2-amino-3-[3-(carboxymethoxy)-5-methyl-1,2-oxazol-4-yl]propanoic acid

• ChemBase ID: 153500
• Molecular Formular: C9H12N2O6
• Molecular Mass: 244.20138
• Monoisotopic Mass: 244.06953611
• SMILES: Cc1c(c(no1)OCC(=O)O)CC(C(=O)O)N
• Canonical SMILES: OC(=O)COc1noc(c1CC(C(=O)O)N)C
• InChI: InChI=1S/C9H12N2O6/c1-4-5(2-6(10)9(14)15)8(11-17-4)16-3-7(12)13/h6H,2-3,10H2,1H3,(H,12,13)(H,14,15)
• InChIKey: OKLRJJIBPYTEDZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-[3-(carboxymethoxy)-5-methyl-1,2-oxazol-4-yl]propanoic acid
• IUPAC Traditional name: 2-amino-3-[3-(carboxymethoxy)-5-methyl-1,2-oxazol-4-yl]propanoic acid
• Synonyms: AMOA; α-Amino-3-(carboxymethoxy)-5-methyl-4-isoxazolepropanoic Acid Hydrate (2:3); (r,s)-2-Amino-3-[3-(carboxymethoxy)-5-methyl-isoxazol-4 -yl]propionic Acid Sesquihydrate; (±)-2-Amino-3-[3-(carboxymethoxy)-5-methyl-isoxazol-4-yl]propionic acid; (±)-α-Amino-3-carbomethoxy-5-methylisoxazole-4-propanoic acid

Database IDs

• CAS Number: 131417-68-0; 209977-56-0
• MDL Number: MFCD00274019
• PubChem SID: 162247639
• PubChem CID: 125406

CALCULATED PROPERTIES

• Acid pKa: 1.6104454
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -4.6726613
• LogD (pH = 7.4): -6.0808473
• Log P: -2.8295426
• Molar Refractivity: 54.5693 cm^3
• Polarizability: 20.836342 Å^3
• Polar Surface Area: 135.88 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble2.5 mg/mL; Hot Methanol; Water
• Apperance: white crystalline; White Crystalline Solid
• Melting Point: 230°C dec.

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C9H12N2O6

DETAILS

Sigma Aldrich - A210

Biochem/physiol Actions
Non-NMDA glutamate receptor antagonist that protects against kainic acid-induced cell damage in vitro.

Toronto Research Chemicals - A603150

A selective inhibitor of [3H]-AMPA binding in rat brain membranes. AMOA shows little affinity for [3H]-kainate binding sites or other sites on the NMDA receptor-channel complex, as represented by binding of [3H]-CPP, [3H]-gly or [3H]-MK-801. AMOA also

REFERENCES

• Frandsden, A., et al.: J. Neurochem., 55, 1821 (1990)
• Krogsgaard-Larsen, P., et al.: J. Med. Chem., 34, 123 (1990)
• Berg, M., et al.: Acta Neuropathalogica, 81, 255 (1991)