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Identification
YMDB IDYMDB00687
NameD-fructose 1,6-bisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-fructose 1,6-bisphosphate, also known as D-fructose-1,6-diphosphoric acid or 1,6-di-O-phosphono-D-fructose, 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. D-fructose 1,6-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-fructose 1,6-bisphosphate 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-diphosphoric acid
  • Fructose-1,6-diphosphoric acid
  • D-Fructose 1,6-bisphosphoric acid
  • SR-FDP
  • Fructose-1,6-diphosphate magnesium salt
  • Fructose-1,6-diphosphate, (L)-isomer
  • Fructose-1,6-diphosphate, (alpha-D)-isomer
  • Fructose-1,6-diphosphate, barium (1:2) salt
  • Strontium fructose-1,6-diphosphate
  • Fructose-1,6-diphosphate, disodium salt
  • Fructose-1,6-diphosphate, sodium salt, monohydrate
  • Fructose-1,6-diphosphate, 2-(18)O-labeled
  • Fructose-1,6-diphosphate, calcium (1:2) salt
  • Fructose-1,6-diphosphate, calcium salt
  • Fructose-1,6-diphosphate, trisodium salt
  • Strontium fructose 1,6-diphosphate
  • Fructose-1,6-diphosphate, (beta-D)-isomer
  • Fructose-1,6-diphosphate, monosodium salt
  • Fructose-1,6-diphosphate, tetrapotassium salt
  • Fructose-1,6-diphosphate, tetrasodium 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
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.