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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:53 UTC
HMDB IDHMDB0001047
Secondary Accession Numbers
  • HMDB01047
Metabolite Identification
Common NameD-Fructose 2,6-bisphosphate
DescriptionD-Fructose 2,6-bisphosphate, also known as phosphofructokinase activator, 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. D-Fructose 2,6-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Fructose 2,6-bisphosphate exists in all living species, ranging from bacteria to humans. D-fructose 2,6-bisphosphate can be converted into fructose 6-phosphate; which is mediated by the enzyme 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1. In humans, D-fructose 2,6-bisphosphate is involved in fructose intolerance, hereditary. The breakdown of Fru-2,6-P2 is catalyzed by the phosphorylation of the bifunctional enzyme, which allows FBPase-2 to dephosphorylate fructose 2,6-bisphosphate to produce fructose 6-phosphate and Pi. Fru-2,6-P2 production is activated when plants are in the dark and photosynthesis and triose phosphates are not produced. The remaining 1/6 of triose phosphate can be converted into sucrose or stored as starch. One such gene is for the expression of TP53-induced glycolysis and apoptosis regulator (TIGAR); an enzyme that inhibits glycolysis, monitors the cellular levels of reactive oxygen species, and protects cells from apoptosis. This kinase phosphorylates the PFK-2/FBPase-2 enzyme at an NH2-terminal Ser residue with ATP to activate the FBPase-2 activity and inhibit the PFK-2 activity of the enzyme, thus reducing levels of Fru-2,6-P2 in the cell.
Structure
Data?1582752173
Synonyms
ValueSource
2,6-Di-O-phosphono-beta-D-fructofuranoseChEBI
2,6-Di-O-phosphono-b-D-fructofuranoseGenerator
2,6-Di-O-phosphono-β-D-fructofuranoseGenerator
D-Fructose 2,6-bisphosphoric acidGenerator
b-D-Fructose 2,6-bisphosphateHMDB
beta-D-Fructose 2,6-bisphosphateHMDB
Fru 2,6-P2, fructose 2,6-diphosphateHMDB
Fructose 2,6-bisphosphateHMDB
Fructose 2,6-biphosphateHMDB
Fructose 2,6-diphosphateHMDB
Phosphofructokinase activation factorHMDB
Phosphofructokinase activatorHMDB
Fructose-2,6-diphosphateHMDB
Chemical FormulaC6H14O12P2
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
IUPAC Name{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
Traditional Namefructose-2,6-diphosphate
CAS Registry NumberNot Available
SMILES
OC[C@@]1(OP(O)(O)=O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
InChI KeyYXWOAJXNVLXPMU-ZXXMMSQZSA-N
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
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.8 g/LALOGPS
logP-1.5ALOGPS
logP-3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.68ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.11 m³·mol⁻¹ChemAxon
Polarizability25.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01dj-0963000000-090736f476a618727455Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00tb-0972000000-e47c74a14376eaabd8c3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01dj-0963000000-090736f476a618727455Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00tb-0972000000-e47c74a14376eaabd8c3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9512000000-82418e0e398490357c5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-2190010000-53cf738181713979e181Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3797000000-cb11e27ce8d0be902a39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9132000000-b908246df46f54e31180Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dm-9600000000-19262e5981934144e1aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-7409000000-0240bd8771cde252759cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-8930f98e412f1b68e30bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fb204edc71835bcbaaadSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022390
KNApSAcK IDC00007441
Chemspider ID94762
KEGG Compound IDC00665
BioCyc IDNot Available
BiGG ID35645
Wikipedia LinkFructose_2,6-bisphosphate
METLIN ID5964
PubChem Compound105021
PDB IDNot Available
ChEBI ID28602
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceShulman, Hagit; Makarov, Carina; Ogawa, Anthony K.; Romesberg, Floyd; Keinan, Ehud. Chemically Reactive Immunogens Lead to Functional Convergence of the Immune Response. Journal of the American Chemical Society (2000), 122(44), 10743-10753.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB3
Uniprot ID:
Q16875
Molecular weight:
57286.965
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Phosphatedetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB4
Uniprot ID:
Q16877
Molecular weight:
54039.34
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Phosphatedetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB1
Uniprot ID:
P16118
Molecular weight:
54680.86
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Phosphatedetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:
PFKFB2
Uniprot ID:
O60825
Molecular weight:
54405.88
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Phosphatedetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphatedetails
General function:
Not Available
Specific function:
Fructose-bisphosphatase hydrolyzing fructose-2,6-bisphosphate as well as fructose-1,6-bisphosphate. Inhibits glycolysis by reducing cellular levels of fructose-2,6-bisphosphate. May protect cells against reactive oxygen species and against apoptosis induced by tp53.
Gene Name:
TIGAR
Uniprot ID:
Q9NQ88
Molecular weight:
30062.295
Reactions
D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Phosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphatedetails