Ergothionine

Ergothioneine

Names
IUPAC name 3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Other names L-Ergothioneine; (+)-Ergothioneine; Thiasine; Sympectothion; Ergothionine; Erythrothioneine; Thiolhistidinebetaine
Identifiers
CAS Number	497-30-3 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:4828 Y
ChemSpider	4508619 Y
ECHA InfoCard	100.007.131
KEGG	C05570 N
PubChem CID	5351619
UNII	BDZ3DQM98W Y
InChI InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1 Y Key: SSISHJJTAXXQAX-ZETCQYMHSA-N Y InChI=1/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1 Key: SSISHJJTAXXQAX-ZETCQYMHBA
SMILES C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-] S=C1N\C(=C/N1)C[C@@H](C([O-])=O)[N+](C)(C)C
Properties
Chemical formula	C9H15N3O2S
Molar mass	229.30 g/mol
Appearance	white solid
Melting point	275 to 277 °C (527 to 531 °F; 548 to 550 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Ergothioneine is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom on the imidazole ring. This compound is made in relatively few organisms, notably Actinobacteria, Cyanobacteria, and certain fungi. Ergothioneine was discovered in 1909 and named after the ergot fungus from which it was first purified, with its structure being determined in 1911.

In vitro assays, as well as in vivo animal models, are used in basic research to identify its potential biological properties.

In humans, ergothioneine is acquired exclusively through the diet and accumulates in erythrocytes, bone marrow, liver, kidney, seminal fluid and eyes. Ergothioneine requires a specific transporter, ETT, also known as OCTN1 (gene symbol SLC22A4), to enter cells. ETT expression has been confirmed in human and animal cell lines and its functional transport of ergothioneine has been observed in preliminary studies in vivo. Although the effect of ergothioneine in vivo is an active area of research, its physiological role in humans is undetermined.

Ergothioneine has been found in bacteria, plants and animals, sometimes at millimolar levels. Foods found to contain ergothioneine include liver, kidney, black beans, kidney bean and oat bran, with the highest levels in bolete and oyster mushrooms. Levels can be variable, even within species and some tissues can contain much more than others. In the human body, the largest amounts of ergothioneine are found in erythrocytes, eye lens and semen, and it is also present in the skin.