Record Information
Version1.0
Creation date2010-04-08 22:04:52 UTC
Update date2015-10-09 22:30:03 UTC
Primary IDFDB001209
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetylneuraminic acid
DescriptionIsol. from eggs, milk and colostrum by acid or enzymic hydrol. of the constit. 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 Number131-48-6
Structure
Thumb
Synonyms
SynonymSource
5-(acetylamino)-3,5-Dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonateHMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonic acidHMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonateHMDB
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonic acidHMDB
5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid, 9CIdb_source
5-(acetylamino)-3,5-Dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonateHMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic acidHMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-delta-galacto-2-nonulosonateHMDB
5-(acetylamino)-3,5-Dideoxy-delta-glycero-delta-galacto-2-nonulosonic acidHMDB
5-acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonatebiospider
5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulosonic acidHMDB
5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulosonateHMDB
5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulosonic acidHMDB
5-N-ACETYL-b-D-neuraminateGenerator
5-N-Acetyl-b-D-neuraminic acidbiospider
5-N-ACETYL-beta-D-neuraminateGenerator
5-N-Acetyl-beta-D-neuraminic acidbiospider
5-N-Acetyl-beta-delta-neuraminic acidbiospider
5-N-Acetyl-D-neuraminatebiospider
5-N-Acetyl-D-neuraminic acidbiospider
5-N-Acetyl-delta-neuraminatebiospider
5-N-Acetyl-delta-neuraminic acidbiospider
5-N-ACETYL-β-D-neuraminateGenerator
5-N-ACETYL-β-D-neuraminic acidGenerator
5-N-Acetylneuraminatebiospider
5-N-Acetylneuraminic acidbiospider
Aceneuramatebiospider
Aceneuramic acidbiospider
Aceneuramic acid, INNdb_source
Acetylneuraminatebiospider
Acetylneuraminic acidbiospider
b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonateHMDB
b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonic acidHMDB
b-Neu5acGenerator
B-sialic acidbiospider
beta-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonateHMDB
beta-5-acetamido-3,5-Dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acidHMDB
beta-Neu5acChEBI
Beta-sialic acidbiospider
Gynaminic aciddb_source
KI 111db_source
Lactaminatebiospider
Lactaminic aciddb_source
N-acetyl-b-d-neuraminatebiospider
N-acetyl-b-d-neuraminic acidbiospider
N-acetyl-b-neuraminatebiospider
N-acetyl-beta-delta-neuraminatebiospider
N-acetyl-beta-delta-neuraminic acidbiospider
N-acetyl-beta-neuraminatebiospider
N-acetyl-d-neuraminatebiospider
N-acetyl-d-neuraminic acidbiospider
N-acetyl-delta-neuraminatebiospider
N-acetyl-delta-neuraminic acidbiospider
N-acetyl-neuraminatebiospider
N-acetyl-neuraminic acidbiospider
N-acetylneuramatebiospider
N-acetylneuramic acidbiospider
N-acetylneuraminatebiospider
N-acetylsialatebiospider
N-acetylsialic acidbiospider
NANbiospider
NANAdb_source
Neu5Acdb_source
Neu5NAcdb_source
O-Sialic aciddb_source
Serolactaminic aciddb_source
SIAbiospider
Sialatebiospider
Sialic acidbiospider
β-neu5acGenerator
Predicted Properties
PropertyValueSource
logP-3.6ChemAxon
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area176.78 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity63.78 m³·mol⁻¹ChemAxon
Polarizability28.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H38N2O18
IUPAC name5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid; 5-acetamido-4,6,7,8,9-pentahydroxy-2-oxononanoic acid
InChI IdentifierInChI=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 KeyInChIKey=RRGVAHSGXJFVRN-UHFFFAOYSA-N
Isomeric SMILESCC(=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 Weight619
Monoisotopic Molecular Weight618
Classification
DescriptionThis compound belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • N-acylneuraminic acid
  • Neuraminic acid
  • Hydroxy fatty acid
  • C-glucuronide
  • Glycosyl compound
  • C-glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Medium-chain keto acid
  • Amino saccharide
  • Amino fatty acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Keto acid
  • Hydroxy acid
  • Gamma-aminoketone
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Alpha-keto acid
  • Alpha-hydroxy acid
  • Acetamide
  • Alpha-hydroxy ketone
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Ketone
  • Hemiacetal
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 42.72%; H 6.19%; N 4.53%; O 46.56%DFC
Melting PointMp 185-187° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -32 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID392810
ChEMBL IDCHEMBL165084
KEGG Compound IDC19910
Pubchem Compound ID445063
Pubchem Substance IDNot Available
ChEBI ID17012
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00230
CRC / DFC (Dictionary of Food Compounds) IDBWJ23-I:BWJ23-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34458
KNApSAcK IDC00019584
HET IDSLB
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDN-Acetylneuraminic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
N-acylneuraminate cytidylyltransferaseCMASQ8NFW8
Sialidase-2NEU2Q9Y3R4
Sialidase-4NEU4Q8WWR8
Sialidase-1NEU1Q99519
Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinaseGNEQ9Y223
Sialic acid synthaseNANSQ9NR45
Sialate O-acetylesteraseSIAEQ9HAT2
N-acetylneuraminate lyaseNPLQ9BXD5
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference