2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-1,2-oxazol-4-yl]propanoic acid

• ChemBase ID: 155082
• Molecular Formular: C11H19N2O7P
• Molecular Mass: 322.251521
• Monoisotopic Mass: 322.09298759
• SMILES: CC(C)(C)c1c(c(no1)OCP(=O)(O)O)CC(C(=O)O)N
• Canonical SMILES: OC(=O)C(Cc1c(noc1C(C)(C)C)OCP(=O)(O)O)N
• InChI: InChI=1S/C11H19N2O7P/c1-11(2,3)8-6(4-7(12)10(14)15)9(13-20-8)19-5-21(16,17)18/h7H,4-5,12H2,1-3H3,(H,14,15)(H2,16,17,18)
• InChIKey: AGSOOCUNMTYPSE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-1,2-oxazol-4-yl]propanoic acid
• IUPAC Traditional name: 2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-1,2-oxazol-4-yl]propanoic acid
• Synonyms: (R,S)-2-Amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl]propionic acid; ATPO

Database IDs

• CAS Number: 252930-37-3
• MDL Number: MFCD03452828
• PubChem SID: 24278239; 162249220
• PubChem CID: 4615193

CALCULATED PROPERTIES

• Acid pKa: 1.271353
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.9557002
• LogD (pH = 7.4): -4.5734916
• Log P: -1.0965358
• Molar Refractivity: 72.4551 cm^3
• Polarizability: 28.205881 Å^3
• Polar Surface Area: 156.11 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M NaOH: soluble7 mg/mL; DMSO: insoluble; H2O: insoluble
• Apperance: solid

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), GRIA3(2892), GRIA4(2893)rat ... Gria1(50592), Grik1(29559), Grin2a(24409)

Product Information

• Empirical Formula (Hill Notation): C11H19N2O7P

DETAILS

Sigma Aldrich - A7845

Biochem/physiol Actions
Competitive antagonist at GluR1-4 (AMPA-preferring) receptors.
Application
The phosphono amino acid, (RS)-2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl+ ++]propio nic acid (ATPO) is a competitive antagonist at GluR1-4 (AMPA-preferring) receptors. ATPO is a structural hybrid between the NMDA antagonist (RS)-2-amino-7-phosphonoheptanoic acid (AP7) and the AMPA/GluR5 agonist, (RS)-2-amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA).