1.0 2010-04-08 22:04:52 UTC 2019-11-26 02:56:06 UTC FDB001209 N-Acetylneuraminic acid Isolated from eggs, milk and colostrum by acid or enzymic hydrolysis of the constituent sialoproteins and oligosaccharides. Most abundant source is the nest cementing glycoprotein of the Chinese swiftlet used in birdsnest soup N-acetylneuraminic acid (NeuAc) or sialic acid is an acetyl derivative of the amino sugar neuraminic acid. It occurs in many glycoproteins, glycolipids, and polysaccharides in both mammals and bacteria. The most abundant sialic acid, NeuAc, is synthesized in vivo from N-acetylated D-mannosamine (ManNAc) or D-glucosamine (GlcNAc). NeuAc and its activated form, CMP-NeuAc, are biosynthesized in five consecutive reactions: UDP-N-acetylglucosamine (UDP-GlcNAc) N-acetylmannosamine (ManNAc) ManNAc 6-phosphate NeuAc 9-phosphate NeuAc CMP-NeuAc. CMP-NeuAc is transported into the Golgi apparatus and, with the aid of specific sialyltransferases, added onto nonreducing positions on oligosaccharide chains of glycoproteins and glycolipids. NeuAc is widely distributed throughout human tissues and found in several fluids, including serum, cerebrospinal fluid, saliva, urine, amniotic fluid, and breast milk. It is found in high levels in the brain, adrenal glands, and the heart. Serum and urine levels of the free acid are elevated in individuals suffering from renal failure. Serum and saliva Neu5Ac levels are also elevated in alcoholics. A disorder known as Salla disease or infantile NeuAc storage disease is also characterized by high serum and urine levels of this compound. The negative charge of is responsible for the slippery feel of saliva and mucins coating the body's organs. This particular sialic acid is known to act as a "decoy" for invading pathogens. NeuAc is also becoming known as an agent necessary for mediating ganglioside distribution and structures in the brain. Sialic acid (SA) is an N-acetylated derivative of neuraminic acid that is an abundant terminal monosaccharide of glycoconjugates. Normal human serum SA is largely bound to glycoproteins or glycolipids (Total sialic acid, TSA, 1.5-2.5 mmol/L), with small amounts of free SA (1-3 umol/L). Negatively charged SA units stabilize glycoprotein conformation in cell surface receptors to increase cell rigidity. This enables signal recognition and adhesion to ligands, antibodies, enzymes and microbes. SA residues are antigenic determinant residues in carbohydrate chains of glycolipids and glycoproteins, chemical messengers in tissue and body fluids, and may regulate glomeruli basement membrane permeability. Sialic acids are structurally unique nine-carbon keto sugars occupying the interface between the host and commensal or pathogenic microorganisms. An important function of host sialic acid is to regulate innate immunity. Sialic acid is the moiety most actively recycled for metabolic purposes in the salvage pathways in glycosphingolipid metabolism. Sialic acid is indispensable for the neuritogenic activities of gangliosides constituents which are unique in that a sialic acid directly binds to the glucose of the cerebroside, they are mutually connected in tandem, and some are located in the internal parts of the sugar chain. Sialylation (sialic acid linked to galactose, N-acetylgalactosamine, or linked to another sialic acid) represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family. (PMID: 11425186, 11287396, 12770781, 16624269, 12510390, 15007099). 5-(acetylamino)-3,5-Dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonate 5-(acetylamino)-3,5-Dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonic acid 5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonate 5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonic acid 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid, 9CI 5-(acetylamino)-3,5-Dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonate 5-(acetylamino)-3,5-Dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic acid 5-(acetylamino)-3,5-Dideoxy-delta-glycero-delta-galacto-2-nonulosonate 5-(acetylamino)-3,5-Dideoxy-delta-glycero-delta-galacto-2-nonulosonic acid 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonate 5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulosonic acid 5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulosonate 5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulosonic acid 5-N-ACETYL-b-D-neuraminate 5-N-Acetyl-b-D-neuraminic acid 5-N-ACETYL-beta-D-neuraminate 5-N-Acetyl-beta-D-neuraminic acid 5-N-Acetyl-beta-delta-neuraminic acid 5-N-Acetyl-D-neuraminate 5-N-Acetyl-D-neuraminic acid 5-N-Acetyl-delta-neuraminate 5-N-Acetyl-delta-neuraminic acid 5-N-ACETYL-β-D-neuraminate 5-N-ACETYL-β-D-neuraminic acid 5-N-Acetylneuraminate 5-N-Acetylneuraminic acid Aceneuramate Aceneuramic acid Aceneuramic acid, INN Acetylneuraminate Acetylneuraminic acid b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonate b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonic acid b-Neu5ac B-sialic acid beta-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonate beta-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acid beta-Neu5ac Beta-sialic acid Gynaminic acid KI 111 Lactaminate Lactaminic acid N-acetyl-b-d-neuraminate N-acetyl-b-d-neuraminic acid N-acetyl-b-neuraminate N-acetyl-beta-delta-neuraminate N-acetyl-beta-delta-neuraminic acid N-acetyl-beta-neuraminate N-acetyl-d-neuraminate N-acetyl-d-neuraminic acid N-acetyl-delta-neuraminate N-acetyl-delta-neuraminic acid N-acetyl-neuraminate N-acetyl-neuraminic acid N-acetylneuramate N-acetylneuramic acid N-acetylneuraminate N-acetylsialate N-acetylsialic acid NAN NANA Neu5Ac Neu5NAc O-Sialic acid Serolactaminic acid SIA Sialate Sialic acid β-neu5ac C22H38N2O18 618.5397 618.211962422 2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid; 4,6,7,8,9-pentahydroxy-5-[(1-hydroxyethylidene)amino]-2-oxononanoic acid 2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid; 4,6,7,8,9-pentahydroxy-5-[(1-hydroxyethylidene)amino]-2-oxononanoic acid 131-48-6 CC(=O)NC(C(O)CC(=O)C(O)=O)C(O)C(O)C(O)CO.CC(=O)NC1C(O)CC(O)(OC1C(O)C(O)CO)C(O)=O InChI=1S/2C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13;1-4(14)12-8(5(15)2-6(16)11(20)21)10(19)9(18)7(17)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19);5,7-10,13,15,17-19H,2-3H2,1H3,(H,12,14)(H,20,21) RRGVAHSGXJFVRN-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Medium-chain keto acids and derivatives Organic compounds Organic acids and derivatives Keto acids and derivatives Medium-chain keto acids and derivatives Acetamides Alpha-hydroxy ketones Alpha-keto acids and derivatives Amino fatty acids Beta-hydroxy ketones Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Monocarboxylic acids and derivatives Monosaccharides Organic oxides Organonitrogen compounds Organopnictogen compounds Polyols Primary alcohols Secondary alcohols Secondary carboxylic acid amides Sugar acids and derivatives Acetamide Alcohol Aliphatic heteromonocyclic compound Alpha-hydroxy ketone Alpha-keto acid Amino fatty acid Beta-hydroxy ketone Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Fatty acyl Hydrocarbon derivative Hydroxy fatty acid Ketone Medium-chain keto acid Monocarboxylic acid or derivatives Monosaccharide Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Polyol Primary alcohol Secondary alcohol Secondary carboxylic acid amide Sugar acid Solid logp -2.35 ALOGPS logs -1.23 ALOGPS solubility 1.82e+01 g/l ALOGPS melting_point Mp 185-187° dec. logp -3.1 ChemAxon pka_strongest_acidic 3.02 ChemAxon pka_strongest_basic 2.09 ChemAxon iupac 2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid; 4,6,7,8,9-pentahydroxy-5-[(1-hydroxyethylidene)amino]-2-oxononanoic acid ChemAxon average_mass 618.5397 ChemAxon mono_mass 618.211962422 ChemAxon smiles CC(=O)NC(C(O)CC(=O)C(O)=O)C(O)C(O)C(O)CO.CC(=O)NC1C(O)CC(O)(OC1C(O)C(O)CO)C(O)=O ChemAxon formula C22H38N2O18 ChemAxon inchi InChI=1S/2C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13;1-4(14)12-8(5(15)2-6(16)11(20)21)10(19)9(18)7(17)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19);5,7-10,13,15,17-19H,2-3H2,1H3,(H,12,14)(H,20,21) ChemAxon inchikey RRGVAHSGXJFVRN-UHFFFAOYSA-N ChemAxon polar_surface_area 180.27 ChemAxon refractivity 64.3 ChemAxon polarizability 27.86 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB00230 17012 SLB #<Reference:0x000055ce31ab7f48> #<Reference:0x000055ce31ab7d90> #<Reference:0x000055ce31ab7bd8> #<Reference:0x000055ce31ab7a20> #<Reference:0x000055ce31ab7868> #<Reference:0x000055ce31ab76b0> #<Reference:0x000055ce31ab74f8> #<Reference:0x000055ce31ab7340> #<Reference:0x000055ce31ab7188> #<Reference:0x000055ce31ab6fd0> #<Reference:0x000055ce31ab6e18> #<Reference:0x000055ce31ab6c60> #<Reference:0x000055ce31ab6aa8> #<Reference:0x000055ce31ab68f0> #<Reference:0x000055ce31ab6738> #<Reference:0x000055ce31ab6580> #<Reference:0x000055ce31ab63c8> #<Reference:0x000055ce31ab6210> #<Reference:0x000055ce31ab6058> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Eggs Unknown generic Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific 249.781625 462.379 37.18425 uM Milk and milk products Unknown generic Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase Q9Y223 GNE N-acetylneuraminate lyase Q9BXD5 NPL N-acylneuraminate cytidylyltransferase Q8NFW8 CMAS Sialate O-acetylesterase Q9HAT2 SIAE Sialic acid synthase Q9NR45 NANS Sialidase-1 Q99519 NEU1 Sialidase-2 Q9Y3R4 NEU2 Sialidase-4 Q8WWR8 NEU4