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Fructose 1-phosphate (M2MDB000243)

Record Information
Version2.0
Creation Date2012-05-31 13:44:38 -0600
Update Date2015-06-03 15:53:42 -0600
Secondary Accession Numbers
  • ECMDB01076
Identification
Name:Fructose 1-phosphate
DescriptionFructose 1-phosphate is an intermediate metabolite in the Fructose and mannose metabolism pathway. It is generated by fructokinase and it is broken down by aldolase B into glyceraldehyde and dihydroxyacetone phosphate (DHAP).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • β-D-fructose-1-P
  • β-D-fructose-1-phosphate
  • β-D-fructose-1-phosphoric acid
  • b-D-Fructose-1-P
  • b-D-Fructose-1-phosphate
  • b-D-Fructose-1-phosphoric acid
  • Beta-D-Fructose-1-P
  • Beta-D-Fructose-1-phosphate
  • beta-D-Fructose-1-phosphoric acid
  • D-Fructose 1-phosphate
  • D-Fructose 1-phosphoric acid
  • D-Fructose-1-P
  • D-Fructose-1-phosphate
  • D-Fructose-1-phosphoric acid
  • Fructose 1-phosphate
  • Fructose 1-phosphoric acid
  • Fructose-1-P
  • Fructose-1-phosphate
  • Fructose-1-phosphoric acid
  • Fructose1P
  • β-D-Fructose-1-P
  • β-D-Fructose-1-phosphate
  • β-D-Fructose-1-phosphoric acid
Chemical Formula:C6H13O9P
Weight:Average: 260.1358
Monoisotopic: 260.029718526
InChI Key:RHKKZBWRNHGJEZ-ARQDHWQXSA-N
InChI:InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1
CAS number:15978-08-2
IUPAC Name:{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid
SMILES:OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.23 m³·mol⁻¹ChemAxon
Polarizability21.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Phosphoenolpyruvic acid + D-Fructose > Fructose 1-phosphate + Pyruvic acid
Adenosine triphosphate + Fructose 1-phosphate > ADP + Fructose 1,6-bisphosphate + Hydrogen ion
Adenosine triphosphate + Fructose 1-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphate
Fructose 1-phosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde
Protein N(pi)-phospho-L-histidine + D-Fructose <> Protein histidine + Fructose 1-phosphate
Fructose 1-phosphate + Water > D-fructose + Phosphate
D-fructose + Phosphoenolpyruvic acid > Fructose 1-phosphate + Pyruvic acid
Adenosine triphosphate + Fructose 1-phosphate > ADP + Fructose 1,6-bisphosphate
Adenosine triphosphate + Fructose 1-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphate
SMPDB Pathways:Not Available
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
  • Phosphotransferase system (PTS) ec02060
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9510000000-71d828159b61f8342118View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-2912320000-08ffe3d23f5fa5d6162cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dm-9470000000-18ac582a370338a3f5f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-7390000000-1a5a72af8bb734e50eb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009y-9100000000-4f151f373d7730140f38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9270000000-5af91634007091008210View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5cf3f457b8c6f6270b68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4e6feccf18943de8c419View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1090000000-03030e5df4374fea160cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9140000000-be637d8fd4ff371117c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-26f483248da003aafbdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-6beaa046be46044471beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p2-6920000000-7fd7dcf4a4f1479d91b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9100000000-60f4d9de70c1b7a7e1deView 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:
  • Alvarez E, Roncero I, Chowen JA, Vazquez P, Blazquez E: Evidence that glucokinase regulatory protein is expressed and interacts with glucokinase in rat brain. J Neurochem. 2002 Jan;80(1):45-53. Pubmed: 11796742
  • 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
  • Malaisse WJ: [Metabolic interactions between glucose and fructose] Bull Mem Acad R Med Belg. 2002;157(7-9):349-52; discussion 352-3. Pubmed: 12647375
  • 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
  • Watford M: Small amounts of dietary fructose dramatically increase hepatic glucose uptake through a novel mechanism of glucokinase activation. Nutr Rev. 2002 Aug;60(8):253-7. Pubmed: 12199300
  • 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:Hara, Yoshito. Ion exchange separation of fructose 1-phosphate by using borate as the eluant. Journal of Biochemistry (Tokyo, Japan) (1959), 46 571-3.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18105
HMDB IDHMDB01076
Pubchem Compound ID439394
Kegg IDC01094
ChemSpider ID8575807
WikipediaFructose 1-phosphate
BioCyc IDFRU1P
EcoCyc IDFRU1P
Ligand ExpoF1X

Enzymes

Protein Details
1. Phosphoenolpyruvate-protein phosphotransferase
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.
Protein Details
2. Fructose-bisphosphate aldolase class 1
General function:
Involved in catalytic activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
fbaB
Uniprot ID:
P0A991
Molecular weight:
38109
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
Protein Details
3. Fructose-bisphosphate aldolase class 2
General function:
Involved in catalytic activity
Specific function:
Catalyzes the aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3- phosphate (G3P) to form fructose 1,6-bisphosphate (FBP) in gluconeogenesis and the reverse reaction in glycolysis
Gene Name:
fbaA
Uniprot ID:
P0AB71
Molecular weight:
39147
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
Protein Details
4. 1-phosphofructokinase
General function:
Involved in 1-phosphofructokinase activity
Specific function:
ATP + D-fructose 1-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
fruK
Uniprot ID:
P0AEW9
Molecular weight:
33755
Reactions
ATP + D-fructose 1-phosphate = ADP + D-fructose 1,6-bisphosphate.
Protein Details
5. PTS system fructose-specific EIIBC component
General function:
Involved in sugar:hydrogen symporter activity
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 fructose transport
Gene Name:
fruA
Uniprot ID:
P20966
Molecular weight:
57519
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
6. Multiphosphoryl transfer protein
General function:
Involved in transporter activity
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 fructose transport
Gene Name:
fruB
Uniprot ID:
P69811
Molecular weight:
39647
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein Details
7. Phosphatase yqaB
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 fructose 1-phosphate and 6-phosphogluconate
Gene Name:
yqaB
Uniprot ID:
P77475
Molecular weight:
20780
Protein Details
8. Phosphocarrier protein HPr
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.

Transporters

Protein Details
1. PTS system fructose-specific EIIBC component
General function:
Involved in sugar:hydrogen symporter activity
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 fructose transport
Gene Name:
fruA
Uniprot ID:
P20966
Molecular weight:
57519
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.