Tryptophol (CHEM027266)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:36:42 UTC
Update Date2016-11-09 01:18:25 UTC
Accession NumberCHEM027266
Identification
Common NameTryptophol
ClassSmall Molecule
DescriptionAn indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
TryptopholHMDB, KEGG
3-(2-Hydroxyethyl)-1H-indoleHMDB
3-(β-Hydroxyethyl)indoleHMDB
3-Indole ethanolHMDB
β-(3-Indole)ethanolHMDB
Chemical FormulaC10H11NO
Average Molecular Mass161.200 g/mol
Monoisotopic Mass161.084 g/mol
CAS Registry Number526-55-6
IUPAC Name2-(1H-indol-3-yl)ethan-1-ol
Traditional Nametryptophol
SMILESOCCC1=CNC2=CC=CC=C12
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1591000000-5b173cc0ac0dc2b874a9Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1591000000-5b173cc0ac0dc2b874a9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0490000000-15708d306e1f75b1e76fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0900000000-d2769447ff27a79be367Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00yi-5690000000-765b6a566d2067c199b0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-593c6fbb6f64e16e7f05Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03e9-0900000000-54f7b6548b8a00c91c3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-003u-0900000000-fb2793cd76eefaaf45c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-016r-0900000000-a97ae0f4c1633b83c415Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-0900000000-d00c24bc728f46156c60Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-593c6fbb6f64e16e7f05Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03e9-0900000000-54f7b6548b8a00c91c3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-003u-0900000000-fb2793cd76eefaaf45c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-016r-0900000000-78c3b34c10c43b6a9317Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-d00c24bc728f46156c60Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-0900000000-d41cd8e81a55b3e00538Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0900000000-aeba8d28d8681fb1473dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-b46601ffc736985fcdf8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-3e7e36fd8027ab6c9e96Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-003u-0900000000-2ba4c5a87b74cfd62e02Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0900000000-5fb5f5b5efe809cbe9adSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-0900000000-44158c348db109504af4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-6900000000-48b709f034a27e74e73fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5927d4ac720f209af38dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-5900000000-4bc97e2ed06c230bbbdeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-4807fdc919bf8c468f72Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-63222dc5b6f22cd7cc13Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9800000000-314e270d78e7a9ec16a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-3f8e0d1410267c0ad66eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-bfeeeabc14ffd14b537eSpectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-20fec68981d54c2e7002Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003447
FooDB IDFDB010973
Phenol Explorer IDNot Available
KNApSAcK IDC00000114
BiGG IDNot Available
BioCyc IDCPD-341
METLIN ID6932
PDB IDNot Available
Wikipedia LinkTryptophol
Chemspider ID10235
ChEBI ID17890
PubChem Compound ID10685
Kegg Compound IDC00955
YMDB IDYMDB00577
ECMDB IDM2MDB005506
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10856636
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12499363
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16664264
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19842066
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23413824
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24032669
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24253838
8. Snyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.
9. Snyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.
10. 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.
11. Schirmer M, Smeekens SP, Vlamakis H, Jaeger M, Oosting M, Franzosa EA, Ter Horst R, Jansen T, Jacobs L, Bonder MJ, Kurilshikov A, Fu J, Joosten LAB, Zhernakova A, Huttenhower C, Wijmenga C, Netea MG, Xavier RJ: Linking the Human Gut Microbiome to Inflammatory Cytokine Production Capacity. Cell. 2016 Nov 3;167(4):1125-1136.e8. doi: 10.1016/j.cell.2016.10.020.
12. 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.