900000000-48b709f034a27e74e73fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-bfeeeabc14ffd14b537eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0900000000-e45fe37e44b99ede037eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2900000000-84aa43c0f5ccfd6511bbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-ae84153e5d93042b79c8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-b04d1b793a892b605239JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-1900000000-eceb6c67d77a5dddf240JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-20fec68981d54c2e7002JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010973
KNApSAcK IDC00000114
Chemspider ID10235
KEGG Compound IDC00955
BioCyc IDCPD-341
BiGG IDNot Available
Wikipedia LinkTryptophol
METLIN ID6932
PubChem Compound10685
PDB IDNot Available
ChEBI ID17890
References
Synthesis ReferenceSnyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.
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 ]
  2. Takahashi S, Godse DD, Naqvi A, Warsh JJ, Stancer HC: 5-Hydroxytryptophol in human cerebrospinal fluid: quantitative determination by gas chromatography-mass spectrometry using a deuterated internal standard. Clin Chim Acta. 1978 Mar 1;84(1-2):55-62. [PubMed:639316 ]
  3. Michnovicz JJ, Bradlow HL: Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990 Jun 6;82(11):947-9. [PubMed:2342128 ]
  4. Cornford EM, Crane PD, Braun LD, Bocash WD, Nyerges AM, Oldendorf WH: Reduction in brain glucose utilization rate after tryptophol (3-indole ethanol) treatment. J Neurochem. 1981 May;36(5):1758-65. [PubMed:7241135 ]
  5. Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]