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Identification
YMDB IDYMDB00657
NameD-Fructose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFructose-1P, also known as D-fructose or fructon, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Fructose-1P is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 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-arabino-hexulose
  • D-Fru
  • delta-(-)-Fructose
  • delta-Fructose
  • FRU
  • Fructon
  • Fructose
  • fruit sugar
  • Hex-2-ulose
  • Laevulose
  • levulose
  • D-(-)-Levulose
  • D-Fructose
CAS number57-48-7
WeightAverage: 180.1559
Monoisotopic: 180.063388116
InChI KeyBJHIKXHVCXFQLS-UYFOZJQFSA-N
InChIInChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6-/m1/s1
IUPAC Name(3S,4R,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
Traditional IUPAC Nameketo-D-fructose
Chemical FormulaC6H12O6
SMILES[H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy ketone
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point119-122 °C
Experimental Properties
PropertyValueReference
Water Solubility778 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility399 g/LALOGPS
logP-2.2ALOGPS
logP-3.3ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)9.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.56 m³·mol⁻¹ChemAxon
Polarizability16.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Fructose MetabolismPW002390 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Fructose and mannose metabolismec00051 Map00051
Galactose metabolismec00052 Map00052
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
Adenosine triphosphate + D-FructoseADP + Beta-D-Fructose 6-phosphate
D-Fructose + Adenosine triphosphateBeta-D-Fructose 6-phosphate + Adenosine triphosphate + hydron
sucrose-6-phosphate + waterD-Fructose + Beta-D-Glucose 6-phosphate
Sucrose + waterD-Fructose + Alpha-D-Glucose
sucrose-6-phosphate + waterD-Fructose + Glucose 6-phosphate
KEGG Reactions
NAD + D-glucitolNADH + D-Fructose + hydron
Adenosine triphosphate + D-FructoseFructose 6-phosphate + hydron + ADP
water + Sucrose D-Fructose + D-Glucose
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1920000000-edcbda13fc8e7419c818JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-1920000000-a09af821de27576754b2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0930000000-82a04b21f0be02924ff8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0930000000-8b1def66209ec997838eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-4a9e1bbc88f9c15ecb02JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0920000000-b0a5097fae72417333e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1920000000-edcbda13fc8e7419c818JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-1920000000-a09af821de27576754b2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0930000000-82a04b21f0be02924ff8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0930000000-8b1def66209ec997838eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-4a9e1bbc88f9c15ecb02JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0920000000-b0a5097fae72417333e3JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9400000000-cbf0535ab90e3a601a7aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-056r-5212930000-7485c1e566587f09d84dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1900000000-87bee64df7fe316d7affJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-eb4eeb92523e2e200555JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-9100000000-3f790be8b14df714880bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0170-7900000000-041fe274da364a106e71JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9300000000-6f545044f1769c501e2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b0a05227494224e23bd2JSpectraViewer
1D NMR13C 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
  • Blazquez, M. A., Lagunas, R., Gancedo, C., Gancedo, J. M. (1993). "Trehalose-6-phosphate, a new regulator of yeast glycolysis that inhibits hexokinases." FEBS Lett 329:51-54.8354408
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.
External Links:
ResourceLink
CHEBI ID15824
HMDB IDHMDB00660
Pubchem Compound ID439709
Kegg IDC00095
ChemSpider ID5764
FOODB IDNot Available
WikipediaFructose
BioCyc IDCPD-535

Enzymes

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
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
Not Available
Uniprot ID:
Q06204
Molecular weight:
48968.80078
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
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
General function:
Involved in zinc ion binding
Specific function:
L-iditol + NAD(+) = L-sorbose + NADH
Gene Name:
SOR1
Uniprot ID:
P35497
Molecular weight:
38165.39844
Reactions
L-iditol + NAD(+) → L-sorbose + NADH.
General function:
Involved in ATP binding
Specific function:
Putative glucokinase involved in phosphorylation of aldohexoses and glucose uptake. Involved in sporulation. Required for the full activation of the early meiotic inducer IME1
Gene Name:
EMI2
Uniprot ID:
Q04409
Molecular weight:
55920.30078
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
Two isoenzymes, hexokinase-1 and hexokinase-2, can phosphorylate keto- and aldohexoses in yeast, whereas a third isoenzyme, GLK, is specific for aldohexoses. All glucose phosphorylating enzymes are involved in glucose uptake
Gene Name:
GLK1
Uniprot ID:
P17709
Molecular weight:
55376.89844
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DSF1
Uniprot ID:
P39941
Molecular weight:
56469.69922
Reactions
D-mannitol + NAD+ → D-fructose + NADH + H+
General function:
Involved in catalytic activity
Specific function:
Catalytic subunit of glucosidase 2, which cleaves sequentially the 2 innermost alpha-1,3-linked glucose residues from the Glc(2)Man(9)GlcNAc(2) oligosaccharide precursor of immature glycoproteins
Gene Name:
ROT2
Uniprot ID:
P38138
Molecular weight:
110265.0
Reactions
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC1
Uniprot ID:
P10594
Molecular weight:
60569.89844
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC3
Uniprot ID:
P10595
Molecular weight:
8649.90039
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC4
Uniprot ID:
P10596
Molecular weight:
60574.80078
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC5
Uniprot ID:
P10597
Molecular weight:
8649.90039
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC2
Uniprot ID:
P00724
Molecular weight:
60638.89844
Reactions
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC7
Uniprot ID:
P07635
Molecular weight:
11248.90039

Transporters

General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT9
Uniprot ID:
P40885
Molecular weight:
62857.19922
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT11
Uniprot ID:
P54862
Molecular weight:
62732.19922
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT10
Uniprot ID:
P43581
Molecular weight:
60661.5
General function:
Involved in transmembrane transporter activity
Specific function:
High-affinity glucose transporter
Gene Name:
HXT6
Uniprot ID:
P39003
Molecular weight:
62704.60156
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT8
Uniprot ID:
P40886
Molecular weight:
63492.0
General function:
Involved in transmembrane transporter activity
Specific function:
High-affinity glucose transporter. Is only indispensable for growth on low glucose-containing media, because S.cerevisiae possesses other sugar transporters
Gene Name:
HXT2
Uniprot ID:
P23585
Molecular weight:
59840.19922
General function:
Involved in transmembrane transporter activity
Specific function:
Low-affinity glucose transporter. HXT1 is as well involved in the transport of mannose
Gene Name:
HXT1
Uniprot ID:
P32465
Molecular weight:
63260.89844
General function:
Involved in transmembrane transporter activity
Specific function:
Low-affinity glucose transporter
Gene Name:
HXT3
Uniprot ID:
P32466
Molecular weight:
62557.19922
General function:
Involved in transmembrane transporter activity
Specific function:
Low-affinity glucose transporter. Can also transport xylose
Gene Name:
HXT4
Uniprot ID:
P32467
Molecular weight:
63909.60156
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT17
Uniprot ID:
P53631
Molecular weight:
62827.69922
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT16
Uniprot ID:
P47185
Molecular weight:
62919.89844
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT5
Uniprot ID:
P38695
Molecular weight:
66251.0
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT13
Uniprot ID:
P39924
Molecular weight:
62733.60156
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT15
Uniprot ID:
P54854
Molecular weight:
62930.89844
General function:
Involved in transmembrane transporter activity
Specific function:
High-affinity glucose transporter
Gene Name:
HXT7
Uniprot ID:
P39004
Molecular weight:
62734.60156