Structure via PubChem · Public domain (PubChem)
ergothioneine
Sign in to saveErgothioneine (EGT) is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom on the imidazole ring. This compound occurs in relatively few organisms, notably actinomycetota, cyanobacteria, and certain fungi. Ergothioneine was discovered by Charles Tanret in 1909 and named after the ergot fungus from which it was first purified, with its structure being determined in 1911.
Chemical data
- Formula
- C9H15N3O2S
- Molecular weight
- 229.3 g/mol
- IUPAC name
- (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
- SMILES
- C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C(=O)[O-]
- InChIKey
- SSISHJJTAXXQAX-ZETCQYMHSA-N
- XLogP
- 0.3
- Polar surface area
- 96.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
1,136 papers- Ergothioneine and its congeners: anti-ageing mechanisms and pharmacophore biosynthesis.Protein & cell · 2024
- Ergothioneine: an underrecognised dietary micronutrient required for healthy ageing?The British journal of nutrition · 2023
- Ergothioneine, recent developments.Redox biology · 2021
- Ergothioneine and its prospects as an anti-ageing compound.Experimental gerontology · 2022
- Ergothioneine in the brain.FEBS letters · 2022
via PubMed
Wikidata facts
- Mass
- 229.088498
Show 7 more facts
- chemical formula
- C₉H₁₅N₃O₂S
- subject has role
- antioxidant
- canonical SMILES
- C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-]
- isomeric SMILES
- C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C(=O)[O-]
- found in taxon
- Caenorhabditis elegans
- Commons category
- Ergothioneine
- time of discovery or invention
- 1909-00-00
via Wikidata · CC0
~5 min read
Encyclopedic overview
10 sectionsContents
- Metabolism and sources
- Biosynthetic pathway
- Industrial sources
- Structure
- Ergothioneine derivatives
- Preliminary research
- Safe intake levels
- See also
- References
- External links
Ergothioneine (EGT) is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom on the imidazole ring. This compound occurs in relatively few organisms, notably actinomycetota, cyanobacteria, and certain fungi. Ergothioneine was discovered by Charles Tanret in 1909 and named after the ergot fungus from which it was first purified, with its structure being determined in 1911.
In humans, ergothioneine is acquired exclusively through the diet and accumulates in erythrocytes, bone marrow, liver, kidney, seminal fluid, and eyes. Although the effect of ergothioneine in vivo is under preliminary research, its physiological role in humans is unknown. Ergothioneine is sold as a dietary supplement.
Excerpted from Wikipedia’s “ergothioneine” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0