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D-Galactosamine 6-phosphate (M2MDB000989)

Record Information
Version2.0
Creation Date2012-05-31 14:29:40 -0600
Update Date2015-06-03 17:19:23 -0600
Secondary Accession Numbers
  • ECMDB20141
Identification
Name:D-Galactosamine 6-phosphate
DescriptionD-galactosamine 6-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. D-Galactosamine 6-phosphate is a metabolite in amino sugar catabolism. The GlcNAc6P deacetylase is an enzyme of the amino sugar catabolic pathway that catalyzes the conversion of the GlcNAc6P into glucosamine 6-phosphate (GlcN6P). (PMID 16630633) Glucosamine 6-phosphate (GlcN-6-P) synthase is an ubiquitous enzyme that catalyses the first committed step in the reaction pathway that leads to formation of uridine 5'-diphospho-N-acetyl-D-glucosamine (UDP-GlcNAc), a precursor of macromolecules that contain amino sugars. (PMID 17681543)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Amino-2-deoxy-6-O-phosphono-D-galactopyranose
  • 2-Amino-2-deoxy-D-galactopyranose 6-(dihydrogen phosphate)
  • 2-amino-2-Deoxy-D-galactopyranose 6-(dihydrogen phosphoric acid)
  • D-Galactosamine 6-phosphoric acid
  • Glucosamine 6-phosphate
  • Glucosamine 6-phosphoric acid
Chemical Formula:C6H14NO8P
Weight:Average: 259.151
Monoisotopic: 259.045702941
InChI Key:XHMJOUIAFHJHBW-GASJEMHNSA-N
InChI:InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3R,4R,5R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:D-galactosamine 6-phosphate
SMILES:[H]C1(O)O[C@]([H])(COP(O)(O)=O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Amino saccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Hemiacetal
  • 1,2-diol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Primary amine
  • Alcohol
  • 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 Solubility34.8 g/LALOGPS
logP-2.6ALOGPS
logP-4.2ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area162.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability21.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
D-Galactosamine 6-phosphate + Water <> D-Tagatose 6-phosphate + Ammonia
D-Galactosamine + Protein N(pi)-phospho-L-histidine <> D-Galactosamine 6-phosphate + Protein histidine
N-Acetyl-D-galactosamine 6-phosphate + Water > D-Galactosamine 6-phosphate + Acetic acid
D-Galactosamine 6-phosphate + Water > D-Tagatose 6-phosphate + Ammonia
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_6_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-3c374446d4c91ce17f62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-7940000000-d6a5dc695f4ff653a09fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fka-9500000000-ef7d98d3e5f6d2a7c45bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0690-8950000000-46dee61503f6654422edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-35a6a1eb1e9b04c8362eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f46b7c78452e48986ad1View 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:
  • Ferreira, F. M., Mendoza-Hernandez, G., Castaneda-Bueno, M., Aparicio, R., Fischer, H., Calcagno, M. L., Oliva, G. (2006). "Structural analysis of N-acetylglucosamine-6-phosphate deacetylase apoenzyme from Escherichia coli." J Mol Biol 359:308-321. Pubmed: 16630633
  • 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
  • Raczynska, J., Olchowy, J., Konariev, P. V., Svergun, D. I., Milewski, S., Rypniewski, W. (2007). "The crystal and solution studies of glucosamine-6-phosphate synthase from Candida albicans." J Mol Biol 372:672-688. Pubmed: 17681543
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18232
HMDB IDNot Available
Pubchem Compound ID5460111
Kegg IDC06377
ChemSpider ID4573772
Wikipedia IDNot Available
BioCyc IDD-GALACTOSAMINE-6-PHOSPHATE
EcoCyc IDD-GALACTOSAMINE-6-PHOSPHATE

Enzymes

Protein Details
1. Putative N-acetylgalactosamine-6-phosphate deacetylase
General function:
Involved in hydrolase activity
Specific function:
N-acetyl-D-galactosamine 6-phosphate + H(2)O = D-galactosamine 6-phosphate + acetate
Gene Name:
agaA
Uniprot ID:
P42906
Molecular weight:
17519
Reactions
N-acetyl-D-galactosamine 6-phosphate + H(2)O = D-galactosamine 6-phosphate + acetate.
Protein Details
2. 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
3. Putative galactosamine-6-phosphate isomerase
General function:
Involved in carbohydrate metabolic process
Specific function:
D-galactosamine 6-phosphate + H(2)O = D- tagatose 6-phosphate + NH(3)
Gene Name:
agaI
Uniprot ID:
P42912
Molecular weight:
27724
Reactions
D-galactosamine 6-phosphate + H(2)O = D-tagatose 6-phosphate + NH(3).
Protein Details
4. 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
5. 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