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Identification
YMDB IDYMDB00011
NameD-Fructose 2,6-bisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Fructose 2,6-bisphosphate, also known as phosphofructokinase activator, 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. D-Fructose 2,6-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Fructose 2,6-bisphosphate exists in all living species, ranging from bacteria to humans. Within yeast, D-fructose 2,6-bisphosphate participates in a number of enzymatic reactions. In particular, D-fructose 2,6-bisphosphate can be biosynthesized from β-D-fructofuranose 6-phosphate through its interaction with the enzyme 6-phosphofructose-2-kinase. In addition, D-fructose 2,6-bisphosphate can be converted into β-D-fructofuranose 6-phosphate through the action of the enzyme fructose-2,6-bisphosphatase. In yeast, D-fructose 2,6-bisphosphate is involved in the metabolic pathway called the fructose metabolism pathway.
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
  • D-Fructose 2,6-diphosphate
  • beta-D-Fructose 2,6-diphosphate
  • β-D-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
Polarizability25.24 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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01dj-0963000000-090736f476a618727455JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00tb-0972000000-e47c74a14376eaabd8c3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01dj-0963000000-090736f476a618727455JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00tb-0972000000-e47c74a14376eaabd8c3JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9512000000-82418e0e398490357c5eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-2190010000-53cf738181713979e181JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, negativesplash10-000i-0019000000-7b58b1d6169f22e732a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, negativesplash10-000m-2496000000-40ad2c4944ae5c0701f3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, negativesplash10-0002-9830000000-a9cbb8a3dba391a8858bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, negativesplash10-002b-9200000000-6dcaff4e5eee3799656fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 50V, negativesplash10-004j-9100000000-9851b59e56acb7c5802cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3797000000-cb11e27ce8d0be902a39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9132000000-b908246df46f54e31180JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dm-9600000000-19262e5981934144e1aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-7409000000-0240bd8771cde252759cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-8930f98e412f1b68e30bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fb204edc71835bcbaaadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0393000000-f7f716e45f745f0bec68JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1920000000-f0eccbb835449758a67cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-9410000000-f9f76bd919e86701aaffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9008000000-d519306c146482d051d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9001000000-2d0e9375a49babbe9d93JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-bc05f33d90e2bf18235cJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0002-9501000000-18bdaa665084a09cbee2JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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