Showing Compound Card for (1R,4R,6R,10S)-4,12,12-Trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane (CDB000214)

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Record Information
Version1.0
Created at2020-03-19 00:24:54 UTC
Updated at2020-11-18 16:34:55 UTC
CannabisDB IDCDB000214
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(1R,4R,6R,10S)-4,12,12-Trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane
DescriptionCaryophyllene oxide belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Caryophyllene oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Caryophyllene oxide is a naturally occurring sesquiterpenederived from Cryophyllene. Caryophyllene oxide is one of the many sesquiterpenes found in cannabis plants and their essential oils (PMID: 6991645 ). Caryophyllene oxide is one of the major compounds found in the essential oil of Salvia spinosa (63.0%). Salvia spinosa essential oil exhibites antimicrobial, cytotoxicity, antioxidant and enzyme inhibitory activities ( Ref:DOI ). Caryophyllene oxide is a volatile compound found in different species of citrus fruits ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Caryophyllene oxideKegg
beta-Caryophyllene oxideMeSH
(-)-Caryophyllene oxidePhytoBank
(-)-EpoxydihydrocaryophyllenePhytoBank
(-)-beta-Caryophyllene epoxidePhytoBank
(-)-β-Caryophyllene epoxidePhytoBank
(-)-beta-Caryophyllene oxidePhytoBank
(-)-β-Caryophyllene oxidePhytoBank
4beta,5alpha-EpoxycaryophyllenePhytoBank
4β,5α-EpoxycaryophyllenePhytoBank
6,7-Epoxy-3(15)-caryophyllenePhytoBank
Caryophyllene 4beta,5alpha-epoxidePhytoBank
Caryophyllene 4β,5α-epoxidePhytoBank
Caryophyllene 4beta,5alpha-oxidePhytoBank
Caryophyllene 4β,5α-oxidePhytoBank
Caryophyllene epoxidePhytoBank
trans-Caryophyllene oxidePhytoBank
beta-Caryophyllene epoxidePhytoBank
β-Caryophyllene epoxidePhytoBank
β-Caryophyllene oxidePhytoBank
beta-Caryophyllene-4beta,5alpha-epoxidePhytoBank
beta-Caryophyllene-4β,5α-epoxidePhytoBank
4,5-Caryophyllene oxidePhytoBank
Chemical FormulaC15H24O
Average Molecular Weight220.36
Monoisotopic Molecular Weight220.1827
IUPAC Name(1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane
Traditional Name(1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane
CAS Registry Number1139-30-6
SMILES
C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2
InChI Identifier
InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1
InChI KeyNVEQFIOZRFFVFW-RGCMKSIDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Caryophyllane sesquiterpenoid
  • Sesquiterpenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
logP3.49ALOGPS
logP3.62ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.21 m³·mol⁻¹ChemAxon
Polarizability26.46 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(1R,4R,6R,10S)-4,12,12-Trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane, non-derivatized, GC-MS Spectrumsplash10-0006-9400000000-9a6b09068a36c82b5822Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00di-2960000000-f7b70b824dbbcfd560372020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-00di-2980000000-dfb6aa501357ff0a0d2b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0kmj-2960000000-160a69cddcceaa4f52c82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0kmj-2950000000-b35d30d4ea970d78410f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0kmj-2950000000-8a87c5152ed2a1ae890d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0kmj-2950000000-d39a843309535799a68c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0kmj-2930000000-574c59f35ddc3bb790eb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0ac1-3910000000-5c2c3565194d3ef7629c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0a5a-4900000000-51f25d5e18143f5e46642020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-0apj-8900000000-fa5ed581ae81aec72a032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0apm-9500000000-8e940a7f31be832a21032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-0aru-9300000000-595cf97ba69a57bc50732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-0ar3-9300000000-9790832083f9a9c3e2b42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-0ar3-9300000000-2700b60615166735a19e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0udi-1940000000-676e73fe8994c6653dab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0aor-0900000000-0cde17272d4e4c32edff2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-014i-0900000000-6cc959b269a7742e56e82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-0006-9000000000-3ff4ad7c215580405f3d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, positivesplash10-052b-1900000000-c435c9aaea08d1f7fc722020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-f8f0be1391f197a799e12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2490000000-b170ea814d2dfe6a38942016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9400000000-360184833a6200ab035e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-0c846f045345079a830d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1190000000-c8390951524f03b712692016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdi-8930000000-6906b65254e00eb839852016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00012483
Chemspider IDNot Available
KEGG Compound IDC16908
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1742210
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 ]