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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
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.9 +/- 2.3 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified10.2 +/- 1.8 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cellular CytoplasmDetected and Quantified16.0 (13.0-19.0) uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified49.6 uMAdult (>18 years old)BothNormal details
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)Download (PDF)
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

General function:
Involved in carbohydrate metabolic process
Specific function:
Seems to trigger calcium oscillations in mammalian eggs. These oscillations serve as the essential trigger for egg activation and early development of the embryo (By similarity).
Gene Name:
GNPDA1
Uniprot ID:
P46926
Molecular weight:
32668.29
Reactions
Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammoniadetails
General function:
Involved in metabolic process
Specific function:
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:
GFPT2
Uniprot ID:
O94808
Molecular weight:
76929.885
Reactions
L-Glutamine + Fructose 6-phosphate → L-Glutamic acid + Glucosamine 6-phosphatedetails
General function:
Involved in metabolic process
Specific function:
Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:
GFPT1
Uniprot ID:
Q06210
Molecular weight:
78805.81
Reactions
L-Glutamine + Fructose 6-phosphate → L-Glutamic acid + Glucosamine 6-phosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKP
Uniprot ID:
Q01813
Molecular weight:
85595.405
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKL
Uniprot ID:
P17858
Molecular weight:
85017.825
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKM
Uniprot ID:
P08237
Molecular weight:
85181.925
Reactions
Adenosine triphosphate + Fructose 6-phosphate → ADP + Fructose 1,6-bisphosphatedetails
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
General function:
Involved in mannose-6-phosphate isomerase activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions.
Gene Name:
MPI
Uniprot ID:
P34949
Molecular weight:
46655.44
Reactions
Mannose 6-phosphate → Fructose 6-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 + Phosphoric aciddetails
Adenosine triphosphate + Fructose 6-phosphate → ADP + D-Fructose 2,6-bisphosphatedetails
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
General function:
Involved in phosphoric ester hydrolase activity
Specific function:
Not Available
Gene Name:
FBP2
Uniprot ID:
O00757
Molecular weight:
36742.84
Reactions
Fructose 1,6-bisphosphate + Water → Fructose 6-phosphate + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
Gene Name:
TALDO1
Uniprot ID:
P37837
Molecular weight:
37539.74
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Fructose 6-phosphatedetails
General function:
Involved in phosphoric ester hydrolase activity
Specific function:
Not Available
Gene Name:
FBP1
Uniprot ID:
P09467
Molecular weight:
36842.145
Reactions
Fructose 1,6-bisphosphate + Water → 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
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
P29401
Molecular weight:
67876.95
General function:
Involved in glucose-6-phosphate isomerase activity
Specific function:
Besides it's role as a glycolytic enzyme, mammalian GPI can function as a tumor-secreted cytokine and an angiogenic factor (AMF) that stimulates endothelial cell motility. GPI is also a neurotrophic factor (Neuroleukin) for spinal and sensory neurons.
Gene Name:
GPI
Uniprot ID:
P06744
Molecular weight:
63146.745
Reactions
Glucose 6-phosphate → Fructose 6-phosphatedetails
General function:
Involved in carbohydrate metabolic process
Specific function:
Not Available
Gene Name:
GNPDA2
Uniprot ID:
Q8TDQ7
Molecular weight:
27090.845
Reactions
Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammoniadetails
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