ChemFOnt: Showing chemical card for N-Acetyl-7-O-acetylneuraminic acid (CFc000000625)

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

CFc000000625

Molecule Identification

Common Name

N-Acetyl-7-O-acetylneuraminic acid

Definition

N-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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetyl-7-O-acetylneuraminate	Generator
7-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate	HMDB
7-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid	HMDB
7-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonate	HMDB
7-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid	HMDB
7-O-Acetyl-N-acetylneuraminate	HMDB
7-O-Acetyl-N-acetylneuraminic acid	HMDB
Neu5,7ac2	HMDB
(2S,4S,5R,6R)-6-[(1R,2R)-1-(Acetyloxy)-2,3-dihydroxypropyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylate	HMDB

Chemical Formula

C₁₃H₂₁NO₁₀

Average Molecular Weight

351.3065

Monoisotopic Molecular Weight

351.116545897

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 Number

18529-63-0

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 Key

DUOKWMWKFGDUDQ-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000785)

Source

Endogenous

Endogenous (HMDB: HMDB0000785)

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	141 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.1	ChemAxon
logS	-0.4	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	31.72 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

HMDB0000785

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022241

KNApSAcK ID

Not Available

Chemspider ID

17216006

KEGG Compound ID

C04016

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5751

PubChem Compound

12315523

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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.

Showing chemical card for N-Acetyl-7-O-acetylneuraminic acid (CFc000000625)

MOL for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

3D MOL for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

3D SDF for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

3D-SDF for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

PDB for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

3D PDB for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

SMILES for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

INCHI for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

Structure for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)

3D Structure for CFc000000625 (N-Acetyl-7-O-acetylneuraminic acid)