Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000047
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
Average Molecular Weight: 260.1358
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
Kingdom Organic compounds
Super ClassOrganophosphorus compounds
Class Organic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct Parent Monoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Organic phosphate
  • Monosaccharide
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic 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:
Pathways:
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
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
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 oxidation-reduction process
Specific function:
D-mannitol 1-phosphate + NAD(+) = D-fructose 6-phosphate + NADH
Gene Name:
mtlD
Locus Tag:
PA2342
Molecular weight:
54.3 kDa
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
Locus Tag:
PA4732
Molecular weight:
61.9 kDa
Reactions
D-glucose 6-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
Locus Tag:
PA2796
Molecular weight:
33.9 kDa
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
Locus Tag:
PA5110
Molecular weight:
37.2 kDa
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
Locus Tag:
PA5549
Molecular weight:
66.3 kDa
Reactions
L-glutamine + D-fructose 6-phosphate = L-glutamate + D-glucosamine 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
Locus Tag:
PA0548
Molecular weight:
72.2 kDa
Reactions
Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate.
General function:
Not Available
Specific function:
Not Available
Gene Name:
cobB
Locus Tag:
PA1273
Molecular weight:
46.5 kDa

Transporters