Showing Compound Card for Fructose (CDB006158)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:22:01 UTC
Updated at2020-11-18 16:34:37 UTC
CannabisDB IDCDB006158
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFructose
DescriptionFructose, or levulose or fruit sugar, is a levorotatory monosaccharide and an isomer of glucose. The chemical formula of fructose is (C6H12O6). . As is the case with all monosaccharides, fructose is a reducing sugar. 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 plants, where it is often bonded to glucose to form the disaccharide sucrose. Fructose is found in many foods and is one of the three most important blood sugars along with glucose and galactose. 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. The greatest dietary sources of fructose are high-fructose corn syrup, agave nectar, honey, molasses, maple syrup, fruit and fruit juices. 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. It is used as a preservative and an intravenous infusion in parenteral feeding. Fructose is a reducing sugar, as are all monosaccharides. The spontaneous addition of single sugar molecules to proteins, known as glycation, is a significant cause of damage in diabetics. Excessive consumption of fructose (especially from sugar-sweetened beverages) may contribute to insulin resistance, obesity, elevated LDL cholesterol and triglycerides, leading to metabolic syndrome (PMID: 26429086 ). Fructose-sweetened food and beverage products cause less of a rise in blood glucose levels than do those manufactured with either sucrose or glucose.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
BETA-L-FRUCTO-furanoseChEBI
b-L-FRUCTO-furanoseGenerator
Β-L-fructo-furanoseGenerator
b-L-FructofuranoseGenerator
Β-L-fructofuranoseGenerator
Chemical FormulaC6H12O6
Average Molecular Weight180.16
Monoisotopic Molecular Weight180.0634
IUPAC Name(2S,3R,4R,5S)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
Traditional Nameβ-L-fructofuranose
CAS Registry Number41579-20-8
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-/m0/s1
InChI KeyRFSUNEUAIZKAJO-AZGQCCRYSA-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
Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point103 °CWikipedia
Boiling PointNot AvailableNot Available
Water Solubility4000 g/LWikipedia
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
Polarizability16.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFructose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0nvj-9800000000-a432e9a4475e87b9a71bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-b3f60381abcbdcb48ac82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-3900000000-71904e4563db1301330c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05a7-9100000000-adcc1736b1bb3c5580532017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-02fc5a461b513bff12f62017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ta-2900000000-bb73e3c08c515665310f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-628908782d8b850cdeeb2017-07-26View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDDB04173
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFructose
METLIN IDNot Available
PubChem Compound439553
PDB IDNot Available
ChEBI ID43703
References
General References
  1. Malik VS, Hu FB: Fructose and Cardiometabolic Health: What the Evidence From Sugar-Sweetened Beverages Tells Us. J Am Coll Cardiol. 2015 Oct 6;66(14):1615-1624. doi: 10.1016/j.jacc.2015.08.025. [PubMed:26429086 ]