Showing metabocard for N-Acetyl-9-O-acetylneuraminic acid (BMDB0000794)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:40 UTC
Update Date2020-04-22 15:05:21 UTC
BMDB IDBMDB0000794
Secondary Accession Numbers
  • BMDB00794
Metabolite Identification
Common NameN-Acetyl-9-O-acetylneuraminic acid
DescriptionN-Acetyl-9-O-acetylneuraminic acid, also known as 9-anana or 9-O-acetylsialic acid, belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety. Based on a literature review a significant number of articles have been published on N-Acetyl-9-O-acetylneuraminic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
9-AnanaChEBI
9-O-Acetyl-N-acetylneuraminic acidChEBI
9-O-Acetylsialic acidChEBI
9-O-Acetyl-N-acetylneuraminateGenerator
9-O-AcetylsialateGenerator
N-Acetyl-9-O-acetylneuraminateGenerator
N,9-O-DiacetylneuraminateHMDB
N,9-O-Diacetylneuraminic acidHMDB
Neu5,9ac2HMDB
Chemical FormulaC13H21NO10
Average Molecular Weight351.3065
Monoisotopic Molecular Weight351.116545897
IUPAC Name(2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
Traditional Name9-O-acetylsialic acid
CAS Registry Number55717-54-9
SMILES
CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)COC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C13H21NO10/c1-5(15)14-9-7(17)3-13(22,12(20)21)24-11(9)10(19)8(18)4-23-6(2)16/h7-11,17-19,22H,3-4H2,1-2H3,(H,14,15)(H,20,21)/t7-,8+,9+,10+,11+,13-/m0/s1
InChI KeyNYWZBRWKDRMPAS-GRRZBWEESA-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
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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-2.4ALOGPS
logP-3.1ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area182.85 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity72.93 m³·mol⁻¹ChemAxon
Polarizability31.82 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 IDHMDB0000794
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022249
KNApSAcK IDNot Available
Chemspider ID110484
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5759
PubChem Compound123962
PDB IDNot Available
ChEBI ID21500
References
Synthesis ReferenceForstner, Michael; Freytag, Katharina; Paschke, Eduard. A simple, one-step synthesis of N-acetyl-9-O-acetylneuraminic acid by enzymic transesterification mediated by porcine pancreas lipase in pyridine. Carbohydrate Research (1989), 193 294-5.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available