Record Information
Version1.0
Creation date2010-04-08 22:09:24 UTC
Update date2019-11-26 03:04:24 UTC
Primary IDFDB010973
Secondary Accession Numbers
  • FDB030938
Chemical Information
FooDB NameTryptophol
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) [HMDB]. Tryptophol is found in many foods, some of which are linden, cupuaçu, black-eyed pea, and mango.
CAS Number526-55-6
Structure
Thumb
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H11NO
IUPAC name2-(1H-indol-3-yl)ethan-1-ol
InChI IdentifierInChI=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
Isomeric SMILESOCCC1=CNC2=CC=CC=C12
Average Molecular Weight161.2004
Monoisotopic Molecular Weight161.084063979
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-20fec68981d54c2e70022015-03-01View Spectrum
GC-MSTryptophol, 2 TMS, GC-MS Spectrumsplash10-0udi-1591000000-5b173cc0ac0dc2b874a9Spectrum
GC-MSTryptophol, non-derivatized, GC-MS Spectrumsplash10-0udi-1591000000-5b173cc0ac0dc2b874a9Spectrum
GC-MSTryptophol, non-derivatized, GC-MS Spectrumsplash10-0udi-0490000000-15708d306e1f75b1e76fSpectrum
Predicted GC-MSTryptophol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-0900000000-d2769447ff27a79be367Spectrum
Predicted GC-MSTryptophol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00yi-5690000000-765b6a566d2067c199b0Spectrum
Predicted GC-MSTryptophol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-593c6fbb6f64e16e7f052012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03e9-0900000000-54f7b6548b8a00c91c3f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-003u-0900000000-fb2793cd76eefaaf45c52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-016r-0900000000-a97ae0f4c1633b83c4152012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-0900000000-d00c24bc728f46156c602012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-593c6fbb6f64e16e7f052017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03e9-0900000000-54f7b6548b8a00c91c3f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-003u-0900000000-fb2793cd76eefaaf45c52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-016r-0900000000-78c3b34c10c43b6a93172017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-d00c24bc728f46156c602017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-0900000000-d41cd8e81a55b3e005382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0900000000-aeba8d28d8681fb1473d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-b46601ffc736985fcdf82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-3e7e36fd8027ab6c9e962021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-003u-0900000000-2ba4c5a87b74cfd62e022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0900000000-5fb5f5b5efe809cbe9ad2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-0900000000-44158c348db109504af42012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-6900000000-48b709f034a27e74e73f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5927d4ac720f209af38d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-5900000000-4bc97e2ed06c230bbbde2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-4807fdc919bf8c468f722021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-63222dc5b6f22cd7cc132021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9800000000-314e270d78e7a9ec16a92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-3f8e0d1410267c0ad66e2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-bfeeeabc14ffd14b537e2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID10235
ChEMBL IDCHEMBL226545
KEGG Compound IDC00955
Pubchem Compound ID10685
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03447
CRC / DFC (Dictionary of Food Compounds) IDFXH84-Q:FXH84-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000114
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
Processing...
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.