Showing Compound Card for Piperitenone (CDB000093)

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Record Information
Version1.0
Created at2020-03-18 23:24:30 UTC
Updated at2020-12-07 19:07:05 UTC
CannabisDB IDCDB000093
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePiperitenone
DescriptionPiperitenone belongs to the class of organic compounds known as menthane monoterpenoids, with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, piperitenone is an isoprenoid lipid molecule. It is very hydrophobic, almost insoluble in water, and relatively neutral. Piperitenone is a minty, phenolic, and sharp-taste ( Ref:DOI ). Piperitenone is found in highest concentrations in spearmints and rosemaries. It was detected in peppermints, herbs and spices, orange mints, citrus, and mentha (mint). This could make piperitenone a potential biomarker for the consumption of these foods. Piperitenone is also found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-oneHMDB
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9ciHMDB
3-Methyl-6-propan-2-ylidenecyclohex-2-en-1-oneHMDB
3-TerpinolenoneHMDB
6-Isopropylidene-3-methyl-2-cyclohexenoneHMDB
FEMA 3560HMDB
PulespenoneHMDB
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
IUPAC Name3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one
Traditional Namepiperitenone
CAS Registry Number491-09-8
SMILES
CC(C)=C1CCC(C)=CC1=O
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3
InChI KeyHKZQJZIFODOLFR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Quinomethane
  • O-quinomethane
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.39ALOGPS
logP2.81ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)18.6ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.96 m³·mol⁻¹ChemAxon
Polarizability17.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPiperitenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f7c-8900000000-f5b1034f0ad5612f0f1eSpectrum
Predicted GC-MSPiperitenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-c4031753132982c55fab2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-7900000000-9a0d9372d2684846d39b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-82fba962be7e9686c5172017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b7c0004066c195aa40892017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-49abeb92134d82dda90e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053s-2900000000-fba0f16e8603dd89ee042017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-7be39bdd81d4a83f56ee2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9300000000-b6529814b27363caeb9a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-51ccd861c84166dd6b2c2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-cfb5c45cee930f53ee1b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-9100000000-afc2d70a9cbeb08c12302021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0036999
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015974
KNApSAcK IDC00010889
Chemspider ID337757
KEGG Compound IDC01951
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound381152
PDB IDNot Available
ChEBI ID17304
References
General References
  1. 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 ]