CHEBI:28490 - L-methionine sulfoximine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name L-methionine sulfoximine
ChEBI ID CHEBI:28490
ChEBI ASCII Name L-methionine sulfoximine
Definition A methionine sulfoximine in which the amino group has S-stereochemistry.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6273, CHEBI:21364
Supplier Information
Download Molfile XML SDF
Formula C5H12N2O3S
Net Charge 0
Average Mass 180.22646
Monoisotopic Mass 180.05686
InChI InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1
InChIKey SXTAYKAGBXMACB-DPVSGNNYSA-N
SMILES CS(=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): EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor
An EC 6.3.* (C1N bond-forming ligase) inhibitor that interferes with the action of glutamateammonia ligase (EC 6.3.1.2).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing L-methionine sulfoximine (CHEBI:28490) has role EC 6.3.1.2 (glutamate—ammonia ligase) inhibitor (CHEBI:24319)
L-methionine sulfoximine (CHEBI:28490) is a L-methionine derivative (CHEBI:84121)
L-methionine sulfoximine (CHEBI:28490) is a methionine sulfoximine (CHEBI:47833)
L-methionine sulfoximine (CHEBI:28490) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
L-methionine sulfoximine (CHEBI:28490) is tautomer of L-methionine sulfoximine zwitterion (CHEBI:87826)
Incoming (2S,5R)-methionine sulfoximine (CHEBI:47832) is a L-methionine sulfoximine (CHEBI:28490)
(2S,5S)-methionine sulfoximine (CHEBI:28227) is a L-methionine sulfoximine (CHEBI:28490)
L-methionine sulfoximine zwitterion (CHEBI:87826) is tautomer of L-methionine sulfoximine (CHEBI:28490)
IUPAC Name
(2S)-2-amino-4-(S-methylsulfonimidoyl)butanoic acid
Synonym Source
L-Methionine sulfoximine KEGG COMPOUND
Manual Xrefs Databases
C03510 KEGG COMPOUND
C03829 KEGG COMPOUND
CPD-9035 MetaCyc
HMDB0029430 HMDB
MSL PDBeChem
View more database links
Registry Numbers Types Sources
15985-39-4 CAS Registry Number ChemIDplus
6175446 Reaxys Registry Number Reaxys
6175446 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
18469098 PubMed citation Europe PMC
21629861 PubMed citation Europe PMC
21769496 PubMed citation Europe PMC
Last Modified
06 October 2015