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D-Galactosamine (M2MDB000990)

Record Information
Version2.0
Creation Date2012-05-31 14:29:43 -0600
Update Date2015-06-03 17:19:24 -0600
Secondary Accession Numbers
  • ECMDB20142
Identification
Name:D-Galactosamine
DescriptionD-galactosamine is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. D-Galactosamine is an amino sugar with unique hepatotoxic properties in animals. (PMID 6338507)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 2-Amino-2-deoxy-D-galactopyranose
  • 2-Amino-2-deoxy-D-galactose
  • Chondrosamine
  • D-2-Amino-2-deoxygalactose
  • D-Chondrosamine
  • D-galactosamine
  • Galactosamine
Chemical Formula:C6H13NO5
Weight:Average: 179.1711
Monoisotopic: 179.079372531
InChI Key:MSWZFWKMSRAUBD-GASJEMHNSA-N
InChI:InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1
CAS number:7535-00-4
IUPAC Name:(3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
Traditional IUPAC Name:galactosamine
SMILES:N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Amino saccharide
  • Oxane
  • 1,2-aminoalcohol
  • Hemiacetal
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Primary amine
  • Primary alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility551 g/LALOGPS
logP-2.7ALOGPS
logP-3ChemAxon
logS0.49ALOGPS
pKa (Strongest Acidic)11.73ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area116.17 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.58 m³·mol⁻¹ChemAxon
Polarizability16.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
D-Galactosamine + Protein N(pi)-phospho-L-histidine <> D-Galactosamine 6-phosphate + Protein histidine
SMPDB Pathways:
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-4c88765919efa0ec2d2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-6900000000-35b62c4724107254a605View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9100000000-3b923e9190cb9ae0466dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9500000000-de552b6c9f3baeb971b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-8900000000-d9a57d2482e40372611bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-59bf0c107fd599151d43View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Camara, D. S., Caruana, J. A. Jr, Schwartz, K. A., Montes, M., Nolan, J. P. (1983). "D-Galactosamine liver injury: absorption of endotoxin and protective effect of small bowel and colon resection in rabbits." Proc Soc Exp Biol Med 172:255-259. Pubmed: 6338507
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28328
HMDB IDNot Available
Pubchem Compound ID24154
Kegg IDC02262
ChemSpider ID22576
Wikipedia IDGalactosamine
BioCyc IDGALACTOSAMINE
EcoCyc IDGALACTOSAMINE

Enzymes

Protein Details
1. N-acetylgalactosamine-specific phosphotransferase enzyme IIB component 1
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:
agaB
Uniprot ID:
P42909
Molecular weight:
17622
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
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

Transporters

Protein Details
1. 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
2. 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