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N-Acetyl-D-galactosamine 1-phosphate (M2MDB001655)

Record Information
Version2.0
Creation Date2012-07-30 14:55:06 -0600
Update Date2015-06-03 17:21:00 -0600
Secondary Accession Numbers
  • ECMDB21247
Identification
Name:N-Acetyl-D-galactosamine 1-phosphate
DescriptionN-Acetyl-D-galactosamine 1-phosphate is an intermediate in amino sugar metabolism. The enzyme UDP-N-acetylgalactosamine diphosphorylase catalyzes the conversion of this metabolite into UDP-N-acetyl-D-galactosamine. In the same pathway, the enzyme N-acetylgalactosamine kinase catalyzes the phosphorylation of this metabolite from N-Acetyl-D-galactosamine using ATP or ITP. These two reactions are irreversible and occur in the cytosol. (BiGG database)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • N- Acetyl-a-D-galactosamine 1-phosphate
  • N- Acetyl-a-D-galactosamine 1-phosphoric acid
  • N- Acetyl-a-delta-galactosamine 1-phosphate
  • N- Acetyl-a-delta-galactosamine 1-phosphoric acid
  • N- Acetyl-a-δ-galactosamine 1-phosphate
  • N- Acetyl-a-δ-galactosamine 1-phosphoric acid
  • N- Acetyl-alpha-D-galactosamine 1-phosphate
  • N- Acetyl-alpha-D-galactosamine 1-phosphoric acid
  • N- Acetyl-alpha-delta-galactosamine 1-phosphate
  • N- Acetyl-alpha-delta-galactosamine 1-phosphoric acid
  • N- Acetyl-α-D-galactosamine 1-phosphate
  • N- Acetyl-α-D-galactosamine 1-phosphoric acid
  • N- Acetyl-α-δ-galactosamine 1-phosphate
  • N- Acetyl-α-δ-galactosamine 1-phosphoric acid
  • N-Acetyl-D-galactosamine 1-phosphate
  • N-Acetyl-D-galactosamine 1-phosphoric acid
Chemical Formula:C8H14NO9P
Weight:Average: 299.1718
Monoisotopic: 299.040617563
InChI Key:FZLJPEPAYPUMMR-JAJWTYFOSA-L
InChI:InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/p-2/t4-,5-,6+,7-,8-/m1/s1
CAS number:Not Available
IUPAC Name:(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl phosphate
Traditional IUPAC Name:(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl phosphate
SMILES:[H]OC([H])([H])[C@@]1([H])O[C@]([H])(OP([O-])([O-])=O)[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@@]([H])(O[H])[C@@]1([H])O[H]
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility51.8 g/LALOGPS
logP-2.2ALOGPS
logP-3.3ChemAxon
logS-0.81ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area171.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.65 m³·mol⁻¹ChemAxon
Polarizability24.74 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + Uridine diphosphate-N-acetylgalactosamine > N-Acetyl-D-galactosamine 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-7dee6cdc2ef63f935dfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2191000000-f590ecb73b66856cac3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r6-9210000000-8a6f355306bbba5b9153View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9430000000-5954701eba8bd70095f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aba-9540000000-f8470d3f4e85ae8bd830View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-2d76753ed2405ffbee42View 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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61970
HMDB IDHMDB06480
Pubchem Compound ID49859685
Kegg IDC18060
ChemSpider ID26332459
Wikipedia IDNot Available
BioCyc IDCPD-7246
EcoCyc IDCPD-7246

Enzymes

Protein Details
1. Protein ushA
General function:
Involved in hydrolase activity
Specific function:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.

Transporters

Protein Details
1. 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
2. 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
3. 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
4. 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