Identification
YMDB IDYMDB00687
NameD-fructose 1,6-bisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFosfructose, also known as SR-FDP, 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. Fosfructose is an extremely weak basic (essentially neutral) compound (based on its pKa). Fosfructose may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • .alpha.-D-Fructofuranose 1,6-diphosphate
  • .alpha.-D-Fructofuranose, 1,6-bis(dihydrogen phosphate)
  • 1,6-di-O-phosphono-D-fructose
  • beta-d-fructofuranose-1,6-diphosphate
  • D-Fructose 1,6-biphosphate
  • D-Fructose 1,6-bis(dihydrogen phosphate)
  • D-Fructose 1,6-bisphosphate
  • D-Fructose 1,6-diphosphate
  • D-fructose-1,6-bisphosphate
  • D-fructose-1,6-diphosphate
  • Diphosphofructose
  • Esafosfan
  • Esafosfina
  • fbp, fructose diphosphate
  • FDP
  • Fosfructose
  • Fructose 1,6-bis
  • Fructose 1,6-bisphosphate
  • Fructose 1,6-diphosphate
  • Fructose 1,6-diphosphic acid
  • fructose-1,6-bisphosphate
  • FRUCTOSE,L,6-DIPHOSPHASE
  • Harden-Young ester
  • Fructose-1,6-diphosphate
  • D-Fructose 1,6-bisphosphoric acid
  • D-Fructose-1,6-diphosphoric acid
  • Fructose-1,6-diphosphoric acid
  • Fructose-1,6-diphosphate, (alpha-D)-isomer
  • Fructose-1,6-diphosphate, sodium salt, monohydrate
  • Fructose-1,6-diphosphate, monosodium salt
  • Fructose-1,6-diphosphate, calcium (1:2) salt
  • Strontium fructose 1,6-diphosphate
  • SR-FDP
  • Fructose-1,6-diphosphate, disodium salt
  • Fructose-1,6-diphosphate, 2-(18)O-labeled
  • Fructose-1,6-diphosphate, (L)-isomer
  • Fructose-1,6-diphosphate, calcium salt
  • Fructose-1,6-diphosphate, tetrapotassium salt
  • Fructose-1,6-diphosphate, (beta-D)-isomer
  • Strontium fructose-1,6-diphosphate
  • Fructose-1,6-diphosphate, tetrasodium salt
  • Fructose-1,6-diphosphate, trisodium salt
  • Fructose-1,6-diphosphate, barium (1:2) salt
  • Fructose-1,6-diphosphate magnesium salt
CAS number488-69-7
WeightAverage: 340.1157
Monoisotopic: 339.996048936
InChI KeyXPYBSIWDXQFNMH-UYFOZJQFSA-N
InChIInChI=1S/C6H14O12P2/c7-3(1-17-19(11,12)13)5(9)6(10)4(8)2-18-20(14,15)16/h3,5-7,9-10H,1-2H2,(H2,11,12,13)(H2,14,15,16)/t3-,5-,6-/m1/s1
IUPAC Name{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]oxy}phosphonic acid
Traditional IUPAC NameD-fructose 1,6-bisphosphate
Chemical FormulaC6H14O12P2
SMILES[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)[C@]([H])(O)C(=O)COP(O)(O)=O
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility13.6 g/LALOGPS
logP-1.6ALOGPS
logP-3.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area211.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity59.31 m³·mol⁻¹ChemAxon
Polarizability25.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Methane metabolismec00680 Map00680
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0955000000-424463ed06df92a04093JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kk-1954000000-c578c6dc8f011032d008JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-8922000000-e52833b8a5a291a52187JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0109000000-5374d73d3b6f0d1d67ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-9100000000-90d958ebad119c7c60f4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00gl-0197000000-2c666d207be881c4ef28JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0kk9-0392000000-2e114e2ff3476fa48de6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-1960000000-d78713458d852ddd22e7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052b-5900000000-d65f29d5f722e387b3ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-3b992f02b655d8e877c3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1249000000-705e8e2d0bf1c8ef0552JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-4921000000-47a02a183df4faa521d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9810000000-9d59b24daf1d7967e6e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002k-5903000000-13d1be2828c65e407664JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-e78f4a266f65b4d059f2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f3dcf179be35cf051b41JSpectraViewer
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:
  • 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
  • Schray, K. J., Fishbein, R., Bullard, W. P., Benkovic, S. J. (1975). "The anomeric form of D-fructose 1,6-bisphosphate used as substrate in the muscle and yeast aldolase reactions." J Biol Chem 250:4883-4887.168195
  • Wurster, B., Hess, B. (1976). "Tautomeric and anomeric specificity of allosteric activation of yeast pyruvate kinase by D-fructose 1, 6-bisphosphate and its relevance in D-glucose catabolism." FEBS Lett 63:17-21.770188
  • Barnett, J. A. (2003). "A history of research on yeasts 5: the fermentation pathway." Yeast 20:509-543.12722184
  • Heinisch, J. (1986). "Isolation and characterization of the two structural genes coding for phosphofructokinase in yeast." Mol Gen Genet 202:75-82.3007939
  • Boles, E., Zimmermann, F. K. (1993). "Saccharomyces cerevisiae phosphoglucose isomerase and fructose bisphosphate aldolase can be replaced functionally by the corresponding enzymes of Escherichia coli and Drosophila melanogaster." Curr Genet 23:187-191.8435847
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16905
HMDB IDHMDB01058
Pubchem Compound ID718
Kegg IDC00354
ChemSpider ID76632
FOODB IDNot Available
WikipediaFructose_1,6-bisphosphate
BioCyc IDFRUCTOSE-16-DIPHOSPHATE

Enzymes

General function:
Involved in 6-phosphofructokinase activity
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
PFK1
Uniprot ID:
P16861
Molecular weight:
107969.0
Reactions
ATP + D-fructose 6-phosphate → ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in 6-phosphofructokinase activity
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
PFK2
Uniprot ID:
P16862
Molecular weight:
104617.0
Reactions
ATP + D-fructose 6-phosphate → ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in phosphoric ester hydrolase activity
Specific function:
D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate
Gene Name:
FBP1
Uniprot ID:
P09201
Molecular weight:
38262.19922
Reactions
D-fructose 1,6-bisphosphate + H(2)O → D-fructose 6-phosphate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3- phosphate (G3P) to form fructose 1,6-bisphosphate (FBP) in gluconeogenesis and the reverse reaction in glycolysis
Gene Name:
FBA1
Uniprot ID:
P14540
Molecular weight:
39620.5
Reactions
D-fructose 1,6-bisphosphate → glycerone phosphate + D-glyceraldehyde 3-phosphate.