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

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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
Supplier Information
Download Molfile XML SDF
Formula C8H18N2O3S
Net Charge 0
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
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 6.3.2.2 (glutamate--cysteine ligase) inhibitor
An acidamino-acid ligase inhibitor that inhibits the action of a glutamatecysteine ligase (EC 6.3.2.2)
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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) is a homocysteines (CHEBI:24610)
S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714) is a non-proteinogenic α-amino acid (CHEBI:83925)
S-butyl-DL-homocysteine (S,R)-sulfoximine (CHEBI:28714) is a sulfoximide (CHEBI:38084)
IUPAC Name
2-amino-4-(S-butylsulfonimidoyl)butanoic acid
Synonyms Sources
2-amino-4-(S-butylsulfonimidoyl)butanoic acid ChEBI
2-amino-4-(S-butylsulfonimidoyl)butyric acid ChEBI
Buthionine sulfoximine KEGG COMPOUND
buthionine sulfoximine ChemIDplus
DL-butathionine-(S,R)-sulfoximine ChEBI
S-Butyl-DL-homocysteine-[S,R]-sulfoximine KEGG COMPOUND
Manual Xrefs Databases
C04543 KEGG COMPOUND
LSM-36606 LINCS
View more database links
Registry Numbers Types Sources
236716 Beilstein Registry Number Beilstein
5072-26-4 CAS Registry Number KEGG COMPOUND
5072-26-4 CAS Registry Number ChemIDplus
Last Modified
26 February 2016
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.