D-Fructose (PAMDB000167)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000167
Identification
Name: D-Fructose
Description:Fructose, or levulose, is a levorotatory monosaccharide and an isomer of glucose (C6H12O6). The chemical composition of fructose is (C6H12O6). Pure fructose has a sweet taste similar to cane sugar, but with a "fruity" aroma. Although fructose is a hexose (6 carbon sugar), it generally exists as a 5-member hemiketal ring (a furanose). This structure is responsible for the long metabolic pathway and high reactivity compared to glucose. Fructose is found in many foods. Honey; tree fruits; berries; melons; and some root vegetables, such as beets, sweet potatoes, parsnips and onions, contain fructose, usually in combination with sucrose and glucose. Fructose is also derived from the digestion of sucrose, a disaccharide consisting of glucose and fructose that is broken down by enzymes during digestion. Fructose is the sweetest naturally occurring sugar, estimated to be twice as sweet as sucrose. Fructose is a reducing sugar, as are all monosaccharides.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • β-D-arabino-hexulose
  • β-D-fructose
  • β-fruit sugar
  • β-Levulose
  • B-D-Arabino-hexulose
  • B-D-Fructofuranose
  • B-D-Fructose
  • b-delta-arabino-Hexulose
  • b-delta-Fructofuranose
  • b-delta-Fructose
  • b-Fruit sugar
  • b-Levulose
  • b-δ-arabino-Hexulose
  • b-δ-Fructofuranose
  • b-δ-Fructose
  • Beta-D-Arabino-hexulose
  • Beta-D-Fructofuranose
  • Beta-D-Fructose
  • Beta-delta-Arabino-hexulose
  • Beta-delta-Fructofuranose
  • Beta-delta-Fructose
  • Beta-Fruit sugar
  • Beta-Levulose
  • D-(-)-Fructose
  • D-Fructose
  • Delta-(-)-Fructose
  • Delta-Fructose
  • FRU
  • Fructon
  • Fructose
  • Levulose
  • β-D-arabino-Hexulose
  • β-D-Fructofuranose
  • β-D-Fructose
  • β-Fruit sugar
  • β-Levulose
  • β-δ-arabino-Hexulose
  • β-δ-Fructofuranose
  • β-δ-Fructose
  • δ-(-)-Fructose
  • δ-Fructose
Chemical Formula: C6H12O6
Average Molecular Weight: 180.1559
Monoisotopic Molecular Weight: 180.063388116
InChI Key: RFSUNEUAIZKAJO-ARQDHWQXSA-N
InChI:InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1
CAS number: 53188-23-1
IUPAC Name:(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
Traditional IUPAC Name: fructose
SMILES:OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent C-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Monosaccharide
  • Oxolane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 119-122°C
Experimental Properties:
PropertyValueSource
Water Solubility:778 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 778.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1110.0 mg/mLALOGPS
logP-2.5ALOGPS
logP-2.8ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.36 m3·mol-1ChemAxon
Polarizability16.52 Å3ChemAxon
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 6-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + D-Fructose > Fructose 1-phosphate + Pyruvic acid
Adenosine triphosphate + D-Fructose > ADP + Fructose 6-phosphate + Hydrogen ion
Fructose 6-phosphate + Water > D-Fructose + Phosphate
D-Glucose <> D-Fructose
Adenosine triphosphate + D-Fructose > ADP + Fructose 6-phosphate
Sucrose + Phosphate <> D-Fructose + Glucose 1-phosphate
β-D-fructofuranose + Adenosine triphosphate + D-Fructose > Adenosine diphosphate + Hydrogen ion + D-tagatofuranose 6-phosphate + ADP
D-Fructose + Adenosine triphosphate + D-Fructose > D-tagatofuranose 6-phosphate + Adenosine diphosphate + Hydrogen ion + ADP
Sucrose + Water <> D-Fructose + D-Glucose + D-Fructose
UDP-Glucose + D-Fructose + D-Fructose <> Sucrose + Phosphate
D-Fructose + Alpha-D-glucose 1-phosphate + D-Fructose <> Phosphate + Sucrose
β-D-fructofuranose + PtsI - his 189 phosphorylated + D-Fructose > β-D-fructofuranose 1-phosphate + PTS enzyme I
β-D-fructofuranose + HPr - phosphorylated + D-Fructose > D-tagatofuranose 6-phosphate + HPr
D-Fructose + HPr - phosphorylated + D-Fructose > HPr + Fructose 6-phosphate + Fructose 6-phosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-2ce9036c30158be73d60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ri-9600000000-a826b29724713036f579View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-007a-9200000000-7621d8d96132cc999f4cView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • 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
  • 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: Liu, Hong; Han, Dong; Meng, Xiang-bao; Li, Zhong-jun. Improved synthesis of fructose-derived 1,3,4-oxadiazole as novel antitumor agents. Journal of Chinese Pharmaceutical Sciences (2005), 14(4), 209-212.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15946
HMDB IDHMDB00660
Pubchem Compound ID439709
Kegg IDC00095
ChemSpider ID388775
WikipediaFRU
BioCyc IDBETA-D-FRUCTOSE
EcoCyc IDBETA-D-FRUCTOSE

Enzymes

Protein Details
• 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
Locus Tag:
PA3560
Molecular weight:
59 kDa
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

Transporters

Protein Details
• 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
Locus Tag:
PA3560
Molecular weight:
59 kDa
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.