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Fructose 1,6-bisphosphate (YMDB00108)

Identification
YMDB IDYMDB00108
NameFructose 1,6-bisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFructose 1,6-bisphosphate (also known as Harden-young ester) is a fructose sugar phosphorylated on carbons 1 and 6. The β-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell will become converted to fructose 1,6-biphosphate at some point. Fructose 1,6-bisphosphate lies within the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate. It is, in turn, broken down into two compounds: glyceraldehyde 3-phosphate and dihydroxyacetone phosphate. It is an allosteric activator of pyruvate kinase. [Wikipedia]
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 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
  • FDP
  • Fosfructose
  • Fructose 1,6-bis
  • Fructose 1,6-bisphosphate
  • Fructose 1,6-diphosphate
  • Fructose 1,6-diphosphic acid
  • Harden-Young ester
  • 2,5-Anhydroglucitol-1,6-biphosphoric acid
  • Fructose 1,6-bisphosphoric acid
CAS number488-69-7
WeightAverage: 324.1163
Monoisotopic: 324.001134314
InChI KeyWSMBXSQDFPTODV-JGWLITMVSA-N
InChIInChI=1S/C6H14O11P2/c7-5-3(1-15-18(9,10)11)17-4(6(5)8)2-16-19(12,13)14/h3-8H,1-2H2,(H2,9,10,11)(H2,12,13,14)/t3-,4+,5-,6-/m1/s1
IUPAC Name{[(2S,3S,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name[(2S,3S,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid
Chemical FormulaC6H14O11P2
SMILES[H]O[C@@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])C([H])([H])OP(=O)(O[H])O[H])C([H])([H])OP(=O)(O[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
  • 1,2-diol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility94 mg/mL [sodium salt, HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility16 g/LALOGPS
logP-1.5ALOGPS
logP-2.8ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.93ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.64 m³·mol⁻¹ChemAxon
Polarizability24.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
Fructose 6-phosphate + Adenosine triphosphate → Fructose 1,6-bisphosphate + ADP
Fructose 1,6-bisphosphate → D-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate
KEGG Reactions
Adenosine triphosphate + D-fructose 1-phosphate → hydron + ADP + Fructose 1,6-bisphosphate
water + Fructose 1,6-bisphosphate → Fructose 6-phosphate + phosphate
Fructose 1,6-bisphosphate ↔ D-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate
Adenosine triphosphate + Fructose 6-phosphate → hydron + ADP + Fructose 1,6-bisphosphate
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
90 ± 70 µM Minimal medium supplemented with ammonia saltsaerobic;resting cellsBaker's yeastPMID: 4578278
3800 ± 3200 µM Minimal medium supplemented with ammonia salts and glucoseaerobic and anaerobic;resting cellsBaker's yeastPMID: 4578278
50 ± 0 µM Minimal medium supplemented with ammonia salts and ethanolaerobic;growing cellsBaker's yeastPMID: 4578278
3500 ± 1000 µM Minimal medium supplemented with ammonia salts and (glucose or galactose)aerobic;growing cellsBaker's yeastPMID: 4578278
1700 ± 10 µM Synthetic medium with 2% glucoseaerobic;growing cellsBaker's yeastPMID: 6229402
410 ± 70 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
530 ± 130 µM Synthetic medium with 2% glucoseanaerobic;resting cellsBaker's yeastPMID: 6229402
2700 ± 600 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9510000000-b61ac58bde76d2a1b23eJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0092-0249000000-eb939046a288ed654b99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-5576a6262edb99fd1ef1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0900000000-5576a6262edb99fd1ef1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1449000000-b8c014f1b120b99df234JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-7394000000-8cf301778bf04bd017a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-7900000000-59986d4e4c4309b9f814JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-6109000000-76c96c0eb2ab1ac20db1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5677f1663b32f68073adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-29c2267c283eb5e5b173JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D 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
  • Blazquez, M. A., Lagunas, R., Gancedo, C., Gancedo, J. M. (1993). "Trehalose-6-phosphate, a new regulator of yeast glycolysis that inhibits hexokinases." FEBS Lett 329:51-54.8354408
  • 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
  • Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
  • 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:Yan, Weiqun. Method for producing fructose-1,6-diphosphate (FDP). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.
External Links:
ResourceLink
CHEBI ID16905
HMDB IDHMDB01058
Pubchem Compound ID718
Kegg IDNot Available
ChemSpider ID21896510
FOODB IDNot Available
WikipediaFructose_1,6-bisphosphate
BioCyc IDFRUCTOSE-16-DIPHOSPHATE

Enzymes

Protein Details
1. 6-phosphofructokinase subunit alpha
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.
Protein Details
2. 6-phosphofructokinase subunit beta
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.
Protein Details
3. Fructose-1,6-bisphosphatase
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.
Protein Details
4. Fructose-bisphosphate aldolase
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.