(2R)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid

• ChemBase ID: 177309
• Molecular Formular: C5H7N3O5
• Molecular Mass: 189.12618
• Monoisotopic Mass: 189.03857034
• SMILES: c1(=O)[nH]c(=O)on1C[C@@H](N)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](Cn1oc(=O)[nH]c1=O)N
• InChI: InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m1/s1
• InChIKey: ASNFTDCKZKHJSW-UWTATZPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
• Synonyms: L-(+)-α-Amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoic Acid; L-Quisqualic Acid; (αS)-α-Amino-3,5-dioxo-1,2,4-Oxadiazolidine-2-propanoic Acid; (+)-Quisqualic Acid

Database IDs

• CAS Number: 52809-07-1
• PubChem SID: 164233219
• PubChem CID: 6603978

CALCULATED PROPERTIES

• Acid pKa: 1.455519
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.7313128
• LogD (pH = 7.4): -4.676513
• Log P: -3.6865237
• Molar Refractivity: 36.5118 cm^3
• Polarizability: 14.785922 Å^3
• Polar Surface Area: 121.96 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Brown Solid
• Melting Point: 185-187°C dec.

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Store in freezer at -20°C

DETAILS

Toronto Research Chemicals - Q825000

An amino acid that is able to function as an agonist at multiple excitatory amino acid receptor substrates in the central nervous system. It also has high affinity for the kainate, AMPA and the metabotropic receptors. Inhibits the Ca2+/Cl-dependent glu

REFERENCES

• Honore, T., et al.: J. Neurochem., 38, 173 (1982)
• Schoepp, D., et al.: J. Neurochem., 50, 1605 (1982)
• Recasens, M., et al.: Neurochem. Int., 13, 463 (1982)
• Subasinghe, N., et al.: J. Med. Chem., 35, 4602 (1992)