Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:55 UTC
HMDB IDHMDB00124
Secondary Accession NumbersNone
Metabolite Identification
Common NameFructose 6-phosphate
DescriptionFructose 6-phosphate is an important intermediate in the Carbohydrates pathway. The interconversion of glucose-6-phosphate and fructose-6-phosphate, the second step of the Embden-Meyerhof glycolytic pathway, is catalyzed by the enzyme phosphoglucose isomerase (PGI). In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate (wikipedia).
Structure
Thumb
Synonyms
  1. D-Fructose 6-phosphate
  2. D-Fructose 6-phosphorate
  3. D-Fructose 6-phosphoric acid
  4. D-Fructose-6-P
  5. D-Fructose-6-phosphate
  6. FPC
  7. Fru-6-P
  8. Fructose 6-phosphate
  9. Fructose-6-P
  10. Fructose-6-phosphate
  11. Fructose-6P
  12. Neuberg ester
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
Traditional IUPAC Name[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxyphosphonic acid
CAS Registry Number643-13-0
SMILES
OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O
InChI Identifier
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1
InChI KeyGSXOAOHZAIYLCY-HSUXUTPPSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • ketohexose monophosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Acyloin
  • Alpha Ketoaldehyde
  • Beta Ketoaldehyde
  • Ketone
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
  • Component of Fructose and mannose metabolism
  • Component of Galactose metabolism
  • Component of Glutamate metabolism
  • Component of Starch and sucrose metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility911 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility23.2 g/LALOGPS
logP-1.9ALOGPS
logP-3.4ChemAxon
logS-1.1ALOGPS
pKa (strongest acidic)1.49ChemAxon
pKa (strongest basic)-3.3ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count6ChemAxon
polar surface area164.75ChemAxon
rotatable bond count7ChemAxon
refractivity48.43ChemAxon
polarizability20.87ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Intestine
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
Fructose and Mannose DegradationSMP00064map00051
GluconeogenesisSMP00128map00010
GlycolysisSMP00040map00010
Pentose Phosphate PathwaySMP00031map00030
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified9.9 +/- 2.3 uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified10.2 +/- 1.8 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cellular CytoplasmDetected and Quantified16.0 (13.0-19.0) uMAdult (>18 years old)BothNormal
Cellular CytoplasmDetected and Quantified49.6 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 IDFDB021896
KNApSAcK IDNot Available
Chemspider ID62713
KEGG Compound IDC00085
BioCyc IDFRUCTOSE-6P
BiGG ID33795
Wikipedia LinkFructose 6-phosphate
NuGOwiki LinkHMDB00124
Metagene LinkHMDB00124
METLIN ID5159
PubChem Compound69507
PDB IDF6R
ChEBI ID15946
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. 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
  3. Roberts NB, Dutton J, Helliwell T, Rothwell PJ, Kavanagh JP: Pyrophosphate in synovial fluid and urine and its relationship to urinary risk factors for stone disease. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):529-34. Pubmed: 1332571
  4. Sanchez B, Champomier-Verges MC, Anglade P, Baraige F, de Los Reyes-Gavilan CG, Margolles A, Zagorec M: Proteomic analysis of global changes in protein expression during bile salt exposure of Bifidobacterium longum NCIMB 8809. J Bacteriol. 2005 Aug;187(16):5799-808. Pubmed: 16077128
  5. Markuszewski MJ, Szczykowska M, Siluk D, Kaliszan R: Human red blood cells targeted metabolome analysis of glycolysis cycle metabolites by capillary electrophoresis using an indirect photometric detection method. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):636-42. Pubmed: 15925468
  6. Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. Epub 2005 Jan 23. Pubmed: 16055050
  7. Karlander S, Roovete A, Vranic M, Efendic S: Glucose and fructose 6-phosphate cycle in humans. Am J Physiol. 1986 Nov;251(5 Pt 1):E530-6. Pubmed: 3777162
  8. Gapparov MM, Virovets OA: [Nonenzymatic glycosylation of serum albumin and thymic DNA by food monosugars and their natural metabolites that form in the body] Vopr Pitan. 1990 Jan-Feb;(1):36-40. Pubmed: 2346009
  9. Alton G, Hasilik M, Niehues R, Panneerselvam K, Etchison JR, Fana F, Freeze HH: Direct utilization of mannose for mammalian glycoprotein biosynthesis. Glycobiology. 1998 Mar;8(3):285-95. Pubmed: 9451038
  10. Gagnon M, Kheadr EE, Le Blay G, Fliss I: In vitro inhibition of Escherichia coli O157:H7 by bifidobacterial strains of human origin. Int J Food Microbiol. 2004 Apr 1;92(1):69-78. Pubmed: 15033269

Enzymes

Gene Name:
GNPDA1
Uniprot ID:
P46926
Reactions
Glucosamine 6-phosphate + Water unknown Fructose 6-phosphate + Ammoniadetails
Gene Name:
GFPT2
Uniprot ID:
O94808
Reactions
L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphatedetails
Gene Name:
GFPT1
Uniprot ID:
Q06210
Reactions
L-Glutamine + Fructose 6-phosphate unknown L-Glutamic acid + Glucosamine 6-phosphatedetails
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:
PFKFB3
Uniprot ID:
Q16875
Reactions
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + D-Fructose 2,6-bisphosphatedetails
Gene Name:
MPI
Uniprot ID:
P34949
Reactions
Mannose 6-phosphate unknown Fructose 6-phosphatedetails
Gene Name:
PFKFB4
Uniprot ID:
Q16877
Reactions
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + D-Fructose 2,6-bisphosphatedetails
Gene Name:
PFKFB1
Uniprot ID:
P16118
Reactions
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + D-Fructose 2,6-bisphosphatedetails
Gene Name:
FBP2
Uniprot ID:
O00757
Reactions
Fructose 1,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails
Gene Name:
TALDO1
Uniprot ID:
P37837
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Fructose 6-phosphatedetails
Gene Name:
FBP1
Uniprot ID:
P09467
Reactions
Fructose 1,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails
Gene Name:
PFKFB2
Uniprot ID:
O60825
Reactions
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate unknown ADP + D-Fructose 2,6-bisphosphatedetails
Gene Name:
TKT
Uniprot ID:
P29401
Gene Name:
GPI
Uniprot ID:
P06744
Reactions
Glucose 6-phosphate unknown Fructose 6-phosphatedetails
Gene Name:
GNPDA2
Uniprot ID:
Q8TDQ7
Reactions
Glucosamine 6-phosphate + Water unknown Fructose 6-phosphate + Ammoniadetails
Gene Name:
TIGAR
Uniprot ID:
Q9NQ88
Reactions
D-Fructose 2,6-bisphosphate + Water unknown Fructose 6-phosphate + Phosphoric aciddetails