Natural Product (NP) Details

General Information of the NP (ID: NP1313)
Name
Beta caryophyllene
Synonyms
BETA-CARYOPHYLLENE; Caryophyllene; (-)-trans-Caryophyllene; 87-44-5; L-Caryophyllene; (-)-beta-caryophyllene; trans-Caryophyllene; (E)-Caryophyllene; (E)-beta-caryophyllene; b-caryophyllene; trans-beta-caryophyllene; Beta-Caryophylene; (-)-Caryophyllene; .beta.-Caryophyllen; .beta.-Caryophyllene; CHEBI:10357; (E)-beta-caryophylene; .beta.-(E)-Caryophyllene; beta-Caryophyllen; (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene; MFCD00075925; UNII-BHW853AU9H; g-Caryophyllene; (1R,9S,E)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; (1S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undec-5-ene; NSC 11906; E-.beta.-caryophyllene; BHW853AU9H; .beta.-Caryophyllene, (-); Tincturoid; NSC11906; Caryophyllene B; beta-cariofillene; (1R,4E,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene; beta-caryophillene; Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-; Bicyclo[7.2.0]undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-; E-beta-caryophyllene; Caryophyllene, (E); beta-(e)-caryophyllene; beta-trans-caryophyllene; (-)- -caryophyllene; (-)-(E)-Caryophyllene; DSSTox_CID_4739; .beta.-trans-Caryophyllene; trans-.beta.-Caryophyllene; (-)-I(2)-caryophyllene; DSSTox_RID_77517; DSSTox_GSID_24739; 8-Methylene-4,11,11-(trimethyl)bicyclo[7.2.0]undec-4-ene; CHEMBL445740; DTXSID8024739; HY-N1415; ZINC8234282; Tox21_301497; BDBM50529607; s6058; (1R,4E,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; AKOS024283988; trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene; LMPR0103120001; beta-Caryophyllene, >=80%, FCC, FG; CAS-87-44-5; NCGC00142620-01; NCGC00255159-01; ST072181; (-)-trans-Caryophyllene, analytical standard; CS-0016839; V0915; C09629; Q421614; W-109317; UNII-K4H93P747O component NPNUFJAVOOONJE-GFUGXAQUSA-N; (-)-trans-Caryophyllene, >=98.5% (sum of enantiomers, GC); trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; 8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene, (1R,4E,9S)-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R- (1R*,4E,9S*)]-
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Species Origin Syzygium aromaticum ...     Click to Show/Hide
Syzygium aromaticum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Myrtales
Family: Myrtaceae
Genus: Syzygium
Species: Syzygium aromaticum
Disease Pain [ICD-11: MG30-MG3Z] Phase 2 [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.482
 
MDCK Permeability
 -4.821
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 0.467
 
PPB
 95.8%
 
BBB
 - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 +++
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 - -
CYP2C9 substrate
 ++
CYP2D6 inhibitor
 - -
CYP2D6 substrate
 ++
CYP3A4 inhibitor
 - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 -
CYP2B6 substrate
 -
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 13.853
 
T1/2
 1.408
Toxicity
DILI
 -
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 - -
 
Respiratory
 -
 
Human Hepatotoxicity
 -
 
Ototoxicity
 - -
 
Drug-induced Nephrotoxicity
 - -
 
Drug-induced Neurotoxicity
 +
 
Hematotoxicity
 -
 
Genotoxicity
 - - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H24
PubChem CID
5281515
Canonical SMILES
CC1=CCCC(=C)C2CC(C2CC1)(C)C
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
InChIKey
NPNUFJAVOOONJE-GFUGXAQUSA-N
CAS Number
CAS 87-44-5
ChEBI ID
CHEBI:10357
TTD Drug ID
D53QMP
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Imipramine      Depression     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model To establish experimental autoimmune encephalomyelitis (EAE) mice, female C57BL/6 mice were actively immunized using two subcutaneous injections with an emulsion containing myelin MOG35-55 (250 g) and an equal volume of CFA (250 g) into dierent sites of each hind ank.
                    Experimental
                    Result(s)		 They reduced the clinical and pathological defects in EAE mice through modulation of both local (microglia) and systemic (lymphocytes and blood) immunity from inflammatory (Th1/Th17/M1) towards anti-inflammatory (Th2/Treg/M2) phenotypes.
Target and Pathway
Target(s) Cannabinoid receptor 2 (CB2)  Molecule Info  [3]
Pyruvate kinase PKM  Molecule Info  [3]
KEGG Pathway Neuroactive ligand-receptor interaction Click to Show/Hide
Reactome Class A/1 (Rhodopsin-like receptors) Click to Show/Hide
2 G alpha (i) signalling events
WikiPathways GPCRs, Class A Rhodopsin-like Click to Show/Hide
2 Small Ligand GPCRs
3 GPCR ligand binding
4 GPCR downstream signaling
References
Reference 1 ClinicalTrials.gov (NCT04794205) Acute Changes In Thermal Pain Response Following Single Oral Dose of Beta-Cary (BCP-Pain). U.S. National Institutes of Health.
Reference 2 Combination of Imipramine, a sphingomyelinase inhibitor, and Beta-caryophyllene improve their therapeutic effects on experimental autoimmune encephalomyelitis (EAE). Int Immunopharmacol. 2019 Dec;77:105923.
Reference 3 The cannabinoid CB1 receptor-selective phytocannabinoid beta-caryophyllene exerts analgesic effects in mouse models of inflammatory and neuropathic pain. Eur Neuropsychopharmacol. 2014 Apr;24(4):608-20.
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