S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714)

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ChEBI Name	S-butyl-DL-homocysteine (S,R)-sulfoximine

ChEBI ID	CHEBI:28714

ChEBI ASCII Name	S-butyl-DL-homocysteine (S,R)-sulfoximine

Definition	A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.

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

Secondary ChEBI IDs	CHEBI:8953, CHEBI:22039

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Formula

C8H18N2O3S

Net Charge

Average Mass

222.30500

Monoisotopic Mass

222.10381

InChI

InChI=1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)

InChIKey

KJQFBVYMGADDTQ-UHFFFAOYSA-N

SMILES

CCCCS(=N)(=O)CCC(N)C(O)=O

Roles Classification
Biological Role(s):	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor An acidamino-acid ligase inhibitor that inhibits the action of a glutamatecysteine ligase (EC 6.3.2.2) ferroptosis inducer Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.

ChEBI Ontology
Outgoing	S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714) has part D-buthionine-(S,R)-sulfoximine (CHEBI:176509) S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714) has part L-buthionine-(S,R)-sulfoximine (CHEBI:94288) S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714) has role EC 6.3.2.2 (glutamate—cysteine ligase) inhibitor (CHEBI:75599) S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714) has role ferroptosis inducer (CHEBI:173085) S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714) is a diastereoisomeric mixture (CHEBI:60915)

IUPAC Name

(2RS)-2-amino-4-(S-butylsulfonimidoyl)butanoic acid

Synonyms	Sources
(2RS)-2-amino-4-(S-butylsulfonimidoyl)butanoic acid	ChEBI
(2RS)-2-amino-4-(S-butylsulfonimidoyl)butyric acid	ChEBI
Buthionine sulfoximine	KEGG COMPOUND
buthionine sulfoximine	ChemIDplus
buthionine sulphoximine	ChemIDplus
DL-butathionine-(S,R)-sulfoximine	ChEBI
DL-buthionine sulfoximine	ChEBI
S-butyl-DL-homocysteine-[S,R]-sulfoximine	KEGG COMPOUND

Last Modified

14 June 2021

General Comment
2011-03-18	A synthetic amino acid, S-butyl-DL-homocysteine (S,R)-sulfoximine is an inhibitor of glutamate—cysteine ligase (γ-glutamylcysteine synthetase, EC 6.3.2.2) and is used as a radiation-protective and radiation-sensitising agent.