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(E)-beta-caryophyllene, beta-caryophyllene, caryophyllene, caryophyllene, (R*,4Z,9S*)-(+-)-isomer, caryophyllene, (R-(R*,4E,9S))-isomer, caryophyllene, (R-(R*,4Z,9S*))-isomer, caryophyllene, (S-(R*,4E,9S*))-isomer, caryophyllene, (S-(R*,4Z,9S*))-isomer, isocaryophyllene, trans-caryophyllene

No.	Title	Href
1	Beta-Caryophyllene Enhances the Anti-Tumor Activity of Cisplatin in Lung Cancer Cell Lines through Regulating Cell Cycle and Apoptosis Signaling Molecules. Molecules. 2022 Nov 30;27(23):8354. doi: 10.3390/molecules27238354.	`Click`
2	Modulation of STAT3 Signaling, Cell Redox Defenses and Cell Cycle Checkpoints by β-Caryophyllene in Cholangiocarcinoma Cells: Possible Mechanisms Accounting for Doxorubicin Chemosensitization and Chemoprevention. Cells. 2020 Apr 2;9(4):858. doi: 10.3390/cells9040858.	`Click`

No.

Title

Href

Beta-Caryophyllene Enhances the Anti-Tumor Activity of Cisplatin in Lung Cancer Cell Lines through Regulating Cell Cycle and Apoptosis Signaling Molecules. Molecules. 2022 Nov 30;27(23):8354. doi: 10.3390/molecules27238354.

Click

Modulation of STAT3 Signaling, Cell Redox Defenses and Cell Cycle Checkpoints by β-Caryophyllene in Cholangiocarcinoma Cells: Possible Mechanisms Accounting for Doxorubicin Chemosensitization and Chemoprevention. Cells. 2020 Apr 2;9(4):858. doi: 10.3390/cells9040858.

Click

Name	Beta-Caryophyllene
PubChem CID	5281515
Molecular Weight	204.35g/mol
Synonyms	(E)-beta-caryophyllene, beta-caryophyllene, caryophyllene, caryophyllene, (R,4Z,9S)-(+-)-isomer, caryophyllene, (R-(R,4E,9S))-isomer, caryophyllene, (R-(R,4Z,9S))-isomer, caryophyllene, (S-(R,4E,9S))-isomer, caryophyllene, (S-(R,4Z,9S*))-isomer, isocaryophyllene, trans-caryophyllene
Formula	C₁₅H₂₄
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	87-44-5
ChEMBL ID	CHEMBL445740
ChEBI ID	CHEBI:10357
Drug Bank ID	DB16854
KEGG ID	C09629
Toxicity	Organism	Test Type	Route(Dose)
	rat	LD50	intraperitoneal(165 mg/kg)
	mouse	LD50	intraperitoneal(254 mg/kg)
	rat	LD50	oral(322 mg/kg)
Structure			Download 2D MOL 3D MOL

Chineses Pinyin	PiJiuHua
Use Part	Female-flower
Habitat	HeiLongJiang, JiLin, LiaoNing, BeiJing, TianJin, HeBei, ShanXi, NeiMengGu, ShanDong
Flavor	Bitter
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Rosales 　　　　-->Family: Cannabaceae 　　　　　-->Genus: Humulus 　　　　　　-->Species: Humulus lupulus

Pair Name	Beta-Caryophyllene, Cisplatin
Partner Name	Cisplatin
Disease Info	[ICD-11: 2C25]	Lung cancer		Investigative
Biological Phenomena	Inhibition-->Epithelial-mesenchymal transition
Gene Regulation	Down-regulation	Expression	BCL2	hsa596
	Up-regulation	Expression	CDH1	hsa999
	Down-regulation	Expression	ZEB2	hsa9839
In Vitro Model	A-549	Lung adenocarcinoma	Homo sapiens (Human)	CVCL_0023
Result	These data indicate that BCP enhances CDDP chemotherapeutic function through regulating the cell cycle, the apoptosis and EMT signaling molecules.

Pair Name	Beta-Caryophyllene, Doxorubicin
Partner Name	Doxorubicin
Disease Info	[ICD-11: 2C17]	Hepatocellular carcinoma		Investigative
Biological Phenomena	Induction-->Blockade of cell cycle in G2/M phase
Gene Regulation	Down-regulation	Phosphorylation	H2AX	hsa3014
Gene Regulation	Down-regulation	Phosphorylation	STAT3	hsa6774
In Vitro Model	Mz-ChA-1	Gallbladder carcinoma	Homo sapiens (Human)	CVCL_6932
Result	This evidence highlighted a possible role of STAT3 as a final effector of a complex network regulated by β-caryophyllene, which leads to an enhanced doxorubicin-sensitivity of cholangiocarcinoma cells and a lowered chemotherapy toxicity in nonmalignant cholangiocytes, thus strengthening the interest for this natural sesquiterpene as a dual-acting chemosensitizing and chemopreventive agent.