ECMDB: N-Acetyl-b-D-galactosamine (ECMDB00853) (M2MDB000193)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)Transporters (7)XML

Proteins (9)

Record Information

Version

2.0

Creation Date

2012-05-31 13:01:37 -0600

Update Date

2015-06-03 15:53:36 -0600

Secondary Accession Numbers

ECMDB00853

Identification

Name:

N-Acetyl-b-D-galactosamine

Description

N-Acetyl-b-D-galactosamine is one of the eight essential sugars. It is important for cell communication. In galactose metabolism pathway, it is converted to N-Acetyl-b-D-galactosamine-6P by N-acetylgalactosamine-specific phosphotransferase enzyme B (EC 2.7.1.69).

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Deoxy-2-acetamido-b-D-galactopyranose
2-Deoxy-2-acetamido-b-delta-galactopyranose
2-Deoxy-2-acetamido-b-δ-galactopyranose
2-Deoxy-2-acetamido-beta-D-galactopyranose
2-Deoxy-2-acetamido-beta-delta-galactopyranose
2-Deoxy-2-acetamido-β-D-galactopyranose
2-Deoxy-2-acetamido-β-δ-galactopyranose
B-D-2-Acetamido-2-deoxy-Galactopyranose
b-delta-2-acetamido-2-Deoxy-galactopyranose
B-N-Acetyl-D-galactosamine
b-N-Acetyl-delta-galactosamine
b-N-Acetyl-δ-galactosamine
B-N-Acetylgalactosamine
b-δ-2-acetamido-2-Deoxy-galactopyranose
Beta-D-2-Acetamido-2-deoxy-Galactopyranose
Beta-delta-2-Acetamido-2-deoxy-Galactopyranose
Beta-N-Acetyl-D-galactosamine
Beta-N-Acetyl-delta-galactosamine
Beta-N-Acetylgalactosamine
β-D-2-acetamido-2-Deoxy-galactopyranose
β-N-Acetyl-D-galactosamine
β-N-Acetyl-δ-galactosamine
β-N-Acetylgalactosamine
β-δ-2-acetamido-2-Deoxy-galactopyranose

Chemical Formula:

C₈H₁₅NO₆

Weight:

Average: 221.2078
Monoisotopic: 221.089937217

InChI Key:

OVRNDRQMDRJTHS-JAJWTYFOSA-N

InChI:

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

CAS number:

14131-60-3

IUPAC Name:

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

Traditional IUPAC Name:

N-acetyl-β-D-galactosamine

SMILES:

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

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:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Water + Globoside <> N-Acetyl-b-D-galactosamine + Globotriaosylceramide
GM2 + Water <> GM3 + N-Acetyl-b-D-galactosamine
G13033 + Water <> G08421 + N-Acetyl-b-D-galactosamine
G06780 + Water <> G08421 + N-Acetyl-b-D-galactosamine
N-Acetyl-b-D-galactosamine + Protein N(pi)-phospho-L-histidine <> N-Acetyl-D-galactosamine 6-phosphate + Protein histidine

SMPDB Pathways:

Galactose metabolism

PW000821

KEGG Pathways:

Galactose metabolism ec00052
Phosphotransferase system (PTS) ec02060

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-6920000000-c07df80c6fb758af9cd2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0007-3331900000-c6fab10d67507eecce65	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1490000000-40dfe33adabe6ad7a7a8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0il0-2940000000-880c7b1fb58ed63f0ee2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9400000000-e1f07558d7921e9f24e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05g0-8920000000-d504941e0508d1593f33	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9820000000-753556be259b7e745ba7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-bad102d081eb3bbc006b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0390000000-3820a7eec5a8c72f49d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h90-9740000000-db880363194a3979c637	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0229-9200000000-cdcf015aa799dc7d6d8b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9500000000-2c2b09cb6bfb29039085	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abc-9540000000-a1f7d557237a521d306a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-18eabe9e3d3657888360	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Barbas C, Garcia A, de Miguel L, Simo C: Evaluation of filter paper collection of urine samples for detection and measurement of organic acidurias by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 15;780(1):73-82. Pubmed: 12383482
Garcia A, Barbas C, Aguilar R, Castro M: Capillary electrophoresis for rapid profiling of organic acidurias. Clin Chem. 1998 Sep;44(9):1905-11. Pubmed: 9732975
Gheri G, Bryk SG, Taddei G, Moncini D, Noci I: Sugar residues content and distribution in atrophic and hyperplastic postmenopausal human endometrium: lectin histochemistry. Histol Histopathol. 1996 Oct;11(4):861-7. Pubmed: 8930627
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
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

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 biotransformat

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	28497
HMDB ID	HMDB00853
Pubchem Compound ID	440552
Kegg ID	C05021
ChemSpider ID	389452
Wikipedia ID	Not Available
BioCyc ID	Not Available
Ligand Expo	NGA

Enzymes

Protein Details

1. N-acetylgalactosamine-specific phosphotransferase enzyme IIB component 2

General function:: Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylgalactosamine transport
Gene Name:: agaV
Uniprot ID:: P42904
Molecular weight:: 17086

Reactions

Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

Protein Details

2. Beta-hexosaminidase

General function:: Involved in beta-N-acetylhexosaminidase activity
Specific function:: Cleaves GlcNAc linked beta-1,4 to MurNAc tripeptides
Gene Name:: nagZ
Uniprot ID:: P75949
Molecular weight:: 37594

Reactions

Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides.

Protein Details

3. N-acetylgalactosamine permease IIC component 1

General function:: Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in N-acetylgalactosamine transport
Gene Name:: agaC
Uniprot ID:: P42910
Molecular weight:: 28645

Protein Details

4. N-acetylgalactosamine permease IID component

General function:: Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in N-acetylgalactosamine transport
Gene Name:: agaD
Uniprot ID:: P42911
Molecular weight:: 29001

Transporters

Protein Details

1. Putative N-acetylgalactosamine permease IIC component 2

General function:: Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in N-acetylgalactosamine transport
Gene Name:: agaW
Uniprot ID:: P42905
Molecular weight:: 13721

Protein Details

2. N-acetylgalactosamine permease IIC component 1

General function:: Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in N-acetylgalactosamine transport
Gene Name:: agaC
Uniprot ID:: P42910
Molecular weight:: 28645

Protein Details

3. N-acetylgalactosamine permease IID component

General function:: Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in N-acetylgalactosamine transport
Gene Name:: agaD
Uniprot ID:: P42911
Molecular weight:: 29001

Protein Details

4. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

5. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

6. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

7. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

N-Acetyl-b-D-galactosamine (ECMDB00853) (M2MDB000193)

Structure for #<Compound:0x84e27960>

Enzymes

Reactions

Reactions

Transporters