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D-fructose 1-phosphate (YMDB00655)

Identification
YMDB IDYMDB00655
NameD-fructose 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-fructose 1-phosphate, also known as 1-O-phosphono-D-fructose, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. D-fructose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-O-phosphono-D-fructose
  • D-Fructose 1-phosphate
  • D-fructose-1-P
  • D-fructose-1-phosphate
  • fructofuranose 1-phosphate
  • fructose 1-phosphate
  • Fructose 1-phosphic acid
  • fructose-1-P
  • fructose-1-phosphate
  • D-Fructose 1-phosphoric acid
  • Fructose-1-phosphoric acid
CAS number15978-08-2
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyZKLLSNQJRLJIGT-UYFOZJQFSA-N
InChIInChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3,5-8,10-11H,1-2H2,(H2,12,13,14)/t3-,5-,6-/m1/s1
IUPAC Name{[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]oxy}phosphonic acid
Traditional IUPAC Namefructose 1-phosphate
Chemical FormulaC6H13O9P
SMILES[H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=O)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Octose monosaccharide
  • Monosaccharide phosphate
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Sugar acid
  • 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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility23.4 g/LALOGPS
logP-1.8ALOGPS
logP-3.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.43 m³·mol⁻¹ChemAxon
Polarizability20.85 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
D-fructose 1-phosphate ↔ D-glyceraldehyde + Dihydroxyacetone phosphate
Adenosine triphosphate + D-fructose 1-phosphate → hydron + ADP + Fructose 1,6-bisphosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dv-9610000000-02ca845189c71078b8f8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-3934870000-59dd8b59f2fffa8ebdafJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0090000000-69e958a21781919936bbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9010000000-09fb21847135e58a6be8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0002-9010000000-9b9929ef874f5c200b1cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5690000000-d7df1ad20a6b23f47261JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kl-9710000000-7b472845d3c649263e2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bu1-9200000000-3489245d9f6a9db937b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0690-8910000000-ee8d111ccdc936caea8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-21f7fc4ed7dab43e8823JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6a6bb84df47427625197JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-3690000000-73991df97ee3e0ff563fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9600000000-beb86194e86a63f5aa98JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-913e6e460093552cee6fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0551-9630000000-cc4ae9d3a3d5e615aeb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9000000000-f02c1b9a3b8134189c4dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kreuzberg, K. (1978). "Interaction of D-fructose and fructose 1-phosphate with yeast phosphofructokinase and its influence on glycolytic oscillations." Biochim Biophys Acta 527:229-238.152653
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.
External Links:
ResourceLink
CHEBI ID18105
HMDB IDHMDB01076
Pubchem Compound ID439394
Kegg IDC02976
ChemSpider ID58741
FOODB IDFDB030864
WikipediaFructose_1-phosphate
BioCyc IDFRU1P

Enzymes

Protein Details
1. Hexokinase-2
General function:
Involved in ATP binding
Specific function:
Main glucose phosphorylating enzyme. May play a regulatory role in both induction and repression of gene expression by glucose
Gene Name:
HXK2
Uniprot ID:
P04807
Molecular weight:
53942.0
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
Protein Details
2. Hexokinase-1
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
HXK1
Uniprot ID:
P04806
Molecular weight:
53737.89844
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
Protein Details
3. Fructose-bisphosphate aldolase
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:
FBA1
Uniprot ID:
P14540
Molecular weight:
39620.5
Reactions
D-fructose 1,6-bisphosphate → glycerone phosphate + D-glyceraldehyde 3-phosphate.