Showing Compound Card for perillene (CDB000298)

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Record Information
Version1.0
Created at2020-03-19 00:29:35 UTC
Updated at2020-11-18 16:35:03 UTC
CannabisDB IDCDB000298
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameperillene
DescriptionPerillene, also known as perillen, belongs to the class of organic compounds known as monoterpenes. 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. Perillene also belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Perillene is a neutral, hydrophobic molecule that is insoluble in water. Perillene exists as a clear, colorless oil and has a woody, flowery, citrus aroma or taste. Perillene has been found in several plants and spices including ginger and oregano. It has also been found in the essential oils of other plants, such as Perilla ocimoides (PMID: 17269047 ), Kenyan Valencia (Citrus sinensis), Australian finger lime (Citrus australasica) peel oil, Neroli (Citrus aurantium) (PMID: 30723488 ) and Boswellia sacra (PMID: 18830149 ). Perillene is one of more than 140 monoterpenes that are known in cannabis plants (PMID: 6991645 ), and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(4-Methyl-3-pentenyl)furanChEBI
PerillenChEBI
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
IUPAC Name3-(4-methylpent-3-en-1-yl)furan
Traditional Name3-(4-methylpent-3-en-1-yl)furan
CAS Registry Number539-52-6
SMILES
CC(C)=CCCC1=COC=C1
InChI Identifier
InChI=1S/C10H14O/c1-9(2)4-3-5-10-6-7-11-8-10/h4,6-8H,3,5H2,1-2H3
InChI KeyXNGKCOFXDHYSGR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point186 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.78ALOGPS
logP3.29ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.42 m³·mol⁻¹ChemAxon
Polarizability18.01 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-MSperillene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-9200000000-f0341154e4be5fa2573fSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-6dcea2710a0949e79b782016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-8900000000-f29bf4a3afaf73292dc02016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9100000000-3a6d857807b0f470e15a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-30f53f9dce61f78cbbdc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-3d680fad94f20130b98a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-3900000000-0c611115b7c5f678041f2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0062147
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007821
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPerillene
METLIN IDNot Available
PubChem Compound68316
PDB IDNot Available
ChEBI ID74039
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. Misra LN, Husain A: The Essential Oil of Perilla ocimoides: A Rich Source of Rosefuran. Planta Med. 1987 Aug;53(4):379-80. doi: 10.1055/s-2006-962743. [PubMed:17269047 ]
  3. Dala-Paula BM, Plotto A, Bai J, Manthey JA, Baldwin EA, Ferrarezi RS, Gloria MBA: Effect of Huanglongbing or Greening Disease on Orange Juice Quality, a Review. Front Plant Sci. 2019 Jan 22;9:1976. doi: 10.3389/fpls.2018.01976. eCollection 2018. [PubMed:30723488 ]
  4. Al-Harrasi A, Al-Saidi S: Phytochemical analysis of the essential oil from botanically certified oleogum resin of Boswellia sacra (Omani Luban). Molecules. 2008 Sep 16;13(9):2181-9. doi: 10.3390/molecules13092181. [PubMed:18830149 ]
  5. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]