Beta-D-Glucose 6-phosphate (YMDB00311)

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Identification

YMDB ID

YMDB00311

Name

Beta-D-Glucose 6-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

beta-D-Glucose 6-phosphate, also known as b-D-glucose 6-phosphoric acid or 6-O-phosphono-b-D-glucopyranose, 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. beta-D-Glucose 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). beta-D-Glucose 6-phosphate exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

beta-D-glucose 6-(dihydrogen phosphate)
beta-D-Glucose 6-phosphate
beta-D-Glucose 6-phosphic acid
6-H2PO3glcbeta
6-O-Phosphono-beta-D-glucopyranose
BETA-D-GLUCOSE-6-phosphATE
6-O-Phosphono-b-D-glucopyranose
6-O-Phosphono-β-D-glucopyranose
b-D-Glucose 6-(dihydrogen phosphate)
b-D-Glucose 6-(dihydrogen phosphoric acid)
beta-D-Glucose 6-(dihydrogen phosphoric acid)
Β-D-glucose 6-(dihydrogen phosphate)
Β-D-glucose 6-(dihydrogen phosphoric acid)
b-D-Glucose 6-phosphate
b-D-Glucose 6-phosphoric acid
beta-D-Glucose 6-phosphoric acid
Β-D-glucose 6-phosphate
Β-D-glucose 6-phosphoric acid
b-D-GLUCOSE-6-phosphate
b-D-GLUCOSE-6-phosphoric acid
beta-D-GLUCOSE-6-phosphoric acid
Β-D-glucose-6-phosphate
Β-D-glucose-6-phosphoric acid

CAS number

Not Available

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

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

Chemical Formula

C₆H₁₃O₉P

SMILES

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

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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
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

Organoleptic Properties

Not Available

SMPDB Pathways

Amino sugar and nucleotide sugar metabolism	PW002413
Ethanol fermentation	PW002448
Fructose Metabolism	PW002390
Glycolysis I	PW002386
Starch and sucrose metabolism	PW002481

KEGG Pathways

Amino sugar and nucleotide sugar metabolism	ec00520
Glycolysis / Gluconeogenesis	ec00010
Pentose phosphate pathway	ec00030
Starch and sucrose metabolism	ec00500

SMPDB Reactions

Adenosine triphosphate + Beta-D-Glucose → ADP + Beta-D-Glucose 6-phosphate

Beta-D-Glucose 6-phosphate ↔ Fructose 6-phosphate

Fructose 6-phosphate → Beta-D-Glucose 6-phosphate

sucrose-6-phosphate + water → D-Fructose + Beta-D-Glucose 6-phosphate

Beta-D-Glucose 6-phosphate ↔ Glucose 1-phosphate

KEGG Reactions

Adenosine triphosphate + D-Glucose → Beta-D-Glucose 6-phosphate + hydron + ADP

aldehydo-D-glucose 6-phosphate ↔ Beta-D-Glucose 6-phosphate

Beta-D-Glucose 6-phosphate ↔ Fructose 6-phosphate

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

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

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Maitra, P. K., Lobo, Z. (1983). "Genetics of yeast glucokinase." Genetics 105:501-515.6357942

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17719
HMDB ID	HMDB03498
Pubchem Compound ID	439427
Kegg ID	C01172
ChemSpider ID	25057696
FOODB ID	FDB031291
Wikipedia	Glucose_6-phosphate
BioCyc ID	Not Available

Enzymes

Protein Details

1. Phosphoglucomutase-2

General function:: Involved in intramolecular transferase activity, phosphotransferases
Specific function:: This enzyme participates in both the breakdown and synthesis of glucose. Can also act on mannose
Gene Name:: PGM2
Uniprot ID:: P37012
Molecular weight:: 63088.0

Reactions

Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.

Protein Details

2. Phosphoglucomutase-1

General function:: Involved in intramolecular transferase activity, phosphotransferases
Specific function:: This enzyme participates in both the breakdown and synthesis of glucose. Can also act on mannose
Gene Name:: PGM1
Uniprot ID:: P33401
Molecular weight:: 63111.30078

Reactions

Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.

Protein Details

3. 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:: PGI1
Uniprot ID:: P12709
Molecular weight:: 61298.89844

Reactions

D-glucose 6-phosphate → D-fructose 6-phosphate.

Protein Details

4. Putative glucokinase-2

General function:: Involved in ATP binding
Specific function:: Putative glucokinase involved in phosphorylation of aldohexoses and glucose uptake. Involved in sporulation. Required for the full activation of the early meiotic inducer IME1
Gene Name:: EMI2
Uniprot ID:: Q04409
Molecular weight:: 55920.30078

Reactions

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

Protein Details

5. Glucokinase-1

General function:: Involved in ATP binding
Specific function:: Two isoenzymes, hexokinase-1 and hexokinase-2, can phosphorylate keto- and aldohexoses in yeast, whereas a third isoenzyme, GLK, is specific for aldohexoses. All glucose phosphorylating enzymes are involved in glucose uptake
Gene Name:: GLK1
Uniprot ID:: P17709
Molecular weight:: 55376.89844

Reactions

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

Protein Details

6. Glucose-6-phosphate 1-epimerase

General function:: Involved in isomerase activity
Specific function:: Catalyzes the interconversion between the alpha and beta anomers from at least three hexose 6-phosphate sugars (Glc6P, Gal6P, and Man6P)
Gene Name:: Not Available
Uniprot ID:: Q03161
Molecular weight:: 33955.69922

Reactions

Alpha-D-glucose 6-phosphate → beta-D-glucose 6-phosphate.

Protein Details

7. Invertase 2

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:: SUC2
Uniprot ID:: P00724
Molecular weight:: 60638.89844

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Structure for #<Compound:0xaa1b0198>

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