N-acetyl-beta-neuraminic acid
Basic information
- CAS
131-48-6- Standard SMILES
CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)O[C@](O)(C(=O)O)C[C@@H]1O- InChIKey
SQVRNKJHWKZAKO-PFQGKNLYSA-N- Molecular formula
- C11H19NO9
- Average molar mass
- 309.27 g/mol
- Monoisotopic mass
- 309.10598118
Overview
N-acetyl-beta-neuraminic acid is N-Acetylneuraminic acid with beta configuration at the anomeric centre. It has a role as an epitope. It is functionally related to a beta-neuraminic acid. It is a conjugate acid of a N-acetyl-beta-neuraminate.
Names & identifiers
- Preferred name
- N-acetyl-beta-neuraminic acid
- IUPAC
- (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
- English name
- N-Acetylneuraminic acid
- Molecular formula
- C11H19NO9
- Molecular weight
- 309.27
Names & synonyms
N-acetyl-beta-neuraminic acidbeta-Neu5Ac19342-33-7TIP79W5HPNCHEBI:45744N-acetyl-beta-D-neuraminic acidDTXSID80864309(-)-N-acetyl-beta-neuraminic acidGlyTouCan:G76571JTRefChem:1048431DTXCID401324324G76571JT
Show more names
SIALIC ACIDNEU5ACNANNeuAc(-)-N-ACETYLNEURAMINIC ACID(2S,4S,5R,6R)-5-AcetaMido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acidN-AcetyIneuraminic acid
131-48-6N-Acetyl-D-neuraminic acidN-acetylneuramic acid5-N-ACETYL-BETA-D-NEURAMINIC ACIDBETA-SIALIC ACIDLactaminic acidNANAAcetylneuraminic acid
Database identifiers
- CAS
131-48-6、19342-33-7、489-46-3、50795-27-2
Properties
Computed structural properties
- XLogP
- -3.5
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 5
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 403
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point186 °C
Physical DescriptionSolid
Collision Cross Section
166.6 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
158.4 Ų [M-H]-
Physicochemical properties
- Melting point
- 184 · 184-186 °C
- alpha
- -32 · -32 º (c=2,water)
- Boiling point
- 449.56 °C · 449.56°C (rough estimate)
- Density
- 1.358 · 1.3580 (rough estimate)
- refractive index
- -32 ° · -32 ° (C=1, H2O)
- storage temp.
- -20 °C · -20°C
- solubility
- 50 g/L · 50 g/L (20°C)
- pka
- 2.41 · 2.41±0.54(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
Regulation (EC) No 258/1997
Regulation (EC) No 258/1997
Neuraminic acid, N-acetyl-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 3-10-23
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29329970
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 22-24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Pharmacology
Tissue LocationsAdrenal Gland
Cellular LocationsCytoplasm
Metabolite PathwaysAmino Sugar Metabolism
Uses & manufacturing
General Manufacturing InformationNeuraminic acid, N-acetyl-: ACTIVE
Applications
DescriptionN-acetylneuraminic acid is an N-acyl derivative of neuraminic or acid amino sugar derivative, derived from N-acetylmannosamine and pyruvic acid. It is an important constituent of glycoproteins and glycolipids. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria.
UsesN-Acetylneuraminic acid is an integral part of sialic acids (SAs), important functional sugars that play an important role in maintaining and improving brain health, detoxification, antibacterial, and immune enhancement. n-Acetylneuraminic acid is biologically useful for neurotransmission, leukocyte extravasation, viral or bacterial infection, and carbohydrate-protein recognition. n- Acetylneuraminic acid is used to study its biochemistry, metabolism and absorption in vivo and in vitro.
Additional notes
DefinitionChEBI: N-Acetylneuraminic acid is n-Acetylneuraminic acid with beta configuration at the anomeric centre. It has a role as an epitope. It is functionally related to a beta-neuraminic acid. It is a conjugate acid of a N-acetyl-beta-neuraminate.
Related reactions
0 records
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Compound notes
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