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Identification
YMDB IDYMDB00311
NameBeta-D-Glucose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionBeta-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
Thumb
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 numberNot Available
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyNBSCHQHZLSJFNQ-VFUOTHLCSA-N
InChIInChI=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 Nameβ-D-glucose 6-phosphate
Chemical FormulaC6H13O9P
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-3.643PhysProp
Predicted Properties
PropertyValueSource
Water Solubility31.4 g/LALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Fructose MetabolismPW002390 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Glycolysis / Gluconeogenesisec00010 Map00010
Pentose phosphate pathwayec00030 Map00030
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
Adenosine triphosphate + Beta-D-GlucoseADP + Beta-D-Glucose 6-phosphate
Beta-D-Glucose 6-phosphateFructose 6-phosphate
Fructose 6-phosphateBeta-D-Glucose 6-phosphate
sucrose-6-phosphate + waterD-Fructose + Beta-D-Glucose 6-phosphate
Beta-D-Glucose 6-phosphateGlucose 1-phosphate
KEGG Reactions
Adenosine triphosphate + D-GlucoseBeta-D-Glucose 6-phosphate + hydron + ADP
aldehydo-D-glucose 6-phosphateBeta-D-Glucose 6-phosphate
Beta-D-Glucose 6-phosphateFructose 6-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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:
ResourceLink
CHEBI ID17719
HMDB IDHMDB03498
Pubchem Compound ID439427
Kegg IDC01172
ChemSpider ID25057696
FOODB IDFDB023183
WikipediaGlucose_6-phosphate
BioCyc IDNot Available

Enzymes

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.
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.
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.
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.
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.
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.
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
Reactions