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MetaCyc Compound Class: D-glucopyranose 6-phosphate

Synonyms: D-glucopyranose-6-P

Superclasses: all carbohydratesa carbohydratea glycana carbohydrate derivativea sugar phosphatea hexose phosphatea hexose 6-phosphateD-glucose 6-phosphate
all carbohydratesa carbohydratea glycana carbohydrate derivativea sugar phosphatea sugar 6-phosphatea hexose 6-phosphateD-glucose 6-phosphate

D-glucopyranose 6-phosphate compound structure

Chemical Formula: C6H11O9P

Instances:
α-D-glucose 6-phosphate,
β-D-glucose 6-phosphate

Molecular Weight: 258.12 Daltons

Monoisotopic Molecular Weight: 260.0297185262 Daltons

SMILES: C(C1(OC(C(C(C1O)O)O)O))OP([O-])([O-])=O

Unification Links: ChEBI:4170, KEGG:C00092

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -319.04593Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) , 1D-myo-inositol hexakisphosphate biosynthesis IV (Dictyostelium) , di-myo-inositol phosphate biosynthesis , mycothiol biosynthesis , myo-inositol biosynthesis , phosphatidylinositol biosynthesis I (bacteria) :
D-glucopyranose 6-phosphate → 1D-myo-inositol 3-monophosphate

formaldehyde oxidation I , heterolactic fermentation , NAD/NADP-NADH/NADPH cytosolic interconversion (yeast) , pentose phosphate pathway (oxidative branch) , superpathway of glycolysis and Entner-Doudoroff :
D-glucopyranose 6-phosphate + NADP+ → 6-phospho D-glucono-1,5-lactone + NADPH + H+

gluconeogenesis III :
D-glucopyranose 6-phosphate + H2O → D-glucopyranose + phosphate

kanamycin biosynthesis , paromamine biosynthesis I , paromamine biosynthesis II :
D-glucopyranose 6-phosphate → 2-deoxy-L-scyllo-inosose + phosphate

kanosamine biosynthesis II :
D-glucopyranose 6-phosphate + NAD+ → 3-dehydro-D-glucose 6-phosphate + NADH + H+

trehalose biosynthesis I :
UDP-α-D-glucose + D-glucopyranose 6-phosphate → α,α-trehalose 6-phosphate + UDP + H+

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

Reactions known to produce the compound:

1,3-propanediol biosynthesis (engineered) , Bifidobacterium shunt , GDP-glucose biosynthesis , glucose and glucose-1-phosphate degradation , glycogen degradation I , glycolysis III (from glucose) , heterolactic fermentation , sucrose biosynthesis II , sucrose degradation III (sucrose invertase) , trehalose degradation II (trehalase) , trehalose degradation IV , trehalose degradation V , UDP-N-acetyl-D-galactosamine biosynthesis II :
D-glucopyranose + ATP → D-glucopyranose 6-phosphate + ADP + H+

glycolysis V (Pyrococcus) :
D-glucopyranose + ADP → D-glucopyranose 6-phosphate + AMP + H+

trehalose degradation I (low osmolarity) :
D-glucopyranose + ATP → D-glucopyranose 6-phosphate + ADP + H+
α,α-trehalose 6-phosphate + H2O → D-glucopyranose 6-phosphate + D-glucopyranose

Not in pathways:
D-glucopyranose + (polyphosphate)(n)D-glucopyranose 6-phosphate + (polyphosphate)(n-1)
α-maltose 6'-phosphate + H2O → D-glucopyranose + D-glucopyranose 6-phosphate
D-cellobiose 6'-phosphate + H2O → D-glucopyranose 6-phosphate + D-glucopyranose

Reactions known to both consume and produce the compound:

1,3-propanediol biosynthesis (engineered) , 1,5-anhydrofructose degradation , Bifidobacterium shunt , chitin biosynthesis , formaldehyde oxidation I , GDP-mannose biosynthesis , gluconeogenesis I , gluconeogenesis II (Methanobacterium thermoautotrophicum) , gluconeogenesis III , glycolysis I (from glucose 6-phosphate) , glycolysis III (from glucose) , glycolysis V (Pyrococcus) , heterolactic fermentation , sucrose biosynthesis I (from photosynthesis) , sucrose biosynthesis III , sucrose degradation III (sucrose invertase) , UDP-N-acetyl-D-galactosamine biosynthesis II , UDP-N-acetyl-D-glucosamine biosynthesis I :
D-glucopyranose 6-phosphate ↔ β-D-fructofuranose 6-phosphate

D-galactose degradation V (Leloir pathway) , GDP-glucose biosynthesis , glucose and glucose-1-phosphate degradation , glycogen biosynthesis I (from ADP-D-Glucose) , glycogen degradation I , glycogen degradation II , starch degradation III , starch degradation V , streptomycin biosynthesis , trehalose degradation V , UDP-glucose biosynthesis :
α-D-glucopyranose 1-phosphate ↔ D-glucopyranose 6-phosphate

sorbitol biosynthesis I :
D-sorbitol 6-phosphate + NADP+D-glucopyranose 6-phosphate + NADPH + H+
D-glucopyranose 6-phosphate ↔ β-D-fructofuranose 6-phosphate

starch biosynthesis :
α-D-glucopyranose 1-phosphate ↔ D-glucopyranose 6-phosphate
D-glucopyranose 6-phosphate ↔ β-D-fructofuranose 6-phosphate

sucrose biosynthesis II :
α-D-glucopyranose 1-phosphate ↔ D-glucopyranose 6-phosphate
D-glucopyranose 6-phosphate ↔ β-D-fructofuranose 6-phosphate

sucrose degradation II (sucrose synthase) :
α-D-glucopyranose 1-phosphate ↔ D-glucopyranose 6-phosphate
D-glucopyranose 6-phosphate ↔ β-D-fructofuranose 6-phosphate

sucrose degradation IV (sucrose phosphorylase) :
α-D-glucopyranose 1-phosphate ↔ D-glucopyranose 6-phosphate
D-glucopyranose 6-phosphate ↔ β-D-fructofuranose 6-phosphate

In Reactions of unknown directionality:

Not in pathways:
α-glucose 1,6-bisphosphate + a phosphoglucomutase = D-glucopyranose 6-phosphate + a phosphorylated phosphoglucomutase
α-D-glucopyranose 1-phosphate = D-glucopyranose 6-phosphate
sn-glycerol 3-phosphate + D-glucopyranose = glycerol + D-glucopyranose 6-phosphate
D-glucopyranose 6-phosphate + NAD+ = 6-phospho D-glucono-1,5-lactone + NADH + H+
D-glucopyranose 6-phosphate + NAD(P)+ = 6-phospho D-glucono-1,5-lactone + NAD(P)H + H+

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + D-glucopyranose[periplasm]D-glucopyranose 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine,
a [PTS enzyme I]-Nπ-phospho-L-histidine + D-glucopyranose[periplasm]D-glucopyranose 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine,
a [PTS enzyme I]-Nπ-phospho-L-histidine + D-glucose[periplasm]D-glucose 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine,
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

Enzymes inhibited by D-glucopyranose 6-phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: trehalose-6-phosphate phosphatase [Friedman71] Inhibitor (Mechanism unknown) of: glycogen phosphorylase [Dombradi85]

This compound has been characterized as an alternative substrate of the following enzymes: phosphoenolpyruvate phosphatase, trehalose-6-phosphate phosphatase, phosphoglucosamine mutase, phosphoenolpyruvate phosphatase


References

Dombradi85: Dombradi V, Hajdu J, Friedrich P, Bot G (1985). "Purification and characterization of glycogen phosphorylase from Drosophila melanogaster." Insect Biochem. Vol. 15, No. 3, pp. 403-410.

Friedman71: Friedman S (1971). "Interactions among sites responsible for trehalose 6-phosphate and trehalose-activated glucose 6-phosphate hydrolysis on trehalose phosphatase isolated from Phormia regina." J Biol Chem 246(13);4122-30. PMID: 4326209

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sat Apr 30, 2016, biocyc13.