ECMDB: D-Fructose (ECMDB00660) (M2MDB000167)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (16)Transporters (11)XML

Proteins (1663)

Record Information

Version

2.0

Creation Date

2012-05-31 13:00:06 -0600

Update Date

2015-09-17 15:41:05 -0600

Secondary Accession Numbers

ECMDB00660

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

MOL SDF PDB SMILES InChI

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

Description

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 Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose (CHEBI:28645 )

Physical Properties

State:

Solid

Charge:

Melting point:

119-122°C

Experimental Properties:

Property	Value	Source
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

Property	Value	Source
Water Solubility	1110 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.8	ChemAxon
logS	0.79	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.36 m³·mol⁻¹	ChemAxon
Polarizability	16.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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 + Inorganic phosphate > D-Fructose + Alpha-D-glucose 1-phosphate
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

SMPDB Pathways:

Lipopolysaccharide biosynthesis	PW000831
Starch and sucrose metabolism	PW000941
colanic acid building blocks biosynthesis	PW000951
fructose metabolism	PW000913
lipopolysaccharide biosynthesis II	PW001905
lipopolysaccharide biosynthesis III	PW002059
peptidoglycan biosynthesis I	PW000906
peptidoglycan biosynthesis I 2	PW002062

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
Fructose and mannose metabolism ec00051
Lipopolysaccharide biosynthesis ec00540
Metabolic pathways eco01100
Starch and sucrose metabolism ec00500

EcoCyc Pathways:

Not Available

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
1383± 112 uM	BL21 DE3	Luria-Bertani (LB) media	Stationary phase cultures (overnight culture)	Shake flask	37 oC	Experimentally Determined Download Details

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-076r-9600000000-f2c06850d0c3db9ec103	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0fb9-5614950000-6ef14e948d063026f7ee	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0900000000-2ce9036c30158be73d60	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ri-9600000000-a826b29724713036f579	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-007a-9200000000-7621d8d96132cc999f4c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-000i-9000000000-f40ae4502b6a2e3ac882	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, negative	splash10-00di-9000000000-a6de82c4270a43535ef4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, negative	splash10-00di-9000000000-f9fa2c446096028a62b8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-f40ae4502b6a2e3ac882	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-a6de82c4270a43535ef4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-f9fa2c446096028a62b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-2afc98a319bf6041adf0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-1dd0cdea93f529e6ccb2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9100000000-d0f08ad6c9dee008067a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-74b62c8ea3678afcff8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ta-1900000000-5a0f3f01ddf8c11c6370	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-93c2b00aa44481aa8630	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-056r-9800000000-b033c19e1db6b17bf7cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9500000000-01306ef5e3c5a271dfb2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-4e87bfc49b1664133053	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-6aefe19f3e63c1b3fbef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03gm-9500000000-d2f178dbda765758ef3d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btd-9000000000-62631cc26542b523e7d7	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View 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)

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Links

External Links:

Resource	Link
CHEBI ID	15946
HMDB ID	HMDB00660
Pubchem Compound ID	439709
Kegg ID	C00095
ChemSpider ID	388775
Wikipedia	FRU
BioCyc ID	BETA-D-FRUCTOSE
EcoCyc ID	BETA-D-FRUCTOSE

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.

D-Fructose (ECMDB00660) (M2MDB000167)

Structure for #<Compound:0xa743577c>

Enzymes

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