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ACTIVE PHARMA INGREDIENTS

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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

Alpha-Amino-3-Hydroxy-5-Methyl-4-Isoxazolepropionic Acid

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

Alpha-Amino-3-Hydroxy-5-Methyl-4-Isoxazolepropionic Acid

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 Formula	C₇H₁₀N₂O₄
Molecular Weight	186.17 g/mol
XLogP3	-3.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	186.06405680 g/mol
Monoisotopic Mass	186.06405680 g/mol
Topological Polar Surface Area	102 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	284
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1