Record Information
Version2.0
Creation Date2012-05-31 14:01:34 -0600
Update Date2015-06-03 15:54:35 -0600
Secondary Accession Numbers
  • ECMDB03971
Identification
Name:beta-D-Fructose 6-phosphate
DescriptionBeta-D-Fructose 6 phosphate (b-F6P) is the beta-anomer of fructose-6-phosphate. There are two anomers of fructose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-fructose 6-phosphate is fructose sugar phosphorylated on carbon 6. Beta-D-Fructose 6-phosphate is a substrate for Fructose-1,6-bisphosphatase, Pyruvate kinase (isozymes R/L), Hexokinase (type I), Fructose-bisphosphate aldolase A, L-lactate dehydrogenase B chain, Glyceraldehyde-3-phosphate dehydrogenase and Transaldolase.
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
  • b-D-Fructose 6-phosphate
  • b-D-Fructose 6-phosphoric acid
  • Beta-D-Fructofuranose 6-phosphate
  • beta-D-Fructofuranose 6-phosphoric acid
  • Beta-D-Fructose 6-phosphate
  • beta-D-Fructose 6-phosphoric acid
  • D-Fructofuranose 6-phosphate
  • D-Fructofuranose 6-phosphoric acid
  • D-Fructose-6-P
  • D-Fructose-6-phosphate
  • D-Fructose-6-phosphoric acid
  • F6P
  • Fru-6-P
  • Fruc6p
  • Fructose-6-P
  • Fructose-6-phosphate
  • Fructose-6-phosphoric acid
  • Fructose-6P
  • β-D-Fructofuranose 6-phosphate
  • β-D-Fructofuranose 6-phosphoric acid
  • β-D-Fructose 6-phosphate
  • β-D-Fructose 6-phosphoric acid
Chemical Formula:C6H13O9P
Weight:Average: 260.1358
Monoisotopic: 260.029718526
InChI Key:BGWGXPAPYGQALX-ARQDHWQXSA-N
InChI:InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:β-D-fructofuranose 6-phosphate
SMILES:OC[C@@]1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility33.4 g/LALOGPS
logP-2.1ALOGPS
logP-2.9ChemAxon
logS-0.89ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.23 m³·mol⁻¹ChemAxon
Polarizability20.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
D-sorbitol degradation IIPW002022 ThumbThumb?image type=greyscaleThumb?image type=simple
Pentose PhosphatePW000893 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
colanic acid building blocks biosynthesisPW000951 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Amino sugar and nucleotide sugar metabolism ec00520
  • Fructose and mannose metabolism ec00051
  • Glycolysis / Gluconeogenesis ec00010
  • Microbial metabolism in diverse environments ec01120
  • Pentose phosphate pathway ec00030
  • Starch and sucrose metabolism ec00500
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
55± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9422000000-bee9b5c8192cd70afd4bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9422000000-bee9b5c8192cd70afd4bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9330000000-5c27e76b48f712dafdf1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0540-8097650000-bd7cf45abb555a5c08daView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9200000000-890d2bc5c099d333bb87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0090000000-9e5a9a987b6541abb2c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0ab9-0000509000-ba24f5137a9692d147abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2980000000-6b021fc643037857d79cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-6950000000-9aeea6f58646b1ddfd2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ds-9300000000-163fede30ff57a757356View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-7390000000-3b9471399e651e34edcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-107d49541ec3b4b1213fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9182363b16cd6b3e720bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3090000000-7ae40fd439a28bd2393eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-53fac253975be4bb66f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-1790000000-cf4773c8e21b0c55570eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9810000000-21980e2a6a612b295b9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9000000000-a08dc200cb22f420d5bcView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • 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
  • 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
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16084
HMDB IDHMDB03971
Pubchem Compound ID440641
Kegg IDC05345
ChemSpider ID389526
Wikipedia IDFructose_6-phosphate
BioCyc IDFRUCTOSE-6P
EcoCyc IDFRUCTOSE-6P
Ligand ExpoF6P

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 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 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:
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.