Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2015-10-09 22:29:53 UTC
Primary IDFDB012528
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Fructose
DescriptionOccurs in honey and a large number of fruits, particularly apples and tomatoes. Fluid and nutrient replenisher, nutritive sweetener. Inulin from dandelion roots has also been used as a source. Present in polymeric form in the inulins, the energy reserve polysaccharides of many plants, e.g. dahlia and Jerusalem artichoke tubers
CAS Number53188-23-1
Structure
Thumb
Synonyms
SynonymSource
(+-)-fructosebiospider
arabino-2-Hexulosebiospider
b-D-arabino-HexuloseGenerator
b-D-FructofuranoseGenerator
b-D-FructoseGenerator
b-Fruit sugarGenerator
b-LevuloseGenerator
beta-D-arabino-HexuloseChEBI
beta-D-FructofuranoseChEBI
beta-D-FructoseChEBI
beta-delta-arabino-HexuloseHMDB
beta-delta-FructofuranoseHMDB
beta-delta-FructoseHMDB
beta-Fruit sugarChEBI
beta-LevuloseChEBI
D-(-)-fructosebiospider
D-(-)-levulosebiospider
D-arabino-hexulosebiospider
D-Fructosebiospider
delta-(-)-FructoseHMDB
delta-FructoseHMDB
DL-fructosebiospider
FRUbiospider
Fructonbiospider
Fructon (TN)biospider
FRUCTOSEChEBI
Fructose (JP15/USP)biospider
Fructose (van)biospider
Fructose [jan]biospider
Fructose, d-biospider
Fructose, purebiospider
Fruit sugarbiospider
FUDbiospider
Fuructonbiospider
Hi-Fructo 970biospider
Keto-d-fructosebiospider
Krystar 300biospider
Levulosebiospider
Methosebiospider
Nevulosebiospider
Sugar, fruitbiospider
β-D-arabino-hexuloseGenerator
β-D-fructofuranoseGenerator
β-D-fructoseGenerator
β-fruit sugarGenerator
β-levuloseGenerator
Predicted Properties
PropertyValueSource
logP-3.3ChemAxon
pKa (Strongest Acidic)9.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity37.56 m³·mol⁻¹ChemAxon
Polarizability16.4 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H36O18
IUPAC name1,3,4,5,6-pentahydroxyhexan-2-one; 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol; 2-(hydroxymethyl)oxane-2,3,4,5-tetrol
InChI IdentifierInChI=1S/3C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6;7-1-3-4(9)5(10)6(11,2-8)12-3;7-1-3(9)5(11)6(12)4(10)2-8/h2*3-5,7-11H,1-2H2;3,5-9,11-12H,1-2H2
InChI KeyInChIKey=JCOXAIPZGMCTBN-UHFFFAOYSA-N
Isomeric SMILESOCC(O)C(O)C(O)C(=O)CO.OCC1OC(O)(CO)C(O)C1O.OCC1(O)OCC(O)C(O)C1O
Average Molecular Weight540
Monoisotopic Molecular Weight540
Classification
DescriptionThis compound belongs to the class of chemical entities known as monosaccharides. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.00%; H 6.71%; O 53.28%DFC
Melting PointMp 102-104°DFC
Boiling PointNot Available
Experimental Water Solubility778 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKapKa1 12.03 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -92.4 (c, 4 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-e57f7f3e433dde4872e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000090000-e57f7f3e433dde4872e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0000090000-e57f7f3e433dde4872e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-a6d766ed6dc42ab853a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000090000-a6d766ed6dc42ab853a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0000090000-a6d766ed6dc42ab853a6View in MoNA
ChemSpider ID388775
ChEMBL IDCHEMBL604608
KEGG Compound IDC02336
Pubchem Compound ID439709
Pubchem Substance IDNot Available
ChEBI ID48095
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00660
CRC / DFC (Dictionary of Food Compounds) IDHHQ70-Q:HHS32-Q
EAFUS ID2020
Dr. Duke IDFRUCTOSE|LEVULOSE
BIGG ID33835
KNApSAcK IDC00033848
HET IDFRU
Flavornet IDNot Available
GoodScent IDrw1098991
SuperScent IDNot Available
Wikipedia IDFructose
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti alcoholic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hangover52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ketoticDUKE
anti nauseant50919 A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.DUKE
laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
neoplasticDUKE
sweetener50505 Substance that sweeten food, beverages, medications, etc.DUKE
Enzymes
NameGene NameUniProt ID
Sucrase-isomaltase, intestinalSIP14410
Lysosomal alpha-glucosidaseGAAP10253
Maltase-glucoamylase, intestinalMGAMO43451
Neutral alpha-glucosidase CGANCQ8TET4
Hexokinase-3HK3P52790
Hexokinase-2HK2P52789
Hexokinase-1HK1P19367
KetohexokinaseKHKP50053
14 kDa phosphohistidine phosphatasePHPT1Q9NRX4
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
Fructose and Mannose DegradationSMP00064 map00051
Galactose MetabolismSMP00043 map00052
Starch and Sucrose MetabolismSMP00058 map00500
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.