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Asparagine, L-

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Chemistry

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Also known as: L-asparagine, 70-47-3, H-asn-oh, Altheine, (s)-asparagine, Aspartamic acid

Molecular Formula

C₄H₈N₂O₃

Molecular Weight

132.12 g/mol

InChI Key

DCXYFEDJOCDNAF-REOHCLBHSA-N

FDA UNII

5Z33R5TKO7

A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed)

1 2D Structure

Asparagine, L-

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2,4-diamino-4-oxobutanoic acid

2.1.2 InChI

InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1

2.1.3 InChI Key

DCXYFEDJOCDNAF-REOHCLBHSA-N

2.1.4 Canonical SMILES

C(C(C(=O)O)N)C(=O)N

2.1.5 Isomeric SMILES

C([C@@H](C(=O)O)N)C(=O)N

2.2 Other Identifiers

2.2.1 UNII

5Z33R5TKO7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. L-asparagine

2.3.2 Depositor-Supplied Synonyms

1. L-asparagine

2. 70-47-3

3. H-asn-oh

4. Altheine

5. (s)-asparagine

6. Aspartamic Acid

7. Agedoite

8. Asparamide

9. Asparagine Acid

10. Crystal Vi

11. (-)-asparagine

12. (s)-2,4-diamino-4-oxobutanoic Acid

13. 2-aminosuccinamic Acid

14. Alpha-aminosuccinamic Acid

15. Asparagine, L-

16. L-asparagine Anhydrous

17. L-aspartamine

18. L-2,4-diamino-4-oxobutanoic Acid

19. L-b-asparagine

20. Aspartic Acid Beta-amide

21. Asn

22. Asparagine (van)

23. Asparagine Anhydrous

24. (2s)-2-amino-3-carbamoylpropanoic Acid

25. L-beta-asparagine (van)

26. 2-aminosuccinamic Acid, L-

27. Butanoic Acid, 2,4-diamino-4-oxo-, (s)-

28. (2s)-2,4-diamino-4-oxobutanoic Acid

29. L-asparatamine

30. L-2-aminosuccinamic Acid

31. Mfcd00064401

32. Nsc 82391

33. 7ng0a2tuhq

34. L-aspartic Acid Beta-amide

35. 2,4-diamino-4-oxobutanoic Acid, (s)-

36. 5z33r5tko7

37. Chebi:17196

38. Nsc-82391

39. (s)-2-amino-3-carbamoylpropanoic Acid

40. L-beta-asparagine

41. (s)-2-aminosuccinic Acid 4-amide

42. L-asn

43. L-(+)-asparagine

44. L-.beta.-asparagine

45. Aspartic Acid B-amide

46. A-aminosuccinamic Acid

47. Aspargine

48. Aspartamate

49. L-asparagin

50. Hsdb 7425

51. A-aminosuccinamate

52. 2-aminosuccinamate

53. Einecs 200-735-9

54. Asn-oh

55. Alpha-aminosuccinamate

56. 4-imino-l-homoserine

57. Alpha Amminosuccinamate

58. L-asparagine (9ci)

59. Asparagine [mi]

60. Aspartic Acid Beta Amide

61. N-lauryl-n-methyltaurine

62. Asparagine [hsdb]

63. Asparagine [inci]

64. Asn Nh3+ Cooh

65. Alpha Amminosuccinamic Acid

66. Asparagine, L- (8ci)

67. Bmse000030

68. Bmse000912

69. Aspartic Acid .beta. Amide

70. L-asparagine [fcc]

71. L-asparagine (h-asn-oh)

72. Asparagine [who-dd]

73. H-asn-2-chlorotrityl Resin

74. L-alpha-aminosuccinamic Acid

75. Unii-5z33r5tko7

76. .alpha.-aminosuccinamic Acid

77. L-(+)-asparagine Anhydrous

78. Chembl58832

79. Asparagine (l) Hydrate

80. Nor Benzphetamine Hydrochloride

81. Gtpl4533

82. P-aminosalicylicacidmagnesiumsalt

83. Schembl3126352

84. L-2,4-diamino-4-oxobutanoate

85. Us9138393, L-asparigine

86. Us9144538, L-asparigine

87. Dtxsid10883220

88. Bdbm181137

89. Pharmakon1600-01301002

90. (s)-2,4-diamino-4-oxobutanoate

91. L-asparagine, >=98% (hplc)

92. Hy-n0667

93. Str07164

94. Zinc1532556

95. B2,4-(s)-diamino-4-oxo-utanoate

96. Nsc760099

97. S5571

98. Asparagine Anhydrous [usp-rs]

99. Akos006239067

100. Ac-4657

101. Am81554

102. Ccg-266117

103. Db00174

104. Nsc-760099

105. B2,4-(s)-diamino-4-oxo-utanoic Acid

106. Ncgc00344576-01

107. Bp-23453

108. A0542

109. Cs-0009702

110. L-asparagine, Vetec(tm) Reagent Grade, 98%

111. A-9031

112. C00152

113. M02998

114. 064a401

115. A937078

116. Q29519883

117. F1905-7151

118. Z1270387291

119. 3c28f6a9-e581-4255-accf-f75597ab288f

120. L-asparagine, Certified Reference Material, Tracecert(r)

121. Asparagine Anhydrous, United States Pharmacopeia (usp) Reference Standard

122. L-asparagine, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₄H₈N₂O₃
Molecular Weight	132.12 g/mol
XLogP3	-3.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	132.05349212 g/mol
Monoisotopic Mass	132.05349212 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	134
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used for nutritional supplementation, also for treating dietary shortage or imbalance.

5 Pharmacology and Biochemistry

5.1 Pharmacology

A non-essential amino acid. Asparagine is critical for the production of the body's proteins, enzymes and muscle tissue. Supplements of this amino acid are claimed to balance nervous system function.

5.2 Mechanism of Action

Asparagine, a non-essential amino acid is important in the metabolism of toxic ammonia in the body through the action of asparagine synthase which attaches ammonia to aspartic acid in an amidation reaction. Asparagine is also used as a structural component in many proteins.

Iron absorption in rats was evaluated with concurrent administration of each of 10 amino acid solutions and ascorbic acid. Asparagine, glycine, serine and ascorbic acid caused a statistically significant increase in iron absorption, with greatest effects for asparagine and glycine. No correlations were found between absorption increases and stability constants of the amino acid-iron complex.

PMID:6491942 Christensen JM et al; J Pharm Sci 73: 1245-1248 (1984)

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