MiMeDB: Showing metabocard for Tryptophol (MMDBc0007020)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 00:21:44 UTC

Update Date

2022-08-31 06:26:37 UTC

Metabolite ID

MMDBc0007020

Metabolite Identification

Common Name

Tryptophol

Description

Tryptophol, 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

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₁₀H₁₁NO

Average Mass

161.2004

Monoisotopic Mass

161.084063979

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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 Key

MBBOMCVGYCRMEA-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	6	Human feces	Metabolic reconstruction; Unknown
Eukaryota/Fungi	Mucoromycota	1	Human feces
Bacteria	Actinobacteria	2

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	31235863
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

Not Available

General References

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. doi: 10.1111/j.1471-4159.1981.tb00428.x. [PubMed:7241135 ]
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 ]
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 ]

Showing metabocard for Tryptophol (MMDBc0007020)

MOL for #<Metabolite:0x0000560be0729290>

3D MOL for #<Metabolite:0x0000560be0729290>

3D SDF for #<Metabolite:0x0000560be0729290>

3D-SDF for #<Metabolite:0x0000560be0729290>

PDB for #<Metabolite:0x0000560be0729290>

3D PDB for #<Metabolite:0x0000560be0729290>

SMILES for #<Metabolite:0x0000560be0729290>

INCHI for #<Metabolite:0x0000560be0729290>

Structure for #<Metabolite:0x0000560be0729290>

3D Structure for #<Metabolite:0x0000560be0729290>