FComEx: N-Acetylneuraminic acid (PC000341)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:02 UTC

Update date

2017-01-19 02:36:20 UTC

FoodComEx ID

PC000341

FoodDB Record

FDB001209

Chemical Information

Name

N-Acetylneuraminic acid

Description

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).

CAS Number

131-48-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
5-(acetylamino)-3,5-Dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonate	HMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonic acid	HMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonate	HMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonic acid	HMDB
5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid, 9CI	db_source
5-(acetylamino)-3,5-Dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonate	HMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic acid	HMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-delta-galacto-2-nonulosonate	HMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-delta-galacto-2-nonulosonic acid	HMDB
5-acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonate	biospider
5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulosonic acid	HMDB
5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulosonate	HMDB
5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulosonic acid	HMDB
5-N-ACETYL-b-D-neuraminate	Generator
5-N-Acetyl-b-D-neuraminic acid	biospider
5-N-ACETYL-beta-D-neuraminate	Generator
5-N-Acetyl-beta-D-neuraminic acid	biospider
5-N-Acetyl-beta-delta-neuraminic acid	biospider
5-N-Acetyl-D-neuraminate	biospider
5-N-Acetyl-D-neuraminic acid	biospider
5-N-Acetyl-delta-neuraminate	biospider
5-N-Acetyl-delta-neuraminic acid	biospider
5-N-ACETYL-β-D-neuraminate	Generator
5-N-ACETYL-β-D-neuraminic acid	Generator
5-N-Acetylneuraminate	biospider
5-N-Acetylneuraminic acid	biospider
Aceneuramate	biospider
Aceneuramic acid	biospider
Aceneuramic acid, INN	db_source
Acetylneuraminate	biospider
Acetylneuraminic acid	biospider
b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonate	HMDB
b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonic acid	HMDB
b-Neu5ac	Generator
B-sialic acid	biospider
beta-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonate	HMDB
beta-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acid	HMDB
beta-Neu5ac	ChEBI
Beta-sialic acid	biospider
Gynaminic acid	db_source
KI 111	db_source
Lactaminate	biospider
Lactaminic acid	db_source
N-acetyl-b-d-neuraminate	biospider
N-acetyl-b-d-neuraminic acid	biospider
N-acetyl-b-neuraminate	biospider
N-acetyl-beta-delta-neuraminate	biospider
N-acetyl-beta-delta-neuraminic acid	biospider
N-acetyl-beta-neuraminate	biospider
N-acetyl-d-neuraminate	biospider
N-acetyl-d-neuraminic acid	biospider
N-acetyl-delta-neuraminate	biospider
N-acetyl-delta-neuraminic acid	biospider
N-acetyl-neuraminate	biospider
N-acetyl-neuraminic acid	biospider
N-acetylneuramate	biospider
N-acetylneuramic acid	biospider
N-acetylneuraminate	biospider
N-acetylsialate	biospider
N-acetylsialic acid	biospider
NAN	biospider
NANA	db_source
Neu5Ac	db_source
Neu5NAc	db_source
O-Sialic acid	db_source
Serolactaminic acid	db_source
SIA	biospider
Sialate	biospider
Sialic acid	biospider
β-neu5ac	Generator

Chemical Formula

C22H38N2O18

IUPAC name

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

InChI Identifier

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)

InChI Key

RRGVAHSGXJFVRN-UHFFFAOYSA-N

Isomeric 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

Average Molecular Weight

618.5397

Monoisotopic Molecular Weight

618.211962422

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents