Record Information
Version2.0
Creation Date2012-05-31 13:44:15 -0600
Update Date2015-09-17 15:41:08 -0600
Secondary Accession Numbers
  • ECMDB01058
Identification
Name:Fructose 1,6-bisphosphate
DescriptionThe hydrolysis of fructose 1,6-bisphosphate is catalized by Fructose-1,6-bisphosphatase (fru-1,6-P2ase, EC 3.1.3.11) to fructose 6-phosphate and inorganic phosphate and provides a mechanism to permit the reversal of the glycolysis reaction (catalyzed by 6-phosphofructo-1-kinase).(OMIM)
Structure
Thumb
Synonyms:
  • β-D-fructose-1,6-diphosphate
  • β-D-fructose-1,6-diphosphoric acid
  • b-D-Fructose-1,6-diphosphate
  • b-D-Fructose-1,6-diphosphoric acid
  • Beta-D-Fructose-1,6-diphosphate
  • beta-D-Fructose-1,6-diphosphoric acid
  • D-Fructose 1,6-biphosphate
  • D-Fructose 1,6-biphosphoric acid
  • D-Fructose 1,6-bis(dihydrogen phosphate)
  • D-Fructose 1,6-bis(dihydrogen phosphoric acid)
  • D-Fructose 1,6-bisphosphate
  • D-Fructose 1,6-bisphosphoric acid
  • D-Fructose 1,6-diphosphate
  • D-Fructose 1,6-diphosphoric acid
  • D-Fructose-1,6-bisphosphate
  • D-Fructose-1,6-bisphosphoric acid
  • D-Fructose-1,6-diphosphate
  • D-Fructose-1,6-diphosphoric acid
  • Diphosphofructose
  • Esafosfan
  • Esafosfina
  • F1,6P
  • FBP
  • FDP
  • Fosfructose
  • Fructose 1,6-bis
  • Fructose 1,6-bisphosphate
  • Fructose 1,6-bisphosphoric acid
  • Fructose 1,6-diphosphate
  • Fructose 1,6-diphosphoric acid
  • Fructose-1,6-biphosphate
  • Fructose-1,6-biphosphoric acid
  • Fructose-1,6-diphosphate
  • Fructose-1,6-diphosphoric acid
  • Harden-Young ester
  • β-D-Fructose-1,6-diphosphate
  • β-D-Fructose-1,6-diphosphoric acid
Chemical Formula:C6H14O12P2
Weight:Average: 340.1157
Monoisotopic: 339.996048936
InChI Key:RNBGYGVWRKECFJ-ZXXMMSQZSA-N
InChI:InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
CAS number:488-69-7
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
SMILES:O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
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
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:94 mg/mL [sodium salt, HMP experimental]PhysProp
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
Reactions:
Fructose 1,6-bisphosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate
Adenosine triphosphate + Fructose 6-phosphate > ADP + Fructose 1,6-bisphosphate + Hydrogen ion
Fructose 1,6-bisphosphate + Water <> Fructose 6-phosphate + Phosphate
Adenosine triphosphate + Fructose 1-phosphate > ADP + Fructose 1,6-bisphosphate + Hydrogen ion
Fructose 1,6-bisphosphate + Water > Fructose 6-phosphate + Phosphate
Fructose 1,6-bisphosphate > Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate
Fructose 1,6-bisphosphate + Water > Fructose 6-phosphate + Inorganic phosphate
Adenosine triphosphate + Fructose 1-phosphate > ADP + Fructose 1,6-bisphosphate
Adenosine triphosphate + Fructose 6-phosphate > ADP + Fructose 1,6-bisphosphate
Adenosine triphosphate + Fructose 6-phosphate <> ADP + Fructose 1,6-bisphosphate
Fructose 6-phosphate + Phosphate + Fructose 6-phosphate > Fructose 1,6-bisphosphate + Water + Fructose 1,6-bisphosphate
Fructose 6-phosphate + Adenosine triphosphate + Fructose 6-phosphate > Fructose 1,6-bisphosphate + Adenosine diphosphate + Hydrogen ion + Fructose 1,6-bisphosphate + ADP
Fructose 1,6-bisphosphate + Fructose 1,6-bisphosphate <> D-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate > Fructose 1,6-bisphosphate + Fructose 1,6-bisphosphate
Fructose 1,6-bisphosphate + Fructose 1,6-bisphosphate > Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphate
Fructose 1,6-bisphosphate + Water + Fructose 1,6-bisphosphate > Phosphate + D-tagatofuranose 6-phosphate
β-D-fructofuranose 1-phosphate + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + Fructose 1,6-bisphosphate + ADP + Fructose 1,6-bisphosphate
Fructose 1,6-bisphosphate + Water <> Fructose 6-phosphate + Phosphate
SMPDB Pathways:
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
Gluconeogenesis from L-malic acidPW000819 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary metabolites: Trehalose Biosynthesis and MetabolismPW000968 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
fructose metabolismPW000913 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolismPW000914 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IIPW000915 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)PW000916 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IV (glycerophosphoglycerol)PW000917 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism V (glycerophosphoserine)PW000918 ThumbThumb?image type=greyscaleThumb?image type=simple
glycolysis and pyruvate dehydrogenasePW000785 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9510000000-b61ac58bde76d2a1b23eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0092-0249000000-eb939046a288ed654b99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-5576a6262edb99fd1ef1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0900000000-5576a6262edb99fd1ef1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1449000000-b8c014f1b120b99df234View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-7394000000-8cf301778bf04bd017a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-7900000000-59986d4e4c4309b9f814View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-6109000000-76c96c0eb2ab1ac20db1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5677f1663b32f68073adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-29c2267c283eb5e5b173View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Yan, Weiqun. Method for producing fructose-1,6-diphosphate (FDP). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16905
HMDB IDHMDB01058
Pubchem Compound ID718
Kegg IDC00354
ChemSpider ID393163
WikipediaFructose 1,6-diphosphate
BioCyc IDFRUCTOSE-16-DIPHOSPHATE
EcoCyc IDFRUCTOSE-16-DIPHOSPHATE
Ligand ExpoAHG

Enzymes

General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkB
Uniprot ID:
P06999
Molecular weight:
32456
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in ATP binding
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkA
Uniprot ID:
P0A796
Molecular weight:
34842
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in catalytic activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
fbaB
Uniprot ID:
P0A991
Molecular weight:
38109
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-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:
fbp
Uniprot ID:
P0A993
Molecular weight:
36834
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate.
General function:
Involved in glycerol metabolic process
Specific function:
D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate
Gene Name:
glpX
Uniprot ID:
P0A9C9
Molecular weight:
35852
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:
fbaA
Uniprot ID:
P0AB71
Molecular weight:
39147
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
General function:
Involved in 1-phosphofructokinase activity
Specific function:
ATP + D-fructose 1-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
fruK
Uniprot ID:
P0AEW9
Molecular weight:
33755
Reactions
ATP + D-fructose 1-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates pyridoxalphosphate and erythrose 4-phosphate
Gene Name:
ybhA
Uniprot ID:
P21829
Molecular weight:
30201
General function:
Involved in glycerol metabolic process
Specific function:
Specific function unknown
Gene Name:
yggF
Uniprot ID:
P21437
Molecular weight:
34323
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
ydjI
Uniprot ID:
P77704
Molecular weight:
30810