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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 21:10:36 UTC
Update Date2023-02-21 17:16:40 UTC
HMDB IDHMDB0003447
Secondary Accession Numbers
  • HMDB03447
Metabolite Identification
Common NameTryptophol
DescriptionTryptophol, also known as indole-3-ethanol, is an indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2. It has a role as a Saccharomyces cerevisiae metabolite, an auxin and a plant metabolite. Tryptophol is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID:30120222 ). Tryptophol production was negatively associated with interferon-gamma production (IFNγ) which suggests that tryptophol has anti-inflammatory properties (PMID:27814509 ). Tryptophol has also been identified as the hypnotic agent in trypanosomal sleeping sickness, and because it is formed in vivo after ethanol or disulfiram treatment, it is also associated with the study of alcoholism (PMID:7241135 ).
Structure
Thumb
Synonyms
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=C1C=CC=C2
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point59 °CNot Available
Boiling Point357.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2749 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.280 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available133.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002126
[M+H]+Not Available133.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00002126
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1295861
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)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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. [PubMed:27814509 ]