Record Information
Version1.0
Creation date2015-05-07 21:30:35 UTC
Update date2019-11-26 03:22:14 UTC
Primary IDFDB031286
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameβ-D-fructofuranose
Descriptionβ-d-fructofuranose, also known as fructose or beta-levulose, is a member of the class of compounds known as C-glycosyl compounds. C-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. β-d-fructofuranose is very soluble (in water) and a very weakly acidic compound (based on its pKa). β-d-fructofuranose can be found in a number of food items such as yardlong bean, red huckleberry, towel gourd, and burdock, which makes β-d-fructofuranose a potential biomarker for the consumption of these food products. β-d-fructofuranose can be found primarily in most biofluids, including cerebrospinal fluid (CSF), feces, urine, and saliva, as well as in human liver, prostate and sperm tissues. β-d-fructofuranose exists in all living organisms, ranging from bacteria to humans. In humans, β-d-fructofuranose is involved in several metabolic pathways, some of which include amino sugar metabolism, fructose intolerance, hereditary, starch and sucrose metabolism, and fructose and mannose degradation. β-d-fructofuranose is also involved in several metabolic disorders, some of which include glycogen synthetase deficiency, salla disease/infantile sialic acid storage disease, mucopolysaccharidosis VI. sly syndrome, and galactosemia. Moreover, β-d-fructofuranose is found to be associated with diabetes mellitus type 2. β-d-fructofuranose is a non-carcinogenic (not listed by IARC) potentially toxic compound. Acute consumption of fructose or high fructose corn syrup is essentially non-toxic. Chronic, excess fructose consumption has been shown to be a cause (or indirect cause) of gout, insulin resistance, hypertension, obesity, fatty liver disease, elevated LDL cholesterol and elevated triglycerides, leading to metabolic syndrome. In Wistar rats, a laboratory model of diabetes, 10% fructose feeding as opposed to 10% glucose feeding was found to increase blood triglyceride levels by 86%, whereas the same amount of glucose had no effect on triglycerides. A 2008 study found a substantial risk of incident gout associated with the consumption of fructose or fructose-rich foods. It is suspected that the fructose found in soft drinks (e.g., carbonated beverages) and other sweetened drinks is the primary reason for this increased incidence (T3DB).
CAS Number53188-23-1
Structure
Thumb
Synonyms
SynonymSource
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
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
Chemical FormulaC6H12O6
IUPAC name(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
InChI IdentifierInChI=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
Isomeric SMILESOC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Foods
  • Sugars
  • Fruits and vegetables:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-076r-9600000000-f2c06850d0c3db9ec103JSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0fb9-5614950000-6ef14e948d063026f7eeJSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-2ce9036c30158be73d60JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ri-9600000000-a826b29724713036f579JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-007a-9200000000-7621d8d96132cc999f4cJSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-2afc98a319bf6041adf0JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-1dd0cdea93f529e6ccb2JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-d0f08ad6c9dee008067aJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-74b62c8ea3678afcff8aJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ta-1900000000-5a0f3f01ddf8c11c6370JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-93c2b00aa44481aa8630JSpectraViewer
    1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound IDNot Available
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDNot Available
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference