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Details

Stereochemistry ACHIRAL
Molecular Formula C9H16N3O2S.Cl
Molecular Weight 265.76
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERGOTHIONEINE HYDROCHLORIDE

SMILES

[Cl-].C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C(O)=O

InChI

InChIKey=DFXLBSRDLIVADK-FJXQXJEOSA-N
InChI=1S/C9H15N3O2S.ClH/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);1H/t7-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C9H15N3O2S
Molecular Weight 229.299
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

ERGO (Ergothioneine) is naturally occurring antioxidant derived from the diet and abundantly contained in golden oyster mushroom (Pleurotus cornucopiae var. citrinopileatus. It is hydrophilic and membrane impermeable, but is well absorbed from the gastrointestinal tract due to the presence of a specific carrier‐mediated transport system, carnitine/organic cation transporter OCTN1/SLC22A4, essential for the beta-oxidation of fatty acids. Numerous in vitro assays have demonstrated the antioxidant and cytoprotective capabilities of ERGO against a wide range of cellular stressors, but an antioxidant role has yet to be fully verified in vivo. Nevertheless, the accumulation, tissue distribution, and scavenging properties, all highlight the potential for EGT to function as a physiological antioxidant. Because ERGO is highly distributed into the brain after oral ingestion, OCTN1 may contribute to the alleviation of oxidative stress and promotion of neuronal differentiation via the uptake of ERGO in the brain, perhaps abating symptoms of neurological disorders.

CNS Activity

Curator's Comment: “Known to be CNS active in mouse. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9H015
Gene ID: 6583.0
Gene Symbol: SLC22A4
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Estimation of ergothioneine in urine, blood and organs by determination of the alkaline perhydrol-labile sulfur.
1952 Oct
Discovery of the ergothioneine transporter.
2005 Apr 5
Patents

Sample Use Guides

in mice: To clarify the exposure of ERGO (ergothioneine) to brain and the possible antidepressant‐like effect after oral ingestion, ERGO or GOME (golden oyster mushroom extract) which contains 1.2% (w/w) ERGO was mixed with feed and provided to mice for 2 weeks, and then ERGO concentration and antidepressant‐like effect were evaluated by LC‐MS/MS and FST (forced swimming test) or TST (tail suspension test), respectively.
Route of Administration: Oral
Human OCTN1 was expressed in 293 cells. Analysis of transport efficiency of stachydrine-related solutes, affinity, and Na+ dependence indicates that the physiological substrate is ergothioneine (ET). Efficiency of transport of ET was as high as 195 μl per min per mg of protein. By contrast, the carnitine transporter OCTN2 from rat did not transport ET at all
Substance Class Chemical
Created
by admin
on Sat Dec 16 12:53:16 GMT 2023
Edited
by admin
on Sat Dec 16 12:53:16 GMT 2023
Record UNII
V688K433V6
Record Status Validated (UNII)
Record Version
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Name Type Language
ERGOTHIONEINE HYDROCHLORIDE
Common Name English
L-ERGOTHIONINE HYDROCHLORIDE
Common Name English
NSC-118378
Code English
Code System Code Type Description
FDA UNII
V688K433V6
Created by admin on Sat Dec 16 12:53:16 GMT 2023 , Edited by admin on Sat Dec 16 12:53:16 GMT 2023
PRIMARY
CAS
6072-08-8
Created by admin on Sat Dec 16 12:53:16 GMT 2023 , Edited by admin on Sat Dec 16 12:53:16 GMT 2023
PRIMARY
PUBCHEM
3037042
Created by admin on Sat Dec 16 12:53:16 GMT 2023 , Edited by admin on Sat Dec 16 12:53:16 GMT 2023
PRIMARY
NSC
118378
Created by admin on Sat Dec 16 12:53:16 GMT 2023 , Edited by admin on Sat Dec 16 12:53:16 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY