Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:55:47 UTC
Update Date2022-08-31 17:40:09 UTC
MiMeDB IDMMDBc0030148
Metabolite Identification
Common Namealpha-N-acetylneuraminate
DescriptionAlpha-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)

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
SynonymsNot Available
Chemical FormulaC11H18NO9
Average Molecular Weight308.2619
Monoisotopic Molecular Weight308.098156179
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
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
InChI KeySQVRNKJHWKZAKO-MMSOYPNASA-M