Record Information
Version1.0
Creation date2010-04-08 22:04:52 UTC
Update date2018-05-28 22:09:46 UTC
Primary IDFDB001209
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetylneuraminic acid
DescriptionIsolated 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 Number131-48-6
Structure
Thumb
Synonyms
SynonymSource
5-N-ACETYL-BETA-D-neuraminIC ACIDChEBI
beta-Neu5acChEBI
5-N-ACETYL-b-D-neuraminateGenerator
5-N-ACETYL-b-D-neuraminic acidGenerator
5-N-ACETYL-beta-D-neuraminateGenerator
5-N-ACETYL-β-D-neuraminateGenerator
5-N-ACETYL-β-D-neuraminic acidGenerator
b-Neu5acGenerator
Β-neu5acGenerator
N-AcetylneuraminateGenerator
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-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-nonulosonateHMDB
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-beta-delta-neuraminic acidHMDB
5-N-Acetyl-D-neuraminateHMDB
5-N-Acetyl-D-neuraminic acidHMDB
5-N-Acetyl-delta-neuraminateHMDB
5-N-Acetyl-delta-neuraminic acidHMDB
5-N-AcetylneuraminateHMDB
5-N-Acetylneuraminic acidHMDB
AceneuramateHMDB
Aceneuramic acidHMDB
AcetylneuraminateHMDB
Acetylneuraminic acidHMDB
b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonateHMDB
b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonic acidHMDB
b-Sialic acidHMDB
beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonateHMDB
beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acidHMDB
beta-Sialic acidHMDB
LactaminateHMDB
Lactaminic acidHMDB
N-Acetyl-b-D-neuraminateHMDB
N-Acetyl-b-D-neuraminic acidHMDB
N-Acetyl-b-neuraminateHMDB
N-Acetyl-beta-delta-neuraminateHMDB
N-Acetyl-beta-delta-neuraminic acidHMDB
N-Acetyl-beta-neuraminateHMDB
N-Acetyl-D-neuraminateHMDB
N-Acetyl-D-neuraminic acidHMDB
N-Acetyl-delta-neuraminateHMDB
N-Acetyl-delta-neuraminic acidHMDB
N-Acetyl-neuraminateHMDB
N-Acetyl-neuraminic acidHMDB
N-AcetylneuramateHMDB
N-Acetylneuramic acidHMDB
N-AcetylsialateHMDB
N-Acetylsialic acidHMDB
NANHMDB
NANAHMDB
Neu5acHMDB
Sialic acidHMDB
Acid, sialicHMDB
Acid, N-acetylneuraminicHMDB
N Acetylneuraminic acidHMDB
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-neuraminic acidbiospider
5-N-Acetyl-beta-D-neuraminic acidbiospider
Aceneuramic acid, INNdb_source
b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonateHMDB
b-5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-nonulopyranosonic acidHMDB
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-sialic acidbiospider
Gynaminic aciddb_source
KI 111db_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
Neu5Acdb_source
Neu5NAcdb_source
O-Sialic aciddb_source
Serolactaminic aciddb_source
SIAbiospider
Sialatebiospider
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 KeyRRGVAHSGXJFVRN-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 Weight618.5397
Monoisotopic Molecular Weight618.211962422
Classification
Description belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • N-acylneuraminic acid
  • Neuraminic acid
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • Alpha-hydroxy acid
  • Pyran
  • Hydroxy acid
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-0fr2-1961000000-3acdbc4b39a5bf685996View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014j-0492000000-8e4279660c77b0c70a30View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)splash10-00l6-1792200000-863a168c10243229e892View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fr2-1961000000-3acdbc4b39a5bf685996View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014j-0492000000-8e4279660c77b0c70a30View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00l6-1792200000-863a168c10243229e892View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h2f-9660000000-f7a1f63f319c23f8e72aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0zfr-4620249000-1d39f85a16504ef9ea46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0190000000-a3a5aaa2e10a6cfed08aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fk9-3900000000-7100e174e13e94736ae7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00si-9300000000-1166885a787fd53086b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1091000000-11c42df33f8993522db0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kc-5090000000-5d0c74aa0d8a2c8d321cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9320000000-cfda0db8085e62f50516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-3391000000-68ee32ef5e2ba6223c42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9110000000-9ae00577454ddf4db073View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-798cb916675bb1245a78View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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