Showing Compound Card for alpha-Humulene epoxide II (CDB000315)

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Record Information
Version1.0
Created at2020-03-19 00:30:30 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000315
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Humulene epoxide II
DescriptionHumulene epoxide II or humulene oxide II is an oxidized or epoxide form of alpha-humulene. Humulene is found in the flowering cone of the hops plant, Humulus lupulus, from which it derives its name as well as in the flowers of related plants such as cannabis. The concentration of humulene varies among different varieties of hops and cannabis but can be up to 40% of the essential oil. Humulene epoxide II belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms (one oxygen and two carbon atoms). Humulene epoxide II is also biochemically classified as a terpenoid or a monocyclic sesquiterpene (C15H24), which includes an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds. Humulene epoxide II exists as a clear, colorless liquid and essentially insoluble in water. Humulene epoxide II is found naturally in a number of plants and foods including allspice, hops, ginger, rosemary, and sage. Multiple epoxides of humulene (such as humulene epoxide I and humulene epoxide II) are produced in the brewing process of beer or in the extraction of cannabis oils. Humulene epoxide II is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645 ). Humulene epoxide II and other caryophyllene sesquiterpeines exhibit larvacidal activities against mosquito larvae (PMID: 20724962 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC15H24O
Average Molecular Weight220.36
Monoisotopic Molecular Weight220.1827
IUPAC Name(1R,3Z,7Z,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene
Traditional Name(1R,3Z,7Z,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene
CAS Registry NumberNot Available
SMILES
C\C1=C\CC(C)(C)\C=C/C[C@@]2(C)O[C@@H]2CC1
InChI Identifier
InChI=1S/C15H24O/c1-12-6-7-13-15(4,16-13)10-5-9-14(2,3)11-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5-,12-8-/t13-,15-/m1/s1
InChI KeyQTGAEXCCAPTGLB-SGRRRNBRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassEpoxides
Sub ClassNot Available
Direct ParentEpoxides
Alternative Parents
Substituents
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP5.03ALOGPS
logP3.98ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.31 m³·mol⁻¹ChemAxon
Polarizability26.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
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 Compound92476330
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. Magalhaes LA, Lima Mda P, Marques MO, Facanali R, Pinto AC, Tadei WP: Chemical composition and larvicidal activity against Aedes aegypti larvae of essential oils from four Guarea species. Molecules. 2010 Aug 19;15(8):5734-41. doi: 10.3390/molecules15085734. [PubMed:20724962 ]