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
Description:N-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
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.65 m3·mol-1ChemAxon
Polarizability24.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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
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

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

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