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]
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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: CHEBI:10357
CAS Number: 87-44-5
TTD ID: D53QMP

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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Acetyl-CoA carboxylase 1 (ACACA)	OT5CQPZY	ACACA_HUMAN	Post-Translational Modifications	[3]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[4]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[4]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[4]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[5]
Fatty acid synthase (FASN)	OTFII9KG	FAS_HUMAN	Gene/Protein Processing	[3]
G1/S-specific cyclin-D1 (CCND1)	OT8HPTKJ	CCND1_HUMAN	Gene/Protein Processing	[4]
Interleukin-6 (IL6)	OTUOSCCU	IL6_HUMAN	Gene/Protein Processing	[4]
Patatin-like phospholipase domain-containing protein 2 (PNPLA2)	OTR3ERMR	PLPL2_HUMAN	Gene/Protein Processing	[3]
Prostaglandin G/H synthase 2 (PTGS2)	OT75U9M4	PGH2_HUMAN	Gene/Protein Processing	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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.
5	The inhibitory effects of beta-caryophyllene, beta-caryophyllene oxide and alpha-humulene on the activities of the main drug-metabolizing enzymes in rat and human liver in vitro. Chem Biol Interact. 2017 Dec 25;278:123-128.