2-amino-3-(4-bromo-3-oxo-2,3-dihydro-1,2-oxazol-5-yl)propanoic acid

• ChemBase ID: 105637
• Molecular Formular: C6H7BrN2O4
• Molecular Mass: 251.03478
• Monoisotopic Mass: 249.95891871
• SMILES: NC(Cc1c(Br)c(=O)[nH]o1)C(=O)O
• Canonical SMILES: OC(=O)C(Cc1o[nH]c(=O)c1Br)N
• InChI: InChI=1S/C6H7BrN2O4/c7-4-3(13-9-5(4)10)1-2(8)6(11)12/h2H,1,8H2,(H,9,10)(H,11,12)
• InChIKey: JRTOQOAGTSUNHA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(4-bromo-3-oxo-2,3-dihydro-1,2-oxazol-5-yl)propanoic acid
• IUPAC Traditional name: 2-amino-3-(4-bromo-3-oxo-2H-1,2-oxazol-5-yl)propanoic acid
• Synonyms: (±)-α-Amino-4-bromo-2,3-dihydro-3-oxo-5-isoxazolepropanoic acid; (±)-4-Bromohomoibotenic acid; (RS)-4-BROMOHOMOIBOTENIC ACID

Database IDs

• CAS Number: 71366-32-0
• MDL Number: MFCD00153776
• PubChem SID: 162092829
• PubChem CID: 2733518

CALCULATED PROPERTIES

• Acid pKa: 0.89777017
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.814706
• LogD (pH = 7.4): -3.9422843
• Log P: -3.0212364
• Molar Refractivity: 46.4018 cm^3
• Polarizability: 17.992302 Å^3
• Polar Surface Area: 101.65 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: moderately soluble
• Apperance: white solid

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301 + H311 + H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Product Information

• Empirical Formula (Hill Notation): C6H7BrN2O4

DETAILS

MP Biomedicals - 02193617

A potent AMPA receptor agonist. Unlike AMPA, it also shows affinity for CaCl₂-dependent L-glutamate binding sites.

Sigma Aldrich - B141

Biochem/physiol Actions
Potent AMPA receptor agonist

REFERENCES

• Chung, et al., J. Neurochem., 63: 133, (1994).