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

ChEBI IDCHEBI:94288
ChEBI NameL-buthionine-(S,R)-sulfoximine
Stars
ASCII NameL-buthionine-(S,R)-sulfoximine
DefinitionA 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.
Last Modified14 June 2021
DownloadsMolfile
FormulaC8H18N2O3S
Net Charge0
Average Mass222.310
Monoisotopic Mass222.10381
SMILESCCCCS(=N)(=O)CC[C@H](N)C(=O)O
InChIInChI=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
InChIKeyKJQFBVYMGADDTQ-CVSPRKDYSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor  An acid—amino-acid ligase inhibitor that inhibits the action of a glutamate—cysteine 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 Relation(s)
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 Relation(s)
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  Source
L-buthionine sulfoximineChemIDplus
L-buthionine (SR)-sulfoximineChemIDplus
L-buthionine-(S,R)-sulfoximineChemIDplus
L-buthionine-(S,R)-sulphoximineChemIDplus
(2S)-2-amino-4-(S-butylsulfonimidoyl)butyric acidChEBI
L-BSOChEBI
Manual XrefsDatabases
LSM-4915LINCS
106767ChemSpider
Registry NumbersSources
Reaxys:2367136Reaxys
CAS:83730-53-4ChemIDplus
Citations