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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:00 UTC
Update Date2019-07-23 06:09:41 UTC
HMDB IDHMDB0031859
Secondary Accession Numbers
  • HMDB31859
Metabolite Identification
Common NameNorfuraneol
DescriptionNorfuraneol, also known as 4Hm-furanone, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Norfuraneol is a sweet, bready, and candy tasting compound. Norfuraneol has been detected, but not quantified in, several different foods, such as beer, blackberries (Rubus), evergreen blackberries (Rubus laciniatus), and fruits. This could make norfuraneol a potential biomarker for the consumption of these foods. Norfuraneol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Norfuraneol.
Structure
Data?1563862181
Synonyms
ValueSource
4-Hydroxy-5-methyl-3(2H)-furanoneMeSH
4-Hydroxy-5-methylfuran-3(2H)-oneMeSH
4Hm-FuranoneMeSH
5-Methyl-4-hydroxy-3(2H)-furanoneMeSH
4-Hydroxy-5-methyl-2,3-dihydrofuran-3-oneHMDB
4-Hydroxy-5-methyl-3-furanoneHMDB
NorfuraneolMeSH
Chemical FormulaC5H6O3
Average Molecular Weight114.0993
Monoisotopic Molecular Weight114.031694058
IUPAC Name4-hydroxy-5-methyl-2,3-dihydrofuran-3-one
Traditional Name4-hydroxy-5-methyl-2H-furan-3-one
CAS Registry Number19322-27-1
SMILES
CC1=C(O)C(=O)CO1
InChI Identifier
InChI=1S/C5H6O3/c1-3-5(7)4(6)2-8-3/h7H,2H2,1H3
InChI KeyDLVYTANECMRFGX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point126.6 - 127.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility616 g/LALOGPS
logP10(-0.83) g/LALOGPS
logP10(-0.36) g/LChemAxon
logS10(0.73) g/LALOGPS
pKa (Strongest Acidic)6.88ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.8 m³·mol⁻¹ChemAxon
Polarizability10.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+128.12130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorfuraneolCC1=C(O)C(=O)CO12037.5Standard polar33892256
NorfuraneolCC1=C(O)C(=O)CO1975.6Standard non polar33892256
NorfuraneolCC1=C(O)C(=O)CO11042.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norfuraneol,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)CO11143.6Semi standard non polar33892256
Norfuraneol,1TMS,isomer #2CC1=C(O)C(O[Si](C)(C)C)=CO11197.1Semi standard non polar33892256
Norfuraneol,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CO11247.8Semi standard non polar33892256
Norfuraneol,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CO11309.9Standard non polar33892256
Norfuraneol,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CO11395.2Semi standard non polar33892256
Norfuraneol,1TBDMS,isomer #2CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=CO11504.6Semi standard non polar33892256
Norfuraneol,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CO11742.6Semi standard non polar33892256
Norfuraneol,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CO11730.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norfuraneol GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-c057722961052e7db7cb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norfuraneol GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-9500000000-44f15f27c3c3c1813bd62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norfuraneol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 10V, Positive-QTOFsplash10-014i-2900000000-bc4ceda0d7268fec73802016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 20V, Positive-QTOFsplash10-014j-9700000000-3cc94b2bfed7a5fbb1352016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 40V, Positive-QTOFsplash10-054p-9000000000-4fda2f9ca6d91ed81b4b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 10V, Negative-QTOFsplash10-03di-1900000000-0a8bbbe75f7fe8274a462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 20V, Negative-QTOFsplash10-03di-4900000000-b1f26dce36a045259cdb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 40V, Negative-QTOFsplash10-0006-9000000000-4c53903862f4136368a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 10V, Positive-QTOFsplash10-066u-9300000000-fb42cca00dbe8013dab42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 20V, Positive-QTOFsplash10-0006-9000000000-923a600b3a1f5143ac692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 40V, Positive-QTOFsplash10-0006-9000000000-856565bd4acb22def6d22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 10V, Negative-QTOFsplash10-022c-9200000000-b403c75353e48c7f21c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 20V, Negative-QTOFsplash10-0a4i-9000000000-193d36314c6367d667502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norfuraneol 40V, Negative-QTOFsplash10-052f-9000000000-29f17cdfee419ec3fa272021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
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
FooDB IDFDB008543
KNApSAcK IDNot Available
Chemspider ID3757733
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4564493
PDB IDNot Available
ChEBI ID74456
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .