Natural Product (NP) Details

General Information of the NP (ID: NP7102)
Name
Elemene
Synonyms
Cyclohexane, 1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, (1R,2R,4S)-rel-; 33880-83-0; beta-Elemene, (-)-; (- )-bete-elemene; EINECS 251-713-0; AC1L1VID; Cyclohexane, 2,4-diisopropenyl-1-methyl-1-vinyl-, (1S,2S,4R)-; OPFTUNCRGUEPRZ-UHFFFAOYSA-N; Cyclohexane, 1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, (1S-(1-alpha,2-beta,4-beta))-; (1alpha,2beta,4beta)-1-Methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane; LS-56795; EN300-296339; 1-Methyl-1-vinyl-2,4-diisopropenylcyclohexane
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Species Origin Pogostemon cablin ...     Click to Show/Hide
Pogostemon cablin
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Pogostemon
Species: Pogostemon cablin
Atractylodes lancea
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Atractylodes
Species: Atractylodes lancea
Abutilon indicum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malvales
Family: Malvaceae
Genus: Abutilon
Species: Abutilon indicum
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Phase 1 [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.679
 
MDCK Permeability
 -4.666
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 0.583
 
PPB
 94.5%
 
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
 10.933
 
T1/2
 0.8
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
6918391
Canonical SMILES
CC(=C)C1CCC(C(C1)C(=C)C)(C)C=C
InChI
1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1
InChIKey
OPFTUNCRGUEPRZ-QLFBSQMISA-N
CAS Number
CAS 33880-83-0
Herb ID
HBIN024973
ETMC ID
991
SymMap ID
SMIT18326
TTD Drug ID
D04VMG
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     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
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP7  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression XIAP  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Up-regulation Cytochrome c release
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 beta-Elemene increases cisplatin chemosensitivity of lung tumor cells by triggering apoptosis.
          Temozolomide      Brain cancer     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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression AKT1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ATM  Molecule Info 
Pathway MAP
Down-regulation Expression ERK1  Molecule Info 
Pathway MAP
Down-regulation Expression H2AFX  Molecule Info 
Pathway MAP
                    In-vitro Model U-87MG ATCC CVCL_0022 Glioblastoma Homo sapiens
T98G CVCL_0556 Glioblastoma Homo sapiens
U-251MG CVCL_0021 Astrocytoma Homo sapiens
LN-229 CVCL_0393 Glioblastoma Homo sapiens
C6 CVCL_0194 Rat malignant glioma Rattus norvegicus
                    Experimental
                    Result(s)		 Beta-elemene enhances both radiosensitivity and chemosensitivity of glioblastoma cells through the inhibition of the ATM signaling pathway.
          Cetuximab      Colorectal cancer     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression CDH1  Molecule Info 
Pathway MAP
Up-regulation Expression CDH1  Molecule Info 
Pathway MAP
Down-regulation Expression CDH2  Molecule Info 
Pathway MAP
Down-regulation Expression GLS2  Molecule Info 
Pathway MAP
Down-regulation Expression GPX4  Molecule Info 
Pathway MAP
Down-regulation Expression HMOX1  Molecule Info 
Pathway MAP
Up-regulation Expression HMOX1  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-9  Molecule Info 
Pathway MAP
Down-regulation Expression SLC40A1  Molecule Info 
Pathway MAP
Down-regulation Expression SLC7A11  Molecule Info 
Pathway MAP
Down-regulation Expression SNAI1  Molecule Info 
Pathway MAP
Down-regulation Expression SNAI2  Molecule Info 
Pathway MAP
Down-regulation Expression TF  Molecule Info 
Pathway MAP
Up-regulation Expression TF  Molecule Info 
Pathway MAP
Down-regulation Expression VIM  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
                    In-vivo Model A volume of 100 ul HCT116-luc cells suspension (2.5*106 cells/ml) was injected subcutaneously into right dorsal flank of mice (5-week-old female BALB/c nude mice).
                    Experimental
                    Result(s)		 Combinative treatment of Beta-elemene and cetuximab is sensitive to KRAS mutant colorectal cancer cells by inducing ferroptosis and inhibiting epithelial-mesenchymal transformation.
          DC/Dribble vaccine      Lung cancer     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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression IFNG  Molecule Info 
Pathway MAP
                    In-vitro Model BNL1MEA.7R.1 Hepatocellular carcinoma Rattus norvegicus
                    Experimental
                    Result(s)		 Beta-elemene combined DC/Dribble vaccine could induce specific immune cells to secrete secretory cells, thus exerting its anti-tumor effect.
          Gefitinib      Lung cancer     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 [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CDH1  Molecule Info 
Pathway MAP
Down-regulation Expression CDH2  Molecule Info 
Pathway MAP
Up-regulation Expression HES1  Molecule Info 
Pathway MAP
Up-regulation Expression MYC  Molecule Info 
Pathway MAP
Up-regulation Expression NOTCH1  Molecule Info 
Pathway MAP
Up-regulation Expression SHH  Molecule Info 
Pathway MAP
Down-regulation Expression SNAI1  Molecule Info 
Pathway MAP
Up-regulation Expression SOX2  Molecule Info 
Pathway MAP
Down-regulation Expression TWIST1  Molecule Info 
Pathway MAP
Down-regulation Expression VIM  Molecule Info 
Pathway MAP
Down-regulation Expression ZEB1  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H1299 CVCL_0060 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Beta-Elemene synergizes with gefitinib to inhibit stem-like phenotypes and progression of lung cancer via down-regulating EZH2.
          TNF-related apoptosis inducing ligand      Lung cancer     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 [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP8  Molecule Info 
Pathway MAP
Up-regulation Expression FADD  Molecule Info 
Pathway MAP
Up-regulation Expression PARP1  Molecule Info 
Pathway MAP
Up-regulation Expression TRAIL-R2  Molecule Info 
Pathway MAP
                    In-vitro Model BGC-823 CVCL_3360 Gastric cancer Homo sapiens
SGC-7901 CVCL_0520 Human gastric cancer Homo sapiens
                    Experimental
                    Result(s)		 Beta-elemene increases the sensitivity of gastric cancer cells to TRAIL by promoting the formation of DISC in lipid rafts.
          Rapamycin      Multiple myeloma     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 [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
                    In-vitro Model FTC-133 CVCL_1219 Thyroid gland follicular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The novel combination of mTOR inhibitor with Beta-elemene synergistically attenuates tumor cell growth in follicular thyroid cancer, which requires additional preclinical validation.
          5-fluorouracil      Solid tumour/cancer     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 [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation c-RAF  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation CYB5R2  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Down-regulation Expression PIK3R1  Molecule Info 
Pathway MAP
                    In-vitro Model BT-549 CVCL_1092 Invasive breast carcinoma Homo sapiens
MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    In-vivo Model MDA-MB-231 cells (5*106 cells in 100 uL of PBS) were subcutaneously injected to the left flank of femal nude mice.
                    Experimental
                    Result(s)		 Beta-Elemene enhances the chemotherapeutic effect of 5-Fluorouracil in triple-negative breast cancer via PI3K/AKT, RAF-MEK-ErK, and NF-KappaB signaling pathways.
          Etoposide      Testicular carcinoma     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 [10]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Synergistic antitumor effect of Beta-elemene and etoposide is mediated via induction of cell apoptosis and cell cycle arrest in non-small cell lung carcinoma cells.
    β. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Oxaliplatin      Colorectal cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [11]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression BECN1  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Up-regulation Expression MAP1LC3A  Molecule Info 
Pathway MAP
Up-regulation Cleavage PAEP  Molecule Info 
Pathway MAP
                    In-vitro Model MHCC97-H CVCL_4972 Adult hepatocellular carcinoma Homo sapiens
HCCLM3 CVCL_6832 Adult hepatocellular carcinoma Homo sapiens
                    In-vivo Model Human HCC cell line MHCC97H were used to estabolish xenograft models in the BALB/c mice.
                    Experimental
                    Result(s)		 Beta-elemene sensitizes hepatocellular carcinoma cells to oxaliplatin by preventing oxaliplatin-induced degradation of copper transporter 1.
References
Reference 1 ClinicalTrials.gov (NCT01679847) Blood Brain Barrier Penetration and Pharmacokinetics of the Elemene in Malignant Patients.. U.S. National Institutes of Health.
Reference 2 beta-Elemene, a novel plant-derived antineoplastic agent, increases cisplatin chemosensitivity of lung tumor cells by triggering apoptosis. Oncol Rep. 2009 Jul;22(1):161-70.
Reference 3 Beta-elemene enhances both radiosensitivity and chemosensitivity of glioblastoma cells through the inhibition of the ATM signaling pathway. Oncol Rep. 2015 Aug;34(2):943-51.
Reference 4 Combinative treatment of beta-elemene and cetuximab is sensitive to KRAS mutant colorectal cancer cells by inducing ferroptosis and inhibiting epithelial-mesenchymal transformation. Theranostics. 2020 Apr 6;10(11):5107-5119.
Reference 5 [Treatment of hepatic cancer in mice by beta-elemene combined DC/Dribble vaccine: an immune mechanism research]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2013 Feb;33(2):214-9.
Reference 6 Beta-Elemene Synergizes With Gefitinib to Inhibit Stem-Like Phenotypes and Progression of Lung Cancer via Down-Regulating EZH2. Front Pharmacol. 2018 Nov 30;9:1413.
Reference 7 Beta-elemene increases the sensitivity of gastric cancer cells to TRAIL by promoting the formation of DISC in lipid rafts. Cell Biol Int. 2018 Sep;42(10):1377-1385.
Reference 8 Combinatorial Antitumor Effect of Rapamycin and Beta-Elemene in Follicular Thyroid Cancer Cells. Biomed Res Int. 2016;2016:6723807.
Reference 9 beta-Elemene Enhances the Chemotherapeutic Effect of 5-Fluorouracil in Triple-Negative Breast Cancer via PI3K/AKT, RAF-MEK-ErK, and NF-kappaB Signaling Pathways. Onco Targets Ther. 2020 Jun 9;13:5207-5222.
Reference 10 Synergistic antitumor effect of Beta-elemene and etoposide is mediated via induction of cell apoptosis and cell cycle arrest in non-small cell lung carcinoma cells. Mol Med Rep. Nov-Dec 2011;4(6):1189-93.
Reference 11 Beta-elemene sensitizes hepatocellular carcinoma cells to oxaliplatin by preventing oxaliplatin-induced degradation of copper transporter 1. Sci Rep. 2016 Feb 12;6:21010.
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