Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000971
Name: beta-D-Fructose 1,6-bisphosphate
Description:Beta-D-fructose 1,6-bisphosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. The hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate is a key reaction of carbohydrate metabolism. (PMID 3008716) Fructose-1,6-bisphosphate (F-1,6-P2) is an allosteric activator of two key enzymes of glycolysis: phosphofructokinase and pyruvate kinase. (PMID 18025560) In gluconeogenesis, fructose 6-phosphate is formed from fructose 1,6-bisphosphate, and if fructose 1,6-bisphosphate were reformed by the phosphofructokinase reaction there would be a "gluconeogenic futile cycle". (PMID 6217196) Fructose-1,6-bisphosphate (FBP) aldolase is an essential glycolytic enzyme that reversibly cleaves its ketohexose substrate into triose phosphates. (PMID 14699122) Fructose 1-phosphate is a metabolite that plays a regulatory role in metabolism and is best measured using an assay based on its conversion to fructose 1,6-bisphosphate by a bacterial fructose-1-phosphate kinase (Fru1PK). (PMID 10833389) For growth, the assimilated fructose is sequentially phosphorylated by ATP and (i) manno(fructo)kinase, to form fructose 6-phosphate, and (ii) phosphofructokinase, to form fructose 1,6-bisphosphate, which is a member of central routes of glycolysis and gluconeogenesis. (PMID 17159144)
  • β-D-fructose-1,6-diphosphate
  • β-D-fructose-1,6-diphosphoric acid
  • 1,6-Di-O-phosphono-b-D-fructofuranose
  • 1,6-Di-O-phosphono-beta-D-fructofuranose
  • 1,6-Di-O-phosphono-β-D-fructofuranose
  • 6055-82-9 (Calcium[1:2] salt)
  • b Fructose 1,6-diphosphate
  • b Fructose 1,6-diphosphoric acid
  • b-D-Fructofuranose 1,6-bis(dihydrogen phosphate)
  • b-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid)
  • b-D-Fructofuranose 1,6-bisphosphate
  • b-D-Fructofuranose 1,6-bisphosphoric acid
  • b-D-Fructofuranose, 1,6-bis(dihydrogen phosphate)
  • b-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid)
  • b-D-Fructose 1,6-bisphosphate
  • b-D-Fructose 1,6-bisphosphoric acid
  • b-D-Fructose-1,6-diphosphate
  • b-D-Fructose-1,6-diphosphoric acid
  • Beta Fructose 1,6-diphosphate
  • beta Fructose 1,6-diphosphoric acid
  • Beta-D-Fructofuranose 1,6-bis(dihydrogen phosphate)
  • beta-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid)
  • Beta-D-Fructofuranose 1,6-bisphosphate
  • beta-D-Fructofuranose 1,6-bisphosphoric acid
  • Beta-D-Fructofuranose, 1,6-bis(dihydrogen phosphate)
  • beta-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid)
  • beta-D-Fructose 1,6-bisphosphoric acid
  • Beta-D-Fructose-1,6-diphosphate
  • beta-D-Fructose-1,6-diphosphoric acid
  • BFP
  • D-Arabino-2-Hexulose-1,6-bis(dihydrogenphosphat)
  • D-Fructofuranose, 1,6-bis(dihydrogen phosphate)
  • D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid)
  • D-Fructose 1,6-bis(dihydrogen phosphate)
  • D-Fructose 1,6-bis(dihydrogen phosphoric acid)
  • D-Fructose, 1,6-bis(dihydrogen phosphate)
  • D-Fructose, 1,6-bis(dihydrogen phosphoric acid)
  • D-Fructose-1,6-bis(dihydrogenphosphat)
  • D-Fructose-1,6-bisphosphate
  • D-Fructose-1,6-bisphosphoric acid
  • D-Fructose-1,6-diphosphate
  • D-Fructose-1,6-diphosphoric acid
  • FBP
  • Fructose 1,6-bisphosphate
  • Fructose 1,6-bisphosphoric acid
  • Fructose 1,6-diphosphate
  • Fructose 1,6-diphosphoric acid
  • Fructose-1,6-biphosphate
  • Fructose-1,6-biphosphoric acid
  • Fructose-1,6-bisphosphate
  • Fructose-1,6-bisphosphoric acid
  • Fructose-1,6-diphosphate
  • Fructose-1,6-diphosphoric acid
  • Harden-young-ester
  • β Fructose 1,6-diphosphate
  • β Fructose 1,6-diphosphoric acid
  • β-D-Fructofuranose 1,6-bis(dihydrogen phosphate)
  • β-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid)
  • β-D-Fructofuranose 1,6-bisphosphate
  • β-D-Fructofuranose 1,6-bisphosphoric acid
  • β-D-Fructofuranose, 1,6-bis(dihydrogen phosphate)
  • β-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid)
  • β-D-Fructose 1,6-bisphosphate
  • β-D-Fructose 1,6-bisphosphoric acid
  • β-D-Fructose-1,6-diphosphate
  • β-D-Fructose-1,6-diphosphoric acid
Chemical Formula: C6H14O12P2
Average Molecular Weight: 340.1157
Monoisotopic Molecular Weight: 339.996048936
CAS number: 125740-83-2
IUPAC Name:{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name: β fructose 1,6-diphosphate
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent C-glycosyl compounds
Alternative Parents
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Oxolane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility16.1 mg/mLALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m3·mol-1ChemAxon
Polarizability25.6 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-014i-0497100000-d0c0dfadfe65ee3cc4e5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)splash10-014r-1779100000-ba60994aacef73cf8691View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)splash10-014r-0779100000-b52ccd042ce4169961edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-6469000000-934f8ed1edcbd28bc667View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-7295000000-a5ca0806e65ba8c99e88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9700000000-02fcc2f4b95b801c5949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-8509000000-2992f67772e061c3ffe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-9ac5383c77bff5f6cb96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9d902dae0eabfe2165daView in MoNA
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137. Pubmed: 11488613
  • Daldal, F., Fraenkel, D. G. (1983). "Assessment of a futile cycle involving reconversion of fructose 6-phosphate to fructose 1,6-bisphosphate during gluconeogenic growth of Escherichia coli." J Bacteriol 153:390-394. Pubmed: 6217196
  • Izard, T., Sygusch, J. (2004). "Induced fit movements and metal cofactor selectivity of class II aldolases: structure of Thermus aquaticus fructose-1,6-bisphosphate aldolase." J Biol Chem 279:11825-11833. Pubmed: 14699122
  • 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
  • Kornberg, H., Lourenco, C. (2006). "A route for fructose utilization by Escherichia coli involving the fucose regulon." Proc Natl Acad Sci U S A 103:19496-19499. Pubmed: 17159144
  • Nghiem, N. P., Cofer, T. M. (2007). "Effect of a nonmetabolizable analog of fructose-1,6-bisphosphate on glycolysis and ethanol production in strains of Saccharomyces cerevisiae and Escherichia coli." Appl Biochem Biotechnol 141:335-347. Pubmed: 18025560
  • Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.
  • Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23. Pubmed: 15158257
  • Veiga-da-Cunha, M., Hoyoux, A., Van Schaftingen, E. (2000). "Overexpression and purification of fructose-1-phosphate kinase from Escherichia coli: application to the assay of fructose 1-phosphate." Protein Expr Purif 19:48-52. Pubmed: 10833389
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
Pubchem Compound ID10267
Kegg IDC05378
ChemSpider ID9848
Wikipedia IDNot Available
Ligand ExpoFBP