Record Information
Version2.0
Creation Date2012-05-31 10:21:23 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00124
Identification
Name:Fructose 6-phosphate
Description:Fructose-6-phosphate is an important intermediate in glycolysis and gluconeogenesis. 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:
  • β-D-fructofuranose 6-phosphate
  • β-D-fructofuranose 6-phosphoric acid
  • A-D-Fructose-6-P
  • b-D-Fructofuranose 6-phosphate
  • b-D-Fructofuranose 6-phosphoric acid
  • Beta-D-Fructofuranose 6-phosphate
  • beta-D-Fructofuranose 6-phosphoric acid
  • D-Fructofuranose 6-phosphate
  • D-Fructofuranose 6-phosphoric acid
  • D-Fructose 6-phosphate
  • D-Fructose 6-phosphorate
  • D-Fructose 6-phosphoric acid
  • D-Fructose-6-P
  • D-Fructose-6-phosphate
  • D-Fructose-6-phosphoric acid
  • F6P
  • FPC
  • Fru-6-P
  • Fruc6p
  • Fructose 6-phosphate
  • Fructose 6-phosphoric acid
  • Fructose-6-P
  • Fructose-6-phosphate
  • Fructose-6-phosphoric acid
  • Fructose-6P
  • Neuberg ester
  • β-D-Fructofuranose 6-phosphate
  • β-D-Fructofuranose 6-phosphoric acid
Chemical Formula:C6H13O9P
Weight:Average: 260.1358
Monoisotopic: 260.029718526
InChI Key:GSXOAOHZAIYLCY-HSUXUTPPSA-N
InChI: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
CAS number:643-13-0
IUPAC Name:{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
Traditional IUPAC Name:D-fructose 6-phosphate
SMILES:OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:911 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility23.2 mg/mLALOGPS
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 Area164.75 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.43 m3·mol-1ChemAxon
Polarizability20.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Fructose 6-phosphate <> Dihydroxyacetone + D-Glyceraldehyde 3-phosphate
Phosphoenolpyruvic acid + D-Fructose > Fructose 6-phosphate + Pyruvic acid
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Erythrose 4-phosphate + Fructose 6-phosphate
D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate
Adenosine triphosphate + Fructose 6-phosphate > ADP + Fructose 1,6-bisphosphate + Hydrogen ion
Fructose 1,6-bisphosphate + Water <> Fructose 6-phosphate + Phosphate
Adenosine triphosphate + D-Fructose > ADP + Fructose 6-phosphate + Hydrogen ion
Glucosamine 6-phosphate + Water > Fructose 6-phosphate + Ammonium
Fructose 6-phosphate + Water > D-Fructose + Phosphate
Mannose 6-phosphate <> Fructose 6-phosphate
NAD + Sorbitol-6-phosphate <> Fructose 6-phosphate + Hydrogen ion + NADH
Sorbitol-6-phosphate + NAD <> Fructose 6-phosphate + Hydrogen ion + NADH
Fructose 6-phosphate + L-Glutamine <> Glucosamine 6-phosphate + L-Glutamate
Glucose 6-phosphate <> Fructose 6-phosphate
D-Allulose-6-phosphate <> Fructose 6-phosphate
Fructose 1,6-bisphosphate + Water <> Fructose 6-phosphate + Phosphate
Glucosamine 6-phosphate + Water <> Fructose 6-phosphate + Ammonia
L-Glutamine + Fructose 6-phosphate <> L-Glutamate + Glucosamine 6-phosphate
Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate
D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate
Fructose 6-phosphate + Adenosine triphosphate > Hydrogen ion + ADP + Fructose 1,6-bisphosphate
Fructose 1,6-bisphosphate + Water > Fructose 6-phosphate + Phosphate
D-Fructose + Adenosine triphosphate > Hydrogen ion + Fructose 6-phosphate + ADP
Glucosamine 6-phosphate + Water <> Hydrogen ion + Fructose 6-phosphate + Ammonia
Fructose 6-phosphate + L-Glutamine > Glucosamine 6-phosphate + L-Glutamate
Sorbitol-6-phosphate + NAD <> Hydrogen ion + Fructose 6-phosphate + NADH
Mannose 6-phosphate <> Fructose 6-phosphate
Glucose 6-phosphate <> Fructose 6-phosphate
D-Allulose-6-phosphate > Fructose 6-phosphate
Fructose 6-phosphate <> Dihydroxyacetone + D-Glyceraldehyde 3-phosphate
Sorbitol-6-phosphate + NAD <> Hydrogen ion + Fructose 6-phosphate + NADH
D-fructose + Phosphoenolpyruvic acid > Fructose 6-phosphate + Pyruvic acid
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> Fructose 6-phosphate + D-Erythrose 4-phosphate
Fructose 1,6-bisphosphate + Water > Fructose 6-phosphate + Inorganic phosphate
Fructose 6-phosphate > Dihydroxyacetone + D-Glyceraldehyde 3-phosphate
Fructose 6-phosphate > Dihydroxyacetone + D-Glyceraldehyde 3-phosphate
Glucose 6-phosphate > Fructose 6-phosphate
L-Glutamine + Fructose 6-phosphate > L-Glutamate + D-glucosamine 6-phosphate
Fructose 1,6-bisphosphate + Water > Fructose 6-phosphate + Inorganic phosphate
Fructose 1,6-bisphosphate + Water > Fructose 6-phosphate + Inorganic phosphate
Adenosine triphosphate + Fructose 6-phosphate > ADP + Fructose 1,6-bisphosphate
Adenosine triphosphate + Fructose 6-phosphate > ADP + Fructose 1,6-bisphosphate
Adenosine triphosphate + D-Fructose > ADP + Fructose 6-phosphate
Mannose 6-phosphate > Fructose 6-phosphate
Mannitol 1-phosphate + NAD > Fructose 6-phosphate + NADH
D-glucosamine 6-phosphate + Water > Fructose 6-phosphate + Ammonia
Sorbitol-6-phosphate + NAD > Fructose 6-phosphate + NADH
Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate > D-Erythrose 4-phosphate + Fructose 6-phosphate
Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate > D-Erythrose 4-phosphate + Fructose 6-phosphate
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Fructose 6-phosphate
Adenosine triphosphate + D-Fructose <> ADP + Fructose 6-phosphate
Mannose 6-phosphate <> Fructose 6-phosphate
Adenosine triphosphate + Fructose 6-phosphate <> ADP + Fructose 1,6-bisphosphate
Sorbitol 6-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion
Mannitol 1-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion
Glucose 6-phosphate <> Fructose 6-phosphate
beta-D-Glucose 6-phosphate > Fructose 6-phosphate + Fructose 6-phosphate
Fructose 6-phosphate + Phosphate + Fructose 6-phosphate > Fructose 1,6-bisphosphate + Water + Fructose 1,6-bisphosphate
Fructose 6-phosphate + Adenosine triphosphate + Fructose 6-phosphate > Fructose 1,6-bisphosphate + Adenosine diphosphate + Hydrogen ion + Fructose 1,6-bisphosphate + ADP
Fructose 6-phosphate + L-Glutamine + Fructose 6-phosphate > L-Glutamic acid + Glucosamine 6-phosphate + L-Glutamate
Fructose 6-phosphate + NADH + Hydrogen ion + Fructose 6-phosphate <> NAD + Mannitol 1-phosphate
D-Fructose + HPr - phosphorylated + D-Fructose > HPr + Fructose 6-phosphate + Fructose 6-phosphate
Sorbitol-6-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion
More...

SMPDB Pathways:
D-sorbitol degradation IIPW002022 Pw002022Pw002022 greyscalePw002022 simple
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
Lipopolysaccharide biosynthesisPW000831 Pw000831Pw000831 greyscalePw000831 simple
Starch and sucrose metabolismPW000941 Pw000941Pw000941 greyscalePw000941 simple
colanic acid building blocks biosynthesisPW000951 Pw000951Pw000951 greyscalePw000951 simple
glycerol metabolismPW000914 Pw000914Pw000914 greyscalePw000914 simple
glycerol metabolism IIPW000915 Pw000915Pw000915 greyscalePw000915 simple
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)PW000916 Pw000916Pw000916 greyscalePw000916 simple
glycerol metabolism IV (glycerophosphoglycerol)PW000917 Pw000917Pw000917 greyscalePw000917 simple
glycerol metabolism V (glycerophosphoserine)PW000918 Pw000918Pw000918 greyscalePw000918 simple
glycolysis and pyruvate dehydrogenasePW000785 Pw000785Pw000785 greyscalePw000785 simple
lipopolysaccharide biosynthesis IIPW001905 Pw001905Pw001905 greyscalePw001905 simple
lipopolysaccharide biosynthesis IIIPW002059 Pw002059Pw002059 greyscalePw002059 simple
KEGG Pathways:
  • Alanine, aspartate and glutamate metabolism ec00250
  • Amino sugar and nucleotide sugar metabolism ec00520
  • Carbon fixation in photosynthetic organisms ec00710
  • Fructose and mannose metabolism ec00051
  • Galactose metabolism ec00052
  • Glycolysis / Gluconeogenesis ec00010
  • Lipopolysaccharide biosynthesis ec00540
  • Metabolic pathways eco01100
  • Methane metabolism ec00680
  • Microbial metabolism in diverse environments ec01120
  • Pentose and glucuronate interconversions ec00040
  • Pentose phosphate pathway ec00030
  • Starch and sucrose metabolism ec00500
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
250± 19 uMK120.2 g/L NH4Cl, 2.0 g/L (NH4)2SO4, 3.25 g/L KH2PO4, 2.5 g/L K2HPO4, 1.5 g/L NaH2PO4, 0.5 g/L MgSO4; trace substances: 10 mg/L CaCl2, 0.5 mg/L ZnSO4, 0.25 mg/L CuCl2, 0.25 mg/L MnSO4, 0.175 mg/L CoCl2, 0.125 mg/L H3BO3, 2.5 mg/L AlCl3, 0.5 mg/L Na2MoO4, 10Stationary Phase, glucose limitedBioreactor, pH controlled, aerated, dilution rate=0.125 L/h37 oCPMID: 11488613
290± 60 uMBW25113M9 Minimal Media, 4 g/L GlucoseMid-Log PhaseBioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h37 oCPMID: 15158257
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-0gba-1943000000-9b9bb3f9964b519fa26bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-014j-1943000000-0be5d726668730e99be0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-014j-1954000000-9fa83268db2925e9478dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-000b-0934000000-eb61ccae8d0b23564bc7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-000b-0934000000-c2a49f4f2d11d3e60a9eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-000j-0925000000-a6b6a121cb447c890019View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0f7a-1934000000-b28e738e5093324060d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)splash10-014i-3966000000-fee84a4ec7828d92e8b6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)splash10-014i-1955000000-32da70382eccbcbbb574View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0gba-1943000000-9b9bb3f9964b519fa26bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014j-1943000000-0be5d726668730e99be0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014j-1954000000-9fa83268db2925e9478dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000b-0934000000-eb61ccae8d0b23564bc7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000b-0934000000-c2a49f4f2d11d3e60a9eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000j-0925000000-a6b6a121cb447c890019View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0f7a-1934000000-b28e738e5093324060d9View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-014i-3966000000-fee84a4ec7828d92e8b6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-014i-1955000000-32da70382eccbcbbb574View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0gba-1933000000-1c8febd80da1382bec31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0229-5090000000-281699f4bce06db0b1b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006x-9730000000-b72576e6bb1ae73e6881View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kbf-9740000000-130bb715a91e870b5480View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0aor-0690000000-b640c7fba12f06d6bfa2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00kb-9710000000-5d6429381cefb6a2bdc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9100000000-51c3f5ca7ef3f190f1dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-054k-9000000000-75c50b162633f723546dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-07895e6c6f3e4a816391View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0aor-0690000000-b640c7fba12f06d6bfa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137. Pubmed: 11488613
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23. Pubmed: 15158257
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15946
HMDB IDHMDB00124
Pubchem Compound ID69507
Kegg IDC00085
ChemSpider ID62713
WikipediaFructose 6-phosphate
BioCyc IDFRUCTOSE-6P
EcoCyc IDFRUCTOSE-6P
Ligand ExpoF6R

Enzymes

General function:
Involved in mannose-6-phosphate isomerase activity
Specific function:
Involved in the conversion of glucose to GDP-L-fucose, which can be converted to L-fucose, a capsular polysaccharide
Gene Name:
manA
Uniprot ID:
P00946
Molecular weight:
42850
Reactions
D-mannose 6-phosphate = D-fructose 6-phosphate.
General function:
Involved in oxidoreductase activity
Specific function:
D-sorbitol 6-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
Gene Name:
srlD
Uniprot ID:
P05707
Molecular weight:
27858
Reactions
D-sorbitol 6-phosphate + NAD(+) = D-fructose 6-phosphate + NADH.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkB
Uniprot ID:
P06999
Molecular weight:
32456
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
General function:
Involved in oxidation-reduction process
Specific function:
D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
Gene Name:
mtlD
Uniprot ID:
P09424
Molecular weight:
41139
Reactions
D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH.
General function:
Involved in glucose-6-phosphate isomerase activity
Specific function:
D-glucose 6-phosphate = D-fructose 6- phosphate
Gene Name:
pgi
Uniprot ID:
P0A6T1
Molecular weight:
61529
Reactions
D-glucose 6-phosphate = D-fructose 6-phosphate.
General function:
Involved in carbohydrate metabolic process
Specific function:
Catalyzes the reversible isomerization-deamination of glucosamine 6-phosphate (GlcN6P) to form fructose 6-phosphate (Fru6P) and ammonium ion
Gene Name:
nagB
Uniprot ID:
P0A759
Molecular weight:
29774
Reactions
D-glucosamine 6-phosphate + H(2)O = D-fructose 6-phosphate + NH(3).
General function:
Involved in ATP binding
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkA
Uniprot ID:
P0A796
Molecular weight:
34842
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:
talA
Uniprot ID:
P0A867
Molecular weight:
35659
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:
talB
Uniprot ID:
P0A870
Molecular weight:
35219
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate.
General function:
Involved in phosphoric ester hydrolase activity
Specific function:
D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate
Gene Name:
fbp
Uniprot ID:
P0A993
Molecular weight:
36834
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate.
General function:
Involved in glycerol metabolic process
Specific function:
D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate
Gene Name:
glpX
Uniprot ID:
P0A9C9
Molecular weight:
35852
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate.
General function:
Involved in metabolic process
Specific function:
Catalyzes the first step in hexosamine metabolism, converting fructose-6P into glucosamine-6P using glutamine as a nitrogen source
Gene Name:
glmS
Uniprot ID:
P17169
Molecular weight:
66894
Reactions
L-glutamine + D-fructose 6-phosphate = L-glutamate + D-glucosamine 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates pyridoxalphosphate and erythrose 4-phosphate
Gene Name:
ybhA
Uniprot ID:
P21829
Molecular weight:
30201
General function:
Transcription
Specific function:
Catalyzes the phosphorylation of fructose to fructose-6- P. Has also low level glucokinase activity in vitro. Is not able to phosphorylate D-ribose, D-mannitol, D-sorbitol, inositol, and L-threonine
Gene Name:
mak
Uniprot ID:
P23917
Molecular weight:
32500
Reactions
ATP + D-fructose = ADP + D-fructose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:
tktA
Uniprot ID:
P27302
Molecular weight:
72211
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate.
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
alsE
Uniprot ID:
P32719
Molecular weight:
26109
General function:
Involved in catalytic activity
Specific function:
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:
tktB
Uniprot ID:
P33570
Molecular weight:
73042
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manX
Uniprot ID:
P69797
Molecular weight:
35047
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the hydrolysis of sugar phosphate to sugar and inorganic phosphate. Has a wide substrate specificity catalyzing the hydrolysis of fructose-1-P most efficiently, but it remains uncertain if this is the real substrate in vivo
Gene Name:
supH
Uniprot ID:
P75792
Molecular weight:
30413
Reactions
Sugar phosphate + H(2)O = sugar + phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
General function:
Involved in glycerol metabolic process
Specific function:
Specific function unknown
Gene Name:
yggF
Uniprot ID:
P21437
Molecular weight:
34323
Reactions
D-fructose 1,6-bisphosphate + H(2)O = D-fructose 6-phosphate + phosphate.
General function:
Involved in catalytic activity
Specific function:
D-fructose 6-phosphate = glycerone + D- glyceraldehyde 3-phosphate
Gene Name:
fsaB
Uniprot ID:
P32669
Molecular weight:
23555
Reactions
D-fructose 6-phosphate = glycerone + D-glyceraldehyde 3-phosphate.
General function:
Involved in catalytic activity
Specific function:
D-fructose 6-phosphate = glycerone + D- glyceraldehyde 3-phosphate
Gene Name:
fsaA
Uniprot ID:
P78055
Molecular weight:
22997
Reactions
D-fructose 6-phosphate = glycerone + D-glyceraldehyde 3-phosphate.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.
General function:
Not Available
Specific function:
Not Available
Gene Name:
cobB
Uniprot ID:
P75960
Molecular weight:
Not Available

Transporters

General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transmembrane transport
Specific function:
Transport protein for sugar phosphate uptake
Gene Name:
uhpT
Uniprot ID:
P0AGC0
Molecular weight:
50606
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368