ChemFOnt: Showing chemical card for N-Acetyl-9-O-acetylneuraminic acid (CFc000000634)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:04 UTC

Chemfont ID

CFc000000634

Molecule Identification

Common Name

N-Acetyl-9-O-acetylneuraminic acid

Definition

N-Acetyl-9-O-acetylneuraminic acid (alternatively 9-O-acetyl-N-acetylneuraminic acid) is an O acetylated sialic acid identified in human colon by using high-pressure liquid chromatography and gas-liquid chromatography/mass spectrometry (PMID 3623000 ). It also has been suggested that 9-O-acetyl-N-acetylneuraminic acid is an essential component of the cell surface receptor of influenza C virus (PMID 3700379 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9-Anana	ChEBI
9-O-Acetyl-N-acetylneuraminic acid	ChEBI
9-O-Acetylsialic acid	ChEBI
9-O-Acetyl-N-acetylneuraminate	Generator
9-O-Acetylsialate	Generator
N-Acetyl-9-O-acetylneuraminate	Generator
N,9-O-Diacetylneuraminate	HMDB
N,9-O-Diacetylneuraminic acid	HMDB
Neu5,9ac2	HMDB

Chemical Formula

C₁₃H₂₁NO₁₀

Average Molecular Weight

351.3065

Monoisotopic Molecular Weight

351.116545897

IUPAC Name

(2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

9-O-acetylsialic acid

CAS Registry Number

55717-54-9

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 Key

NYWZBRWKDRMPAS-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Neuraminic 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetyl-O-acetylneuraminic acid (CHEBI:21500 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000794)

Source

Endogenous

Endogenous (HMDB: HMDB0000794)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	103 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.1	ChemAxon
logS	-0.53	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	182.85 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.93 m³·mol⁻¹	ChemAxon
Polarizability	31.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000794

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022249

KNApSAcK ID

Not Available

Chemspider ID

110484

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5759

PubChem Compound

123962

PDB ID

Not Available

ChEBI ID

21500

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Forstner, 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.

Showing chemical card for N-Acetyl-9-O-acetylneuraminic acid (CFc000000634)

MOL for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

3D MOL for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

3D SDF for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

3D-SDF for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

PDB for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

3D PDB for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

SMILES for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

INCHI for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

Structure for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)

3D Structure for CFc000000634 (N-Acetyl-9-O-acetylneuraminic acid)