ChemFOnt: Showing chemical card for N-Acetyl-4-O-acetylneuraminic acid (CFc000000636)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:05 UTC

Chemfont ID

CFc000000636

Molecule Identification

Common Name

N-Acetyl-4-O-acetylneuraminic acid

Definition

N-Acetyl-4-O-acetylneuraminic acid is a component of glycoprotein- and glycolipid-bound sialic acids present in the human erythrocyte membrane (RBC). (PMID: 12527384 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetyl-4-O-acetylneuraminate	Generator
N,4-O-Diacetylneuraminate	HMDB
N,4-O-Diacetylneuraminic acid	HMDB
4-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate	HMDB
4-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid	HMDB
4-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonate	HMDB
4-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid	HMDB
4-O-Acetyl-N-acetylneuraminate	HMDB
4-O-Acetyl-N-acetylneuraminic acid	HMDB
Neu4,5ac2	HMDB
N-Acetyl-4-O-acetylneuraminic acid	Generator

Chemical Formula

C₁₃H₂₁NO₁₀

Average Molecular Weight

351.3065

Monoisotopic Molecular Weight

351.116545897

IUPAC Name

(2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

Traditional Name

(2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

CAS Registry Number

16655-75-7

SMILES

CC(=O)N[C@@H]1[C@H](C[C@](O)(O[C@H]1C(O)C(O)CO)C(O)=O)OC(C)=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 Key

LVBIMVQYUKOENY-FODKYPIKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide sulfate
Monosaccharide
Oxane
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Acetamide
1,2-diol
Carboxamide group
Hemiacetal
Secondary alcohol
Secondary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucosamine sulfate (CHEBI:28132 )
amino monosaccharide (CHEBI:28132 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000796)

Source

Endogenous

Endogenous (HMDB: HMDB0000796)

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	135 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.1	ChemAxon
logS	-0.42	ALOGPS
pKa (Strongest Acidic)	2.97	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	31.77 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

HMDB0000796

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022250

KNApSAcK ID

Not Available

Chemspider ID

389185

KEGG Compound ID

C04015

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5761

PubChem Compound

440197

PDB ID

Not Available

ChEBI ID

32844

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Ogura, 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

Showing chemical card for N-Acetyl-4-O-acetylneuraminic acid (CFc000000636)

MOL for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

3D MOL for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

3D SDF for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

3D-SDF for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

PDB for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

3D PDB for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

SMILES for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

INCHI for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

Structure for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)

3D Structure for CFc000000636 (N-Acetyl-4-O-acetylneuraminic acid)