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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: α-D-glucose 6-phosphate

Synonyms: α-glucose 6-phosphate, α-D-glucose-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 D-glucopyranose 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

Chemical Formula: C6H11O9P

Molecular Weight: 258.12 Daltons

Monoisotopic Molecular Weight: 260.0297185262 Daltons

SMILES: C(OP(=O)([O-])[O-])C1(OC(O)C(O)C(O)C(O)1)

InChI: InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/p-2/t2-,3-,4+,5-,6+/m1/s1

InChIKey: InChIKey=NBSCHQHZLSJFNQ-DVKNGEFBSA-L

Unification Links: ChEBI:58225 , ChemSpider:10239175 , KEGG:C00668 , PubChem:21604864

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

Reactions known to consume the compound:

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

trehalose biosynthesis III :
GDP-α-D-glucose + α-D-glucose 6-phosphate → GDP + α,α-trehalose 6-phosphate + H+

Not in pathways:
α-D-glucose 6-phosphate + H2O → α-D-glucose + phosphate

1D-myo-inositol hexakisphosphate biosynthesis III (Spirodela polyrrhiza) , 1D-myo-inositol hexakisphosphate biosynthesis IV (Dictyostelium) , di-myo-inositol phosphate biosynthesis , L-1-phosphatidyl-inositol biosynthesis (Mycobacteria) , mycothiol biosynthesis , myo-inositol biosynthesis :
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+


a sugar phosphate + H2O → a sugar + phosphate

Reactions known to produce the compound:

sucrose degradation III (sucrose invertase) :
α-D-glucose + ATP → α-D-glucose 6-phosphate + ADP + H+

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

GDP-glucose biosynthesis II , 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


an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

Reactions known to both consume and produce the compound:

chitin biosynthesis , sucrose degradation III (sucrose invertase) :
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

GDP-glucose biosynthesis :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

GDP-glucose biosynthesis II , glycogen degradation I :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate

glucose and glucose-1-phosphate degradation :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

glycogen biosynthesis I (from ADP-D-Glucose) :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

starch biosynthesis :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

starch degradation III :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

starch degradation V :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

streptomycin biosynthesis :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

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

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

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

trehalose biosynthesis II :
α-D-glucose 6-phosphate + ADP-α-D-glucose ↔ α,α-trehalose 6-phosphate + ADP + H+

trehalose degradation V :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

UDP-glucose biosynthesis :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 6-phosphate ↔ β-D-glucose 6-phosphate

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 + α-D-glucose[periplasmic space]α-D-glucose 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine ,
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 α-D-glucose 6-phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: trehalose-6-phosphate phosphatase [Friedman71]

Inhibitor (Mechanism unknown) of: glycogen phosphorylase [Dombradi85]


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 SRI International Pathway Tools version 18.5 on Sat Dec 20, 2014, BIOCYC14B.