Showing Compound Card for piperitone oxide (CDB000301)

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Record Information
Version1.0
Created at2020-03-19 00:29:45 UTC
Updated at2020-11-18 16:35:03 UTC
CannabisDB IDCDB000301
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namepiperitone oxide
DescriptionPiperitone oxide is an oxidized derivative of Piperitone. It belongs to the class of organic compounds known cyclic monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Piperitone oxide exists as two isomers, cis-Piperitone oxide and trans-Piperitone oxide. It is a colorless to pale yellow clear liquid that is neutral, hydrophobic and essentially insoluble in water. Piperitone oxide can be found in cornmint, orange mint, peppermint, and spearmint, which makes piperitone oxide a potential biomarker for the consumption of these food products. It has also been detected in the essential oils of other mint species, such as apple mint (Mentha suaveolens) (PMID: 25985361 ). Piperitone oxide has also been detected in Cannabis sativa plants (PMID: 6991645 ). It is one of more than 140 terpenoids found in cannabis and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC10H16O2
Average Molecular Weight168.24
Monoisotopic Molecular Weight168.115
IUPAC Name(1S,3R,6S)-6-methyl-3-(propan-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one
Traditional Name(1S,3R,6S)-3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one
CAS Registry Number4713-38-6
SMILES
CC(C)[C@H]1CC[C@]2(C)O[C@@H]2C1=O
InChI Identifier
InChI=1S/C10H16O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h6-7,9H,4-5H2,1-3H3/t7-,9-,10+/m1/s1
InChI KeyIAFONZHDZMCORS-QNSHHTMESA-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
  • Aldehyde
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.96ALOGPS
logP2.26ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)19.7ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.95 m³·mol⁻¹ChemAxon
Polarizability18.97 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-MSpiperitone oxide, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSpiperitone oxide, 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 Compound6430800
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Bozovic M, Pirolli A, Ragno R: Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry. Molecules. 2015 May 13;20(5):8605-33. doi: 10.3390/molecules20058605. [PubMed:25985361 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  3. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]