Record Information
Version1.0
Creation Date2016-09-30 22:34:28 UTC
Update Date2020-06-04 20:58:44 UTC
BMDB IDBMDB0000660
Secondary Accession Numbers
  • BMDB00660
Metabolite Identification
Common NameD-Fructose
DescriptionD-Fructose, also known as D-tagatose or D-lyxo-2-hexulose, 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. D-Fructose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Fructose exists in all living species, ranging from bacteria to humans. D-Fructose participates in a number of enzymatic reactions, within cattle. In particular, D-Fructose can be biosynthesized from sorbitol through its interaction with the enzyme sorbitol dehydrogenase. In addition, D-Fructose can be biosynthesized from Beta-D-fructose 2-phosphate through the action of the enzyme 14 kda phosphohistidine phosphatase. In cattle, D-fructose is involved in the metabolic pathway called the fructose and mannose degradation pathway. D-Fructose is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
beta-D-Arabino-hexuloseChEBI
beta-D-FructoseChEBI
beta-Fruit sugarChEBI
beta-LevuloseChEBI
FRUCTOSEChEBI
b-D-Arabino-hexuloseGenerator
Β-D-arabino-hexuloseGenerator
b-D-FructoseGenerator
Β-D-fructoseGenerator
b-Fruit sugarGenerator
Β-fruit sugarGenerator
b-LevuloseGenerator
Β-levuloseGenerator
beta-D-FructofuranoseHMDB
beta-delta-Arabino-hexuloseHMDB
beta-delta-FructofuranoseHMDB
beta-delta-FructoseHMDB
D-(-)-FructoseHMDB
delta-(-)-FructoseHMDB
delta-FructoseHMDB
FRUHMDB
FructonHMDB
LevuloseHMDB
Braun brand OF fructoseHMDB
Fleboplast levulosaHMDB
Fresenius kabi brand OF fructoseHMDB
Instituto farmacologico brand OF fructoseHMDB
LevulosaHMDB
Levulosa ifeHMDB
Grifols brand OF fructoseHMDB
Levulosa baxterHMDB
Levulosado braunHMDB
Ern brand OF fructoseHMDB
Levulosa grifolsHMDB
Levulosa meinHMDB
Levulosado vituliaHMDB
Apir levulosaHMDB
Baxter brand OF fructoseHMDB
Bieffe brand OF fructoseHMDB
Levulosa braunHMDB
Levulosa ibysHMDB
Levulosa, apirHMDB
Levulosa, fleboplastHMDB
Levulosado bieffe meditHMDB
Plast apyr levulosa meinHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
Traditional Namefructose
CAS Registry Number53188-23-1
SMILES
OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O
InChI Identifier
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
InChI KeyRFSUNEUAIZKAJO-ARQDHWQXSA-N
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.
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point119 - 122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility778 mg/mL at 20 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified763.813 +/- 751.731 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified2415.813 +/- 1248.434 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000660
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031286
KNApSAcK IDC00001117
Chemspider ID388775
KEGG Compound IDC02336
BioCyc IDBETA-D-FRUCTOSE
BiGG ID33835
Wikipedia LinkFructose
METLIN ID135
PubChem Compound439709
PDB IDFRU
ChEBI ID28645
References
Synthesis ReferenceLiu, 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)Not Available
General References
  1. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  2. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Polyol dehydrogenase that catalyzes the reversible NAD(+)-dependent oxidation of various sugar alcohols. Is mostly active with xylitol, D-sorbitol (D-glucitol) and L-iditol as substrates, leading to the C2-oxidized products D-xylulose, D-fructose and L-sorbose, respectively (PubMed:9143345). Is a key enzyme in the polyol pathway that interconverts glucose and fructose via sorbitol, which constitutes an important alternate route for glucose metabolism. May play a role in sperm motility by using sorbitol as an alternative energy source for sperm motility (By similarity). Cannot use NADP(+) as the electron acceptor. Has no activity on ethanol, methanol, glycerol, galactitol and fructose 6-phosphate (PubMed:9143345).
Gene Name:
SORD
Uniprot ID:
Q58D31
Molecular weight:
38099.0
Reactions
Sorbitol + NAD → D-Fructose + NADHdetails
General function:
Carbohydrate transport and metabolism
Specific function:
Essential for the degradation of glycogen in lysosomes (PubMed:10723725). Has highest activity on alpha-1,4-linked glycosidic linkages, but can also hydrolyze alpha-1,6-linked glucans.
Gene Name:
GAA
Uniprot ID:
Q9MYM4
Molecular weight:
104757.0
Reactions
Sucrose + Water → D-Galactose + D-Fructosedetails
Alpha-D-Glucose + D-Fructose → Sucrose + Waterdetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:
HK1
Uniprot ID:
P27595
Molecular weight:
103064.0
Reactions
D-Fructose + Adenosine triphosphate → Fructose 6-phosphate + ADPdetails
Adenosine triphosphate + D-Fructose → ADP + Beta-D-Fructose 6-phosphatedetails
General function:
Involved in sodium ion binding
Specific function:
Involved in the sodium-dependent cotransport of myo-inositol (MI) with a Na(+):MI stoichiometry of 2:1. Exclusively responsible for apical MI transport and absorption in intestine. Also can transport D-chiro-inositol (DCI) but not L-fructose. Exhibits stereospecific cotransport of both D-glucose and D-xylose. May induce apoptosis through the TNF-alpha, PDCD1 pathway. May play a role in the regulation of MI concentration in serum, involving reabsorption in at least the proximal tubule of the kidney.
Gene Name:
SLC5A11
Uniprot ID:
Q3ZC26
Molecular weight:
73957.0
General function:
Carbohydrate transport and metabolism
Specific function:
Insulin-regulated facilitative hexose transporter that mediates the transport of glucose and fructose. Also able to mediate the transport of dehydroascorbate.
Gene Name:
SLC2A8
Uniprot ID:
P58354
Molecular weight:
51417.0
General function:
Carbohydrate transport and metabolism
Specific function:
Functions as a fructose transporter that has only low activity with other monosaccharides. Can mediate the uptake of deoxyglucose, but with low efficiency. Essential for fructose uptake in the small intestine. Plays a role in the regulation of salt uptake and blood pressure in response to dietary fructose. Required for the development of high blood pressure in response to high dietary fructose intake.
Gene Name:
SLC2A5
Uniprot ID:
P58353
Molecular weight:
55393.0
General function:
Not Available
Specific function:
Exhibits phosphohistidine phosphatase activity.
Gene Name:
PHPT1
Uniprot ID:
Q32PA4
Molecular weight:
13931.0
Reactions
Beta-D-Fructose 2-phosphate + Water → D-Fructose + Hydrogen phosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
KHK
Uniprot ID:
Q0II75
Molecular weight:
37868.0
Reactions
D-Fructose + Adenosine triphosphate → Fructose 1-phosphate + ADPdetails