Eugenol, Phenol, 2-methoxy-4-(2-propenyl)-
| Name | Eugenol | ||
| PubChem CID | 3314 | ||
| Molecular Weight | 164.20g/mol | ||
| Synonyms |
Eugenol, Phenol, 2-methoxy-4-(2-propenyl)- |
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| Formula | C₁₀H₁₂O₂ | ||
| SMILES | COC1=C(C=CC(=C1)CC=C)O | ||
| InChI | 1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 | ||
| InChIKey | RRAFCDWBNXTKKO-UHFFFAOYSA-N | ||
| CAS Number | 97-53-0 | ||
| ChEMBL ID | CHEMBL42710 | ||
| ChEBI ID | CHEBI:4917 | ||
| Herb ID | HBIN026067 | ||
| Drug Bank ID | DB09086 | ||
| KEGG ID | C10453 | ||
| 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 | 
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Download
2D
MOL
3D
MOL
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| Chineses Pinyin | DingXiang | ||
| Use Part | Flower bud | ||
| Habitat | GuangDong, HaiNan | ||
| Flavor | Pungent | ||
| Meridian Tropism | Spleen; Stomach; Lung; Kidney | ||
| Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Myrtales
-->Family: Myrtaceae
-->Genus: Syzygium
-->Species: Syzygium aromaticum
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| Pair Name | Eugenol, Cisplatin | |||
| Partner Name | Cisplatin | |||
| Disease Info | [ICD-11: 2C77] | Cervical cancer | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Up-regulation | Expression | BAX | hsa581 |
| Down-regulation | Expression | BCL2 | hsa596 | |
| Up-regulation | Activity | CASP3 | hsa836 | |
| Up-regulation | Expression | CASP9 | hsa842 | |
| Up-regulation | Expression | CYCS | hsa54205 | |
| Down-regulation | Expression | IL1B | hsa3553 | |
| Down-regulation | Expression | PTGS2 | hsa5743 | |
| In Vitro Model | HeLa | Human papillomavirus-related cervical adenocarcinoma | Homo sapiens (Human) | CVCL_0030 |
| Result | Eugenol showed antiproliferative and cytotoxic effects via apoptosis and also synergism with cisplatin and ionizing radiation in the human cervical cancer cell line. | |||
| Pair Name | Eugenol, Cisplatin | |||
| Partner Name | Cisplatin | |||
| Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
| Biological Phenomena | Inhibition-->Epithelial-mesenchymal transition | |||
| Gene Regulation | Up-regulation | Expression | BAX | hsa581 |
| Up-regulation | Cleavage | CASP3 | hsa836 | |
| Up-regulation | Cleavage | CASP9 | hsa842 | |
| Down-regulation | Phosphorylation | CDH13 | hsa1012 | |
| Down-regulation | Expression | MMP2 | hsa4313 | |
| Down-regulation | Expression | MMP9 | hsa4318 | |
| Up-regulation | Cleavage | PARP1 | hsa142 | |
| Down-regulation | Phosphorylation | RELA | hsa5970 | |
| In Vitro Model | MDA-MB-231 | Breast adenocarcinoma | Homo sapiens (Human) | CVCL_0062 |
| MDA-MB-468 | Breast adenocarcinoma | Homo sapiens (Human) | CVCL_0419 | |
| BT-20 | Invasive breast carcinoma | Homo sapiens (Human) | CVCL_0178 | |
| In Vivo Model | Breast cancer xenografts were created 4-6 week female nude mice by subcutaneous injection of the MDA-MB-231 cells (5×10⁶) into the right leg of each mouse. | |||
| Result | These results provide strong preclinical justification for combining cisplatin with eugenol as therapeutic approach for triple-negative breast cancers through targeting the resistant ALDH-positive cells and inhibiting the NF-κB pathway. | |||
| Pair Name | Eugenol, 2-methoxyestradiol | |||
| Partner Name | 2-methoxyestradiol | |||
| Disease Info | [ICD-11: 2C82] | Prostate cancer | Investigative | |
| Biological Phenomena | Induction-->Blockade of cell cycle in G2/M phase | |||
| Gene Regulation | Up-regulation | Expression | BAX | hsa581 |
| Down-regulation | Expression | BCL2 | hsa596 | |
| In Vitro Model | LNCaP | Prostate carcinoma | Homo sapiens (Human) | CVCL_0395 |
| PC-3 | Prostate carcinoma | Homo sapiens (Human) | CVCL_0035 | |
| DU145 | Prostate carcinoma | Homo sapiens (Human) | CVCL_0105 | |
| Result | Combining these agents may allow ameliorating any adverse effects of either 2-ME(2) or eugenol alone by reducing their individual concentrations should these two agents be developed for human use. | |||
| Pair Name | Eugenol, Gemcitabine | |||
| Partner Name | Gemcitabine | |||
| Disease Info | [ICD-11: 2C77] | Cervical cancer | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Down-regulation | Expression | BCL2 | hsa596 |
| Down-regulation | Expression | COX2 | hsa4513 | |
| Down-regulation | Expression | IL1B | hsa3553 | |
| In Vitro Model | HeLa | Human papillomavirus-related cervical adenocarcinoma | Homo sapiens (Human) | CVCL_0030 |
| Result | The results suggest that eugenol exerts its anticancer activities via apoptosis induction and anti-inflammatory properties and also provide the first evidence demonstrating synergism between eugenol and gemcitabine, which may enhance The therapeutic index of prevention and/or treatment of cervical cancer. | |||
| Pair Name | Eugenol, Fluorouracil | |||
| Partner Name | Fluorouracil | |||
| Disease Info | [ICD-11: 2C77] | Cervical cancer | Investigative | |
| Biological Phenomena | Induction-->Blockade of cell cycle in S and G2/M phase | |||
| In Vitro Model | HeLa | Human papillomavirus-related cervical adenocarcinoma | Homo sapiens (Human) | CVCL_0030 |
| Result | Eugenol interacts synergistically with 5-fluorouracil against human cervical cancer, HeLa cell lines, by blocking the cell cycle and inducing apoptosis | |||
| Pair Name | Eugenol, Sorafenib | |||
| Partner Name | Sorafenib | |||
| Disease Info | [ICD-11: 2D10.Z] | Thyroid cancer | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Up-regulation | Cleavage | CASP8 | hsa841 |
| Down-regulation | Cleavage | CASP9 | hsa842 | |
| In Vitro Model | 8305C | Thyroid gland anaplastic carcinoma | Homo sapiens (Human) | CVCL_1053 |
| Result | The most potent apoptotic effect was achieved with sorafenib and eugenol at their IC50. Lower doses of sorafenib could be used with eugenol to improve its efficacy while reducing its side effects. | |||
| No. | Title | Href |
|---|---|---|
| 1 | Eugenol: A New Option in Combination Therapy with Sorafenib for the Treatment of Undifferentiated Thyroid Cancer. Iran J Allergy Asthma Immunol. 2022 Jun 18;21(3):313-321. doi: 10.18502/ijaai.v21i3.9804. | Click |
| 2 | Eugenol Exerts Apoptotic Effect and Modulates the Sensitivity of HeLa Cells to Cisplatin and Radiation. Molecules. 2019 Nov 3;24(21):3979. doi: 10.3390/molecules24213979. | Click |
| 3 | Eugenol potentiates cisplatin anti-cancer activity through inhibition of ALDH-positive breast cancer stem cells and the NF-κB signaling pathway. Mol Carcinog. 2018 Mar;57(3):333-346. doi: 10.1002/mc.22758. | Click |
| 4 | Combination of 2-methoxyestradiol (2-ME2) and eugenol for apoptosis induction synergistically in androgen independent prostate cancer cells. J Steroid Biochem Mol Biol. 2009 Jan;113(1-2):25-35. doi: 10.1016/j.jsbmb.2008.11.002. | Click |
| 5 | Eugenol enhances the chemotherapeutic potential of gemcitabine and induces anticarcinogenic and anti-inflammatory activity in human cervical cancer cells. Cancer Biother Radiopharm. 2011 Oct;26(5):519-27. doi: 10.1089/cbr.2010.0925. | Click |
| 6 | Combination of phenylpropanoids with 5-fluorouracil as anti-cancer agents against human cervical cancer (HeLa) cell line. Phytomedicine. 2013 Jan 15;20(2):151-8. doi: 10.1016/j.phymed.2012.10.009. | Click |
