L-ethionine (CHEBI:4886)

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ChEBI Name	L-ethionine

ChEBI ID	CHEBI:4886

ChEBI ASCII Name	L-ethionine

Definition	An S-ethylhomocysteine that has S-configuration at the chiral centre.

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

Supplier Information	ChemicalBook:CB9426830, eMolecules:537882, ZINC000001532201

Download	Molfile XML SDF

Wikipedia	License
Ethionine is a non-proteinogenic amino acid structurally related to methionine, with an ethyl group in place of the methyl group. Ethionine is an antimetabolite and methionine antagonist. It prevents amino acid incorporation into proteins and interferes with cellular use of adenosine triphosphate (ATP). Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen. Ethionine has been found to naturally occur in the edible pulp of the durian fruit, and postulated to be a biosynthetic precursor for ethanethiol and other strong odorants found in the fruit.
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Formula

C6H13NO2S

Net Charge

Average Mass

163.23800

Monoisotopic Mass

163.06670

InChI

InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1

InChIKey

GGLZPLKKBSSKCX-YFKPBYRVSA-N

SMILES

CCSCC[C@H](N)C(O)=O

Roles Classification
Chemical Role(s):	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):	antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization. carcinogenic agent A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.

ChEBI Ontology
Outgoing	L-ethionine (CHEBI:4886) has role antimetabolite (CHEBI:35221) L-ethionine (CHEBI:4886) has role carcinogenic agent (CHEBI:50903) L-ethionine (CHEBI:4886) is a S-ethylhomocysteine (CHEBI:68662) L-ethionine (CHEBI:4886) is enantiomer of D-ethionine (CHEBI:68663)

Incoming	DL-ethionine (CHEBI:68664) has part L-ethionine (CHEBI:4886) D-ethionine (CHEBI:68663) is enantiomer of L-ethionine (CHEBI:4886)

IUPAC Name

S-ethyl-L-homocysteine

Synonyms	Sources
(+)-ethionine	ChEBI
(+)-S-ethyl-L-homocysteine	ChEBI
(2S)-2-amino-4-(ethylsulfanyl)butanoic acid	IUPAC
Ethionine	KEGG COMPOUND
L-2-amino-4-(ethylthio)butanoic acid	ChEBI
L-2-amino-4-(ethylthio)butyric acid	ChemIDplus
L-S-ethylhomocysteine	ChemIDplus

Last Modified

28 July 2014