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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:48 UTC
HMDB IDHMDB01047
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Fructose 2,6-bisphosphate
DescriptionD-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
Thumb
Synonyms
  1. b-D-Fructose 2,6-bisphosphate
  2. beta-D-Fructose 2,6-bisphosphate
  3. D-Fructose 2,6-bisphosphate
  4. Fru 2,6-P2, Fructose 2,6-diphosphate
  5. Fructose 2,6-bisphosphate
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 IUPAC Name[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxyphosphonic acid
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
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassPentoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Monosaccharide Phosphates
  • ketohexose bisphosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentPentoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 area203.44ChemAxon
rotatable bond count6ChemAxon
refractivity58.11ChemAxon
polarizability25.37ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022390
KNApSAcK IDNot Available
Chemspider ID94762
KEGG Compound IDC00665
BioCyc IDCPD-535
BiGG ID35645
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01047
Metagene LinkHMDB01047
METLIN ID5964
PubChem Compound105021
PDB IDFDP
ChEBI ID28602
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 + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphoric aciddetails
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 + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphoric aciddetails
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 + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphoric aciddetails
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 + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphoric aciddetails
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 + Phosphoric aciddetails
D-Fructose 2,6-bisphosphate + Water → Beta-D-Fructose 6-phosphate + Phosphoric aciddetails