ChemFOnt: Showing chemical card for Ergothioneine (CFc000001761)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:28 UTC

Chemfont ID

CFc000001761

Molecule Identification

Common Name

Ergothioneine

Definition

Ergothioneine is a naturally occurring metabolite of histidine that has antioxidant properties. -- Pubchem. Ergothioneine is a product of plant origin that accumulates in animal tissues. Ergothioneine is biosynthesized exclusively by fungi and mycobacteria and is captured by plants through their roots. As an ingredient of human food, ET is distributed very unevenly. By far, the highest levels of Ergothioneine have been found in mushrooms (0.1-1 mg/g dried material). Ergothioneine is rapidly cleared from the circulation and then avidly retained with minimal metabolism: the whole-body half-life of ingested Ergothioneine in rats is 1 month. The content of Ergothioneine varies greatly among tissues and is strongly dependent on its dietary level. In addition to erythrocytes and bone marrow, high Ergothioneine levels have also been found in seminal fluid. The precise physiological role of ET has remained elusive since its discovery in 1909. It is known that Ergothioneine is a powerful scavenger of hydroxyl radicals and an inhibitor of iron or copper ion-dependent generation of hydroxyl radicals from hydrogen peroxide (H2O2). A specific ergothioneine transporter has recently been identified (gene symbol SLC22A4 - PMID: 15795384 ). Ergothioneine appears to play a pivotal protective role in monocytes, because the occurrence of rheumatoid arthritis and Crohn's disease has very recently been linked to variant ergothioneine transporter genes (PMID: 15795384 ). SLC22A4 is highly expressed in the kidney, where it is thought to aid in active secretion of organic cations, and may facilitate the active reabsorption of ergothioneine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₉H₁₆N₃O₂S

Average Molecular Weight

230.307

Monoisotopic Molecular Weight

230.096322461

IUPAC Name

[1-carboxy-2-(2-sulfanyl-1H-imidazol-5-yl)ethyl]trimethylazanium

Traditional Name

[1-carboxy-2-(2-sulfanyl-3H-imidazol-4-yl)ethyl]trimethylazanium

CAS Registry Number

497-30-3

SMILES

C[N+](C)(C)C(CC1=CN=C(S)N1)C(O)=O

InChI Identifier

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)/p+1

InChI Key

SSISHJJTAXXQAX-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
Aralkylamine
Imidazole-2-thione
Azole
Imidazole
Quaternary ammonium salt
Heteroaromatic compound
Tetraalkylammonium salt
Thiourea
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic salt
Organic nitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24392160)

Organ

Placenta (HMDB: HMDB0003045)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0003045)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cereal and cereal product

Cereal

Oat (FooDB: FOOD00022)

Vegetable

Mushrooms (HMDB: HMDB0003045)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0003045)
Antioxidant (HMDB: HMDB0003045)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	5.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.52 m³·mol⁻¹	ChemAxon
Polarizability	23.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004217

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergothioneine

METLIN ID

Not Available

PubChem Compound

10344

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Xu, Jinzhu; Yadan, Jean Claude. Synthesis of L-(+)-Ergothioneine. Journal of Organic Chemistry (1995), 60(20), 6296-301.

Showing chemical card for Ergothioneine (CFc000001761)

MOL for CFc000001761 (Ergothioneine)

3D MOL for CFc000001761 (Ergothioneine)

3D SDF for CFc000001761 (Ergothioneine)

3D-SDF for CFc000001761 (Ergothioneine)

PDB for CFc000001761 (Ergothioneine)

3D PDB for CFc000001761 (Ergothioneine)

SMILES for CFc000001761 (Ergothioneine)

INCHI for CFc000001761 (Ergothioneine)

Structure for CFc000001761 (Ergothioneine)

3D Structure for CFc000001761 (Ergothioneine)