Common NameBeta-d-glucose 6-phosphate
Descriptionbeta-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 glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways. 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 into glycogen, especially if blood glucose levels are high.
Structure
Molecular FormulaC6H13O9P
Average Mass260.13580
Monoisotopic Mass260.02972
IUPAC Name{[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4s,5r,6r)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number15209-12-8
SMILESO=P([O-])([O-])OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=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
InChI KeyNBSCHQHZLSJFNQ-VFUOTHLCSA-N
CHEBI IDCHEBI:58247
HMDB IDHMDB0003498
Pathways
NameSMPDB/PathBank
pentose phosphate pathway
Glycolysis
Gluconeogenesis
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease
Trehalose Degradation
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
Glycogenosis, Type VII. Tarui disease
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)
Fructose-1,6-diphosphatase deficiency
Triosephosphate isomerase
Fanconi-bickel syndrome
Glycogenosis, Type IB
Glycogenosis, Type IC
Glycogenosis, Type IA. Von gierke disease
Warburg Effect
StateSolid
Water Solubility3.14e+01 g/l
logP-2.06
logS-0.92
pKa (Strongest Acidic)1.22
pKa (Strongest Basic)-3.65
Hydrogen Acceptor Count8
Hydrogen Donor Count6
Polar Surface Area156.91 Ų
Rotatable Bond Count3
Physiological Charge-2
Formal Charge0
Refractivity46.80 m³·mol⁻¹
Polarizability20.96

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