Details of the Drug

General Information of Drug (ID: DM7583A)

Drug 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*)]-
Indication
Disease Entry ICD 11 Status REF
Pain MG30-MG3Z Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 204.35
Logarithm of the Partition Coefficient (xlogp) 4.4
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 0
Chemical Identifiers
Formula
C15H24
IUPAC Name
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Canonical SMILES
C/C/1=C\\CCC(=C)[C@H]2CC([C@@H]2CC1)(C)C
InChI
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
Cross-matching ID
PubChem CID
5281515
ChEBI ID
CHEMBL10357
CAS Number
87-44-5
UNII
NRY8I0KNIR
DrugBank ID
DB16854
TTD ID
D53QMP
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cannabinoid receptor 2 (CB2) TTMSFAW CNR2_HUMAN Agonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Acetyl-CoA carboxylase 1 (ACACA) OT5CQPZY ACACA_HUMAN Post-Translational Modifications [3]
Patatin-like phospholipase domain-containing protein 2 (PNPLA2) OTR3ERMR PLPL2_HUMAN Gene/Protein Processing [3]
Transcription factor p65 (RELA) OTUJP9CN TF65_HUMAN Gene/Protein Processing [4]
Tyrosine-protein kinase JAK1 (JAK1) OT0X3D17 JAK1_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Pain
ICD Disease Classification MG30-MG3Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cannabinoid receptor 2 (CB2) DTT CNR2 3.82E-02 -0.43 -1.18
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

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.
2 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.
3 -Caryophyllene attenuates palmitate-induced lipid accumulation through AMPK signaling by activating CB2 receptor in human HepG2 hepatocytes. Mol Nutr Food Res. 2016 Oct;60(10):2228-2242. doi: 10.1002/mnfr.201600197. Epub 2016 Jun 16.
4 JAK1/STAT3 regulatory effect of -caryophyllene on MG-63 osteosarcoma cells via ROS-induced apoptotic mitochondrial pathway by DNA fragmentation. J Biochem Mol Toxicol. 2020 Aug;34(8):e22514. doi: 10.1002/jbt.22514. Epub 2020 May 2.