Showing Compound Card for gamma-Caryophyllene (CDB000711)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:52:31 UTC
Updated at2020-12-07 19:07:42 UTC
CannabisDB IDCDB000711
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namegamma-Caryophyllene
DescriptionIso-caryophyllene also called cis-beta-caryophyllene (E-BCP) is a cis-double-bond isomer of trans-beta-caryophyllene. Caryophyllene has three isomers, cis-beta-caryophyllene, trans-beta-caryophyllene and alpha-caryophyllene (also called alpha humulene). All three isomers are found together in plants. Iso-caryophyllene belongs to the class of organic compounds known as sesquiterpenoids. It is formally classified as a polycyclic hydrocarbon although it is biochemically a bicyclic sesquiterpenoid as it is synthesized via multiple isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Thus, isocaryophyllene is considered to be an isoprenoid lipid molecule. Iso-caryophyllene is a neutral, hydrophobic molecule, that is practically insoluble in water. It has a woody, spicy odor and can be used as a perfuming agent and a food additive (PMID: 27696789 ). Iso-caryophyllene is a naturally occurring sesquiterpenoid found in allspice, anise, basil, cinnamon, lime, black pepper, sage, spearmint, cloves, rosemary and hops and is widespread in plants (Jasminum, Origanum, and Pimpinella species). It is also one of more than 140 terpenoids that are found in cannabis plants (PMID:6991645 ) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. Iso-caryophyllene is also called a phytocannabinoid and is able to bind to the CB2 (cannabinoid) receptor (PMID: 27696789 ). Binding to CB2 results in the activation of Gαi/o protein, which leads to decline of cAMP production and in consequence inhibition of adenylyl cyclase. In addition, ligand‐coupled CB2 activate Gγβ proteins and stimulate both mitogen‐activated protein kinase (MAPK) and phosphoinositide 3‐kinase (PI3K) signaling pathways (PMID: 27696789 ). Iso-caryophyllene is thought to possess anti-cancer and anti-angiogenic activities through induction of apoptosis (2) repression of cell cycle, and (3) inhibition of angiogenesis and metastasis (PMID: 27696789 )
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Gamma-CaryophylleneHMDB
g-CaryophylleneHMDB
Γ-caryophylleneHMDB
Caryophyllene, (r*,4Z,9S*)-(+-)-isomerHMDB
CaryophylleneHMDB
Caryophyllene, (R-(r*,4E,9S))-isomerHMDB
Caryophyllene, (R-(r*,4Z,9S*))-isomerHMDB
Caryophyllene, (S-(r*,4E,9S*))-isomerHMDB
Caryophyllene, (S-(r*,4Z,9S*))-isomerHMDB
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Traditional Nameisocaryophyllene
CAS Registry Number118-65-0
SMILES
C\C1=C\CCC(=C)[C@H]2CC(C)(C)[C@@H]2CC1
InChI Identifier
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m1/s1
InChI KeyNPNUFJAVOOONJE-FLFDDASRSA-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
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.35ALOGPS
logP4.52ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.45 m³·mol⁻¹ChemAxon
Polarizability26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSiso-caryophyllene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-2900000000-666e65f6b538d4a0eeeaSpectrum
Predicted GC-MSiso-caryophyllene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-de2a6b536bb38d3c29512017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3950000000-6dc317c917393691dfef2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-6900000000-5f5ee8e9f24e0511e1862017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d6c31402204fa765cbc02017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-48307d26c19d0c84ce742017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2900000000-741197d2390e8d4bc1042017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-18da8cef0774773a46642021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-7930000000-0de14671750170215e532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9400000000-c0fc2f9446fefc8829182021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0980000000-9f708eefb54c5860f0032021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0061779
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00012474
Chemspider IDNot Available
KEGG Compound IDC09691
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281522
PDB IDNot Available
ChEBI ID5993
References
General References
  1. Pavlovic R, Nenna G, Calvi L, Panseri S, Borgonovo G, Giupponi L, Cannazza G, Giorgi A: Quality Traits of "Cannabidiol Oils": Cannabinoids Content, Terpene Fingerprint and Oxidation Stability of European Commercially Available Preparations. Molecules. 2018 May 20;23(5). pii: molecules23051230. doi: 10.3390/molecules23051230. [PubMed:29783790 ]
  2. Nissen L, Zatta A, Stefanini I, Grandi S, Sgorbati B, Biavati B, Monti A: Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.). Fitoterapia. 2010 Jul;81(5):413-9. doi: 10.1016/j.fitote.2009.11.010. Epub 2009 Dec 4. [PubMed:19969046 ]
  3. Hernandez T, Canales M, Avila JG, Garcia AM, Martinez A, Caballero J, de Vivar AR, Lira R: Composition and antibacterial activity of essential oil of Lantana achyranthifolia Desf. (Verbenaceae). J Ethnopharmacol. 2005 Jan 15;96(3):551-4. doi: 10.1016/j.jep.2004.09.044. [PubMed:15619577 ]
  4. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  5. Jirovetz L, Buchbauer G, Ngassoum MB, Geissler M: Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry. J Chromatogr A. 2002 Nov 8;976(1-2):265-75. doi: 10.1016/s0021-9673(02)00376-x. [PubMed:12462618 ]
  6. Fidyt K, Fiedorowicz A, Strzadala L, Szumny A: beta-caryophyllene and beta-caryophyllene oxide-natural compounds of anticancer and analgesic properties. Cancer Med. 2016 Oct;5(10):3007-3017. doi: 10.1002/cam4.816. Epub 2016 Sep 30. [PubMed:27696789 ]
  7. 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 ]