NP-MRD: Showing NP-Card for N-Acetyl-beta-D-galactosamine (NP0334605)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-10 19:06:52 UTC

Updated at

2024-09-10 19:06:52 UTC

NP-MRD ID

NP0334605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-beta-D-galactosamine

Description

N-Acetyl-b-D-galactosamine, also known as beta-galnac or β-galnac, 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. An N-acetyl-D-galactosamine having beta-configuration at the anomeric centre. N-Acetyl-b-D-galactosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-b-D-galactosamine exists in all living organisms, ranging from bacteria to humans. Outside of the human body, N-Acetyl-b-D-galactosamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, purple mangosteens, savoy cabbages, common beets, and wax gourds. N-Acetyl-beta-D-galactosamine was first documented in 1999 (PMID: 10732728). This could make N-acetyl-b-D-galactosamine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231216422D          

 15 15  0  0  1  0            999 V2000
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334605

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C8H15NO6

> <MOLECULAR_WEIGHT>
221.2078

> <EXACT_MASS>
221.089937217

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.03656445486596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.60

> <JCHEM_LOGP>
-3.220574411666667

> <ALOGPS_LOGS>
0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.811681816701025

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.604129514800581

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7815744979932194

> <JCHEM_POLAR_SURFACE_AREA>
119.25000000000001

> <JCHEM_REFRACTIVITY>
47.024699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-β-D-galactosamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

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 Mass

221.2078 Da

Monoisotopic Mass

221.08994 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

FoodDB 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

Good Scents ID

Not Available

References

General References

Sediva A, Stejskal J, Bartunkova J, Smetana K Jr, Gabius HJ: Detection of alpha(beta)-N-acetyl-D-galactosamine-binding sites in kidney--relation to Henoch-Schonlein-associated IgA nephropathy. Folia Biol (Praha). 1999;45(4):147-50. [PubMed:10732728 ]

Showing NP-Card for N-Acetyl-beta-D-galactosamine (NP0334605)

MOL for NP0334605 (N-Acetyl-beta-D-galactosamine)

3D MOL for NP0334605 (N-Acetyl-beta-D-galactosamine)

3D SDF for NP0334605 (N-Acetyl-beta-D-galactosamine)

3D-SDF for NP0334605 (N-Acetyl-beta-D-galactosamine)

PDB for NP0334605 (N-Acetyl-beta-D-galactosamine)

3D PDB for NP0334605 (N-Acetyl-beta-D-galactosamine)

SMILES for NP0334605 (N-Acetyl-beta-D-galactosamine)

INCHI for NP0334605 (N-Acetyl-beta-D-galactosamine)

Structure for NP0334605 (N-Acetyl-beta-D-galactosamine)

3D Structure for NP0334605 (N-Acetyl-beta-D-galactosamine)