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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:31:05 UTC
HMDB IDHMDB0000796
Secondary Accession Numbers
  • HMDB00796
Metabolite Identification
Common NameN-Acetyl-4-O-acetylneuraminic acid
DescriptionN-Acetyl-4-O-acetylneuraminic acid, also known as N,4-O-diacetylneuraminate or neu4,5ac2, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-4-O-acetylneuraminic 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-4-O-acetylneuraminic acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on N-Acetyl-4-O-acetylneuraminic acid.
Structure
Thumb
Synonyms
ValueSource
N-Acetyl-4-O-acetylneuraminateGenerator
N,4-O-DiacetylneuraminateHMDB
N,4-O-Diacetylneuraminic acidHMDB
4-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonateHMDB
4-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acidHMDB
4-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonateHMDB
4-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acidHMDB
4-O-Acetyl-N-acetylneuraminateHMDB
4-O-Acetyl-N-acetylneuraminic acidHMDB
Neu4,5ac2HMDB
N-Acetyl-4-O-acetylneuraminic acidGenerator
Chemical FormulaC13H21NO10
Average Molecular Weight351.3065
Monoisotopic Molecular Weight351.116545897
IUPAC Name(2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
CAS Registry Number16655-75-7
SMILES
CC(=O)N[C@@H]1[C@H](C[C@](O)(O[C@H]1C(O)C(O)CO)C(O)=O)OC(C)=O
InChI Identifier
InChI=1S/C13H21NO10/c1-5(16)14-9-8(23-6(2)17)3-13(22,12(20)21)24-11(9)10(19)7(18)4-15/h7-11,15,18-19,22H,3-4H2,1-2H3,(H,14,16)(H,20,21)/t7?,8-,9+,10?,11+,13-/m0/s1
InChI KeyLVBIMVQYUKOENY-FODKYPIKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide sulfate
  • Monosaccharide
  • Oxane
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Acetamide
  • 1,2-diol
  • Carboxamide group
  • Hemiacetal
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022250
KNApSAcK IDNot Available
Chemspider ID389185
KEGG Compound IDC04015
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5761
PubChem Compound440197
PDB IDNot Available
ChEBI ID32844
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1897321
References
Synthesis ReferenceOgura, Haruo; Furuhata, Kimio; Sato, Shingo; Anazawa, Katsuko; Shidori, Yoshiyasu; Ito, Masayoshi. A process for preparation of N-acetyl-4-O-acetylneuraminic acid, a ganglioside intermediate. Jpn. Kokai Tokkyo Koho (1988), 7 pp. CODEN: JKXXAF JP 63044587 A 19880225 Showa. CAN 109:110857 AN 1988:510857
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bulai T, Bratosin D, Pons A, Montreuil J, Zanetta JP: Diversity of the human erythrocyte membrane sialic acids in relation with blood groups. FEBS Lett. 2003 Jan 16;534(1-3):185-9. [PubMed:12527384 ]