Record Information
Version1.0
Creation date2011-09-21 00:10:39 UTC
Update date2015-07-21 06:57:04 UTC
Primary IDFDB022234
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetyl-alpha-neuraminic acid
DescriptionN-Acetyl-a-neuraminic acid, also known as alpha-neu5ac or O-sialIC ACID, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-Acetyl-a-neuraminic acid exists in all living organisms, ranging from bacteria to humans. N-Acetyl-a-neuraminic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-acetyl-a-neuraminic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on N-Acetyl-a-neuraminic acid.
CAS Number21646-00-4
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility227 g/LALOGPS
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
Polarizability28.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H19NO9
IUPAC name(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
InChI IdentifierInChI=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-YRMXFSIDSA-N
Isomeric 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
Average Molecular Weight309.2699
Monoisotopic Molecular Weight309.105981211
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
Ontology
Disposition

Source:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-9370000000-a2a8e1f2580c7bb97655Spectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pb9-2390148000-6c04c73ad5de1e54ba0eSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TBDMS_5_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, "N-Acetyl-a-neuraminic acid,5TBDMS,#15" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-alpha-neuraminic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1092000000-ca2f76604846382a30322015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kc-6190000000-7e304e9fa3125067d3522015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-9240000000-65d03a6c6f60a71416c62015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-074j-4961000000-bc80694ae9687db9a3652015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9210000000-c1d9f41a64bc464147dd2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-a1d857dc5ad7118647b32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03kc-0095000000-8f7746cc3f652b12033f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-1392000000-3e251c9d2583e71f866a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7910000000-ba41b78e53cb934a9b192021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3039000000-4348eff0515b0da3bc082021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-6290000000-5ac6f13cca0827ab0dd02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-9100000000-ac22477eeca403481eff2021-09-24View Spectrum
NMRNot Available
ChemSpider ID392681
ChEMBL IDCHEMBL1234621
KEGG Compound IDC19909
Pubchem Compound ID444885
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00773
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDSIA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference