Showing Compound N-Acetylneuraminic acid (FDB001209)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:52 UTC

Update date

2019-11-26 02:56:06 UTC

Primary ID

FDB001209

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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
N-Acetylneuraminate	Generator
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

Predicted Properties

Property	Value	Source
Water Solubility	18.2 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.1	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.02	ChemAxon
pKa (Strongest Basic)	2.09	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	180.27 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	64.3 m³·mol⁻¹	ChemAxon
Polarizability	27.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Classification

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

Substituents

Medium-chain keto acid
Amino fatty acid
Hydroxy fatty acid
Sugar acid
Alpha-keto acid
Beta-hydroxy ketone
Monosaccharide
Fatty acyl
Acetamide
Alpha-hydroxy ketone
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Ketone
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Alcohol
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 42.72%; H 6.19%; N 4.53%; O 46.56%	DFC
Melting Point	Mp 185-187° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]22D -32 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17012

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00230

CRC / DFC (Dictionary of Food Compounds) ID

BWJ23-I:BWJ23-I

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34458

KNApSAcK ID

C00019584

HET ID

SLB

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

N-Acetylneuraminic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
N-acylneuraminate cytidylyltransferase	CMAS	Q8NFW8
Sialidase-2	NEU2	Q9Y3R4
Sialidase-4	NEU4	Q8WWR8
Sialidase-1	NEU1	Q99519
Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase	GNE	Q9Y223
Sialic acid synthase	NANS	Q9NR45
Sialate O-acetylesterase	SIAE	Q9HAT2
N-acetylneuraminate lyase	NPL	Q9BXD5