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aldehydo-D-glucose 6-phosphate (YMDB00582)

Identification
YMDB IDYMDB00582
Namealdehydo-D-glucose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionaldehydo-D-glucose 6-phosphate, also known as glucose-6-phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. aldehydo-D-glucose 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). aldehydo-D-glucose 6-phosphate may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (2R,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexyl dihydrogen phosphate
  • (2R,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexyl dihydrogen phosphoric acid
  • Aldehydo-D-glucose 6-phosphoric acid
  • Glucose-6-phosphate
  • Glucose 6 phosphate
  • Aldohexose 6-phosphoric acid
CAS numberNot Available
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyVFRROHXSMXFLSN-SLPGGIOYSA-N
InChIInChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h1,3-6,8-11H,2H2,(H2,12,13,14)/t3-,4+,5+,6+/m0/s1
IUPAC Name{[(2R,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexyl]oxy}phosphonic acid
Traditional IUPAC Namealdohexose 6-phosphate
Chemical FormulaC6H13O9P
SMILES[H]C(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(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
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility21.7 g/LALOGPS
logP-1.8ALOGPS
logP-3.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.22 m³·mol⁻¹ChemAxon
Polarizability20.67 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
aldehydo-D-glucose 6-phosphate + Uridine diphosphate glucose → Uridine 5'-diphosphate + hydron + Trehalose 6-phosphate
aldehydo-D-glucose 6-phosphate + NADP → NADPH + hydron + 6-Phosphonoglucono-D-lactone
aldehydo-D-glucose 6-phosphate ↔ Beta-D-Glucose 6-phosphate
aldehydo-D-glucose 6-phosphate ↔ Fructose 6-phosphate
Adenosine triphosphate + D-Glucose → aldehydo-D-glucose 6-phosphate + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9640000000-89efc5d69e8c7bfb4553JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-3590000000-c4a61ad12acec8747b35JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c04-9610000000-2669606b86e055f34ce4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-e505553192dc14593d6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0699-9820000000-e830f41d1e0ca6ab55c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-21a0d89fb15d8c0b8834JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7110f9b68f151d8b446bJSpectraViewer
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
References
References:
  • 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
  • De Virgilio, C., Burckert, N., Bell, W., Jeno, P., Boller, T., Wiemken, A. (1993). "Disruption of TPS2, the gene encoding the 100-kDa subunit of the trehalose-6-phosphate synthase/phosphatase complex in Saccharomyces cerevisiae, causes accumulation of trehalose-6-phosphate and loss of trehalose-6-phosphate phosphatase activity." Eur J Biochem 212:315-323.8444170
  • Entian, K. D., Kopetzki, E., Frohlich, K. U., Mecke, D. (1984). "Cloning of hexokinase isoenzyme PI from Saccharomyces cerevisiae: PI transformants confirm the unique role of hexokinase isoenzyme PII for glucose repression in yeasts." Mol Gen Genet 198:50-54.6394965
  • Nogae, I., Johnston, M. (1990). "Isolation and characterization of the ZWF1 gene of Saccharomyces cerevisiae, encoding glucose-6-phosphate dehydrogenase." Gene 96:161-169.2269430
  • Boles, E., Zimmermann, F. K. (1993). "Saccharomyces cerevisiae phosphoglucose isomerase and fructose bisphosphate aldolase can be replaced functionally by the corresponding enzymes of Escherichia coli and Drosophila melanogaster." Curr Genet 23:187-191.8435847
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15954
HMDB IDNot Available
Pubchem Compound ID23616120
Kegg IDC03251
ChemSpider ID24534258
FOODB IDNot Available
WikipediaGlucose_6-phosphate
BioCyc IDNot Available

Enzymes

Protein Details
1. Phosphoglucomutase-2
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.
Protein Details
2. Phosphoglucomutase-1
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.
Protein Details
3. Hexokinase-2
General function:
Involved in ATP binding
Specific function:
Main glucose phosphorylating enzyme. May play a regulatory role in both induction and repression of gene expression by glucose
Gene Name:
HXK2
Uniprot ID:
P04807
Molecular weight:
53942.0
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
Protein Details
4. Hexokinase-1
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
HXK1
Uniprot ID:
P04806
Molecular weight:
53737.89844
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
Protein Details
5. Glucose-6-phosphate isomerase
General function:
Involved in glucose-6-phosphate isomerase activity
Specific function:
D-glucose 6-phosphate = D-fructose 6- phosphate
Gene Name:
PGI1
Uniprot ID:
P12709
Molecular weight:
61298.89844
Reactions
D-glucose 6-phosphate → D-fructose 6-phosphate.
Protein Details
6. Glucokinase-1
General function:
Involved in ATP binding
Specific function:
Two isoenzymes, hexokinase-1 and hexokinase-2, can phosphorylate keto- and aldohexoses in yeast, whereas a third isoenzyme, GLK, is specific for aldohexoses. All glucose phosphorylating enzymes are involved in glucose uptake
Gene Name:
GLK1
Uniprot ID:
P17709
Molecular weight:
55376.89844
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.
Protein Details
7. Trehalose synthase complex regulatory subunit TPS3
General function:
Involved in catalytic activity
Specific function:
Regulatory subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process. May stabilize the trehalose synthase complex
Gene Name:
TPS3
Uniprot ID:
P38426
Molecular weight:
118834.0
Reactions
Protein Details
8. Glucose-6-phosphate 1-dehydrogenase
General function:
Involved in glucose-6-phosphate dehydrogenase activity
Specific function:
D-glucose 6-phosphate + NADP(+) = D-glucono- 1,5-lactone 6-phosphate + NADPH
Gene Name:
ZWF1
Uniprot ID:
P11412
Molecular weight:
57521.10156
Reactions
D-glucose 6-phosphate + NADP(+) → 6-phospho-D-glucono-1,5-lactone + NADPH.
Protein Details
9. Inositol-3-phosphate synthase
General function:
Involved in inositol-3-phosphate synthase activity
Specific function:
D-glucose 6-phosphate = 1D-myo-inositol 3- phosphate
Gene Name:
INO1
Uniprot ID:
P11986
Molecular weight:
59641.60156
Reactions
D-glucose 6-phosphate → 1D-myo-inositol 3-phosphate.