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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:17:15 UTC
Update Date2023-02-21 17:25:33 UTC
HMDB IDHMDB0037044
Secondary Accession Numbers
  • HMDB37044
Metabolite Identification
Common NameRotundifolone
DescriptionRotundifolone belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Rotundifolone is a herbal and minty tasting compound. Rotundifolone is found, on average, in the highest concentration within spearmints (Mentha spicata) and cornmints (Mentha arvensis). Rotundifolone has also been detected, but not quantified in, herbs and spices. This could make rotundifolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Rotundifolone.
Structure
Data?1677000333
Synonyms
ValueSource
1,2-Epoxy-P-menth-4(8)-en-3-oneHMDB
2,3-Epoxy-6-isopropylidene-3-methylcyclohexanoneHMDB
6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9ciHMDB
Piperitenone oxideHMDB
Chemical FormulaC10H14O2
Average Molecular Weight166.217
Monoisotopic Molecular Weight166.099379692
IUPAC Name6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one
Traditional Name6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one
CAS Registry Number5945-46-0
SMILES
CC(C)=C1CCC2(C)OC2C1=O
InChI Identifier
InChI=1S/C10H14O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h9H,4-5H2,1-3H3
InChI KeyAKASWINDKIEEBO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxepanes
Sub ClassNot Available
Direct ParentOxepanes
Alternative Parents
Substituents
  • Oxepane
  • Ketone
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point27.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.95 g/LALOGPS
logP1.61ALOGPS
logP2.07ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.56 m³·mol⁻¹ChemAxon
Polarizability18.49 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.11731661259
DarkChem[M-H]-134.66331661259
DeepCCS[M+H]+137.2830932474
DeepCCS[M-H]-133.45330932474
DeepCCS[M-2H]-170.88930932474
DeepCCS[M+Na]+146.42730932474
AllCCS[M+H]+135.632859911
AllCCS[M+H-H2O]+131.332859911
AllCCS[M+NH4]+139.732859911
AllCCS[M+Na]+140.832859911
AllCCS[M-H]-139.632859911
AllCCS[M+Na-2H]-140.532859911
AllCCS[M+HCOO]-141.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RotundifoloneCC(C)=C1CCC2(C)OC2C1=O1809.7Standard polar33892256
RotundifoloneCC(C)=C1CCC2(C)OC2C1=O1290.3Standard non polar33892256
RotundifoloneCC(C)=C1CCC2(C)OC2C1=O1360.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rotundifolone,1TMS,isomer #1CC(C)=C1CCC2(C)OC2=C1O[Si](C)(C)C1387.1Semi standard non polar33892256
Rotundifolone,1TMS,isomer #1CC(C)=C1CCC2(C)OC2=C1O[Si](C)(C)C1331.6Standard non polar33892256
Rotundifolone,1TBDMS,isomer #1CC(C)=C1CCC2(C)OC2=C1O[Si](C)(C)C(C)(C)C1649.7Semi standard non polar33892256
Rotundifolone,1TBDMS,isomer #1CC(C)=C1CCC2(C)OC2=C1O[Si](C)(C)C(C)(C)C1546.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rotundifolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00o4-9300000000-28ac35eefccb97ecf8f72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rotundifolone 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 - Rotundifolone 10V, Positive-QTOFsplash10-014i-0900000000-0d2244bb050ca70a3c492015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 20V, Positive-QTOFsplash10-014i-4900000000-a49b13c97830692f36f02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 40V, Positive-QTOFsplash10-067i-9100000000-5d3ca3ad1a2c8d2541172015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 10V, Negative-QTOFsplash10-014i-0900000000-ab194c3e028cf03581b82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 20V, Negative-QTOFsplash10-014i-1900000000-a1934865dd6aa8ca0d4a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 40V, Negative-QTOFsplash10-0a59-9600000000-37561a809cd7b097631e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 10V, Negative-QTOFsplash10-014i-0900000000-349584a3f625d5b5807f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 20V, Negative-QTOFsplash10-014i-0900000000-d1252c53df5aa0366a662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 40V, Negative-QTOFsplash10-014i-9300000000-442ba93afe2056decf392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 10V, Positive-QTOFsplash10-014i-1900000000-d8e5853d91f1eb90687c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 20V, Positive-QTOFsplash10-00kf-9300000000-0dfe3b6fd9baf52e4fd72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotundifolone 40V, Positive-QTOFsplash10-014l-9100000000-6c52be035dfdc4e36ed22021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 IDFDB016026
KNApSAcK IDC00003058
Chemspider ID55800
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61942
PDB IDNot Available
ChEBI IDNot Available
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.. .