Showing Compound Card for Verbenone (CDB000675)

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Record Information
Version1.0
Created at2020-03-19 00:50:31 UTC
Updated at2020-11-18 16:35:24 UTC
CannabisDB IDCDB000675
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameVerbenone
DescriptionVerbenone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing 2 rings, which are 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. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP can undergo several cyclization reactions to yield a diverse number of cyclic arrangements. Verbenone and its analogs are insect pheromones. In particular, verbenone has shown an important role to control bark beetles (DOI:10.1021/bk-2013-1141.ch004). It is also a part of the essential oils of a variety of plants. Verbenone is one of the monoterpenes found to occur in Cannabis sativa plants (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-VerbenoneChEBI
(1R)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-oneChEBI
(1R,5R)-(+)-2-Pinen-4-oneChEBI
(1R,5R)-(+)-Pin-2-en-4-oneChEBI
(1R,5R)-2-Pinen-4-oneChEBI
(1R,5R)-Pin-2-en-4-oneChEBI
(1R-cis)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-oneChEBI
D-VerbenoneChEBI
VerbenoneChEBI
Verbenone, (+-)-isomerMeSH
Verbenone, (1R)-isomerMeSH
Verbenone, (1S)-isomerMeSH
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
IUPAC Name(1R,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
Traditional Nameverbenone
CAS Registry Number80-57-9
SMILES
CC1=CC(=O)[C@@H]2C[C@H]1C2(C)C
InChI Identifier
InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m1/s1
InChI KeyDCSCXTJOXBUFGB-SFYZADRCSA-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
  • Cyclohexenone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point6.5 °CWikipedia
Boiling Point227 to 228 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.3ALOGPS
logP2.24ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)19.84ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.37 m³·mol⁻¹ChemAxon
Polarizability17.37 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-MSVerbenone, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
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
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
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 LinkVerbenone
METLIN IDNot Available
PubChem Compound65724
PDB IDNot Available
ChEBI ID9955
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. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]