L-buthionine-(S,R)-sulfoximine (CHEBI:94288)

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ChEBI Name	L-buthionine-(S,R)-sulfoximine

ChEBI ID	CHEBI:94288

ChEBI ASCII Name	L-buthionine-(S,R)-sulfoximine

Definition	A 2-amino-4-(S-butylsulfonimidoyl)butanoic acid which has S-configuration. It is a inhibitor of γ-glutamylcysteine synthetase and glutathione (GSH) biosynthesis and is capable of enhancing the apoptotic effects of several chemotherapeutic agents.

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

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Formula

C8H18N2O3S

Net Charge

Average Mass

222.300

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)/t7-,14?/m0/s1

InChIKey

KJQFBVYMGADDTQ-CVSPRKDYSA-N

SMILES

CCCCS(=N)(=O)CC[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):	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. 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)

ChEBI Ontology
Outgoing	L-buthionine-(S,R)-sulfoximine (CHEBI:94288) has role EC 6.3.2.2 (glutamate—cysteine ligase) inhibitor (CHEBI:75599) L-buthionine-(S,R)-sulfoximine (CHEBI:94288) has role ferroptosis inducer (CHEBI:173085) L-buthionine-(S,R)-sulfoximine (CHEBI:94288) is a 2-amino-4-(S-butylsulfonimidoyl)butanoic acid (CHEBI:176510)

Incoming	S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714) has part L-buthionine-(S,R)-sulfoximine (CHEBI:94288)

IUPAC Name

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

Synonyms	Sources
(2S)-2-amino-4-(butylsulfonimidoyl)butanoic acid	ChEBI
(2S)-2-amino-4-(S-butylsulfonimidoyl)butyric acid	ChEBI
L-BSO	ChEBI
L-buthionine (SR)-sulfoximine	ChemIDplus
L-buthionine sulfoximine	ChemIDplus
L-buthionine-(S,R)-sulfoximine	ChemIDplus
L-buthionine-(S,R)-sulphoximine	ChemIDplus

Last Modified

14 June 2021