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β-D-fructofuranose 1-phosphate (M2MDB006364)

Record Information
Version2.0
Creation Date2015-09-08 17:50:23 -0600
Update Date2015-09-14 16:46:45 -0600
Secondary Accession Numbers
  • ECMDB24247
Identification
Name:β-D-fructofuranose 1-phosphate
Descriptionbeta-D-fructofuranose 1-phosphate is an intermediate in fructose degradation pathway in E.coli. It is a substrate for the enzyme 1-phosphofructokinase which catalyzes the reaction ATP + beta-D-fructofuranose 1-phosphate -> ADP + fructose 1,6-bisphosphate + H+ (BioCyc compound: FRU1P).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • β-D-fructofuranose 1-phosphoric acid
Chemical Formula:C6H11O9P
Weight:Average: 258.12
Monoisotopic: 258.015166092
InChI Key:RHKKZBWRNHGJEZ-UHFFFAOYSA-L
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)/p-2
CAS number:Not Available
IUPAC Name:[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl phosphate
Traditional IUPAC Name:[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl phosphate
SMILES:OCC1OC(O)(COP([O-])([O-])=O)C(O)C1O
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
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxolane
  • Hemiacetal
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility73.3 g/LALOGPS
logP-2.1ALOGPS
logP-2.9ChemAxon
logS-0.6ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area162.57 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.99 m³·mol⁻¹ChemAxon
Polarizability20.38 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
β-D-fructofuranose 1-phosphate + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + Fructose 1,6-bisphosphate + ADP + Fructose 1,6-bisphosphate
β-D-fructofuranose + PtsI - his 189 phosphorylated + D-Fructose > β-D-fructofuranose 1-phosphate + PTS enzyme I
SMPDB Pathways:
fructose metabolismPW000913 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-5590000000-ea64b3b2ab9bacdf8e4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-3290000000-2e29c507350b4be28235View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002g-9200000000-d87c855790228ff626faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3190000000-60c6e5dcf4caf0ace898View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-6490000000-a3ce8f7ad66d34e877cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-46af478d80947cae61c1View 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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID74050557
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 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
2. 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
3. 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.

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.