Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000236
Identification
Name: Fructose 1,6-bisphosphate
Description:The 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
Average Molecular Weight: 340.1157
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent C-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not 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 Solubility16.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.64 m3·mol-1ChemAxon
Polarizability24.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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 phosphoric ester hydrolase activity
Specific function:
D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate
Gene Name:
fbp
Locus Tag:
PA5110
Molecular weight:
37.2 kDa
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate.
General function:
Involved in 1-phosphofructokinase activity
Specific function:
ATP + D-fructose 1-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
fruK
Locus Tag:
PA3561
Molecular weight:
33.4 kDa
Reactions
ATP + D-fructose 1-phosphate = ADP + D-fructose 1,6-bisphosphate.