Structure Database (LMSD)
Common Name
beta-Caryophyllene
Systematic Name
Synonyms
3D model of beta-Caryophyllene
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
β-Caryophyllene is a sesquiterpene that has been found in plants, including C. sativa, C. indica, and hemp, and has diverse biological activities, including lipid metabolic, antioxidant, anti-neuroinflammatory, anti-proliferative, and antinociceptive properties.1,2,3,4,5,6 It is an agonist of the cannabinoid (CB) receptor CB2 (Ki = 155 nM) that inhibits cAMP production induced by forskolin in CHO-K1 cells expressing CB2 receptors (EC50 = 38 nM).7 β-Caryophyllene is also an agonist of peroxisome proliferator-activated receptor α (PPARα; EC50 = 9.58 µM in a reporter assay).2 β-Caryophyllene (1 and 2.5 µM) reduces the production of reactive oxygen species (ROS) in and protects against cytotoxicity of SH-SY5Y cells induced by 1-methyl-4-pheylpyridinium (MPP+).3 It also decreases the β-amyloid burden in the hippocampus and cerebral cortex and improves memory in an APP/PS1 transgenic mouse model of Alzheimer’s disease, decreasing the latency to find the platform in the Morris water maze during training and increasing the time spent in the target quadrant during testing when administered at a dose of 48 mg/kg per day.4 β-Caryophyllene (50 mg/kg) increases the number of entries into and the time spent in the open arms of the elevated plus maze and the time spent immobile in the forced swim test, indicating anxiolytic-like and antidepressant-like activity, effects that can be blocked by the CB2 receptor antagonist AM630 .5
This information has been provided by Cayman Chemical
References
2. Hazekamp, A., Tejkalová, K., and Papadimitriou, S. Cannabis: From cultivar to chemovar II—A metabolomics approach to Cannabis classification. Cannabis Cannabinoid Res. 1(1), 202-215 (2016).
6. Wang, G., Ma, W., and Du, J. β-Caryophyllene (BCP) ameliorates MPP+ induced cytotoxicity. Biomed. Pharmacother. 103, 1086-1091 (2018).
String Representations
InChiKey (Click to copy)
NPNUFJAVOOONJE-GFUGXAQUSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@]12([H])C(C[C@]1([H])C(=C)CCC=C(C)CC2)(C)C
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
15
Rings
2
Aromatic Rings
0
Rotatable Bonds
0
Van der Waals Molecular Volume
238.06
Topological Polar Surface Area
0.00
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
0
logP
4.73
Molar Refractivity
66.74
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Created at
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Updated at
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