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

• ChemBase ID: 1822
• Molecular Formular: C7H10N2O4
• Molecular Mass: 186.1653
• Monoisotopic Mass: 186.06405681
• SMILES: Cc1c(C[C@H](N)C(=O)O)c(O)no1
• Canonical SMILES: OC(=O)[C@H](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)/t5-/m0/s1
• InChIKey: UUDAMDVQRQNNHZ-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoic acid
• IUPAC Traditional name: AMPA
• Synonyms: (S)-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid; (S)-AMPA; 1-Aminomethylphosphonic acid; AMPA

Database IDs

• CAS Number: 83643-88-3; 1066-51-9
• MDL Number: MFCD00672630
• PubChem SID: 24890421; 46505942; 160965277
• PubChem CID: 158397

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.49
• LOG S: -0.88
• Solubility (Water): 2.45e+01 g/l

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK1(2897)mouse ... Gria1(14799)rat ... Gria1(50592), Gria2(29627), Gria3(29628), Gria4(29629), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409), Grin2b(24410), Grm6(24419)

Product Information

• Purity: ≥98%

DETAILS

DrugBank - DB02057

• Drug Groups: experimental
• Description: AMPA is a specific agonist for the AMPA receptor.
• External Links: Wikipedia

Sigma Aldrich - A0326

Biochem/physiol Actions
Active enantiomer of (RS)-AMPA zwitterion. Potent agonist at the AMPA subclass of ionotropic glutamate receptors.