ERGOTHIONEINE
(2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Molecular Identity
ERGOTHIONEINE
(2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
PubChem CID: 5351619
Ergothioneine is a L-histidine derivative that is Nalpha,Nalpha,Nalpha-trimethyl-L-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a mercapto group. A naturally occurring metabolite of histidine synthesized by bacteria and fungi with antioxidant properties. It is found ubiquitously in plants and animals and is present in many human foodstuffs. It has a role as an antioxidant, a chelator, a xenobiotic metabolite, a plant metabolite and a fungal metabolite. It is an amino-acid betaine, a sulfur-containing amino acid and a L-histidine derivative. It is a conjugate base of an ergothioneine(1+). It is a tautomer of an ergothioneine thione form.
2D Structure
Properties
C9H15N3O2S
Molecular Formula
229.30
Molecular Weight
g/mol
229.0885
Exact Mass
Da
0.3
XLogP
Drug-like (Lipinski: < 5)
96.3
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
3
H-Bond Acceptors
314
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
ERGOTHIONEINE497-30-3L-ErgothioneineSympectothionErgothionineThioneinel-ThioneineThiasineL(+)-ErgothioneineThiolhistidine-betaineBDZ3DQM98WDTXSID901020082(2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoateCHEBI:4828(2S)-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Data from PubChem (NCBI)
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