Showing metabocard for N-Acetyl-7-O-acetylneuraminic acid (BMDB0000785)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:31 UTC
Update Date2020-04-22 15:05:18 UTC
BMDB IDBMDB0000785
Secondary Accession Numbers
  • BMDB00785
Metabolite Identification
Common NameN-Acetyl-7-O-acetylneuraminic acid
DescriptionN-Acetyl-7-O-acetylneuraminic acid, also known as 7-O-acetyl-N-acetylneuraminate or neu5,7ac2, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Based on a literature review a small amount of articles have been published on N-Acetyl-7-O-acetylneuraminic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
N-Acetyl-7-O-acetylneuraminateGenerator
7-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonateHMDB
7-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acidHMDB
7-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonateHMDB
7-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acidHMDB
7-O-Acetyl-N-acetylneuraminateHMDB
7-O-Acetyl-N-acetylneuraminic acidHMDB
Neu5,7ac2HMDB
(2S,4S,5R,6R)-6-[(1R,2R)-1-(Acetyloxy)-2,3-dihydroxypropyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylateHMDB
Chemical FormulaC13H21NO10
Average Molecular Weight351.3065
Monoisotopic Molecular Weight351.116545897
IUPAC Name(2S,4S,5R,6R)-6-[(1R,2R)-1-(acetyloxy)-2,3-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-6-[(1R,2R)-1-(acetyloxy)-2,3-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid
CAS Registry Number18529-63-0
SMILES
CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](OC(C)=O)[C@H](O)CO)C(O)=O
InChI Identifier
InChI=1S/C13H21NO10/c1-5(16)14-9-7(18)3-13(22,12(20)21)24-11(9)10(8(19)4-15)23-6(2)17/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 KeyDUOKWMWKFGDUDQ-GRRZBWEESA-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
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Oxane
  • Pyran
  • Acetamide
  • Carboxamide group
  • Carboxylic acid ester
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Primary alcohol
  • 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-2.3ALOGPS
logP-3.1ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)2.97ChemAxon
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
Polarizability31.72 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 IDHMDB0000785
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022241
KNApSAcK IDNot Available
Chemspider ID17216006
KEGG Compound IDC04016
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5751
PubChem Compound12315523
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceDiaz, Sandra; Higa, Herman H.; Hayes, Bradley K.; Varki, Ajit. O-Acetylation and de-O-acetylation of sialic acids. 7- and 9-O-acetylation of a2,6-linked sialic acids on endogenous N-linked glycans in rat liver Golgi vesicles. Journal of Biological Chemistry (1989), 264(32), 19416-26.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available