2-amino-4-[butyl(imino)oxo-$l^{6}-sulfanyl]butanoic acid

• ChemBase ID: 92417
• Molecular Formular: C8H18N2O3S
• Molecular Mass: 222.30512
• Monoisotopic Mass: 222.10381345
• SMILES: S(=N)(=O)(CCCC)CCC(C(=O)O)N
• Canonical SMILES: CCCCS(=O)(=N)CCC(C(=O)O)N
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-[butyl(imino)oxo-$l^{6}-sulfanyl]butanoic acid; 2-amino-4-[butyl(imino)oxo-λ^6-sulfanyl]butanoic acid
• IUPAC Traditional name: buthionine sulfoximine; 2-amino-4-[butyl(imino)oxo-λ^6-sulfanyl]butanoic acid
• Synonyms: DL-Buthionine-sulfoximine; 2-Amino-4-(S-butylsulfonimidoyl)butanoic Acid; S-(3-Amino-3-carboxypropyl)-S-butylsulfoximine; Buthionine Sulfoximine; NSC 381100; D,L-Buthionine-(S,R)-sulfoximine; 2-Amino-4-(S-butylsulphonimidoyl)butanoic acid; S-(3-Amino-3-carboxypropyl)-S-butylsulphoximine; D,L-Buthionine (S,R)-sulphoximine; β-Glutamylcysteine; 2-Amino-4-(S-butylsulfoninidoyl)butanoic acid; S-(n-butyl)homo cysteine sulfoximine; DL-BUTHIONINE-S,R-SULFOXIMINE; Buthionine sulfoximine; DL-Buthionine-(S,R)-sulfoximine; DL-丁硫氨酸-(S,R)-亚砜亚胺

Database IDs

• CAS Number: 5072-26-4
• MDL Number: MFCD00070309
• Beilstein Number: 2367136
• PubChem SID: 162079115; 24851509
• PubChem CID: 21157
• CHEBI ID: 28714
• Chemspider ID: 19896
• MeSH Name: Buthionine+sulfoximine
• Wikipedia Title: Buthionine_sulfoximine

CALCULATED PROPERTIES

• Acid pKa: 2.181531
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.9740744
• LogD (pH = 7.4): -2.9773746
• Log P: -2.9709322
• Molar Refractivity: 54.0074 cm^3
• Polarizability: 22.389696 Å^3
• Polar Surface Area: 104.24 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear to almost clear, colorless; Soluble in Water (62 mg in 1 mL)
• Apperance: White Crystalline Solid
• Melting Point: 214-215°C; 214-215°C; 215 °C (dec.)(lit.); 215°C; 225-227°C
• Boiling Point: 382.3°C
• Density: 1.29 g/mL

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• Storage Warning: Irritant/Store at -20°C
• RTECS: EK7713435
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:22
• Safety Statements: 26-36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (TLC); 98%
• Linear Formula: CH3(CH2)3S(O)(=NH)CH2CH2CH(NH2)CO2H
• Empirical Formula (Hill Notation): C8H18N2O3S

DETAILS

MP Biomedicals - 02150533

γ-Glutamylcysteine synthetase inhibitor

Apollo Scientific Ltd - OR9025T

Racemic mixture. A potent & specific inhibitor of g-glutamylcysteine synthetase.

Sigma Aldrich - 19176

Other Notes
Depletes glutathionine in isolated cells2,3
Biochem/physiol Actions
Augments the antiproliferative action of reactive oxygen species (e.g., hydrogen peroxide), and agents that indirectly cause accumulation of reactive oxygen species (e.g., 2-methoxyestradiol, which increases intracellular superoxide anion).1

Toronto Research Chemicals - B690250

A potent and specific inhibitor of alpha-glutamyl cysteine synthetase.

REFERENCES

• Griffith, O.W., et al.: J. Biol. Chem., 254, 16, 7558 (1979)
• Griffith, O.W., et al.: Methods Enzymol., 77, 59 (1979)