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MetaCyc Compound Class: D-glucopyranose 6-phosphate

Synonyms: D-glucopyranose-6-P

Superclasses: all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a hexose phosphate a hexose 6-phosphate D-glucose 6-phosphate
all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a sugar 6-phosphate a hexose 6-phosphate D-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 Change Formation (ΔfG in kcal/mol): -319.04593 Inferred 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

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+

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

Reactions known to produce the compound:

D-galactose degradation V (Leloir pathway) , glycogen degradation II (eukaryotic) :
α-D-glucopyranose 1-phosphate → D-glucopyranose 6-phosphate

GDP-glucose biosynthesis , glycogen degradation I (bacterial) , glycolysis VI (metazoan) , trehalose degradation I (low osmolarity) , trehalose degradation IV :
D-glucopyranose + ATP → D-glucopyranose 6-phosphate + ADP + H+

Not in pathways:
α-maltose 6'-phosphate + H2O → D-glucopyranose + D-glucopyranose 6-phosphate

Reactions known to both consume and produce the compound:

1,5-anhydrofructose degradation , gluconeogenesis III , glycolysis VI (metazoan) :
D-glucopyranose 6-phosphate ↔ β-D-fructofuranose 6-phosphate

In Reactions of unknown directionality:

Not in pathways:
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[periplasmic space]D-glucopyranose 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine ,
a [PTS enzyme I]-Nπ-phospho-L-histidine + D-glucose[periplasmic space]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: phosphoglucosamine mutase , phosphoenolpyruvate phosphatase , trehalose-6-phosphate phosphatase , 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."


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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 SRI International Pathway Tools version 19.0 on Tue Jul 28, 2015, biocyc14.