beta-D-Glucose 1-phosphate (ECMDB20124) (M2MDB000972)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (113)
Record Information
Version2.0
Creation Date2012-05-31 14:28:45 -0600
Update Date2015-06-03 17:19:21 -0600
Secondary Accession Numbers
  • ECMDB20124
Identification
Name:beta-D-Glucose 1-phosphate
DescriptionBeta-D-glucose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Trehalose phosphorylase from Thermoanaerobacter sp. is a glycoside hydrolase family 65 enzyme which catalyzes the reversible breakdown of trehalose [D-glucopyranosyl-alpha(1,1)alpha-D-glucopyranose] to beta-D-glucose 1-phosphate and D-glucose. (PMID 20383018) SgrS is an Hfq-binding small RNA that is induced under glucose phosphate stress in Escherichia coli. (PMID 18650387)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • .alpha.-D-Glucose, 1-phosphate
  • .alpha.-D-glucose, 1-phosphoric acid
  • 1-O-phosphono-b-D-Glucopyranose
  • 1-O-Phosphono-beta-D-glucopyranose
  • 1-O-phosphono-β-D-Glucopyranose
  • 1-phospho-b-D-Glucopyranose
  • 1-Phospho-beta-D-glucopyranose
  • 1-phospho-β-D-Glucopyranose
  • b-D-Glucopyranose 1-(dihydrogen phosphate)
  • b-D-Glucopyranose 1-(dihydrogen phosphoric acid)
  • b-D-Glucose 1-phosphate
  • b-D-Glucose 1-phosphoric acid
  • Beta-D-Glucopyranose 1-(dihydrogen phosphate)
  • beta-D-Glucopyranose 1-(dihydrogen phosphoric acid)
  • beta-D-Glucose 1-phosphoric acid
  • Cori ester
  • Dol-p-GLC
  • Dolichol monophosphate glucose
  • Dolichol monophosphoric acid glucose
  • Dolichol-D-glucosylmonophosphate
  • Dolichol-D-glucosylmonophosphoric acid
  • Dolichyl monophosphate glucose
  • Dolichyl monophosphoric acid glucose
  • Dolichylglucose phosphate
  • Dolichylglucose phosphoric acid
  • Glucosylphosphodolichol
  • phospho-b-D-Glucoside
  • Phospho-beta-D-glucoside
  • phospho-β-D-Glucoside
  • β-D-Glucopyranose 1-(dihydrogen phosphate)
  • β-D-Glucopyranose 1-(dihydrogen phosphoric acid)
  • β-D-Glucose 1-phosphate
  • β-D-Glucose 1-phosphoric acid
Chemical Formula:C6H13O9P
Weight:Average: 260.1358
Monoisotopic: 260.029718526
InChI Key:HXXFSFRBOHSIMQ-DVKNGEFBSA-N
InChI:InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6+/m1/s1
CAS number:55607-88-0
IUPAC Name:{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:β-D-glucose 1-phosphate
SMILES:[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OP(O)(O)=O)[C@]1([H])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
  • Organic phosphoric acid derivative
  • Oxane
  • Alkyl phosphate
  • Phosphoric acid ester
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility32.3 g/LALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.36 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
beta-D-Glucose 1-phosphate <> beta-D-Glucose 6-phosphate
Glucose 1-phosphate > beta-D-Glucose 1-phosphate
beta-D-Glucose 1-phosphate Glucose 6-phosphate
beta-D-Glucose 1-phosphate > beta-D-Glucose 6-phosphate
SMPDB Pathways:
Starch and sucrose metabolismPW000941 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_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-d6ee97f6c2cc4c529090View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-06ae450e49c3ed95f599View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-983003b6233add18ea51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-9380000000-95d403c269465c6fe3adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-23bfc860bd8a296d442cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeView 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:
  • 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
  • Maki, K., Uno, K., Morita, T., Aiba, H. (2008). "RNA, but not protein partners, is directly responsible for translational silencing by a bacterial Hfq-binding small RNA." Proc Natl Acad Sci U S A 105:10332-10337. Pubmed: 18650387
  • Van Hoorebeke, A., Stout, J., Van der Meeren, R., Kyndt, J., Van Beeumen, J., Savvides, S. N. (2010). "Crystallization and X-ray diffraction studies of inverting trehalose phosphorylase from Thermoanaerobacter sp." Acta Crystallogr Sect F Struct Biol Cryst Commun 66:442-447. Pubmed: 20383018
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16218
HMDB IDNot Available
Pubchem Compound ID122250
Kegg IDC00663
ChemSpider ID109022
Wikipedia IDGlucose-1-phosphate
BioCyc IDCPD-448
EcoCyc IDCPD-448
Ligand ExpoXGP

Enzymes

Protein Details
1. Putative beta-phosphoglucomutase
General function:
Involved in beta-phosphoglucomutase activity
Specific function:
Reversible transformation of glucose 6-phosphate and beta-glucose 1-phosphate
Gene Name:
ycjU
Uniprot ID:
P77366
Molecular weight:
23565
Reactions
Beta-D-glucose 1-phosphate = beta-D-glucose 6-phosphate.