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Glucosamine-1P (M2MDB000256)

Record Information
Version2.0
Creation Date2012-05-31 13:45:20 -0600
Update Date2015-09-17 15:41:08 -0600
Secondary Accession Numbers
  • ECMDB01109
Identification
Name:Glucosamine-1P
DescriptionGlucosamine-1p is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Glucosamine-1P is a substrate of enzyme UDP-N-acetylglucosamine diphosphorylase [EC 2.7.7.23] (KEGG).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • α-D-glucosamine 1-phosphate
  • α-D-glucosamine 1-phosphoric acid
  • α-D-glucosamine 1P
  • a-D-Glucosamine 1-phosphate
  • a-D-Glucosamine 1-phosphoric acid
  • a-D-Glucosamine 1P
  • a-delta-Glucosamine 1-phosphate
  • a-delta-Glucosamine 1-phosphoric acid
  • a-delta-Glucosamine 1P
  • a-δ-Glucosamine 1-phosphate
  • a-δ-Glucosamine 1-phosphoric acid
  • a-δ-Glucosamine 1P
  • Alpha-D-Glucosamine 1-phosphate
  • alpha-D-Glucosamine 1-phosphoric acid
  • Alpha-D-Glucosamine 1P
  • Alpha-delta-glucosamine 1-phosphate
  • alpha-delta-Glucosamine 1-phosphoric acid
  • Alpha-delta-glucosamine 1P
  • Glucosamine-1P
  • 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
  • α-D-Glucosamine 1P
  • α-δ-Glucosamine 1-phosphate
  • α-δ-Glucosamine 1-phosphoric acid
  • α-δ-Glucosamine 1P
Chemical Formula:C6H14NO8P
Weight:Average: 259.151
Monoisotopic: 259.045702941
InChI Key:YMJBYRVFGYXULK-UKFBFLRUSA-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:{[3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name: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 DescriptorsNot Available
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
Polarizability21.26 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Uridine triphosphate + Glucosamine-1P <> Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
Acetyl-CoA + alpha-D-Glucosamine 1-phosphate <> Coenzyme A + Glucosamine-1P
Glucosamine-1P + Acetyl-CoA > Hydrogen ion + <i>N</i>-acetyl-&alpha;-D-glucosamine 1-phosphate + Coenzyme A
Glucosamine-1P <> Glucosamine 6-phosphate
Glucosamine 6-phosphate <> Glucosamine-1P + Glucosamine-1P
Glucosamine-1P + Acetyl-CoA + Glucosamine-1P > N-Acetyl-glucosamine 1-phosphate + Coenzyme A + Hydrogen ion + N-Acetyl-glucosamine 1-phosphate
D-glucosamine 6-phosphate <> Glucosamine-1P
Uridine triphosphate + Glucosamine-1P <> Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
Acetyl-CoA + alpha-D-Glucosamine 1-phosphate <> Coenzyme A + Glucosamine-1P
SMPDB Pathways:
1,6-anhydro-<i>N</i>-acetylmuramic acid recyclingPW002064 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
O-antigen building blocks biosynthesisPW002089 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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:
  • 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 ID16446
HMDB IDHMDB01109
Pubchem Compound ID740
Kegg IDC04501
ChemSpider ID720
Wikipedia IDNot Available
BioCyc IDGLUCOSAMINE-1P
EcoCyc IDGLUCOSAMINE-1P

Enzymes

Protein Details
1. Bifunctional protein glmU
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.
Protein Details
2. Phosphoglucosamine mutase
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.