Identification
YMDB IDYMDB00970
Namealpha-D-glucose 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionα-D-Glucose 1-phosphate, also known as alpha-D-glucose-1-phosphate or cori ester, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. α-D-Glucose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). α-D-Glucose 1-phosphate exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • 1-O-phosphono-alpha-D-glucopyranose
  • a-D-Glucopyranosyl phosphate
  • a-D-Glucose 1-phosphate
  • alpha-D-Glucopyranosyl phosphate
  • alpha-D-Glucose 1-phosphate
  • alpha-d-glucose-1-phosphate
  • alpha-delta-Glucopyranosyl phosphate
  • alpha-delta-Glucose 1-phosphate
  • alpha-delta-glucose-1-phosphate
  • cori ester
  • D-Glucopyranose 1-phosphate
  • D-glucose 1-phosphate
  • D-Glucose alpha-1-phosphate
  • D-glucose-1-P
  • D-Glucose-1-phosphate
  • delta-Glucopyranose 1-phosphate
  • delta-glucose 1-phosphate
  • delta-glucose-1-P
  • delta-Glucose-1-phosphate
  • glucose 1-phosphate
  • Glucose 1-phosphic acid
  • Glucose monophosphate
  • Glucose-1-phosphate
  • glucose-1P
  • 1-O-Phosphono-a-D-glucopyranose
  • 1-O-Phosphono-α-D-glucopyranose
  • Glucose 1-phosphoric acid
  • a-D-Glucopyranosyl phosphoric acid
  • alpha-D-Glucopyranosyl phosphoric acid
  • α-D-Glucopyranosyl phosphate
  • α-D-Glucopyranosyl phosphoric acid
  • a-D-Glucose-1-phosphate
  • a-D-Glucose-1-phosphoric acid
  • alpha-D-Glucose-1-phosphoric acid
  • α-D-Glucose-1-phosphate
  • α-D-Glucose-1-phosphoric acid
  • D-Glucose 1-phosphoric acid
  • D-Glucose a-1-phosphate
  • D-Glucose a-1-phosphoric acid
  • D-Glucose alpha-1-phosphoric acid
  • D-Glucose α-1-phosphate
  • D-Glucose α-1-phosphoric acid
  • alpha-Glucose-1-phosphate
  • a-D-Glucose 1-phosphoric acid
  • alpha-D-Glucose 1-phosphoric acid
  • α-D-Glucose 1-phosphoric acid
  • α-D-Glucose 1-phosphate
CAS number59-56-3
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyHXXFSFRBOHSIMQ-VFUOTHLCSA-N
InChIInChI=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
IUPAC Name{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Nameα-D-glucose 1-phosphate
Chemical FormulaC6H13O9P
SMILESOC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL [MERCK INDEX (1996); extremely soluble]PhysProp
LogPNot AvailablePhysProp
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
Polarizability20.72 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
Leloir PathwayPW002397 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Galactose metabolismec00052 Map00052
Glycolysis / Gluconeogenesisec00010 Map00010
Pentose and glucuronate interconversionsec00040 Map00040
Starch and sucrose metabolismec00500 Map00500
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0890000000-cb800147fb5e99a510e7JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0090000000-2a3b56296e3be19cb31eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-5190000000-fdc51a7b0fd975e56650JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-69de35d5ce6872252869JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-9963fa05cb28ee4e9750JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-817af0fa07de830dfcf8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0090000000-2322457ec511bd92510dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-5090000000-d986f523677b1a7addcdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-ce71459726865b116c97JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-41baf1958afa8e1bca49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-bfea8e3efab209c2697eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-1090000000-8e32630bfab3f0ed6178JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0090000000-0c85f2f24f79558bd95eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9030000000-cc7fbcb760461482d91aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9100000000-41a1f7e48ed2619c083cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9100000000-7c0c1db3eeeec90afc60JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-1f32b398f51ac98aaa87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-2785b12981c99944620aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-9000000000-abfc53ea34b8f04f9f65JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9200000000-1e94374a7c4c5c6c58eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-0a7885872856fe43526bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-b437590c213fb263989dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0532-9100000000-97504a02d14244b901cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9360000000-98c3aee1d36863dc12abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-92ad15ffc9eae3eed039JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Daran, J. M., Dallies, N., Thines-Sempoux, D., Paquet, V., Francois, J. (1995). "Genetic and biochemical characterization of the UGP1 gene encoding the UDP-glucose pyrophosphorylase from Saccharomyces cerevisiae." Eur J Biochem 233:520-530.7588797
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID29042
HMDB IDHMDB01586
Pubchem Compound ID65533
Kegg IDC00103
ChemSpider ID24604707
FOODB IDFDB021830
WikipediaGlucose_1-phosphate
BioCyc IDGLC-1-P

Enzymes

General function:
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose
Gene Name:
GAL7
Uniprot ID:
P08431
Molecular weight:
42384.69922
Reactions
UDP-glucose + alpha-D-galactose 1-phosphate → alpha-D-glucose 1-phosphate + UDP-galactose.
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways
Gene Name:
Not Available
Uniprot ID:
P38709
Molecular weight:
55999.80078
Reactions
UTP + alpha-D-glucose 1-phosphate → diphosphate + UDP-glucose.
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways
Gene Name:
UGP1
Uniprot ID:
P32861
Molecular weight:
55987.39844
Reactions
UTP + alpha-D-glucose 1-phosphate → diphosphate + UDP-glucose.