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    alpha Amino 3 hydroxy 5 methyl 4 isoxazolepropionic Acid

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: Ampa, 77521-29-0, (rs)-ampa, 74341-63-2, (r,s)-ampa, Ampa (pharmaceutical)
    Molecular Formula
    C7H10N2O4
    Molecular Weight
    186.17  g/mol
    InChI Key
    UUDAMDVQRQNNHZ-UHFFFAOYSA-N
    FDA UNII
    J090588E6X
    An IBOTENIC ACID homolog and glutamate agonist. The compound is the defining agonist for the AMPA subtype of glutamate receptors (RECEPTORS, AMPA). It has been used as a radionuclide imaging agent but is more commonly used as an experimental tool in cell biological studies.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-amino-3-(5-methyl-3-oxo-1,2-oxazol-4-yl)propanoic acid
    2.1.2 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)
    2.1.3 InChI Key
    UUDAMDVQRQNNHZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(C(=O)NO1)CC(C(=O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    J090588E6X
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Alpha Amino 3 Hydroxy 5 Methyl 4 Isoxazolepropionic Acid

    2. Ampa

    3. Ampa, (+-)-isomer

    4. Ampa, (r)-isomer

    5. Ampa, (r)-isomer, Monohydrobromide

    6. Ampa, (s)-isomer

    7. Ampa, (s)-isomer, Monohydrobromide

    2.3.2 Depositor-Supplied Synonyms

    1. Ampa

    2. 77521-29-0

    3. (rs)-ampa

    4. 74341-63-2

    5. (r,s)-ampa

    6. Ampa (pharmaceutical)

    7. Chembl13378

    8. Chebi:34018

    9. Alpha-amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic Acid

    10. J090588e6x

    11. L-ampa

    12. 2-amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)-propionic Acid

    13. (+/-)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    14. 2-amino-3-(5-methyl-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)propanoic Acid

    15. 2-amino-3-(5-methyl-3-oxo-2,3-dihydroisoxazol-4-yl)propanoic Acid

    16. (r,s)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    17. C7h10n2o4

    18. 4-isoxazolepropanoic Acid, A-amino-2,3-dihydro-5-methyl-3-oxo-

    19. Gnf-pf-2579

    20. Unii-j090588e6x

    21. 4-isoxazolepropanoic Acid, Alpha-amino-2,3-dihydro-5-methyl-3-oxo-

    22. Gamma-amino-3-hydroxy-5-methylisoxazole-4-propionic Acid

    23. Dl-alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic Acid

    24. (+-)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    25. Alpha-amino-2,3-dihydro-5-methyl-3-oxoisoxazolepropionic Acid

    26. D,l-alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic Acid

    27. Ampa [mi]

    28. [3h]ampa

    29. (r,s) Ampa

    30. Ampa, D,l-

    31. Lopac0_000581

    32. Schembl68799

    33. Gtpl4077

    34. Gtpl4131

    35. Dtxsid20868301

    36. 2-amino-3-(5-methyl-3-oxo-1,2-oxazol-4-yl)propanoic Acid

    37. Hms3266a13

    38. Hms3411a07

    39. Hms3675a07

    40. Zca34163

    41. 4-isoxazolepropanoic Acid, .alpha.-amino-2,3-dihydro-5-methyl-3-oxo-

    42. Bdbm50002370

    43. Mfcd00069214

    44. Pdsp1_001835

    45. Pdsp2_001818

    46. Akos017343917

    47. Ab02804

    48. Ccg-204670

    49. Hy-100815b

    50. Sb38931

    51. Sb38934

    52. Sdccgsbi-0050563.p002

    53. Ncgc00015458-04

    54. Ncgc00015458-05

    55. Ncgc00024481-03

    56. Da-02875

    57. Db-016844

    58. Cs-0021074

    59. Ft-0661849

    60. Ft-0762346

    61. Ft-0772278

    62. M01253

    63. L000026

    64. Sr-01000075447-3

    65. Q66370552

    66. ( )-a-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    67. (rs)-?-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    68. (rs)-a-amino-3-hydroxy-5-methylisoxazole-4-propanoic Acid

    69. 2-amino-3-(5-methyl-3-oxo-isoxazol-4-yl)propanoic Acid

    70. 2-ammonio-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoate

    71. (r,s)-

    72. A-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    73. (rs)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    74. 2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)-propionic Acid

    75. 2-amino-3-(5-methyl-3-oxo-1,2-oxazol-4-yl)propanoic Acid.

    76. (r,s)-a-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    77. (r,s)-alpha-amino-3-hydroxy-5-methyl-4-isooxazole-propionic Acid

    78. (rs)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)-propionicacid

    79. .alpha.-amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic Acid

    80. .gamma.-amino-3-hydroxy-5-methylisoxazole-4-propionic Acid

    81. 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propanoic Acid

    82. (+/-)-.alpha.-amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid

    83. 2-amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)-propionic Acid(dl-ampa)

    84. Dl-.alpha.-amino-3-hydroxy-5-methylisoxazole-4-propionic Acid

    85. 110592-37-5

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 186.17 g/mol
    Molecular Formula C7H10N2O4
    XLogP3-3.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count3
    Exact Mass186.06405680 g/mol
    Monoisotopic Mass186.06405680 g/mol
    Topological Polar Surface Area102 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity284
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Excitatory Amino Acid Agonists

    Drugs that bind to and activate excitatory amino acid receptors. (See all compounds classified as Excitatory Amino Acid Agonists.)