2-amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid

• ChemBase ID: 75536
• Molecular Formular: C7H10N2O4
• Molecular Mass: 186.1653
• Monoisotopic Mass: 186.06405681
• SMILES: n1c(O)c(c(o1)C)CC(C(=O)O)N
• Canonical SMILES: OC(=O)C(Cc1c(C)onc1O)N
• InChI: InChI=1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)
• InChIKey: UUDAMDVQRQNNHZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid
• IUPAC Traditional name: AMPA; AMeP
• Synonyms: D,L-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic Acid; γ-Amino-3-hydroxy-5-methylisoxazole-4-propionic Αcid; (R,S)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid; (R,S)-2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid; AMPA; (±)-α-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID HYDRATE

Database IDs

• CAS Number: 74341-63-2
• MDL Number: MFCD00069214
• PubChem SID: 162040454
• PubChem CID: 1221

CALCULATED PROPERTIES

• Acid pKa: 1.5563054
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.4256098
• LogD (pH = 7.4): -3.4511206
• Log P: -2.3328915
• Molar Refractivity: 44.0024 cm^3
• Polarizability: 16.434475 Å^3
• Polar Surface Area: 109.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >200°C (dec.); 240-250(dec.)°C

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• Storage Warning: Irritant

Product Information

• Purity: >98%

DETAILS

MP Biomedicals - 02158828

Hydrate
Purity: >98%
Potent and selective glutamate agonist.

Apollo Scientific Ltd - OR1150T

A selective agonist of the exitatory neurotransmitter L-glutamic acid. AMPA does not interfere with binding sites for kainic acid in vitro.

Toronto Research Chemicals - A611500

A potent and selective agonist of the putative, excitatory neurotransmitter L-glutamic acid. AMPA does not interfere with binding sites for kainic acid in vitro, and AMPA- induced neuronal excitation is not significantly affected by NMDA antagonists.

REFERENCES

• Krogsgaard-Larson, P. et al., Nature , 282 : 64, (1980).
• Krogsgaard-Larsen, et al.: Nature, 284, 64 (1980)
• Honore, T., et al.: J. Neurochem., 38, 173 (1980)
• MacDonald, J.F., et al.: Science, 253, 1132 (1991)