Showing Compound Card for Rotundifolone (CDB000203)

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Record Information
Version1.0
Created at2020-03-18 23:28:36 UTC
Updated at2020-12-07 19:07:15 UTC
CannabisDB IDCDB000203
Secondary Accession NumbersNot Available
Cannabis Compound 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 neutral compound. Rotundifolone has an herbal and minty taste. Rotundifolone is found in highest concentrations in spearmints and cornmints. Rotundifolone has also been detected in herbs and spices. This could make rotundifolone a potential biomarker for the consumption of these foods. Rotundifolone is the major chemical constituent (around 70%) of Mentha crispa essential oil which exibits several biological activities, including antinociceptive, spasmolytic, antimicrobial, larvicidal, trypanocidal, cytotoxic, and antitumoral (PMID: 30057673 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC10H14O2
Average Molecular Weight166.22
Monoisotopic Molecular Weight166.0994
IUPAC Name(1R,6R)-6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one
Traditional Name(1R,6R)-6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one
CAS Registry NumberNot Available
SMILES
CC(C)=C1CC[C@@]2(C)O[C@H]2C1=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/t9-,10+/m0/s1
InChI KeyAKASWINDKIEEBO-VHSXEESVSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability18.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRotundifolone, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124301339
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turkez H, Tozlu OO, Lima TC, de Brito AEM, de Sousa DP: A Comparative Evaluation of the Cytotoxic and Antioxidant Activity of Mentha crispa Essential Oil, Its Major Constituent Rotundifolone, and Analogues on Human Glioblastoma. Oxid Med Cell Longev. 2018 Jul 2;2018:2083923. doi: 10.1155/2018/2083923. eCollection 2018. [PubMed:30057673 ]