Showing metabocard for N-Acetyl-4-O-acetylneuraminic acid (BMDB0000796)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:43 UTC
Update Date2020-04-22 15:05:21 UTC
BMDB IDBMDB0000796
Secondary Accession Numbers
  • BMDB00796
Metabolite Identification
Common NameN-Acetyl-4-O-acetylneuraminic acid
DescriptionN-Acetyl-4-O-acetylneuraminic acid belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety. N-Acetyl-4-O-acetylneuraminic acid is a moderately basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-Acetyl-4-O-acetylneuraminateGenerator
(2S,4S,5R,6R)-4-(Acetyloxy)-2-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator
Chemical FormulaC13H21NO10
Average Molecular Weight351.308
Monoisotopic Molecular Weight351.11654588
IUPAC Name(2S,4S,5R,6R)-4-(acetyloxy)-2-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Nameneu4,5ac2
CAS Registry NumberNot Available
SMILES
[H]C(O)(CO)[C@@]([H])(O)[C@]1([H])O[C@@](O)(C[C@]([H])(OC(C)=O)[C@@]1([H])N=C(C)O)C(O)=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-QLEAHAHXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentNeuraminic acids
Alternative Parents
Substituents
  • Neuraminic acid
  • C-glucuronide
  • C-glycosyl compound
  • Glycosyl compound
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Pyran
  • Oxane
  • Carboxylic acid ester
  • Hemiacetal
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-2.7ChemAxon
logS-0.83ALOGPS
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)2.05ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.34 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity73.45 m³·mol⁻¹ChemAxon
Polarizability31.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25201413
PDB IDNot Available
ChEBI IDNot Available
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 ReferencesNot Available