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Identification
YMDB IDYMDB00582
Namealdehydo-D-glucose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAldehydo-D-glucose 6-phosphate is the linear form of D-glucose 6-phosphate. Glucose 6-phosphate (G6P) is produced in the cell by phosphorylation of glucose on the sixth carbon. G6P is then converted into pyruvate during the glycolysis. [Biocyc GLYCOLYSIS]
Structure
Thumb
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
  • 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
DescriptionThis compound belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Organic phosphate
  • Monosaccharide
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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-1.9ALOGPS
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 glucoseUridine 5'-diphosphate + hydron + Trehalose 6-phosphate
aldehydo-D-glucose 6-phosphate + NADPNADPH + hydron + 6-Phosphonoglucono-D-lactone
aldehydo-D-glucose 6-phosphateBeta-D-Glucose 6-phosphate
aldehydo-D-glucose 6-phosphateFructose 6-phosphate
Adenosine triphosphate + D-Glucosealdehydo-D-glucose 6-phosphate + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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 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
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
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.
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.
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
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.
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.