Showing Compound Card for Pinocarvone (CDB000067)

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Record Information
Version1.0
Created at2020-03-18 23:23:33 UTC
Updated at2020-11-18 16:34:43 UTC
CannabisDB IDCDB000067
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePinocarvone
DescriptionPinocarvone or (-)-Pinocarvone, also known as 2(10)-pinen-3-one, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing 2 rings, fused to each other. 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-eritritol-phosphate (MEP) pathway in plant cell plastids (PMID: 23746261 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes (PMID: 23911730 ). GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Thus, (-)-pinocarvone is an isoprenoid lipid molecule. Pinocarvone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Pinocarvone is a volatile, minty tasting compound. Pinocarvone is found in higher concentrations in hyssops. It has also been detected in cauliflowers, spearmints, sweet bay and in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
IUPAC Name(1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-one
Traditional Name(1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-one
CAS Registry Number19890-00-7
SMILES
CC1(C)[C@H]2C[C@@H]1C(=C)C(=O)C2
InChI Identifier
InChI=1S/C10H14O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-8H,1,4-5H2,2-3H3/t7-,8+/m0/s1
InChI KeyTZDMGBLPGZXHJI-JGVFFNPUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP2.28ALOGPS
logP2.19ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.34 m³·mol⁻¹ChemAxon
Polarizability17.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPinocarvone, 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 Compound12314319
PDB IDNot Available
ChEBI IDNot Available
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 ]
  2. Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. [PubMed:23746261 ]
  3. Kulkarni R, Pandit S, Chidley H, Nagel R, Schmidt A, Gershenzon J, Pujari K, Giri A, Gupta V: Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit. Plant Physiol Biochem. 2013 Oct;71:121-31. doi: 10.1016/j.plaphy.2013.07.006. Epub 2013 Jul 16. [PubMed:23911730 ]