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

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


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 SRI International Pathway Tools version 19.0 on Thu Oct 8, 2015, biocyc14.