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Identification
YMDB IDYMDB00288
NameGlucose 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlucose 1-phosphate, also known as cori ester or GLC-1-p, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Glucose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glucose 1-phosphate exists in all living species, ranging from bacteria to humans. Within yeast, glucose 1-phosphate participates in a number of enzymatic reactions. In particular, glucose 1-phosphate can be biosynthesized from Beta-D-glucose 6-phosphate through the action of the enzyme phosphoglucomutase. In addition, glucose 1-phosphate and uridine triphosphate can be converted into uridine diphosphate glucose and UDP ; which is mediated by the enzyme uridinephosphoglucose pyrophosphorylase. In yeast, glucose 1-phosphate is involved in the metabolic pathway called the amino sugar and nucleotide sugar metabolism pathway. Glucose 1-phosphate is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 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-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-D-glucopyranose
  • GLC-1-p
  • D-Glucose 1-phosphoric acid
  • Glucose 1-phosphoric acid
  • Galactose 1-phosphoric acid
CAS number59-56-3
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyHXXFSFRBOHSIMQ-GASJEMHNSA-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{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Nameglucose 1-phosphate
Chemical FormulaC6H13O9P
SMILES[H]OC([H])([H])[C@@]1([H])OC([H])(OP(=O)(O[H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
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
Polarizability20.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
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 Reactions
Glucose 1-phosphate + waterD-Glucose + phosphate
Galactose 1-phosphate + Uridine diphosphate glucoseGlucose 1-phosphate + UDP-D-galactose
UDP-D-galactose + Glucose 1-phosphateUridine diphosphate glucose + Galactose 1-phosphate
Glucose 1-phosphateGlucose 6-phosphate
Beta-D-Glucose 6-phosphateGlucose 1-phosphate
KEGG Reactions
Glycogen + phosphateGlucose 1-phosphate
Glucose 1-phosphatealdehydo-D-glucose 6-phosphate
Galactose 1-phosphate + Uridine diphosphate glucoseUDP-D-galactose + Glucose 1-phosphate
Uridine triphosphate + Glucose 1-phosphate + hydronPyrophosphate + Uridine diphosphate glucose
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
100 ± 0 µM Minimal medium supplemented with ammonia salts and glucoseaerobic;resting cellsBaker's yeastPMID: 4578278
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-003r-5591470000-4932aa0d35a53458633dJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0390000000-9e3307d6125b74ed8579JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-05mk-2960000000-4950cd68ef81b4267967JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0230-5970000000-4c2745937c6f87f89f17JSpectraViewer | 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 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:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • DOUGLAS, H. C., HAWTHORNE, D. C. (1964). "ENZYMATIC EXPRESSION AND GENETIC LINKAGE OF GENES CONTROLLING GALACTOSE UTILIZATION IN SACCHAROMYCES." Genetics 49:837-844.14158615
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
Synthesis Reference:Weinhausel, Andreas; Nidetzky, Bernd; Kysela, Christian; Kulbe, Klaus D. Application of Escherichia coli maltodextrin-phosphorylase for the continuous production of glucose-1-phosphate. Enzyme and Microbial Technology (1995), 17(2), 140-6.
External Links:
ResourceLink
CHEBI ID16077
HMDB IDHMDB01586
Pubchem Compound ID65533
Kegg IDC00103
ChemSpider ID24604707
FOODB IDFDB001159
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 catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP2 and PHO5
Gene Name:
NPP1
Uniprot ID:
P25353
Molecular weight:
84733.20313
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and PHO5
Gene Name:
NPP2
Uniprot ID:
P39997
Molecular weight:
57354.10156
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose. Can also act on mannose
Gene Name:
PGM2
Uniprot ID:
P37012
Molecular weight:
63088.0
Reactions
Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose. Can also act on mannose
Gene Name:
PGM1
Uniprot ID:
P33401
Molecular weight:
63111.30078
Reactions
Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.
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.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:
Not Available
Uniprot ID:
Q03262
Molecular weight:
71068.60156
Reactions
Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
Gene Name:
GPH1
Uniprot ID:
P06738
Molecular weight:
103274.0
Reactions
(1,4-alpha-D-glucosyl)(n) + phosphate → (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.