Record Information
Version2.0
Creation Date2012-05-31 13:00:06 -0600
Update Date2015-09-17 15:41:05 -0600
Secondary Accession Numbers
  • ECMDB00660
Identification
Name:D-Fructose
DescriptionFructose, 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
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
Weight:Average: 180.1559
Monoisotopic: 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
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Pentose monosaccharide
  • Monosaccharide
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.36 m³·mol⁻¹ChemAxon
Polarizability16.26 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 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
fructose metabolismPW000913 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
1383± 112 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
Download Details
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-076r-9600000000-f2c06850d0c3db9ec103View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0fb9-5614950000-6ef14e948d063026f7eeView in MoNA
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-2afc98a319bf6041adf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-1dd0cdea93f529e6ccb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-d0f08ad6c9dee008067aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-74b62c8ea3678afcff8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ta-1900000000-5a0f3f01ddf8c11c6370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-93c2b00aa44481aa8630View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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

General function:
Involved in xylose isomerase activity
Specific function:
D-xylose = D-xylulose
Gene Name:
xylA
Uniprot ID:
P00944
Molecular weight:
49742
Reactions
D-xylose = D-xylulose.
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.
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.
General function:
Involved in catalytic activity
Specific function:
May play a role in regulating the intracellular level of maltotriose. Cleaves glucose from the reducing end of maltotriose and longer maltodextrins with a chain length of up to 7 glucose units
Gene Name:
malZ
Uniprot ID:
P21517
Molecular weight:
69172
Reactions
Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of alpha-D-glucose.
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:
Exhibits hydrolysis activity against alpha-glucosyl fluoride, although natural substrates, such as alpha-glucobioses are scarcely hydrolyzed
Gene Name:
yihQ
Uniprot ID:
P32138
Molecular weight:
77274
Reactions
Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of alpha-D-glucose.
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
Gene Name:
frvB
Uniprot ID:
P32154
Molecular weight:
51120
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
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 mannose transport
Gene Name:
manX
Uniprot ID:
P69797
Molecular weight:
35047
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
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.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the hydrolysis of sugar phosphate to sugar and inorganic phosphate. Has a wide substrate specificity catalyzing the hydrolysis of fructose-1-P most efficiently, but it remains uncertain if this is the real substrate in vivo
Gene Name:
supH
Uniprot ID:
P75792
Molecular weight:
30413
Reactions
Sugar phosphate + H(2)O = sugar + phosphate.
General function:
Involved in catalytic activity
Specific function:
Sucrose + phosphate = D-fructose + alpha-D- glucose 1-phosphate
Gene Name:
ycjM
Uniprot ID:
P76041
Molecular weight:
64185
Reactions
Sucrose + phosphate = D-fructose + alpha-D-glucose 1-phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
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.
General function:
Not Available
Specific function:
Not Available
Gene Name:
yniC
Uniprot ID:
P77247
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfbT
Uniprot ID:
P77625
Molecular weight:
Not Available

Transporters

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.
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
Gene Name:
frvB
Uniprot ID:
P32154
Molecular weight:
51120
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:
setC
Uniprot ID:
P31436
Molecular weight:
43493
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane
Gene Name:
frwC
Uniprot ID:
P32672
Molecular weight:
37086
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane
Gene Name:
fryC
Uniprot ID:
P77579
Molecular weight:
43966
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368