Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DM7583A)

Drug Name
Beta-caryophyllene Drug Info
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]
Cross-matching ID
PubChem CID
5281515
ChEBI ID
CHEMBL10357
CAS Number
CAS 87-44-5
TTD Drug ID
DM7583A

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Cannabinoid receptor 2 (CB2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Guanfacine extended release DMB1CZ8 Attention deficit hyperactivity disorder 6A05.Z Approved [5]
NABILONE DMVRYT2 Insomnia 7A00-7A0Z Approved [6]
GW-42004 DMY3KSU Lipid metabolism disorder 5C52.Z Phase 2 [7]
KHK-6188 DMF6CTI Neuropathic pain 8E43.0 Phase 2 [8]
LY-2828360 DMO8IEZ Pain MG30-MG3Z Phase 2 [8]
APD371 DM3XT5V Crohn disease DD70 Phase 2 [9]
S-777469 DMZGNOJ Atopic dermatitis EA80 Phase 2 [10]
842166X DMOV0AP Pain MG30-MG3Z Phase 2 [11]
Vicasinabin DMF16CU Diabetic retinopathy 9B71.0 Phase 2 [12]
Tedalinab DM58J7E Pain MG30-MG3Z Phase 1 [13]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Tyrosine-protein kinase JAK1 (JAK1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [14]
Quercetin DM3NC4M Obesity 5B81 Approved [15]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [16]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [17]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [18]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [19]
Tofacitinib DMBS370 Rheumatoid arthritis FA20 Approved [20]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [21]
Clozapine DMFC71L Schizophrenia 6A20 Approved [22]
Zoledronate DMIXC7G Adenocarcinoma 2D40 Approved [23]
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Drug(s) Affected By Transcription factor p65 (RELA)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [24]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [25]
Selenium DM25CGV N. A. N. A. Approved [26]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [27]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [28]
Deoxycholic acid DM3GYAL Subcutaneous fat disorder EF02 Approved [29]
Quercetin DM3NC4M Obesity 5B81 Approved [15]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [30]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [16]
Glucosamine DM4ZLFD Osteoarthritis FA00-FA05 Approved [31]
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Drug(s) Affected By Acetyl-CoA carboxylase 1 (ACACA)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [32]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [33]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [34]
Quercetin DM3NC4M Obesity 5B81 Approved [35]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [36]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [37]
Crizotinib DM4F29C Non-small-cell lung cancer 2C25.Y Approved [38]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [39]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [17]
Glucosamine DM4ZLFD Osteoarthritis FA00-FA05 Approved [40]
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Drug(s) Affected By Patatin-like phospholipase domain-containing protein 2 (PNPLA2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [21]
Hydrocortisone DMGEMB7 Acne vulgaris ED80 Approved [41]
Dexamethasone DMMWZET Acute adrenal insufficiency Approved [42]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [43]
Urethane DM7NSI0 N. A. N. A. Phase 4 [44]
GSK2110183 DMZHB37 leukaemia 2A60-2B33 Phase 2 [45]
(+)-JQ1 DM1CZSJ Testicular cancer 2C80 Phase 1 [46]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [47]
bisphenol A DM2ZLD7 Discovery agent N.A. Investigative [48]
D-glucose DMMG2TO Discovery agent N.A. Investigative [49]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas
Download the Complete Interaction Atlas for Visualization in Cytoscape

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]

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 Posttraining activation of CB1 cannabinoid receptors in the CA1 region of the dorsal hippocampus impairs object recognition long-term memory. Neurobiol Learn Mem. 2008 Sep;90(2):374-81.
6 Novel 1',1'-chain substituted hexahydrocannabinols: 9-hydroxy-3-(1-hexyl-cyclobut-1-yl)-hexahydrocannabinol (AM2389) a highly potent cannabinoid r... J Med Chem. 2010 Oct 14;53(19):6996-7010.
7 Company report (Gwpharm)
8 Recent Development of CB2 Selective and Peripheral CB1/CB2 Cannabinoid Receptor Ligands. Current Medicinal Chemistry . 10/2013; 21(2).
9 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
10 Emerging drugs for atopic dermatitis. Expert Opin Emerg Drugs. 2009 Mar;14(1):165-79.
11 The agonist binding mechanism of human CB2 receptor studied by molecular dynamics simulation, free energy calculation and 3D-QSAR studies. Yao Xue Xue Bao. 2013 Sep;48(9):1436-49.
12 Clinical pipeline report, company report or official report of Roche
13 Cannabinoid CB2 receptor (CNR2). SciBX 3(46); doi:10.1038/scibx.2010.1384. Dec. 2 2010
14 Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802.
15 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
16 Differential modulation of PI3-kinase/Akt pathway during all-trans retinoic acid- and Am80-induced HL-60 cell differentiation revealed by DNA microarray analysis. Biochem Pharmacol. 2004 Dec 1;68(11):2177-86.
17 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
18 Arsenic trioxide induces differentiation of cancer stem cells in hepatocellular carcinoma through inhibition of LIF/JAK1/STAT3 and NF-kB signaling pathways synergistically. Clin Transl Med. 2021 Feb;11(2):e335. doi: 10.1002/ctm2.335.
19 Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
20 JAK inhibitors: treatment efficacy and safety profile in patients with psoriasis. J Immunol Res. 2014;2014:283617. doi: 10.1155/2014/283617. Epub 2014 May 5.
21 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
22 Toxicoproteomics reveals an effect of clozapine on autophagy in human liver spheroids. Toxicol Mech Methods. 2023 Jun;33(5):401-410. doi: 10.1080/15376516.2022.2156005. Epub 2022 Dec 19.
23 Interleukin-19 as a translational indicator of renal injury. Arch Toxicol. 2015 Jan;89(1):101-6.
24 Cannabidiol Modulates the Immunophenotype and Inhibits the Activation of the Inflammasome in Human Gingival Mesenchymal Stem Cells. Front Physiol. 2016 Nov 24;7:559. doi: 10.3389/fphys.2016.00559. eCollection 2016.
25 -Carotene Induces Apoptosis in Human Esophageal Squamous Cell Carcinoma Cell Lines via the Cav-1/AKT/NF-B Signaling Pathway. J Biochem Mol Toxicol. 2016 Mar;30(3):148-57. doi: 10.1002/jbt.21773. Epub 2016 Jan 6.
26 Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
27 Differential gene expression of sulindac-treated human breast epithelial cells. Int J Oncol. 2005 Dec;27(6):1727-36.
28 Suppression of RAGE as a basis of simvastatin-dependent plaque stabilization in type 2 diabetes. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2716-23.
29 Prevention of deoxycholate-induced gastric apoptosis by aspirin: roles of NF-kappaB and PKC signaling. J Surg Res. 2008 Mar;145(1):66-73. doi: 10.1016/j.jss.2007.04.039. Epub 2007 Jul 20.
30 Peroxisome proliferator-activated receptor-gamma agonists inhibit respiratory syncytial virus-induced expression of intercellular adhesion molecule-1 in human lung epithelial cells. Immunology. 2007 May;121(1):71-81. doi: 10.1111/j.1365-2567.2006.02539.x.
31 Glucosamine regulation of LPS-mediated inflammation in human bronchial epithelial cells. Eur J Pharmacol. 2010 Jun 10;635(1-3):219-26. doi: 10.1016/j.ejphar.2010.02.044. Epub 2010 Mar 20.
32 Antidepressant drug sertraline modulates AMPK-MTOR signaling-mediated autophagy via targeting mitochondrial VDAC1 protein. Autophagy. 2021 Oct;17(10):2783-2799. doi: 10.1080/15548627.2020.1841953. Epub 2020 Nov 9.
33 Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses. PLoS One. 2010 Dec 17;5(12):e14352. doi: 10.1371/journal.pone.0014352.
34 Drug-induced hepatic steatosis in absence of severe mitochondrial dysfunction in HepaRG cells: proof of multiple mechanism-based toxicity. Cell Biol Toxicol. 2021 Apr;37(2):151-175. doi: 10.1007/s10565-020-09537-1. Epub 2020 Jun 14.
35 Multifaceted preventive effects of single agent quercetin on a human prostate adenocarcinoma cell line (PC-3): implications for nutritional transcriptomics and multi-target therapy. Med Oncol. 2011 Dec;28(4):1395-404. doi: 10.1007/s12032-010-9603-3. Epub 2010 Jul 2.
36 Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicol In Vitro. 2017 Mar;39:93-103.
37 Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
38 Multi-parameter in vitro toxicity testing of crizotinib, sunitinib, erlotinib, and nilotinib in human cardiomyocytes. Toxicol Appl Pharmacol. 2013 Oct 1;272(1):245-55.
39 Adipocyte differentiation, mitochondrial gene expression and fat distribution: differences between zidovudine and tenofovir after 6 months. Antivir Ther. 2009;14(8):1089-100. doi: 10.3851/IMP1457.
40 Comparative effects of fructose and glucose on lipogenic gene expression and intermediary metabolism in HepG2 liver cells. PLoS One. 2011;6(11):e26583. doi: 10.1371/journal.pone.0026583. Epub 2011 Nov 11.
41 Prenatal caffeine exposure increases the susceptibility to non-alcoholic fatty liver disease in female offspring rats via activation of GR-C/EBP-SIRT1 pathway. Toxicology. 2019 Apr 1;417:23-34. doi: 10.1016/j.tox.2019.02.008. Epub 2019 Feb 15.
42 Identification of mechanisms of action of bisphenol a-induced human preadipocyte differentiation by transcriptional profiling. Obesity (Silver Spring). 2014 Nov;22(11):2333-43.
43 Identification of novel low-dose bisphenol a targets in human foreskin fibroblast cells derived from hypospadias patients. PLoS One. 2012;7(5):e36711. doi: 10.1371/journal.pone.0036711. Epub 2012 May 4.
44 Ethyl carbamate induces cell death through its effects on multiple metabolic pathways. Chem Biol Interact. 2017 Nov 1;277:21-32.
45 Novel ATP-competitive Akt inhibitor afuresertib suppresses the proliferation of malignant pleural mesothelioma cells. Cancer Med. 2017 Nov;6(11):2646-2659. doi: 10.1002/cam4.1179. Epub 2017 Sep 27.
46 Inhibition of BRD4 attenuates tumor cell self-renewal and suppresses stem cell signaling in MYC driven medulloblastoma. Oncotarget. 2014 May 15;5(9):2355-71.
47 Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
48 Alternatives for the worse: Molecular insights into adverse effects of bisphenol a and substitutes during human adipocyte differentiation. Environ Int. 2021 Nov;156:106730. doi: 10.1016/j.envint.2021.106730. Epub 2021 Jun 27.
49 Calorie restriction-induced changes in the secretome of human adipocytes, comparison with resveratrol-induced secretome effects. Biochim Biophys Acta. 2014 Sep;1844(9):1511-22. doi: 10.1016/j.bbapap.2014.04.023. Epub 2014 May 5.