ChemFOnt: Showing chemical card for N-Acetyl-b-D-galactosamine (CFc000000679)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:08 UTC

Chemfont ID

CFc000000679

Molecule Identification

Common Name

N-Acetyl-b-D-galactosamine

Definition

N-Acetyl-b-D-galactosamine is an oligosaccharide residue found in the lining and glandular epithelium, the stroma and the vessels (capillary and large vessels of the human postmenopausal endometrium. (PMID: 8930627 ). It is suspected that N-Acetyl-b-D-galactosamine is a molecule that binds to IgA in the glomerular mesangium in Henoch-Schoenlein purpura associated nephropathy (the most common vasculitis of childhood). (PMID: 10732728 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Acetamido-2-deoxy-beta-D-galactopyranoside	ChEBI
beta-GalNAc	ChEBI
BGalNAc	ChEBI
2-Acetamido-2-deoxy-b-D-galactopyranoside	Generator
2-Acetamido-2-deoxy-β-D-galactopyranoside	Generator
b-GalNAc	Generator
Β-galnac	Generator
2-Deoxy-2-acetamido-b-D-galactopyranose	HMDB
2-Deoxy-2-acetamido-beta-D-galactopyranose	HMDB
2-Deoxy-2-acetamido-beta-delta-galactopyranose	HMDB
b-D-2-Acetamido-2-deoxy-galactopyranose	HMDB
b-N-Acetyl-D-galactosamine	HMDB
b-N-Acetylgalactosamine	HMDB
beta-D-2-Acetamido-2-deoxy-galactopyranose	HMDB
beta-delta-2-Acetamido-2-deoxy-galactopyranose	HMDB
beta-N-Acetyl-D-galactosamine	HMDB
beta-N-Acetyl-delta-galactosamine	HMDB
beta-N-Acetylgalactosamine	HMDB
2 Acetamido 2 D galactopyranose	HMDB
2-Acetamido-2-deoxy-D-galactose	HMDB
2 Acetamido 2 deoxy D galactose	HMDB
2-Acetamido-2-D-galactopyranose	HMDB
Acetylgalactosamine	HMDB
2 Acetamido 2 deoxygalactose	HMDB
N-Acetyl-D-galactosamine	HMDB
2-Acetamido-2-deoxygalactose	HMDB
N Acetyl D galactosamine	HMDB
N-Acetyl-β-D-galactosamine	HMDB
N-Acetyl-b-D-galactosamine	Generator

Chemical Formula

C₈H₁₅NO₆

Average Molecular Weight

221.2078

Monoisotopic Molecular Weight

221.089937217

IUPAC Name

N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Traditional Name

N-acetyl-β-D-galactosamine

CAS Registry Number

14131-60-3

SMILES

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

InChI Identifier

InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1

InChI Key

OVRNDRQMDRJTHS-JAJWTYFOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide
Oxane
Hemiacetal
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alcohol
Organonitrogen compound
Organic nitrogen compound
Primary alcohol
Organopnictogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetyl-D-galactosamine (CHEBI:28497 )

Functional Ontology

Not Available

Feces (PMID: 25037050)

Source

Endogenous

Endogenous (HMDB: HMDB0000853)

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	254 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	21.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000853

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031024

KNApSAcK ID

Not Available

Chemspider ID

389452

KEGG Compound ID

C05021

BioCyc ID

CPD-12557

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5816

PubChem Compound

440552

PDB ID

Not Available

ChEBI ID

28497

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Chaplin, David; Crout, David H. G.; Bornemann, Stephen; Hutchinson, David W.; Khan, Riaz. Conversion of 2-acetamido-2-deoxy-b-D-glucopyranose (N-acetylglucosamine) into 2-acetamido-2-deoxy-b-D-galactopyranose (N-acetylgalactosamine using a biotransformation to generate a selectively deprotected substrate for SN2 inversion. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1992), (2), 235-7.

Showing chemical card for N-Acetyl-b-D-galactosamine (CFc000000679)

MOL for CFc000000679 (N-Acetyl-b-D-galactosamine)

3D MOL for CFc000000679 (N-Acetyl-b-D-galactosamine)

3D SDF for CFc000000679 (N-Acetyl-b-D-galactosamine)

3D-SDF for CFc000000679 (N-Acetyl-b-D-galactosamine)

PDB for CFc000000679 (N-Acetyl-b-D-galactosamine)

3D PDB for CFc000000679 (N-Acetyl-b-D-galactosamine)

SMILES for CFc000000679 (N-Acetyl-b-D-galactosamine)

INCHI for CFc000000679 (N-Acetyl-b-D-galactosamine)

Structure for CFc000000679 (N-Acetyl-b-D-galactosamine)

3D Structure for CFc000000679 (N-Acetyl-b-D-galactosamine)