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Chemistry

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Also known as: 131-48-6, N-acetyl-beta-neuraminic acid, N-acetylneuramic acid, N-acetyl-d-neuraminic acid, Lactaminic acid, Nana
Molecular Formula
C11H19NO9
Molecular Weight
309.27  g/mol
InChI Key
SQVRNKJHWKZAKO-PFQGKNLYSA-N
FDA UNII
TIP79W5HPN

N-Acetyl-D-neuraminate
An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518)
1 2D Structure

N-Acetyl-D-neuraminate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
2.1.2 InChI
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1
2.1.3 InChI Key
SQVRNKJHWKZAKO-PFQGKNLYSA-N
2.1.4 Canonical SMILES
CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O
2.1.5 Isomeric SMILES
CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
TIP79W5HPN
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, N-acetylneuraminic

2. Acid, Sialic

3. N Acetylneuraminic Acid

4. N-acetylneuraminic Acid

5. Sialic Acid

2.3.2 Depositor-Supplied Synonyms

1. 131-48-6

2. N-acetyl-beta-neuraminic Acid

3. N-acetylneuramic Acid

4. N-acetyl-d-neuraminic Acid

5. Lactaminic Acid

6. Nana

7. Sialic Acid

8. Beta-neu5ac

9. Beta-sialic Acid

10. 19342-33-7

11. N-acetylsialic Acid

12. 5-acetamido-3,5-dideoxy-d-glycero-d-galactononulosonic Acid

13. Tip79w5hpn

14. (2s,4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic Acid

15. Chembl165084

16. Chebi:45744

17. (2s,4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-((1r,2r)-1,2,3-trihydroxypropyl)tetrahydro-2h-pyran-2-carboxylic Acid

18. Acide Aceneuramique

19. 489-46-3

20. O-sialic Acid

21. Mfcd00006620

22. 5-acetamido-3,5-dideoxy-d-glycero-beta-d-galacto-non-2-ulopyranosonic Acid

23. Slb

24. 5-n-acetylneuraminic Acid

25. N-acetylneuraminicacid

26. Unii-tip79w5hpn

27. Lactaminate

28. Sialomucin

29. Aceneuramic-acid

30. N-acetylsialate

31. B-sialic Acid

32. Nsc111756

33. N-acetylneuramate

34. 4mmp

35. 4mnp

36. N-acetyl-neuraminate

37. Neu-5ac

38. 5-n-acetylneuraminate

39. N-acetyl-b-neuraminate

40. N-acetyl-d-neuraminate

41. 126934-33-6

42. N-acetyl-b-d-neuraminate

43. Neuraminic Acid, N-acetyl

44. 5-n-acetyl-d-neuraminate

45. N-acetyl-delta-neuraminate

46. Schembl22412

47. 5-n-acetyl-delta-neuraminate

48. Mls002207179

49. Nan

50. N-acetyl-b-d-neuraminic Acid

51. Neuraminic Acid, N-acetyl- Starburst 4th Generation

52. 5-acetamido-3,5-dideoxy-d-glycero-d-galacto-nonulopyranosonic Acid

53. N-acetyl-delta-neuraminic Acid

54. N-acetyl-beta-delta-neuraminate

55. N-acetyl-beta-d-neuraminic Acid

56. 5-n-acetyl-b-d-neuraminic Acid

57. Dtxsid80864309

58. 5-n-acetyl-delta-neuraminic Acid

59. (-)-n-acetyl-beta-neuraminic Acid

60. N-acetyl-beta-delta-neuraminic Acid

61. Zinc3793840

62. N-(-)-acetylneuraminic Acid

63. Bdbm50063302

64. S4792

65. 5-n-acetyl-beta-delta-neuraminic Acid

66. Akos016004587

67. Am83978

68. Ccg-267571

69. Db04265

70. N-acetyl-.beta.-neuraminic Acid

71. Ac-24185

72. As-13907

73. Smr000857174

74. .beta.-neuraminic Acid, N-acetyl-

75. N-acetyl-.beta.-d-neuraminic Acid

76. N-acetylneuraminic Acid, Analytical Standard

77. N-acetylneuraminic Acid, Synthetic, >=95%

78. A1105

79. (-)-n-acetyl-.beta.-neuraminic Acid

80. A-1600

81. C19910

82. En300-174088

83. N-acetyl-.beta.-neuraminic Acid, (-)-

84. 131a486

85. (-)-n-acetylneuraminic Acid, Synthetic, Crystalline

86. N-acetylneuraminic Acid, Cell Culture Tested, >=95%

87. Q27120624

88. N-acetylneuraminic Acid, From Escherichia Coli, >=98%

89. Z1741971506

90. 5-acetamido-3,5-dideoxy-d-glycero-d-galacto-nonulosonate

91. 028d6d24-32a0-45ed-857e-4138653435fb

92. 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-2-nonulosonate

93. 5-acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonate

94. 5-acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonic Acid

95. B-5-acetamido-3,5-dideoxy-d-glycero-d-galacto-nonulopyranosonate

96. Wurcs=2.0/1,1,0/[aad21122h-2b_2-6_5*ncc/3=o]/1/

97. 5-(acetylamino)-3,5-dideoxy-d-glycero-b-d-galacto-2-nonulopyranosonate

98. 5-(acetylamino)-3,5-dideoxy-d-glycero-b-d-galacto-2-nonulopyranosonic Acid

99. 5-(acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonate

100. 5-(acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonic Acid

101. B-5-acetamido-3,5-dideoxy-d-glycero-d-galacto-nonulopyranosonic Acid

102. Beta-5-acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonate

103. 5-(acetylamino)-3,5-dideoxy-d-glycero-beta-d-galacto-non-2-ulopyranosonic Acid

104. 5-(acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonate

105. 5-(acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic Acid

106. Beta-5-acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonic Acid

107. D-glycero-.beta.-d-galacto-2-nonulopyranosonic Acid, 5-(acetylamino)-3,5-dideoxy-

108. D-glycero-d-galacto-nonulopyranosonic Acid, 5-acetamido-3,5-dideoxy-, .beta.-

109. (2s,4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic Acid

110. N-acetylneuraminic Acid; Sialic Acid; O-sialic Acid; 5-n-acetyl-beta-d-neuraminic Acid; Beta-sialic Acid

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 309.27 g/mol
Molecular Formula C11H19NO9
XLogP3-3.5
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count9
Rotatable Bond Count5
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area177
Heavy Atom Count21
Formal Charge0
Complexity403
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Treatment of distal myopathy, Nonaka type (hereditary inclusion-body myopathy)


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