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Record Information
Version1.0
Creation Date2016-09-30 22:27:07 UTC
Update Date2020-05-21 16:28:28 UTC
BMDB IDBMDB0000230
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Lysosome
  • Membrane
  • Myelin sheath
  • Nucleus
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Lysosome
  • Membrane
  • Myelin sheath
  • Nucleus
Biospecimen Locations
  • Adrenal Gland
  • Brain
  • Milk
  • Neuron
  • Placenta
  • Prostate Tissue
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal GlandExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified462.379 uMNot SpecifiedNot Specified
Normal
    • The N-acetyl neur...
details
MilkDetected and Quantified32.334 - 42.0345 uMNot SpecifiedNot Specified
Normal
    • International Dai...
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
NeuronExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000230
DrugBank IDDB04265
Phenol Explorer Compound IDNot Available
FooDB 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.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the cleavage of N-acetylneuraminic acid (sialic acid) to form pyruvate and N-acetylmannosamine via a Schiff base intermediate. It prevents sialic acids from being recycled and returning to the cell surface. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway (By similarity).
Gene Name:
NPL
Uniprot ID:
Q29RY9
Molecular weight:
35166.0
Reactions
N-Acetylneuraminic acid → N-Acetyl-D-mannosamine + Pyruvic aciddetails
General function:
Involved in N-acylneuraminate cytidylyltransferase acti
Specific function:
Catalyzes the activation of N-acetylneuraminic acid (NeuNAc) to cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-NeuNAc), a substrate required for the addition of sialic acid. Has some activity toward NeuNAc, N-glycolylneuraminic acid (Neu5Gc) or 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN) (By similarity).
Gene Name:
CMAS
Uniprot ID:
Q3SZM5
Molecular weight:
48438.0
Reactions
N-Acetylneuraminic acid + Cytidine triphosphate → Cytidine monophosphate N-acetylneuraminic acid + Pyrophosphatedetails
General function:
Involved in exo-alpha-sialidase activity
Specific function:
Plays a role in modulating the ganglioside content of the lipid bilayer at the level of membrane-bound sialyl glycoconjugates.
Gene Name:
NEU3
Uniprot ID:
O97859
Molecular weight:
47917.0
General function:
Involved in exo-alpha-sialidase activity
Specific function:
Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moieties from glycoproteins and glycolipids. To be active, it is strictly dependent on its presence in the multienzyme complex. Appears to have a preference for alpha 2-3 and alpha 2-6 sialyl linkage (By similarity).
Gene Name:
NEU1
Uniprot ID:
A6BMK7
Molecular weight:
45433.0
General function:
Involved in calcium-dependent protein binding
Specific function:
Not Available
Gene Name:
SELP
Uniprot ID:
A6QPF9
Molecular weight:
71273.0
General function:
Involved in G-protein coupled receptor protein signalin
Specific function:
Receptor for a number of inflammatory CC-chemokines including MIP-1-alpha, MIP-1-beta and RANTES and subsequently transduces a signal by increasing the intracellular calcium ion level. May play a role in the control of granulocytic lineage proliferation or differentiation (By similarity).
Gene Name:
CCR5
Uniprot ID:
Q2HJ17
Molecular weight:
40235.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
NANS
Uniprot ID:
Q1RMX7
Molecular weight:
40217.0
Reactions
N-Acetyl-D-mannosamine + Phosphoenolpyruvic acid + Water → N-Acetylneuraminic acid + Hydrogen phosphatedetails