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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-07-23 16:07:02 UTC
HMDB IDHMDB0001047
Secondary Accession Numbers
  • HMDB01047
Metabolite Identification
Common NameD-Fructose 2,6-bisphosphate
DescriptionD-Fructose 2,6-bisphosphate (CAS: 77164-51-3), 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 a regulatory molecule controlling the activity of the enzyme phosphofructokinase-1 or PFK1 (in mammals). PFK1, in turn, is the key regulatory enzyme in the central metabolic pathway glycolysis. D-Fructose 2,6-bisphosphate has the effect of increasing the activity of PFK1, thus increasing the rate at which the principle food molecule glucose is broken down. At the same time, this regulatory molecule also inhibits the opposing enzyme (FBPase1) in the reverse pathway (gluconeogenesis) so that the synthesis of glucose is not taking place in the same cell where glucose is being broken down (which would be wasteful) (Wikipedia ).
Structure
Data?1595520422
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-biphosphateMeSH, HMDB
Fructose 2,6-diphosphateMeSH, HMDB
Phosphofructokinase activation factorMeSH, HMDB
Phosphofructokinase activatorMeSH, HMDB
Fructose-2,6-diphosphateMeSH, HMDB
D-Fructose 2,6-diphosphateHMDB
beta-D-Fructose 2,6-diphosphateHMDB
β-D-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 Number79082-92-1
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, negativesplash10-000i-0019000000-7b58b1d6169f22e732a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, negativesplash10-000m-2496000000-40ad2c4944ae5c0701f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, negativesplash10-0002-9830000000-a9cbb8a3dba391a8858bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, negativesplash10-002b-9200000000-6dcaff4e5eee3799656fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 50V, negativesplash10-004j-9100000000-9851b59e56acb7c5802cSpectrum
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
FooDB IDFDB022390
KNApSAcK IDC00007441
Chemspider ID94762
KEGG Compound IDC00665
BioCyc IDCPD-535
BiGG ID35645
Wikipedia LinkFructose_2,6-bisphosphate
METLIN ID5964
PubChem Compound105021
PDB IDNot Available
ChEBI ID28602
Food Biomarker OntologyNot Available
VMH IDF26BP
MarkerDB ID
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