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Identification
YMDB IDYMDB00011
NameD-Fructose 2,6-bisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Fructose 2,6-bisphosphate is a regulatory molecule controlling the activity of the phosphofructokinase-1 (PFK1) which is the key regulatory enzyme of glycolysis.
Structure
Thumb
Synonyms
  • 2,6-Di-O-phosphono-b-D-fructofuranose
  • 2,6-Di-O-phosphono-beta-D-fructofuranose
  • 2,6-Di-O-phosphono-β-D-fructofuranose
  • b-D-fructose 2,6-bisphosphate
  • beta-D-fructose 2,6-bisphosphate
  • D-Fructose 2,6-bisphosphate
  • D-Fructose 2,6-bisphosphic acid
  • D-Fructose 2,6-bisphosphoric acid
  • Fru 2,6-P2, Fructose 2,6-diphosphate
  • Fructose 2,6-biphosphate
  • fructose 2,6-bisphosphate
  • Fructose 2,6-diphosphate
  • Phosphofructokinase activation factor
  • Phosphofructokinase activator
  • Fructose-2,6-diphosphate
CAS numberNot Available
WeightAverage: 340.1157
Monoisotopic: 339.996048936
InChI KeyYXWOAJXNVLXPMU-ZXXMMSQZSA-N
InChIInChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
IUPAC Name{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Namefructose-2,6-diphosphate
Chemical FormulaC6H14O12P2
SMILES[H]OC([H])([H])[C@@]1(OP(=O)(O[H])O[H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility15.8 g/LALOGPS
logP-1.5ALOGPS
logP-3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.68ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m³·mol⁻¹ChemAxon
Polarizability25.37 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Fructose MetabolismPW002390 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
SMPDB Reactions
β-D-fructofuranose 6-phosphate + Adenosine triphosphateADP + hydron + D-Fructose 2,6-bisphosphate
D-Fructose 2,6-bisphosphate + waterphosphate + β-D-fructofuranose 6-phosphate
KEGG Reactions
Adenosine triphosphate + Fructose 6-phosphateD-Fructose 2,6-bisphosphate + hydron + ADP
D-Fructose 2,6-bisphosphate + waterFructose 6-phosphate + phosphate
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1200 ± 200 µM Synthetic medium with 2% glucoseaerobic;growing cellsBaker's yeastPMID: 6229402
360 ± 1 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
510 ± 20 µM Synthetic medium with 2% glucoseanaerobic;resting cellsBaker's yeastPMID: 6229402
1700 ± 200 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
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
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Francois, J., Van Schaftigen, E., Hers, H. G. (1988). "Characterization of phosphofructokinase 2 and of enzymes involved in the degradation of fructose 2,6-bisphosphate in yeast." Eur J Biochem 171:599-608.2831055
  • Kretschmer, M., Schellenberger, W., Otto, A., Kessler, R., Hofmann, E. (1987). "Fructose-2,6-bisphosphatase and 6-phosphofructo-2-kinase are separable in yeast." Biochem J 246:755-759.2825652
  • Goncalves, P., Planta, R. J. (1998). "Starting up yeast glycolysis." Trends Microbiol 6:314-319.9746941
  • Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
  • Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
Synthesis Reference:Shulman, Hagit; Makarov, Carina; Ogawa, Anthony K.; Romesberg, Floyd; Keinan, Ehud. Chemically Reactive Immunogens Lead to Functional Convergence of the Immune Response. Journal of the American Chemical Society (2000), 122(44), 10743-10753.
External Links:
ResourceLink
CHEBI ID28602
HMDB IDHMDB01047
Pubchem Compound ID105021
Kegg IDC00665
ChemSpider ID24534245
FOODB IDFDB022390
WikipediaFructose_2,6-bisphosphate
BioCyc IDCPD-535

Enzymes

General function:
Involved in catalytic activity
Specific function:
This is predominantly if not solely a fructose-2,6- bisphosphatase
Gene Name:
FBP26
Uniprot ID:
P32604
Molecular weight:
52594.5
Reactions
Beta-D-fructose 2,6-bisphosphate + H(2)O → D-fructose 6-phosphate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Synthesis of fructose 2,6-bisphosphate
Gene Name:
PFK27
Uniprot ID:
Q12471
Molecular weight:
45317.10156
Reactions
ATP + D-fructose 6-phosphate → ADP + beta-D-fructose 2,6-bisphosphate.
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate
Gene Name:
Not Available
Uniprot ID:
Q06137
Molecular weight:
58385.19922
Reactions
Beta-D-fructose 2,6-bisphosphate + H(2)O → D-fructose 6-phosphate + phosphate.
ATP + D-fructose 6-phosphate → ADP + beta-D-fructose 2,6-bisphosphate.
General function:
Involved in catalytic activity
Specific function:
Synthesis of fructose 2,6-bisphosphate
Gene Name:
PFK26
Uniprot ID:
P40433
Molecular weight:
93416.20313
Reactions
ATP + D-fructose 6-phosphate → ADP + beta-D-fructose 2,6-bisphosphate.
General function:
Involved in catalytic activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
PHO8
Uniprot ID:
P11491
Molecular weight:
63003.60156
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
(2E,6E)-farnesyl diphosphate + H(2)O → (2E,6E)-farnesol + diphosphate.
beta-D-fructose 2,6-bisphosphate + H2O → beta-D-fructofuranose 2-phosphate + phosphate