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N-Acetyl-alpha-neuraminate (M2MDB003607)

Record Information
Version2.0
Creation Date2012-10-10 12:22:30 -0600
Update Date2015-09-16 14:50:11 -0600
Secondary Accession Numbers
  • ECMDB23217
Identification
Name:N-Acetyl-alpha-neuraminate
DescriptionN-Acetyl-alpha-neuraminate is a sialic acid. Sialic acids are an important family of related 9-carbon sugars acids, present on the surface of many different cells and functioning in a wide range of different biological processes. They can be utilized by pathogens to evade the host immune response. N-acetylneuraminic acid is the most common sialic acid. A number of bacteria that can colonize humans (such as E. coli) make use of N-acetylneuraminic acid as a nutrient source. Production of the enzymes involved in N-acetylneuraminate degradation is induced by growth on sialic acid as the sole source of carbon, which is due to transcriptional regulation by the repressor NanR.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2R,4S,5R,6R)-5-acetamido-2,4-Dihydroxy-6-(1R,2R)-1,2,3-trihydroxypropyloxane-2-carboxylate
  • (2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-(1R,2R)-1,2,3-trihydroxypropyloxane-2-carboxylic acid
  • 5-(acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-Nonulopyranosonate
  • 5-(acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-Nonulopyranosonic acid
  • 5-(acetylamino)-3,5-Dideoxy-delta-glycero-a-delta-galacto-2-nonulopyranosonate
  • 5-(acetylamino)-3,5-Dideoxy-delta-glycero-a-delta-galacto-2-nonulopyranosonic acid
  • 5-(acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-Nonulopyranosonate
  • 5-(acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-Nonulopyranosonic acid
  • 5-(acetylamino)-3,5-Dideoxy-δ-glycero-a-δ-galacto-2-nonulopyranosonate
  • 5-(acetylamino)-3,5-Dideoxy-δ-glycero-a-δ-galacto-2-nonulopyranosonic acid
  • 5-(acetylamino)-3,5-Dideoxy-δ-glycero-α-δ-galacto-2-nonulopyranosonate
  • 5-(acetylamino)-3,5-Dideoxy-δ-glycero-α-δ-galacto-2-nonulopyranosonic acid
  • 5-acetamido-3,5-dideoxy-a-D-glycero-D-galacto-Nonulopyranosonate
  • 5-acetamido-3,5-dideoxy-a-D-glycero-D-galacto-Nonulopyranosonic acid
  • 5-acetamido-3,5-Dideoxy-a-delta-glycero-delta-galacto-nonulopyranosonate
  • 5-acetamido-3,5-Dideoxy-a-delta-glycero-delta-galacto-nonulopyranosonic acid
  • 5-acetamido-3,5-Dideoxy-a-δ-glycero-δ-galacto-nonulopyranosonate
  • 5-acetamido-3,5-Dideoxy-a-δ-glycero-δ-galacto-nonulopyranosonic acid
  • 5-acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-Nonulopyranosonate
  • 5-acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-Nonulopyranosonic acid
  • 5-acetamido-3,5-Dideoxy-α-δ-glycero-δ-galacto-nonulopyranosonate
  • 5-acetamido-3,5-Dideoxy-α-δ-glycero-δ-galacto-nonulopyranosonic acid
  • 8)-a-NeuNAC-(2->n
  • 8)-alpha-NeuNAC-(2->n
  • 8)-α-NeuNAC-(2->n
  • a-Neu5ac
  • a-Neu5ac-(2->8)N
  • Alpha-Neu5Ac
  • Alpha-Neu5Ac-(2->8)n
  • N-Acetyl-a-D-neuraminate
  • N-Acetyl-a-D-neuraminic acid
  • N-Acetyl-a-delta-neuraminate
  • N-Acetyl-a-delta-neuraminic acid
  • N-Acetyl-a-neuraminate
  • N-Acetyl-a-neuraminic acid
  • N-Acetyl-a-δ-neuraminate
  • N-Acetyl-a-δ-neuraminic acid
  • N-Acetyl-alpha-delta-neuraminate
  • N-Acetyl-alpha-delta-neuraminic acid
  • N-Acetyl-alpha-neuraminic acid
  • N-Acetyl-α-neuraminate
  • N-Acetyl-α-neuraminic acid
  • N-Acetyl-α-δ-neuraminate
  • N-Acetyl-α-δ-neuraminic acid
  • N-Acetylated a-(2->8)-linked homosialopolysaccharide
  • N-acetylated alpha-(2->8)-linked homosialopolysaccharide
  • N-Acetylated α-(2->8)-linked homosialopolysaccharide
  • Poly-a-(2->8)-neu5ac
  • Poly-a-(2->8)-neunac
  • Poly-alpha-(2->8)-Neu5Ac
  • Poly-alpha-(2->8)-NeuNAc
  • Poly-α-(2->8)-neu5ac
  • Poly-α-(2->8)-neunac
  • Polyalpha-Neu5Ac-(2->8)
  • α-Neu5ac
  • α-Neu5ac-(2->8)N
Chemical Formula:C11H19NO9
Weight:Average: 309.2699
Monoisotopic: 309.105981211
InChI Key:SQVRNKJHWKZAKO-YRMXFSIDSA-N
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
CAS number:21646-00-4
IUPAC Name:(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional IUPAC Name:N-acetylneuraminic acid
SMILES:[H][C@]1(O[C@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • N-acylneuraminic acid
  • Neuraminic acid
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • Alpha-hydroxy acid
  • Pyran
  • Hydroxy acid
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility227 g/LALOGPS
logP-2.8ALOGPS
logP-3.6ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area176.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.78 m³·mol⁻¹ChemAxon
Polarizability28.19 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
N-Acetyl-alpha-neuraminate > N-Acetylneuraminic acid
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9370000000-a2a8e1f2580c7bb97655View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0pb9-2390148000-6c04c73ad5de1e54ba0eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_5_15) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("N-Acetyl-a-neuraminic acid,5TBDMS,#15" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1092000000-ca2f76604846382a3032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kc-6190000000-7e304e9fa3125067d352View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-9240000000-65d03a6c6f60a71416c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-074j-4961000000-bc80694ae9687db9a365View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9210000000-c1d9f41a64bc464147ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-a1d857dc5ad7118647b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03kc-0095000000-8f7746cc3f652b12033fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-1392000000-3e251c9d2583e71f866aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7910000000-ba41b78e53cb934a9b19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3039000000-4348eff0515b0da3bc08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-6290000000-5ac6f13cca0827ab0dd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-9100000000-ac22477eeca403481effView in MoNA
References
References:
  • Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. Pubmed: 890917
Synthesis Reference:Baumberger, Franz; Vasella, Andrea. , Synthesis of N-acetylneuraminic acid and N-acetyl-4-epineuraminic acid. Helvetica Chimica Acta (1986), 69(5), 1205-15.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID58770
HMDB IDHMDB00773
Pubchem Compound ID444885
Kegg IDC19909
ChemSpider ID392681
Wikipedia IDNot Available
BioCyc IDNot Available
EcoCyc IDNot Available
Ligand ExpoSIA

Enzymes

Protein Details
1. N-acetylneuraminate epimerase
General function:
Involved in racemase and epimerase activity, acting on
Specific function:
Converts alpha-N-acetylneuranimic acid (Neu5Ac) to the beta-anomer, accelerating the equilibrium between the alpha- and beta-anomers. Probably facilitates sialidase-negative bacteria to compete sucessfully for limited amounts of extracellular Neu5Ac, which is likely taken up in the beta-anomer. In addition, the rapid removal of sialic acid from solution might be advantageous to the bacterium to damp down host responses
Gene Name:
nanM
Uniprot ID:
P39371
Molecular weight:
39572
Reactions
N-acetyl-alpha-neuraminate = N-acetyl-beta-neuraminate.