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Record Information
Version	2.0
Creation Date	2012-05-31 14:40:18 -0600
Update Date	2015-07-07 12:21:05 -0600
Secondary Accession Numbers	ECMDB20347
Identification
Name:	alpha-N-acetylneuraminate
Description	Alpha-n-acetylneuraminate belongs to the class of Neuraminic Acid Derivatives. These are compounds containingor dervivated from a neuraminic acid moeity (5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid), which is a 9-carbon monosaccharide. (inferred from compound structure)<br/><br/> N-acetyl-D-neuraminic acid (Neu5Ac) is a precursor for producing many pharmaceutical drugs such as zanamivir which have been used in clinical trials to treat and prevent the infection with influenza virus, such as the avian influenza virus H5N1 and the current 2009 H1N1. (PMID 19888576) E. coli Neu5Ac synthase is the Neu5Ac-9-P synthase. The Neu5Ac-9-P synthase is a cytosolic enzyme and ubiquitously distributed in mouse various tissues. (PMID 10873658) A prerequisite for the synthesis of sialylated glycoconjugates is the activated sugar-nucleotide cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-Neu5Ac), which provides a substrate for Golgi sialyltransferases. (PMID 9689047) The CMP-sialic acid synthetase (CMP-Neu5Ac, synthetase) is responsible for the synthesis of CMP-Neu5Ac, which is the donor used by sialyltransferases to attach sialic acid to acceptor hydroxyl groups in various polysaccharides, glycolipids, and glycoproteins. (PMID 12135555)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x5a0e7a4> Close
Synonyms:	α-N-acetylneuraminate α-n-acetylneuraminate α-n-acetylneuraminic acid α-Neu5Ac a-N-Acetylneuraminate a-N-Acetylneuraminic acid a-Neu5ac Alpha-N-Acetylneuraminic acid Alpha-Neu5Ac α-N-Acetylneuraminate α-N-Acetylneuraminic acid α-Neu5ac
Chemical Formula:	C11H18NO9
Weight:	Average: 308.2619 Monoisotopic: 308.098156179
InChI Key:	SQVRNKJHWKZAKO-MMSOYPNASA-M
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)/p-1/t5-,6-,7?,8?,9+,11+/m0/s1
CAS number:	Not Available
IUPAC Name:	N-[(2R,4S,6R)-6-carboxy-4,6-dihydroxy-2-[(2S)-1,2,3-trihydroxypropyl]oxan-3-yl]ethanecarboximidate
Traditional IUPAC Name:	N-[(2R,4S,6R)-6-carboxy-4,6-dihydroxy-2-[(2S)-1,2,3-trihydroxypropyl]oxan-3-yl]ethanecarboximidate
SMILES:	[H][C@](O)(CO)C([H])(O)[C@]1([H])O[C@](O)(C[C@]([H])(O)C1([H])N=C(C)[O-])C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Neuraminic acids
Alternative Parents	C-glucuronides C-glycosyl compounds Pyrans Oxanes Alpha hydroxy acids and derivatives Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Carboximidic acids Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic anions
Substituents	Neuraminic acid C-glucuronide Glycosyl compound C-glycosyl compound Pyran Oxane Hydroxy acid Alpha-hydroxy acid Secondary alcohol Hemiacetal Oxacycle Organoheterocyclic compound Polyol Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Carboximidic acid derivative Carboximidic acid Organic nitrogen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary alcohol Organonitrogen compound Carbonyl group Alcohol Organic anion Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 110 g/L ALOGPS logP -2.2 ALOGPS logP -3.1 ChemAxon logS -0.47 ALOGPS pKa (Strongest Acidic) 3.02 ChemAxon pKa (Strongest Basic) 2.1 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 10 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 183.1 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 74.85 m³·mol⁻¹ ChemAxon Polarizability 28.03 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	alpha-N-acetylneuraminate <> beta-N-acetylneuraminate alpha-N-acetylneuraminate <> N-Acetylneuraminic acid
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-2069000000-310a8ed2162a8510b485 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03fs-7190000000-6a4f6bb48b45c9d3293a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-9110000000-5a948d1f1c992ef7f516 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4l-5493000000-809b8fe0ef32ab8a0a3f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-9420000000-d2fac964875ab3eb3957 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4r-9200000000-73cbdd0a5128c6b9fc79 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 25203632 Kegg ID C19909 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CPD0-1122 EcoCyc ID CPD0-1122