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Identification
YMDB IDYMDB00078
NameFructose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFructose 6-phosphate is an important intermediate in the carbohydrates pathway. In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate.
Structure
Thumb
Synonyms
  • D-Fructose 6-phosphate
  • D-Fructose 6-phosphorate
  • D-Fructose 6-phosphoric acid
  • D-fructose-6-P
  • D-fructose-6-phosphate
  • FPC
  • fru-6-P
  • Fructose 6-phosphate
  • Fructose 6-phosphic acid
  • fructose-6-P
  • Fructose-6-phosphate
  • fructose-6P
  • Neuberg ester
  • Fructose-6-phosphoric acid
  • Fructose 6-phosphoric acid
  • Fructose-6-phosphate, (alpha-D)-isomer
  • Fructose-6-phosphate, (beta-D)-isomer
  • Fructose-6-phosphate, disodium salt, (D)-isomer
  • Fructose-6-phosphate, (D)-isomer
  • Fructose-6-phosphate, 1-(14)C-labeled, (D)-isomer
  • Fructose-6-phosphate, 2-(14)C-labeled, (D)-isomer
  • Fructose-6-phosphate, barium (1:1) salt, (D)-isomer
  • Fructose-6-phosphate, barium salt, (D)-isomer
  • Fructose-6-phosphate, sodium salt, (D)-isomer
  • Fructose-6-phosphate, calcium salt, (D)-isomer
  • Fructose-6-phosphate, magnesium (1:1) salt, (D)-isomer
  • Fructose-6-phosphate, sodium salt
CAS number643-13-0
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyGSXOAOHZAIYLCY-HSUXUTPPSA-N
InChIInChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1
IUPAC Name{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
Traditional IUPAC NameD-fructose 6-phosphate
Chemical FormulaC6H13O9P
SMILES[H]OC([H])([H])C(=O)[C@@]([H])(O[H])[C@]([H])(O[H])[C@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]
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
  • 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
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility911 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility23.2 g/LALOGPS
logP-1.9ALOGPS
logP-3.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.43 m³·mol⁻¹ChemAxon
Polarizability20.87 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
SMPDB Reactions
Fructose 6-phosphateGlucose 6-phosphate
Beta-D-Glucose 6-phosphateFructose 6-phosphate
Fructose 6-phosphateBeta-D-Glucose 6-phosphate
Fructose 6-phosphate + Adenosine triphosphateFructose 1,6-bisphosphate + ADP
KEGG Reactions
Adenosine triphosphate + Fructose 6-phosphateD-Fructose 2,6-bisphosphate + hydron + ADP
D-Fructose 2,6-bisphosphate + waterFructose 6-phosphate + phosphate
water + Fructose 1,6-bisphosphateFructose 6-phosphate + phosphate
water + Glucosamine 6-phosphateFructose 6-phosphate + Ammonium
Beta-D-Glucose 6-phosphateFructose 6-phosphate
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
400 ± 30 µM 20 ml 2% (wt/vol) glucose, 0.5% (wt/vol) ammonium sulfate, 0.17% (wt/vol) yeast nitrogen base without amino acids (Difco, Detroit, MI) and 100 mM potassium phthalate at pH 5.0, supplemented with required nutrients (40 mg/L uracil, 40 mg/L Ltryptophan, 60 aerobicBaker's yeastPMID: 11135551
650 ± 30 µM Synthetic medium with 2% glucoseaerobic;growing cellsBaker's yeastPMID: 6229402
94 ± 13 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
90 ± 30 µM Synthetic medium with 2% glucoseanaerobic;resting cellsBaker's yeastPMID: 6229402
120 ± 50 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
  • Raamsdonk, L. M., Teusink, B., Broadhurst, D., Zhang, N., Hayes, A., Walsh, M. C., Berden, J. A., Brindle, K. M., Kell, D. B., Rowland, J. J., Westerhoff, H. V., van Dam, K., Oliver, S. G. (2001). "A functional genomics strategy that uses metabolome data to reveal the phenotype of silent mutations." Nat Biotechnol 19:45-50.11135551
  • 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
  • Goncalves, P., Planta, R. J. (1998). "Starting up yeast glycolysis." Trends Microbiol 6:314-319.9746941
  • Fonzi, W. A., Shanley, M., Opheim, D. J. (1979). "Relationship of glycolytic intermediates, glycolytic enzymes, and ammonia to glycogen metabolism during sporulation in the yeast Saccharomyces cerevisiae." J Bacteriol 137:285-294.368017
  • Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
  • Senac, T., Hahn-Hagerdal, B. (1990). "Intermediary Metabolite Concentrations in Xylulose- and Glucose-Fermenting Saccharomyces cerevisiae Cells." Appl Environ Microbiol 56:120-126.16348083
  • Heinisch, J. (1986). "Isolation and characterization of the two structural genes coding for phosphofructokinase in yeast." Mol Gen Genet 202:75-82.3007939
  • Banki, K., Halladay, D., Perl, A. (1994). "Cloning and expression of the human gene for transaldolase. A novel highly repetitive element constitutes an integral part of the coding sequence." J Biol Chem 269:2847-2851.8300619
  • Watzele, G., Tanner, W. (1989). "Cloning of the glutamine:fructose-6-phosphate amidotransferase gene from yeast. Pheromonal regulation of its transcription." J Biol Chem 264:8753-8758.2656689
  • 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
  • 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:Not Available
External Links:
ResourceLink
CHEBI ID15946
HMDB IDHMDB00124
Pubchem Compound ID69507
Kegg IDC00085
ChemSpider ID62713
FOODB IDFDB021896
WikipediaFructose_6-phosphate
BioCyc IDFRUCTOSE-6P

Enzymes

General function:
Involved in metabolic process
Specific function:
Involved in amino sugar synthesis (formation of chitin, supplies the amino sugars of asparagine-linked oligosaccharides of glycoproteins)
Gene Name:
Not Available
Uniprot ID:
A2P2R3
Molecular weight:
29272.0
Reactions
L-glutamine + D-fructose 6-phosphate → L-glutamate + D-glucosamine 6-phosphate.
General function:
Involved in metabolic process
Specific function:
Involved in amino sugar synthesis (formation of chitin, supplies the amino sugars of asparagine-linked oligosaccharides of glycoproteins)
Gene Name:
GFA1
Uniprot ID:
P14742
Molecular weight:
80046.0
Reactions
L-glutamine + D-fructose 6-phosphate → L-glutamate + D-glucosamine 6-phosphate.
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 ATP binding
Specific function:
Main glucose phosphorylating enzyme. May play a regulatory role in both induction and repression of gene expression by glucose
Gene Name:
HXK2
Uniprot ID:
P04807
Molecular weight:
53942.0
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
HXK1
Uniprot ID:
P04806
Molecular weight:
53737.89844
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
General function:
Involved in catalytic activity
Specific function:
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:
TKL2
Uniprot ID:
P33315
Molecular weight:
75028.79688
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-ribose 5-phosphate + D-xylulose 5-phosphate.
General function:
Involved in mannose-6-phosphate isomerase activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions
Gene Name:
PMI40
Uniprot ID:
P29952
Molecular weight:
48188.30078
Reactions
D-mannose 6-phosphate → D-fructose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:
NQM1
Uniprot ID:
P53228
Molecular weight:
37253.30078
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-erythrose 4-phosphate + D-fructose 6-phosphate.
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 catalytic activity
Specific function:
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:
TKL1
Uniprot ID:
P23254
Molecular weight:
73805.0
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-ribose 5-phosphate + D-xylulose 5-phosphate.
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 glucose-6-phosphate isomerase activity
Specific function:
D-glucose 6-phosphate = D-fructose 6- phosphate
Gene Name:
PGI1
Uniprot ID:
P12709
Molecular weight:
61298.89844
Reactions
D-glucose 6-phosphate → D-fructose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:
TAL1
Uniprot ID:
P15019
Molecular weight:
37036.0
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-erythrose 4-phosphate + D-fructose 6-phosphate.