N-Acetyl-7-O-acetylneuraminic acid (CHEM034957)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:22:04 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034957
Identification
Common NameN-Acetyl-7-O-acetylneuraminic acid
ClassSmall Molecule
DescriptionN-Acetyl-7-O-acetylneuraminic acid is a component of glycoprotein- and glycolipid-bound sialic acids present in the human erythrocyte membrane (RBC). (PMID: 12527384) N-Acetyl-7-O-acetylneuraminic acid has been detected in basaliomas and normal human skin. (PMID: 11180001) Determination of N-Acetyl-7-O-acetylneuraminic acid in human serum has been obtained by fluorometric high-performance liquid chromatography. (PMID: 2757191) [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass351.307 g/mol
Monoisotopic Mass351.117 g/mol
CAS Registry Number18529-63-0
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
SMILESCC(=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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility141 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-9243000000-d7ccc05692a4d75fb4ebSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00fr-3630159000-2547f8b04d7846614cacSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-0039000000-c810a0ad05cb6acc1105Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029x-2297000000-d44cbff0cda2e28ac99fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vo-9280000000-9973498389c59055966fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ll0-4796000000-91d87281166861a3c89aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9110000000-bd618fcb099eec6501fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-a3290b1a5a9d7dc02128Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0039000000-ed6b9256db9e6e59cd12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0292000000-8b38cd58da6690723f3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0296-9650000000-6bb12602eb7afffd25c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1029000000-9076b066f53831f14270Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9171000000-f7c8d0647e111d524a49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9210000000-b33c36ac1971ebaba9bdSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000785
FooDB IDFDB022241
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5751
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216006
ChEBI IDNot Available
PubChem Compound ID12315523
Kegg Compound IDC04016
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Diaz, 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.
2. 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.
3. Fahr C, Schauer R: Detection of sialic acids and gangliosides with special reference to 9-O-acetylated species in basaliomas and normal human skin. J Invest Dermatol. 2001 Feb;116(2):254-60.
4. Hara S, Yamaguchi M, Takemori Y, Furuhata K, Ogura H, Nakamura M: Determination of mono-O-acetylated N-acetylneuraminic acids in human and rat sera by fluorometric high-performance liquid chromatography. Anal Biochem. 1989 May 15;179(1):162-6.