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Chemistry

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Also known as: 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-2-nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-2-nonulosonic acid, 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-non-2-nonulosonic acid, 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-non-2-ulopyranosonic acid, D-glycero-5-acetamido-3,5-dideoxy-d-galacto-non-2-ulo-pyranosonic acid, N-acetylneuraminic acid

Molecular Formula

C₁₁H₁₉NO₉

Molecular Weight

309.27 g/mol

InChI Key

SQVRNKJHWKZAKO-LUWBGTNYSA-N

N-Acetylneuraminic acid is a metabolite found in the aging mouse brain.

1 2D Structure

N-Acetyl-Neuraminic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(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-LUWBGTNYSA-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](CC(O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O)O

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-2-nonulopyranosonic Acid

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

3. 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-non-2-nonulosonic Acid

4. 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-non-2-ulopyranosonic Acid

5. D-glycero-5-acetamido-3,5-dideoxy-d-galacto-non-2-ulo-pyranosonic Acid

6. N-acetylneuraminic Acid

7. Neu5ac

8. N-acetylneuraminate

9. Neuac

10. Acidium Aceneuramicum

11. 131-48-6

12. O-sialic Acid

13. Neuraminic Acid, N-acetyl-

14. Acide Aceneuramique

15. Chembl4280954

16. Chebi:17012

17. Nsc 111756

18. 5-acetamido-3,5-dideoxy-d-glycero-d-galacto-2-nonulosonic Acid

19. 5-n-acetylneuraminic Acid

20. 489-46-3

21. Nsc111756

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

23. Bmse000057

24. Epitope Id:146100

25. Schembl236448

26. Bdbm50468556

27. Akos025311078

28. C00270

29. A806270

30. F_full_00010000000000_gs_6869

31. Wurcs=2.0/1,1,0/[aad21122h-2x_2-6_5*ncc/3=o]/1/

32. 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-2-nonulosonicaci;galactononulosonic Acid

33. (4s,5r,6r)-5-acetamido-2,4-bis(oxidanyl)-6-[(1r,2r)-1,2,3-tris(oxidanyl)propyl]oxane-2-carboxylic Acid

34. (4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic Acid

35. 6alpha-[(1r,2r)-1,2,3-trihydroxypropyl]-5beta-(acetylamino)-2,4alpha-dihydroxytetrahydro-2h-pyran-2-carboxylic Acid

2.3 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₉NO₉
Molecular Weight	309.27 g/mol
XLogP3	-3.5
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	309.10598118 g/mol
Monoisotopic Mass	309.10598118 g/mol
Topological Polar Surface Area	177 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	403
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1