ECMDB: beta-D-Glucose 6-phosphate (ECMDB03498) (M2MDB000506)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (11)Transporters (1)XML

Proteins (1819)

Record Information

Version

2.0

Creation Date

2012-05-31 13:59:22 -0600

Update Date

2015-06-03 15:54:24 -0600

Secondary Accession Numbers

ECMDB03498

Identification

Name:

beta-D-Glucose 6-phosphate

Description

Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

β-D-glucose-6-P
b-D-Glucose 6-(dihydrogen phosphate)
b-D-Glucose 6-(dihydrogen phosphoric acid)
b-D-Glucose 6-phosphate
b-D-Glucose 6-phosphoric acid
b-D-Glucose-6-P
Beta-D-Glucose 6-(dihydrogen phosphate)
beta-D-Glucose 6-(dihydrogen phosphoric acid)
Beta-D-Glucose 6-phosphate
beta-D-Glucose 6-phosphoric acid
Beta-D-Glucose-6-P
D-Glucose-6-P
D-Glucose-6-phosphate
D-Glucose-6-phosphoric acid
Glucose-6-P
Glucose-6-phosphate
Glucose-6-phosphoric acid
β-D-Glucose 6-(dihydrogen phosphate)
β-D-Glucose 6-(dihydrogen phosphoric acid)
β-D-Glucose 6-phosphate
β-D-Glucose 6-phosphoric acid
β-D-Glucose-6-P

Chemical Formula:

C₆H₁₃O₉P

Weight:

Average: 260.1358
Monoisotopic: 260.029718526

InChI Key:

NBSCHQHZLSJFNQ-VFUOTHLCSA-N

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)/t2-,3-,4+,5-,6-/m1/s1

CAS number:

Not Available

IUPAC Name:

{[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid

Traditional IUPAC Name:

β-D-glucose 6-phosphate

SMILES:

O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

Hexose phosphate
Monosaccharide phosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Phosphoric acid ester
Hemiacetal
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucopyranose 6-phosphate (CHEBI:17719 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-3.643	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	31.4 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.1	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.8 m³·mol⁻¹	ChemAxon
Polarizability	20.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Amino sugar and nucleotide sugar metabolism III	PW000895
Galactose metabolism	PW000821
Pentose Phosphate	PW000893
Secondary metabolites: Trehalose Biosynthesis and Metabolism	PW000968
Starch and sucrose metabolism	PW000941
colanic acid building blocks biosynthesis	PW000951
galactose degradation/Leloir Pathway	PW000884
glycerol metabolism	PW000914
glycerol metabolism II	PW000915
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)	PW000916
glycerol metabolism IV (glycerophosphoglycerol)	PW000917
glycerol metabolism V (glycerophosphoserine)	PW000918
glycolysis and pyruvate dehydrogenase	PW000785
inner membrane transport	PW000786

KEGG Pathways:

Galactose metabolism ec00052
Glycolysis / Gluconeogenesis ec00010
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Pentose phosphate pathway ec00030
Starch and sucrose metabolism ec00500

EcoCyc Pathways:

GDP-mannose biosynthesis PWY-5659
fructoselysine and psicoselysine degradation PWY0-521
gluconeogenesis I GLUCONEO-PWY
glucose and glucose-1-phosphate degradation GLUCOSE1PMETAB-PWY
glycogen degradation I GLYCOCAT-PWY
glycolysis I GLYCOLYSIS
pentose phosphate pathway (oxidative branch) OXIDATIVEPENT-PWY
superpathway of glycolysis and Entner-Doudoroff GLYCOLYSIS-E-D
trehalose degradation I (low osmolarity) TREDEGLOW-PWY
trehalose degradation II (trehalase) PWY0-1182

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9740000000-a6e81224fb97751dc2e6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001i-5572890000-1bd34b89c6cb6aadc13c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0490000000-1a5b3049c27a2a9b8996	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dm-4940000000-cbc695bef22278b36879	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uka-8900000000-320e52be29673422365e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-6290000000-e76ad7d6142e19f5a9c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-e27be76de6d71ada7083	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9540d84c7e74555e7a01	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6s-9060000000-b446300429049a22bea4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-d5aaca13a836cb9f1725	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dm-0970000000-40dbaf3d3c72cf65bf47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-7900000000-00bc03290b6c0bfb7f84	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9000000000-7a6ff6606f1dbc2f0ae4	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17719
HMDB ID	HMDB03498
Pubchem Compound ID	439427
Kegg ID	C01172
ChemSpider ID	388538
Wikipedia ID	Not Available
BioCyc ID	GLC-6-P
EcoCyc ID	GLC-6-P
Ligand Expo	BG6

Enzymes

Protein Details

1. Glucose-6-phosphate isomerase

General function:: Involved in glucose-6-phosphate isomerase activity
Specific function:: D-glucose 6-phosphate = D-fructose 6- phosphate
Gene Name:: pgi
Uniprot ID:: P0A6T1
Molecular weight:: 61529

Reactions

D-glucose 6-phosphate = D-fructose 6-phosphate.

Protein Details

2. Glucokinase

General function:: Involved in glucokinase activity
Specific function:: Not highly important in E.coli as glucose is transported into the cell by the PTS system already as glucose 6-phosphate
Gene Name:: glk
Uniprot ID:: P0A6V8
Molecular weight:: 34723

Reactions

ATP + D-glucose = ADP + D-glucose 6-phosphate.

Protein Details

3. Glucose-6-phosphate 1-dehydrogenase

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:: zwf
Uniprot ID:: P0AC53
Molecular weight:: 55704

Reactions

D-glucose 6-phosphate + NADP(+) = 6-phospho-D-glucono-1,5-lactone + NADPH.

Protein Details

4. 6-phospho-beta-glucosidase BglB

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Can hydrolyze salicin and arbutin
Gene Name:: bglB
Uniprot ID:: P11988
Molecular weight:: 53161

Reactions

6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.

Protein Details

5. 6-phospho-beta-glucosidase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Hydrolyzes a wide variety of P-beta-glucosides including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P, methyl- beta-glucoside-6P and p-nitrophenyl-beta-D-glucopyranoside-6P. Is also able to hydrolyze phospho-N,N'-diacetylchitobiose
Gene Name:: chbF
Uniprot ID:: P17411
Molecular weight:: 50512

Reactions

6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.

Protein Details

6. 6-phospho-beta-glucosidase AscB

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Can hydrolyze salicin, cellobiose, and probably arbutin
Gene Name:: ascB
Uniprot ID:: P24240
Molecular weight:: 53935

Reactions

6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.

Protein Details

7. Glucose-specific phosphotransferase enzyme IIA component

General function:: Involved in sugar:hydrogen symporter activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
Gene Name:: crr
Uniprot ID:: P69783
Molecular weight:: 18251

Reactions

Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.

Protein Details

8. PTS system glucose-specific EIICB component

General function:: Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
Gene Name:: ptsG
Uniprot ID:: P69786
Molecular weight:: 50676

Reactions

Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

Protein Details

9. Putative beta-phosphoglucomutase

General function:: Involved in beta-phosphoglucomutase activity
Specific function:: Reversible transformation of glucose 6-phosphate and beta-glucose 1-phosphate
Gene Name:: ycjU
Uniprot ID:: P77366
Molecular weight:: 23565

Reactions

Beta-D-glucose 1-phosphate = beta-D-glucose 6-phosphate.

Protein Details

10. 6-phospho-beta-glucosidase BglA

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: 6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate
Gene Name:: bglA
Uniprot ID:: Q46829
Molecular weight:: 55361

Reactions

6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.

Protein Details

11. conserved protein

General function:: Not Available
Specific function:: Not Available
Gene Name:: yeaD
Uniprot ID:: P39173
Molecular weight:: Not Available

Transporters

Protein Details

1. PTS system glucose-specific EIICB component

General function:: Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
Gene Name:: ptsG
Uniprot ID:: P69786
Molecular weight:: 50676

Reactions

Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

beta-D-Glucose 6-phosphate (ECMDB03498) (M2MDB000506)

Structure for #<Compound:0xa958e16c>

Enzymes

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Transporters

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