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Record Information
Version3.6
Creation Date2006-08-12 21:10:36 UTC
Update Date2016-02-11 01:06:17 UTC
HMDB IDHMDB03447
Secondary Accession NumbersNone
Metabolite Identification
Common NameTryptophanol
DescriptionIndole-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 ). 3-Indole ethanol 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 ).
Structure
Thumb
Synonyms
ValueSource
1H-Indole-3-ethanolChEBI
1H-Indolyl-3-ethanolChEBI
2-(indol-3-yl)EthanolChEBI
3-(2-Hydroxyethyl)indoleChEBI
Indole-3-ethanolChEBI
TryptophanolChEBI
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
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 KeyInChIKey=MBBOMCVGYCRMEA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.72 m3·mol-1ChemAxon
Polarizability17.88 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1591000000-5b173cc0ac0dc2b874a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0900000000-5fb5f5b5efe809cbe9adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-0900000000-44158c348db109504af4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-6900000000-48b709f034a27e74e73fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-593c6fbb6f64e16e7f05View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03e9-0900000000-54f7b6548b8a00c91c3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-003u-0900000000-fb2793cd76eefaaf45c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-016r-0900000000-a97ae0f4c1633b83c415View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-0900000000-d00c24bc728f46156c60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-ae84153e5d93042b79c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-b04d1b793a892b605239View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-1900000000-eceb6c67d77a5dddf240View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-bfeeeabc14ffd14b537eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0900000000-e45fe37e44b99ede037eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2900000000-84aa43c0f5ccfd6511bbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-20fec68981d54c2e7002View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB010973
KNApSAcK IDC00000114
Chemspider ID10235
KEGG Compound IDC00955
BioCyc IDCPD-341
BiGG IDNot Available
Wikipedia LinkIEA
NuGOwiki LinkHMDB03447
Metagene LinkHMDB03447
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. [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. [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. [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. [7241135 ]