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NCGC00024507-01

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13EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: L-serine, 56-45-1, (s)-2-amino-3-hydroxypropanoic acid, (s)-serine, H-ser-oh, Beta-hydroxyalanine

Molecular Formula

C₃H₇NO₃

Molecular Weight

105.09 g/mol

InChI Key

MTCFGRXMJLQNBG-REOHCLBHSA-N

FDA UNII

452VLY9402

A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.

1 2D Structure

Serine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-amino-3-hydroxypropanoic acid

2.1.2 InChI

InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1

2.1.3 InChI Key

MTCFGRXMJLQNBG-REOHCLBHSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

452VLY9402

2.3 Synonyms

2.3.1 MeSH Synonyms

1. L Serine

2. L-serine

2.3.2 Depositor-Supplied Synonyms

1. L-serine

2. 56-45-1

3. (s)-2-amino-3-hydroxypropanoic Acid

4. (s)-serine

5. H-ser-oh

6. Beta-hydroxyalanine

7. L-ser

8. L-(-)-serine

9. (2s)-2-amino-3-hydroxypropanoic Acid

10. L-serin

11. Serine, L-

12. Serinum [latin]

13. Serina [spanish]

14. Serine (van)

15. L-3-hydroxy-alanine

16. (-)-serine

17. Beta-hydroxy-l-alanine

18. L-2-amino-3-hydroxypropionic Acid

19. Serine [usan:inn]

20. Ser (iupac Abbrev)

21. Alpha-amino-beta-hydroxypropionic Acid

22. 2-amino-3-hydroxypropionic Acid

23. L-3-hydroxy-2-aminopropionic Acid

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

25. Hsdb 680

26. (s)-(-)-serine

27. 2-amino-3-hydroxypropanoic Acid, (s)-

28. Propanoic Acid, 2-amino-3-hydroxy-, (s)-

29. Mfcd00064224

30. Brn 1721404

31. Ser

32. Chebi:17115

33. (s)-alpha-amino-beta-hydroxypropionic Acid

34. (2s)-2-amino-3-hydroxy-propanoic Acid

35. 6898-95-9

36. Serine (l-serine)

37. 452vly9402

38. Nsc-118365

39. (s)-2-amino-3-hydroxy-propanoic Acid

40. (s)-(+)-2-amino-3-hydroxypropionic Acid

41. Serinum

42. Serene

43. Serina

44. .beta.-hydroxyalanine

45. B-hydroxy-l-alanine

46. Einecs 200-274-3

47. Nsc 118365

48. Rac-serine

49. Racemic Serine

50. 2-amino-3-hydroxypropanoate

51. Unii-452vly9402

52. 3h-l-serine

53. L-serine;

54. H-ser

55. (s)-a-amino-b-hydroxypropionic Acid

56. Serine (usp)

57. 3-hydroxy-l-alanine

58. L-serine,(s)

59. Tocris-0226

60. Tocris-0227

61. L-serine (jp17)

62. Serine [vandf]

63. Serine [hsdb]

64. Serine [inci]

65. Serine [usan]

66. L-alanine, 3-hydroxy-

67. Serine [inn]

68. Serine [who-dd]

69. Lopac-s-4250

70. Serine [ii]

71. Serine [mi]

72. L-serine [fcc]

73. L-serine [jan]

74. Serine [mart.]

75. (l)-serine

76. Bmse000048

77. Bmse000809

78. Bmse000867

79. Bmse000885

80. Epitope Id:150900

81. Ec 200-274-3

82. Schembl1775

83. L-serine [usp-rs]

84. Gtpl726

85. 4-04-00-03118 (beilstein Handbook Reference)

86. Chembl11298

87. Serine [ep Monograph]

88. L-3-hydroxy-2-aminopropionate

89. Serine [usp Monograph]

90. (s)-a-amino-b-hydroxypropionate

91. (s)-b-amino-3-hydroxypropionate

92. Dtxsid60883230

93. (s)-2-amino-3-hydroxypropanoate

94. Dtxsid301031857

95. Pharmakon1600-01301010

96. Zinc895034

97. L-serine - Cas 56-45-1

98. (s)-2-amino-3-hydroxy-propanoate

99. Act08366

100. Hy-n0650

101. L-2-amino-3-hydroxypropanoic Acid

102. L-serine, Vetec(tm), 98.5%

103. Str02557

104. (s)-beta-amino-3-hydroxypropionate

105. Fmoc-(2-aminomethylphenyl)aceticacid

106. L-2-amino-3-hydroxy-propanoic Acid

107. L-serine, >=99.0% (nt)

108. Bdbm50357212

109. Nsc760115

110. (s)-b-amino-3-hydroxypropionic Acid

111. Akos015854115

112. (s)-alpha-amino-beta-hydroxypropionate

113. Ac-1190

114. Ccg-266038

115. Cs-w020136

116. Db00133

117. Nsc-760115

118. (s)-beta-amino-3-hydroxypropionic Acid

119. L-serine, Tested According To Ph.eur.

120. (2s)-2-amino-3-hydroxypropanoic Acid.

121. Ncgc00015952-01

122. Ncgc00024507-01

123. Ncgc00024507-02

124. Bp-13282

125. L-serine, Bioultra, >=99.5% (nt)

126. Sy002847

127. 2-amino-3-hydroxypropanoic Acid-, (s)-

128. Db-029983

129. Propanoic Acid, 2-amino-3-hydroxy-, (s)

130. Am20100375

131. S0035

132. S9353

133. L-serine, Reagentplus(r), >=99% (hplc)

134. L-serine, Vetec(tm) Reagent Grade, >=99%

135. A20660

136. C00065

137. D00016

138. L-serine, Cell Culture Reagent (h-l-ser-oh)

139. 064s224

140. Q183290

141. Sr-01000597708

142. .alpha.-amino-.beta.-hydroxypropionic Acid-, (s)-

143. Sr-01000597708-1

144. L-serine, Certified Reference Material, Tracecert(r)

145. F1905-7047

146. Serine, European Pharmacopoeia (ep) Reference Standard

147. Z1270387256

148. 3ab40d3a-043a-488f-8361-d1bf309f842c

149. L-serine, United States Pharmacopeia (usp) Reference Standard

150. (s)-2-amino-3-hydroxypropanoicacid;2-amion-3-hydroxypropionicacid

151. L-serine, Pharmaceutical Secondary Standard; Certified Reference Material

152. L-serine, From Non-animal Source, Meets Ep, Usp Testing Specifications, Suitable For Cell Culture, 98.5-101.0%

153. L-serine, Pharmagrade, Ajinomoto, Ep, Usp, Jp, Manufactured Under Appropriate Controls For Use In Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

154. L-serine, Pharmagrade, Ajinomoto, Ep, 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	C₃H₇NO₃
Molecular Weight	105.09 g/mol
XLogP3	-3.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	105.042593085 g/mol
Monoisotopic Mass	105.042593085 g/mol
Topological Polar Surface Area	83.6 Å²
Heavy Atom Count	7
Formal Charge	0
Complexity	72.6
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 as a natural moisturizing agent in some cosmetics and skin care products.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Serine is classified as a nutritionally non-essential amino acid. Serine is critical for the production of the body's proteins, enzymes and muscle tissue. Serine is needed for the proper metabolism of fats and fatty acids. It also helps in the production of antibodies. Serine is used as a natural moisturizing agent in some cosmetics and skin care products. The main source of essential amino acids is from the diet, non-essential amino acids are normally synthesize by humans and other mammals from common intermediates.

5.2 Absorption, Distribution and Excretion

IN PT AGE 2-9 YR, SERINE PRESENT IN ACID MUCOPOLYSACCHARIDES. EXCESSIVE ACCUMULATION & EXCRETION IN URINE OF MUCOPOLYSACCHARIDES MAY BE RELATED TO ABNORMAL BONDING BETWEEN MUCOPOLYSACCHARIDES & PROTEIN.

RENNERT OM, DEKABAN AS; AMINO ACID METAB IN PT WITH HURLER'S SYNDROME; METAB, CLIN EXP; 15(5) 429 (1966)

IN PT AGE 2-9 YR, URINARY SERINE EXCRETION INCR FROM 0.059-0.162 UMOL/24 HR & PLASMA SERINE LEVELS INCR FROM 0.102-0.158 UMOL/ML.

RENNERT OM, DEKABAN AS; AMINO ACID METAB IN PT WITH HURLER'S SYNDROME; METAB, CLIN EXP; 15(5) 429 (1966)

IN PT AGE 2-9 YR, SERINE IS PROBABLY NOT ESTERIFIED THROUGH ITS BETA-HYDROXYL GROUP TO ACID MUCOPOLYSACCHARIDES BUT IS LINKED BY CARBOXYL GROUP.

RENNERT OM, DEKABAN AS; AMINO ACID METAB IN PT WITH HURLER'S SYNDROME; METAB, CLIN EXP; 15(5) 429 (1966)

DETERMINATION OF SERINE LEVELS IN 13 REGIONS OF THE RAT CEREBRAL CORTEX FAILED TO SHOW ANY MARKED DIFFERENCES IN THE AMINO ACID CONTENTS OF CORTEX AREAS OF DIVERSE FUNCTIONS.

ELEKES I ET AL; DRUGS, BIOCHEM METAB, SCI MATER PAP COLLOQ 37 (1981)

5.3 Mechanism of Action

L-Serine plays a role in cell growth and development (cellular proliferation). The conversion of L-serine to glycine by serine hydroxymethyltransferase results in the formation of the one-carbon units necessary for the synthesis of the purine bases, adenine and guanine. These bases when linked to the phosphate ester of pentose sugars are essential components of DNA and RNA and the end products of energy producing metabolic pathways, ATP and GTP. In addition, L-serine conversion to glycine via this same enzyme provides the one-carbon units necessary for production of the pyrimidine nucleotide, deoxythymidine monophosphate, also an essential component of DNA.

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