Showing Metabocard for D-fructose 6-phosphate (BASm0004132)

Common NameD-fructose 6-phosphate
DescriptionFructose 6-phosphate (F6P) 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. F6P is a derivative of fructose, which has been phosphorylated at the 6-hydroxy group. Fructose 6-phosphate is a fundamental metabolite and exists in all living species, ranging from bacteria to plants to humans. The great majority of glucose is converted to fructose 6-phosphate as part of the glycolytic metabolic pathway (glycolysis). Specifically, F6P is produce is produced by the isomerisation of glucose 6-phosphate via the enzyme phosphoglucose isomerase. F6P is in turn further phosphorylated to fructose-1,6-bisphosphate by the enzyme phosphofructokinase-1. Glycolysis is the metabolic pathway that converts glucose into pyruvic acid. The free energy released in this process is used to form ATP and reduced nicotinamide adenine dinucleotide (NADH). In addition to its key involvement in glycolysis, fructose 6-phosphate can also be biosynthesized from glucosamine 6-phosphate via the enzyme glucosamine-6-phosphate isomerase 1. In addition, fructose 6-phosphate and L-glutamine can be converted into glucosamine 6-phosphate and L-glutamic acid through the action of the enzyme glutamine--fructose-6-phosphate aminotransferase.
Structure
Molecular FormulaC6H13O9P
Average Mass260.13580
Monoisotopic Mass260.02972
IUPAC Name{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
Traditional Name[(2r,3r,4s)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxyphosphonic acid
CAS Registry Number643-13-0
SMILESO=P([O-])([O-])OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1
InChI KeyGSXOAOHZAIYLCY-HSUXUTPPSA-N
CHEBI IDCHEBI:61527
HMDB IDHMDB0000124
Pathways
NameSMPDB/PathBank
Fructose and mannose metabolism
pentose phosphate pathway
Glycolysis
Amino Sugar Metabolism
Glutamate Metabolism
Gluconeogenesis
2-Hydroxyglutric Aciduria (D And L Form)
Sialuria or French Type Sialuria
Salla Disease/Infantile Sialic Acid Storage Disease
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Hyperinsulinism-Hyperammonemia Syndrome
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease
Homocarnosinosis
Tay-Sachs Disease
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
Glycogenosis, Type VII. Tarui disease
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)
Fructosuria
Fructose-1,6-diphosphatase deficiency
Triosephosphate isomerase
Succinic semialdehyde dehydrogenase deficiency
Fanconi-bickel syndrome
Glycogenosis, Type IB
Glycogenosis, Type IC
Glycogenosis, Type IA. Von gierke disease
Warburg Effect
Fructose intolerance, hereditary
StateSolid
Water Solubility2.32e+01 g/l
logP-1.86
logS-1.05
pKa (Strongest Acidic)1.49
pKa (Strongest Basic)-3.33
Hydrogen Acceptor Count8
Hydrogen Donor Count6
Polar Surface Area164.75 Ų
Rotatable Bond Count7
Physiological Charge-2
Formal Charge0
Refractivity48.43 m³·mol⁻¹
Polarizability20.87

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