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Identification
YMDB IDYMDB01413
Namevitispirane
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionVitispirane belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Vitispirane is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 2,10,10-trimethyl-6-methylidene-1-oxaspiro[4.5]dec-7-ene
  • 6,9-Epoxy-3,5(13)-megastigmadiene
CAS number65416-59-3
WeightAverage: 192.2973
Monoisotopic: 192.151415262
InChI KeyDUPDJVDPPBFBPL-UHFFFAOYSA-N
InChIInChI=1S/C13H20O/c1-10-6-5-8-12(3,4)13(10)9-7-11(2)14-13/h5-6,11H,1,7-9H2,2-4H3
IUPAC Name2,10,10-trimethyl-6-methylidene-1-oxaspiro[4.5]dec-7-ene
Traditional IUPAC Name2,10,10-trimethyl-6-methylidene-1-oxaspiro[4.5]dec-7-ene
Chemical FormulaC13H20O
SMILES[H]C([H])=C1C([H])=C([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C11OC([H])(C([H])([H])[H])C([H])([H])C1([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydrofurans
Sub ClassNot Available
Direct ParentTetrahydrofurans
Alternative Parents
Substituents
  • Tetrahydrofuran
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP4.25ALOGPS
logP3.15ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.03 m³·mol⁻¹ChemAxon
Polarizability22.83 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
EarthyFDB015765
FloralFDB015765
FruityFDB015765
WoodyFDB015765
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gv-2900000000-2739a1eb76ca5414d126JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-744c2618d9fcad65a6ebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-6900000000-eda4218a528077619319JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-0940e73441b1b0b4f7eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-593d1022019da0a50f12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e5d36e0a67335cf33415JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-3900000000-57f58811e3bfef9b8148JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-9cc3e24333b35d1cc976JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-5900000000-868d984a13f8e20c1337JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9500000000-1e1f155e383051c8cb17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-14436e4d9ff8d032db54JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-f2d4c7e0561b1f59c4d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02tl-4900000000-f45993d01a55623763bfJSpectraViewer
References
References:
  • Gallardo-Chacon, J. J., Vichi, S., Lopez-Tamames, E., Buxaderas, S. (2010). "Changes in the Sorption of Diverse Volatiles by Saccharomyces cerevisiae Lees during Sparkling Wine Aging." J Agric Food Chem :.21073195
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0036818
Pubchem Compound ID6450832
Kegg IDNot Available
ChemSpider ID4953381
FOODB IDFDB015765
Wikipedia IDNot Available
BioCyc IDNot Available