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Record Information
Version1.0
Creation Date2016-09-30 22:27:07 UTC
Update Date2020-06-04 20:56:29 UTC
MCDB ID BMDB0000230
Secondary Accession Numbers
  • BMDB00230
Metabolite Identification
Common NameN-Acetylneuraminic acid
DescriptionN-Acetylneuraminic acid, also known as N-acetylneuraminate or sialic acid, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-Acetylneuraminic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. N-Acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans. N-Acetylneuraminic acid participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylneuraminic acid can be biosynthesized from N-acetylmannosamine and phosphoenolpyruvic acid; which is catalyzed by the enzyme sialic acid synthase. In addition, N-Acetylneuraminic acid can be converted into N-acetylmannosamine and pyruvic acid; which is mediated by the enzyme N-acetylneuraminate lyase. In cattle, N-acetylneuraminic acid is involved in the metabolic pathway called the amino sugar metabolism pathway. N-Acetylneuraminic acid is a potentially toxic compound. N-Acetylneuraminic acid has been found to be associated with several diseases known as sialidosis, normosomatic type, irritable bowel syndrome, ulcerative colitis, and colorectal cancer; also n-acetylneuraminic acid has been linked to the inborn metabolic disorders including salla disease.
Structure
Thumb
Synonyms
ValueSource
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
N-Acetyl-beta-D-neuraminic acidHMDB
N-Acetyl-beta-neuraminic acidHMDB
N-Acetyl-β-D-neuraminic acidHMDB
N-Acetyl-β-neuraminic acidHMDB
N-Acetylneuraminic acidHMDB
Chemical FormulaC11H19NO9
Average Molecular Weight309.2699
Monoisotopic Molecular Weight309.105981211
IUPAC Name(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Nameβ-neu5ac
CAS Registry Number131-48-6
SMILES
[H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1
InChI KeySQVRNKJHWKZAKO-PFQGKNLYSA-N
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point186 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.8ALOGPS
logP-3.6ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area176.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.78 m³·mol⁻¹ChemAxon
Polarizability27.82 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified32 - 42 uM
  • International Dai...
details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected and Quantified462 uM
  • The N-acetyl neur...
details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
HMDB IDHMDB0000230
DrugBank IDDB04265
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID392810
KEGG Compound IDC19910
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Acetylneuraminic acid
METLIN IDNot Available
PubChem Compound445063
PDB IDNot Available
ChEBI ID45744
References
Synthesis ReferenceYamamoto, Toshihiro; Teshima, Tadashi; Inami, Kaoru; Shiba, Tetsuo. Synthesis of sialic acid through aldol condensation of glucose with oxalacetic acid. Tetrahedron Letters (1992), 33(3), 325-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Paul McJarrow, Janneke van Amelsfort-Schoonbeek (2004). International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579. International Dairy Journal.
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  3. P. A. Morrissey (1973). The N-acetyl neuraminic-acid content of the milk of various species Journal of Dairy Research (1973), 40: 421-425 Cambridge University Press doi: 10.1017/S0022029900014795 (About doi) . Journal of Dairy Research.