Structure Database (LMSD)
Common Name
Humulene
Systematic Name
Tetramethylcycloundeca-1E,4E,8E-triene
Synonyms
- alpha-caryophyllene
3D model of Humulene
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
α-Humulene is a sesquiterpene that has been found in C. sativa, C. indica, and hemp with diverse biological activities.1,2,3,4,5 It is lethal to A. subpictus, A. albopictus, and C. tritaeniorhynchus mosquito larvae (LC50s = 6.19, 7.39, and 12.05 mg/ml, respectively).2 α-Humulene reduces growth of MCF-7 breast cancer cells by approximately 50% when used at a concentration of 32 mg/ml.3 It also reduces viability of Caco-2 cells in a concentration-dependent manner (IC50 = 24.4 mg/ml) but has no effect on viability of rat hepatocytes.4 In vivo, α-humulene (50 mg/kg) reduces histamine-induced paw edema in mice as well as carrageenan-induced TNF-α and IL-1β production and paw edema in mice and rats.5 It also reduces carrageenan-induced production of prostaglandin E2 (PGE2) and expression of inducible nitric oxide synthase (iNOS) and COX-2 in rats.
This information has been provided by Cayman Chemical
References
1. Govindarajan, M., and Benelli, G. α-Humulene and β-elemene from Syzygium zeylanicum (Myrtaceae) essential oil: highly effective and eco-friendly larvicides against Anopheles subpictus, Aedes albopictus, and Culex tritaeniorhynchus (Diptera: Culicidae). Parasitol. Res. 115(7), 2771-2778 (2016).
4. Fernandes, E.S., Passos, G.F., Medeiros, R., et al. Anti-inflammatory effects of compounds α-humulene and (−)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea. Eur. J. Pharmacol. 569(3), 228-236 (2007).
5. 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).
String Representations
InChiKey (Click to copy)
FAMPSKZZVDUYOS-HRGUGZIWSA-N
InChi (Click to copy)
InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6+,13-7+,14-10+
SMILES (Click to copy)
C1C(C)(C)CC=C(C)CCC=C(C)CC=1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
15
Rings
1
Aromatic Rings
0
Rotatable Bonds
0
Van der Waals Molecular Volume
247.78
Topological Polar Surface Area
0.00
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
0
logP
5.04
Molar Refractivity
68.90
Admin
Created at
-
Updated at
19th Dec 2023