2-amino-4-(S-butylsulfonimidoyl)butanoic acid
Basic information
- CAS
5072-26-4- Standard SMILES
CCCCS(=N)(=O)CCC(N)C(=O)O- InChIKey
KJQFBVYMGADDTQ-UHFFFAOYSA-N- Molecular formula
- C8H18N2O3S
- Average molar mass
- 222.31 g/mol
- Monoisotopic mass
- 222.10381361
Overview
S-butyl-DL-homocysteine (S,R)-sulfoximine is a sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl. It has a role as a ferroptosis inducer and an EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor. It contains a D-buthionine-(S,R)-sulfoximine and a L-buthionine-(S,R)-sulfoximine.
Names & identifiers
- Preferred name
- 2-amino-4-(S-butylsulfonimidoyl)butanoic acid
- IUPAC
- 2-amino-4-(butylsulfonimidoyl)butanoic acid
- English name
- DL-Buthionine-[s,r]-sulfoximine
- Molecular formula
- C8H18N2O3S
- Molecular weight
- 222.31
Names & synonyms
2-Amino-4-(S-butylsulfonimidoyl)butanoic acidCHEBI:176510RefChem:10621805072-26-4BUTHIONINE SULFOXIMINEButionine sulfoximine2-Amino-4-(butylsulfonimidoyl)butanoic acidButhionine sulfoxamineD,L-Buthionine-(S,R)-sulfoximineButhionine sulphoximineButanoic acid, 2-amino-4-(S-butylsulfonimidoyl)-Buthionine-S,R-sulfoximine
Show more names
buthioninesulfoximineNSC 381100butioninesulfoximinebuthioninesulfoxaminebuthioninesulphoximineDL-BUTHIONINE-SULFOXIMINEDL-BUTHIONINE (S,R)-SULPHOXIMEDL-BUTHIONINE (R,S)-SULFOXIMINEDL-Buthionine-[s,r]-sulfoximineDL-Buthionine-sulfoximine
dl-buthionine (s,r)-sulfoximineNSC-3811002-azaniumyl-4-(butylsulfonimidoyl)butanoateDL-Buthionine-S,R-sulfoximineLW4108Q0BV2-amino-4-(S-butylsulfonimidoyl)butyric acidDL-butathionine-(S,R)-sulfoximineMFCD00070309
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 284
Physicochemical properties
- Melting point
- 215 °C · 215 °C (dec.)(lit.)
- Boiling point
- 382.3 · 382.3±52.0 °C(Predicted)
- Density
- 1.29 · 1.29±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL, clear, colorless
- form
- Fluffy Powder
- color
- White
- biological source
- synthetic (organic)
- Water Solubility
- 50 mg/mL, · water: 50mg/mL, clear to very slightly hazy, colorless to yellow
- Merck
- 13 · 13,1520
- BRN
- 2367136 · 2367136
- 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
- CAS DataBase Reference
- 5072 · 5072-26-4(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- EK7713435
- hs_code
- 29309090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesA potent and specific inhibitor of alpha-glutamyl cysteine synthetase
UsesDL-Buthionine-sulfoximine is suitable for use to:examine whether the inhibition of glutathione by BSO enhances the apoptotic effect of estrogen on antihormone-resistant human breast cancer cellsinvestigate the effect of BSO on development of bovine embryosinhibit GSH in several studiesinvestigate the effect of GSH synthesis on oocyte maturationIt may be used to inhibit GSH and evaluate the hepatotoxicity and nephrotoxicity of natural food colorants in the absence of GSH
UsesBiological tool for depletion of glutathione.
General DescriptionDL-buthionine-SR-sulfoximine (BSO) is an amino acid analogue, which acts as an inhibitor of γ-glutamylcysteine synthetase. BSO increases the sensitivity of Trypanosoma cruzi to antiparasitic drugs, such as nifurtimox or benznidazole.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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