Record Information
Version2.0
Creation Date2012-08-15 08:51:37 -0600
Update Date2015-06-03 17:22:02 -0600
Secondary Accession Numbers
  • ECMDB21662
Identification
Name:alpha-D-Glucosamine 1-phosphate
DescriptionAlpha-D-glucosamine 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. It is involved and amino sugar and nucleotide sugar metabolism.
Structure
Thumb
Synonyms:
  • 2-amino-2-Deoxy-1-O-phosphono-a-D-glucopyranose
  • 2-Amino-2-deoxy-1-O-phosphono-alpha-D-glucopyranose
  • 2-amino-2-Deoxy-1-O-phosphono-α-D-glucopyranose
  • 2-amino-2-Deoxy-a-D-glucopyranose 1-(dihydrogen phosphate)
  • 2-amino-2-Deoxy-a-D-glucopyranose 1-(dihydrogen phosphoric acid)
  • 2-Amino-2-deoxy-alpha-D-glucopyranose 1-(dihydrogen phosphate)
  • 2-amino-2-Deoxy-alpha-D-glucopyranose 1-(dihydrogen phosphoric acid)
  • 2-amino-2-Deoxy-α-D-glucopyranose 1-(dihydrogen phosphate)
  • 2-amino-2-Deoxy-α-D-glucopyranose 1-(dihydrogen phosphoric acid)
  • a-D-Glucosamine 1-phosphate
  • a-D-Glucosamine 1-phosphoric acid
  • Alpha-D-Glucosamine 1-phosphate
  • alpha-D-Glucosamine 1-phosphoric acid
  • D-Glucosamine 1-phosphate
  • D-Glucosamine 1-phosphoric acid
  • GLUCOSAMINE 1-PHOSPHATE
  • GLUCOSAMINE 1-phosphoric acid
  • N-Acetyl-a-D-glucosamine 1-phosphate
  • N-Acetyl-a-D-glucosamine 1-phosphoric acid
  • N-Acetyl-alpha-D-glucosamine 1-phosphate
  • N-Acetyl-alpha-D-glucosamine 1-phosphoric acid
  • N-Acetyl-α-D-glucosamine 1-phosphate
  • N-Acetyl-α-D-glucosamine 1-phosphoric acid
  • α-D-Glucosamine 1-phosphate
  • α-D-Glucosamine 1-phosphoric acid
Chemical Formula:C6H14NO8P
Weight:Average: 259.151
Monoisotopic: 259.045702941
InChI Key:YMJBYRVFGYXULK-QZABAPFNSA-N
InChI:InChI=1S/C6H14NO8P/c7-3-5(10)4(9)2(1-8)14-6(3)15-16(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,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:α-D-glucosamine 1-phosphate
SMILES:N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Amino saccharide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Primary alcohol
  • Primary amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • 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 Solubility35.1 g/LALOGPS
logP-2.6ALOGPS
logP-4.2ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)8.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area162.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability21.24 ųChemAxon
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:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9010000000-4a4369962a02bbefd288View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-1390000000-19b3065167a88b742febView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ow-9550000000-52be51437d4b754c9a4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-b0eb00d809084bbdb3d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054t-9010000000-da9819227ffe756d390bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-42c6841338922884a12aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-21af41c3ae65f0ccd866View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27625
HMDB IDNot Available
Pubchem Compound ID25243931
Kegg IDC06156
ChemSpider ID26331214
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoGP1

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the last two sequential reactions in the de novo biosynthetic pathway for UDP-GlcNAc. Responsible for the acetylation of Glc-N-1-P to give GlcNAc-1-P and for the uridyl transfer from UTP to GlcNAc-1-P which produces UDP-GlcNAc
Gene Name:
glmU
Uniprot ID:
P0ACC7
Molecular weight:
49190
Reactions
Acetyl-CoA + alpha-D-glucosamine 1-phosphate = CoA + N-acetyl-alpha-D-glucosamine 1-phosphate.
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate = diphosphate + UDP-N-acetyl-D-glucosamine.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Catalyzes the conversion of glucosamine-6-phosphate to glucosamine-1-phosphate. Can also catalyze the formation of glucose-6-P from glucose-1-P, although at a 1400-fold lower rate
Gene Name:
glmM
Uniprot ID:
P31120
Molecular weight:
47543
Reactions
Alpha-D-glucosamine 1-phosphate = D-glucosamine 6-phosphate.