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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:15:16 UTC
Update Date2018-03-12 21:55:50 UTC
HMDB IDHMDB0041561
Secondary Accession Numbers
  • HMDB41561
Metabolite Identification
Common NameD-1,5-Anhydrofructose
DescriptionD-1,5-Anhydrofructose belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. D-1,5-Anhydrofructose exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, D-1,5-anhydrofructose is primarily located in the cytoplasm. Outside of the human body, D-1,5-anhydrofructose can be found in fruits. This makes D-1,5-anhydrofructose a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
1,5-anhydro-D-FructoseHMDB
1,5-AnhydrofructoseHMDB
15-anhydro-D-FRUCTOSEHMDB
1:5-anhydro-D-FructoseHMDB
Chemical FormulaC6H10O5
Average Molecular Weight162.1406
Monoisotopic Molecular Weight162.05282343
IUPAC Name4,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
Traditional Name4,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
CAS Registry Number75414-43-6
SMILES
OCC1OCC(=O)C(O)C1O
InChI Identifier
InChI=1S/C6H10O5/c7-1-4-6(10)5(9)3(8)2-11-4/h4-7,9-10H,1-2H2
InChI KeyOCLOLUFOLJIQDC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oxanes. These are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxanes
Sub ClassNot Available
Direct ParentOxanes
Alternative Parents
Substituents
  • Oxane
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107 - 112 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility965 g/LALOGPS
logP-1.8ALOGPS
logP-2.1ChemAxon
logS0.77ALOGPS
pKa (Strongest Acidic)11.27ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.05 m³·mol⁻¹ChemAxon
Polarizability14.77 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9400000000-6a2c86d0cbf668aaa216View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0l90-7679000000-3923b2f90f522329a8b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-cbe44c73ecfc238d255eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r2-2900000000-f11ae6616ad28f125f1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i0-9200000000-598cdf214a959b4a72ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-4b04da39ac4457064187View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03kc-5900000000-fdc01e18caf26a201fd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9100000000-17bf9cfa9059c522cc05View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021549
KNApSAcK IDNot Available
Chemspider ID11479177
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14299935
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Not Available
Specific function:
Catalyzes the NADPH-dependent reduction of 1,5-anhydro-D-fructose (AF) to 1,5-anhydro-D-glucitol. Can also catalyze the reduction of various aldehydes and quinones (By similarity). Has low NADPH-dependent reductase activity towards 9,10-phenanthrenequinone (in vitro).
Gene Name:
AKR1E2
Uniprot ID:
Q96JD6
Molecular weight:
36588.935
Reactions
1,5-Anhydrosorbitol + NADP → D-1,5-Anhydrofructose + NADPHdetails