S-(2-succinyl)-L-cysteine (CHEBI:144907)

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ChEBI Name	S-(2-succinyl)-L-cysteine

ChEBI ID	CHEBI:144907

ChEBI ASCII Name	S-(2-succinyl)-L-cysteine

Definition	An L-cysteine thioether that is L-cysteine in which the hydrogen of the thiol group has been replaced by a 1,2-dicarboxyethyl group. It is a chemical modification which occurs in tissue proteins and formed by a Michael addition of cysteine to fumaric acid.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Mark Williams

Supplier Information	ChemicalBook:CB2376433, eMolecules:31267389, eMolecules:530483, ZINC000008214783

Download	Molfile XML SDF

Formula

C7H11NO6S

Net Charge

Average Mass

237.230

Monoisotopic Mass

237.03071

InChI

InChI=1S/C7H11NO6S/c8-3(6(11)12)2-15-4(7(13)14)1-5(9)10/h3-4H,1-2,8H2,(H,9,10)(H,11,12)(H,13,14)/t3-,4?/m0/s1

InChIKey

XPKKFTKCRVIDAG-WUCPZUCCSA-N

SMILES

S(C(CC(O)=O)C(O)=O)C[C@H](N)C(O)=O

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	Found in heart (BTO:0000562). See: MetaboLights Study

Roles Classification
Chemical Role(s):	Maillard reaction product Any thermal degradation product obtained as a result of a chemical reaction between an amino acid and a reducing sugar (Maillard reaction, a non-enzymatic browning procedure that usually imparts flavour to starch-based food products). Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

ChEBI Ontology
Outgoing	S-(2-succinyl)-L-cysteine (CHEBI:144907) has role human metabolite (CHEBI:77746) S-(2-succinyl)-L-cysteine (CHEBI:144907) has role Maillard reaction product (CHEBI:77523) S-(2-succinyl)-L-cysteine (CHEBI:144907) is a L-cysteine thioether (CHEBI:27532) S-(2-succinyl)-L-cysteine (CHEBI:144907) is a tricarboxylic acid (CHEBI:27093)

IUPAC Name

2-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid

Synonyms	Sources
2-[[(2R)-2-amino-2-carboxyethyl]thio]butanedioic acid	ChEBI
[[(2R)-2-amino-2-carboxyethyl]thio]succinic acid	ChEBI
S-(1,2-dicarboxyethyl)-L-cysteine	ChEBI
S-(2-succino)-L-cysteine	ChEBI

Last Modified

22 August 2023