EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

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

Default Structure
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:
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 acid—amino-acid ligase inhibitor that inhibits the action of a glutamate—cysteine ligase (EC 6.3.2.2)
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
(2S)-2-amino-4-(butylsulfonimidoyl)butanoic acidChEBI
(2S)-2-amino-4-(S-butylsulfonimidoyl)butyric acidChEBI
L-BSOChEBI
L-buthionine (SR)-sulfoximineChemIDplus
L-buthionine-(S,R)-sulfoximineChemIDplus
L-buthionine-(S,R)-sulphoximineChemIDplus
Manual XrefsDatabases
106767ChemSpider
LSM-4915LINCS
Registry NumbersSources
Reaxys:2367136Reaxys
CAS:83730-53-4ChemIDplus
Citations