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Chemistry

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Also known as: L-alanine, 56-41-7, (s)-alanine, H-ala-oh, L-alpha-alanine, (s)-2-aminopropanoic acid

Molecular Formula

C₃H₇NO₂

Molecular Weight

89.09 g/mol

InChI Key

QNAYBMKLOCPYGJ-REOHCLBHSA-N

FDA UNII

OF5P57N2ZX

A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.

Alanine is an Amino Acid.

1 2D Structure

L-Alanine API

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-aminopropanoic acid

2.1.2 InChI

InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1

2.1.3 InChI Key

QNAYBMKLOCPYGJ-REOHCLBHSA-N

2.1.4 Canonical SMILES

CC(C(=O)O)N

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

OF5P57N2ZX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Abufne

2. Alanine, L Isomer

3. Alanine, L-isomer

4. L Alanine

5. L-alanine

6. L-isomer Alanine

2.3.2 Depositor-Supplied Synonyms

1. L-alanine

2. 56-41-7

3. (s)-alanine

4. H-ala-oh

5. L-alpha-alanine

6. (s)-2-aminopropanoic Acid

7. L-2-aminopropionic Acid

8. (2s)-2-aminopropanoic Acid

9. L-(+)-alanine

10. L-2-aminopropanoic Acid

11. 2-aminopropionic Acid

12. Alpha-alanine

13. L-alpha-aminopropionic Acid

14. Alpha-aminopropionic Acid

15. L-2-aminopropionsaeure

16. Alaninum [latin]

17. (s)-(+)-alanine

18. L-s-aminopropionic Acid

19. (l)-alanine

20. Alanine (van)

21. (s)-2-aminopropionsaeure

22. Poly-l-alanine

23. 2-aminopropanoic Acid, L-

24. (s)-alpha-aminopropionsaeure

25. Alanine [usan:inn]

26. Alanina [dcit,spanish]

27. Alanine, L-

28. L-alanine, Homopolymer

29. L-a-aminopropionic Acid

30. L-alanin

31. (s)-2-aminopropionic Acid

32. Propanoic Acid, 2-amino-, (s)-

33. 25191-17-7

34. Hsdb 1801

35. Nsc 206315

36. L-alanine Homopolymer

37. Mfcd00064410

38. Of5p57n2zx

39. Chembl279597

40. Chebi:16977

41. Alanine (l-alanine)

42. Polyalanine

43. Alaninum

44. A-alanine

45. Poly-dl-alanine

46. L-a-alanine

47. 14c-l-alanine

48. A-aminopropionic Acid

49. (2s)-2-aminopropanoate

50. (c14)l-alanine

51. .alpha.-alanine

52. 18875-37-1

53. L-.alpha.-alanine

54. L-&alpha-alanine

55. Alanine (usp)

56. L-alanine (9ci)

57. 2-ammoniopropanoate

58. Propanoic Acid, 2-amino-

59. .alpha.-aminopropionic Acid

60. L-alanine, N-coco Alkyl Derivs.

61. L-alanine, Labeled With Carbon-14

62. Einecs 200-273-8

63. L-.alpha.-aminopropionic Acid

64. Unii-of5p57n2zx

65. Ritalanine

66. Racemic Alanine

67. A-aminopropionate

68. L-alanine, Labeled With Tritium

69. 3h-l-alanine

70. L-alanine Powder

71. Propanoic Acid, 2-amino-, (s)

72. [3h]alanine

73. L-a-aminopropionate

74. L-ala

75. [14c]alanine

76. [3h]-alanine

77. Alpha-aminopropanoate

78. Alpha-aminopropionate

79. L-2-aminopropanoate

80. L-2-aminopropionate

81. L-alanine,(s)

82. [14c]-alanine

83. L-alpha-aminopropionate

84. Tocris-0205

85. 2-ammoniopropanoic Acid

86. Ala-oh

87. Starbld0003382

88. L-alanine (jp17)

89. (s)-2-aminopropanoate

90. Alanine [vandf]

91. Alanine [hsdb]

92. Alanine [inci]

93. Alanine [usan]

94. Alanine [inn]

95. Alpha-aminopropanoic Acid

96. Alanine [ii]

97. Alanine [mi]

98. L-ala-2

99. L-alanine [fcc]

100. L-alanine [jan]

101. (s)-2-amino-propanoate

102. Alanine [who-dd]

103. L-alanine, >=99%

104. Bmse000028

105. Bmse000994

106. Ec 200-273-8

107. L-ch3ch(nh2)cooh

108. L-alanine [usp-rs]

109. Gtpl720

110. (s)-2-amino-propanoic Acid

111. 26336-61-8

112. (2s)-2-azanylpropanoic Acid

113. Alanine [ep Monograph]

114. Alanine, L- (7ci,8ci)

115. Gtpl4542

116. Gtpl4543

117. Alanine [usp Monograph]

118. Dtxsid20873899

119. L-alanine, >=98% (tlc)

120. L-alanine, 99%, Natural, Fg

121. F4f207ff-8ff8-4789-99a1-147ae0a36673

122. Hy-n0229

123. Str01663

124. Zinc4658553

125. L-alanine, >=99.0% (nt)

126. Ac-014

127. Bdbm50000099

128. S5631

129. (s)-2-aminopropanoic Acid;h-ala-oh

130. Akos010367904

131. Akos015840030

132. Ccg-266017

133. Cs-w020002

134. Db00160

135. L-alanine, Purum, >=98.0% (nt)

136. Serine Impurity A [ep Impurity]

137. Valine Impurity A [ep Impurity]

138. Ncgc00024494-01

139. 130380-93-7

140. 6898-94-8

141. Ac-24031

142. Bp-13281

143. L-alanine, Bioultra, >=99.5% (nt)

144. Db-029940

145. L-alanine, Saj Special Grade, >=99.0%

146. A0179

147. Am20100374

148. A15652

149. C00041

150. D00012

151. D84362

152. Lysine Acetate Impurity C [ep Impurity]

153. L-alanine, Cell Culture Reagent (h-l-ala-oh)

154. 064a410

155. A803529

156. Q218642

157. Sr-01000597687

158. J-015860

159. Q-201274

160. Sr-01000597687-3

161. L-alanine, Certified Reference Material, Tracecert(r)

162. Alanine, European Pharmacopoeia (ep) Reference Standard

163. F0001-2354

164. Z940713326

165. L-alanine, United States Pharmacopeia (usp) Reference Standard

166. L-alanine, Pharmaceutical Secondary Standard; Certified Reference Material

167. 115967-49-2

168. 77160-91-9

169. L-alanine, From Non-animal Source, Meets Ep, Usp Testing Specifications, Suitable For Cell Culture, >=98.5%

170. L-alanine, Pharmagrade, Ajinomoto, Ep, Jp, Usp, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₃H₇NO₂
Molecular Weight	89.09 g/mol
XLogP3	-3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	89.047678466 g/mol
Monoisotopic Mass	89.047678466 g/mol
Topological Polar Surface Area	63.3 Å²
Heavy Atom Count	6
Formal Charge	0
Complexity	61.8
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 Therapeutic Uses

Exptl Ther: ... Therapy of acute water diarrhea is reported in 94 male patients, aged 6-59 yr, of whom 49 were given a standard dextrose (glucose) based formula, to a total dose of 105-1719 ml/kg, and 45 were given the same soln with added alanine 90 uM/l, to a total dose of 60-1035 ml/kg. All patients were also given iv injections of replacement soln and oral tetracycline. The median stool output/kg body weight during the initial 24 hr of treatment until diarrhea stopped was reduced in those given the soln containing alanine as compared to controls. Intake of oral rehydration soln was reduced in those given alanine. Two patients given alanine soln and 18 given the standard treatment required unscheduled rapid iv replacement soln to correct signs of dehydration during oral therapy.

Patra FC et al; Br Med J 298: 1353-6 (1989)

DIETARY SUPPLEMENT

Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 29

Used in pharmaceutical preparations for injection or infusion; dietary supplement and flavor compounds in maillard reaction products; stimulant of glucagon secretion

Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA2 80-4

4.2 Drug Indication

Used for protein synthesis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Is an important source of energy for muscle tissue, the brain and central nervous system; strengthens the immune system by producing antibodies; helps in the metabolism of sugars and organic acids.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

ALANINE

5.2.2 FDA UNII

OF5P57N2ZX

5.2.3 Pharmacological Classes

Chemical Structure [CS] - Amino Acids

5.3 Mechanism of Action

L-Alanine is a non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and the central nervous system. BCAAs are used as a source of energy for muscle cells. During prolonged exercise, BCAAs are released from skeletal muscles and their carbon backbones are used as fuel, while their nitrogen portion is used to form another amino acid, Alanine. Alanine is then converted to Glucose by the liver. This form of energy production is called the Alanine-Glucose cycle, and it plays a major role in maintaining the body's blood sugar balance.

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