Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-03-12 22:21:28 UTC
HMDB IDHMDB01058
Secondary Accession Numbers
  • HMDB03973
Metabolite Identification
Common NameFructose 1,6-bisphosphate
DescriptionFructose 1,6-bisphosphate is fructose sugar or fructosephosphate that has been phosphorylated on carbons 1 and 6. The beta-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell is converted to fructose 1,6-bisphosphate at some point. Fructose 1,6-bisphosphate is a key component in the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate The enzyme phosphofructokinase uses ATP to transfer a phosphate group to fructose 6-phosphate to form fructose 1, 6-bisphosphate. fructose The enzyme aldolase splits fructose 1, 6-bisphosphate into two sugars that are isomers of each other. These two sugars are dihydroxyacetone phosphate and glyceraldehyde phosphate. Fructose 1,6-bisphosphate is an allosteric activator of pyruvate kinase.
Structure
Thumb
Synonyms
  1. D-Fructose 1,6-biphosphate
  2. D-Fructose 1,6-bis(dihydrogen phosphate)
  3. D-Fructose 1,6-bisphosphate
  4. D-Fructose 1,6-diphosphate
  5. D-Fructose-1,6-bisphosphate
  6. D-Fructose-1,6-diphosphate
  7. Diphosphofructose
  8. Esafosfan
  9. Esafosfina
  10. FDP
  11. Fosfructose
  12. Fructose 1,6-bis
  13. Fructose 1,6-bisphosphate
  14. Fructose 1,6-diphosphate
  15. Harden-Young ester
Chemical FormulaC6H14O12P2
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
IUPAC Name{[(2S,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Namefructose 1,6-bisphosphate
CAS Registry Number488-69-7
SMILES
O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
InChI Identifier
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
InChI KeyRNBGYGVWRKECFJ-ZXXMMSQZSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassPentoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Monosaccharide Phosphates
Substituents
  • 1,2 Diol
  • Dialkyl Ether
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct ParentPentoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
  • Component of Galactose metabolism
  • Component of Inositol metabolism
  • Protein component
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility94 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility16.1 g/LALOGPS
logP-1.5ALOGPS
logP-3ChemAxon
logS-1.3ALOGPS
pKa (strongest acidic)0.89ChemAxon
pKa (strongest basic)-3.7ChemAxon
physiological charge-4ChemAxon
hydrogen acceptor count10ChemAxon
hydrogen donor count7ChemAxon
polar surface area203.44ChemAxon
rotatable bond count6ChemAxon
refractivity58.11ChemAxon
polarizability25.28ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
GluconeogenesisSMP00128map00010
GlycolysisSMP00040map00010
Pentose Phosphate PathwaySMP00031map00030
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified3.8 +/- 0.7 uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified1.2 +/- 0.4 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cellular CytoplasmDetected and Quantified7.60 (3.60-11.6) uMAdult (>18 years old)BothNormal
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 IDFDB022397
KNApSAcK IDNot Available
Chemspider ID393165
KEGG Compound IDC00354
BioCyc IDFRUCTOSE-16-DIPHOSPHATE
BiGG ID34717
Wikipedia LinkFructose 1,6-diphosphate
NuGOwiki LinkHMDB01058
Metagene LinkHMDB01058
METLIN ID147
PubChem Compound172313
PDB IDAFP
ChEBI ID16905
References
Synthesis ReferenceYan, Weiqun. Method for producing fructose-1,6-diphosphate (FDP). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  2. Nakai A, Shigematsu Y, Liu YY, Kikawa Y, Sudo M: Urinary sugar phosphates and related organic acids in fructose-1,6-diphosphatase deficiency. J Inherit Metab Dis. 1993;16(2):408-14. Pubmed: 8412001
  3. Riedel BJ, Gal J, Ellis G, Marangos PJ, Fox AW, Royston D: Myocardial protection using fructose-1,6-diphosphate during coronary artery bypass graft surgery: a randomized, placebo-controlled clinical trial. Anesth Analg. 2004 Jan;98(1):20-9, table of contents. Pubmed: 14693576
  4. Acan NL, Ozer N: Modification of human erythrocyte pyruvate kinase by an active site-directed reagent: bromopyruvate. J Enzyme Inhib. 2001 Nov;16(5):457-64. Pubmed: 11916152
  5. Ahn SM, Yoon HY, Lee BG, Park KC, Chung JH, Moon CH, Lee SH: Fructose-1,6-diphosphate attenuates prostaglandin E2 production and cyclo-oxygenase-2 expression in UVB-irradiated HaCaT keratinocytes. Br J Pharmacol. 2002 Oct;137(4):497-503. Pubmed: 12359631
  6. Norne JE, Lilja H, Lindman B, Einarsson R, Zeppezauer M: Pt(CN)2-4 and Au(CN)-2: potential general probes for anion-binding sites of proteins. 35Cl and 81Br nuclear-magnetic-resonance studies. Eur J Biochem. 1975 Nov 15;59(2):463-73. Pubmed: 1204623

Enzymes

Gene Name:
PFKP
Uniprot ID:
Q01813
Reactions
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + Fructose 1,6-bisphosphatedetails
Gene Name:
PFKL
Uniprot ID:
P17858
Reactions
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + Fructose 1,6-bisphosphatedetails
Gene Name:
PFKM
Uniprot ID:
P08237
Reactions
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + Fructose 1,6-bisphosphatedetails
Gene Name:
FBP2
Uniprot ID:
O00757
Reactions
Fructose 1,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails
Gene Name:
FBP1
Uniprot ID:
P09467
Reactions
Fructose 1,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails
Gene Name:
ALDOA
Uniprot ID:
P04075
Reactions
Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
Gene Name:
ALDOC
Uniprot ID:
P09972
Reactions
Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
Gene Name:
ALDOB
Uniprot ID:
P05062
Reactions
Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
Gene Name:
Not Available
Uniprot ID:
Q8NHT3
Gene Name:
ALDOC
Uniprot ID:
A8MVZ9
Gene Name:
Not Available
Uniprot ID:
A4UCT0
Gene Name:
Not Available
Uniprot ID:
A4UCS9
Gene Name:
ALDOB
Uniprot ID:
Q5T7D5
Gene Name:
Not Available
Uniprot ID:
A8K430