Natural Product (NP) Details
| General Information of the NP (ID: NP3478) | |||||
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| Name |
Eugenol
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| Synonyms |
4-Allyl-2-methoxyphenol; 4-Allylguaiacol; Eugenic acid; Allylguaiacol; Caryophyllic acid; p-Allylguaiacol; p-Eugenol; 2-Methoxy-4-prop-2-enylphenol; Engenol; 2-Methoxy-4-allylphenol; Phenol, 2-methoxy-4-(2-propenyl)-; 1,3,4-Eugenol; 4-Allylcatechol-2-methyl ether; Synthetic eugenol; 2-Methoxy-4-(2-propenyl)phenol; 2-Methoxy-1-hydroxy-4-allylbenzene; 4-Allyl-1-hydroxy-2-methoxybenzene; 1-Hydroxy-2-methoxy-4-allylbenzene; 5-Allylguaiacol; 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene
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| Species Origin | Coreopsis tinctoria ... | Click to Show/Hide | |||
| Coreopsis tinctoria | |||||
| Myristica fragrans | |||||
| Narcissus tazetta | |||||
| Hedychium coronarium | |||||
| Osmanthus fragrans | |||||
| Cinnamomum burmannii | |||||
| Psidium guajava | |||||
| Syringa villosa | |||||
| Cestrum nocturnum | |||||
| Disease | Keratitis [ICD-11: 9A71] | Investigative | [1] | ||
| Structure |
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Click to Download Mol2D MOL |
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| Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product | |||||
| Formula |
C10H12O2
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| PubChem CID | |||||
| Canonical SMILES |
COC1=C(C=CC(=C1)CC=C)O
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| InChI |
1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
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| InChIKey |
RRAFCDWBNXTKKO-UHFFFAOYSA-N
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| CAS Number |
CAS 97-53-0
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| Herb ID | |||||
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| TTD Drug ID | |||||
| Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally | ||||||
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| 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
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| Molecule(s)
Regulation |
Up-regulation | Expression | BAX | Molecule Info |
Pathway MAP
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| Up-regulation | Cleavage | CASP3 | Molecule Info |
Pathway MAP
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| Up-regulation | Cleavage | CASP9 | Molecule Info |
Pathway MAP
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| Down-regulation | Expression | MMP-2 | Molecule Info |
Pathway MAP
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| Down-regulation | Expression | MMP-9 | Molecule Info |
Pathway MAP
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| Down-regulation | Phosphorylation | p105 | Molecule Info |
Pathway MAP
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| Up-regulation | Cleavage | PARP1 | Molecule Info |
Pathway MAP
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| Down-regulation | Phosphorylation | RELA | Molecule Info |
Pathway MAP
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| In-vitro Model | MDA-MB-231 | CVCL_0062 | Breast adenocarcinoma | Homo sapiens | ||
| MDA-MB-468 | CVCL_0419 | Breast adenocarcinoma | Homo sapiens | |||
| BT-20 | CVCL_0178 | Invasive breast carcinoma | Homo sapiens | |||
| In-vivo Model | Breast cancer xenografts were created 4-6week female nude mice by subcutaneous injection of the MDA-MB-231 cells (5*106) into the right leg of each mouse. | |||||
| Experimental
Result(s) |
Eugenol potentiates cisplatin anti-cancer activity through inhibition of ALDH-positive breast cancer stem cells and the NF-kappaB signaling pathway. | |||||
| 2-methoxyestradiol | Pulmonary hypertension | 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
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| Molecule(s)
Regulation |
Up-regulation | Expression | BAX | Molecule Info |
Pathway MAP
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| Down-regulation | Expression | BCL-2 | Molecule Info |
Pathway MAP
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| In-vitro Model | LNCaP | CVCL_0395 | Prostate carcinoma | Homo sapiens | ||
| PC-3 | CVCL_0035 | Prostate carcinoma | Homo sapiens | |||
| DU145 | CVCL_0105 | Prostate carcinoma | Homo sapiens | |||
| Experimental
Result(s) |
Combining 2-ME(2) with eugenol (i) inhibited growth of prostate cancer cells and induced apoptosis at lower concentrations than either single agent alone. | |||||
| Gemcitabine | Solid tumour/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 | [4] | |||||
| Detail(s) |
Combination Info
click to show the detail info of this combination
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| Molecule(s)
Regulation |
Down-regulation | Expression | BCL-2 | Molecule Info |
Pathway MAP
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| Down-regulation | Expression | COX-2 | Molecule Info |
Pathway MAP
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| Down-regulation | Expression | IL1B | Molecule Info |
Pathway MAP
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| In-vitro Model | HeLa | CVCL_0030 | Endocervical adenocarcinoma | Homo sapiens | ||
| Experimental
Result(s) |
Eugenol enhances the chemotherapeutic potential of gemcitabine and induces anticarcinogenic and anti-inflammatory activity in human cervical cancer cells. | |||||
| 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 | [5] | |||||
| Detail(s) |
Combination Info
click to show the detail info of this combination
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| Biological
Regulation |
Induction | Cell cycle arrest in S and G2/M phase | ||||
| In-vitro Model | HeLa | CVCL_0030 | Endocervical adenocarcinoma | Homo sapiens | ||
| Experimental
Result(s) |
Eugenol interacts synergistically with 5-fluorouracil against human cervical cancer, HeLa cell lines, by blocking the cell cycle and inducing apoptosis. | |||||
| Target and Pathway | ||||
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| Target(s) | Androgen receptor (AR) | Molecule Info | [6] | |
| Monoamine oxidase B (MAO-B) | Molecule Info | [7] | ||
| BioCyc | Superpathway of tryptophan utilization | Click to Show/Hide | ||
| 2 | Tryptophan degradation via tryptamine | |||
| 3 | Dopamine degradation | |||
| 4 | Putrescine degradation III | |||
| 5 | Noradrenaline and adrenaline degradation | |||
| KEGG Pathway | Oocyte meiosis | Click to Show/Hide | ||
| 2 | Pathways in cancer | |||
| 3 | Prostate cancer | |||
| 4 | Glycine, serine and threonine metabolism | |||
| 5 | Arginine and proline metabolism | |||
| 6 | Histidine metabolism | |||
| 7 | Tyrosine metabolism | |||
| 8 | Phenylalanine metabolism | |||
| 9 | Tryptophan metabolism | |||
| 10 | Drug metabolism - cytochrome P450 | |||
| 11 | Metabolic pathways | |||
| 12 | Serotonergic synapse | |||
| 13 | Dopaminergic synapse | |||
| 14 | Cocaine addiction | |||
| 15 | Amphetamine addiction | |||
| 16 | Alcoholism | |||
| NetPath Pathway | EGFR1 Signaling Pathway | Click to Show/Hide | ||
| 2 | AndrogenReceptor Signaling Pathway | |||
| 3 | FSH Signaling Pathway | |||
| Panther Pathway | Adrenaline and noradrenaline biosynthesis | Click to Show/Hide | ||
| 2 | 5-Hydroxytryptamine degredation | |||
| 3 | Dopamine receptor mediated signaling pathway | |||
| Pathway Interaction Database | Regulation of nuclear SMAD2/3 signaling | Click to Show/Hide | ||
| 2 | Coregulation of Androgen receptor activity | |||
| 3 | Regulation of Androgen receptor activity | |||
| 4 | Nongenotropic Androgen signaling | |||
| 5 | Regulation of nuclear beta catenin signaling and target gene transcription | |||
| 6 | FOXA1 transcription factor network | |||
| 7 | Notch-mediated HES/HEY network | |||
| 8 | Alpha-synuclein signaling | |||
| Reactome | Nuclear Receptor transcription pathway | Click to Show/Hide | ||
| 2 | Activated PKN1 stimulates transcription of AR (androgen receptor) regulated genes KLK2 and KLK3 | |||
| WikiPathways | SIDS Susceptibility Pathways | Click to Show/Hide | ||
| 2 | Integrated Pancreatic Cancer Pathway | |||
| 3 | Prostate Cancer | |||
| 4 | Integrated Breast Cancer Pathway | |||
| 5 | Nuclear Receptors | |||
| 6 | Androgen receptor signaling pathway | |||
| 7 | Tryptophan metabolism | |||
| 8 | Dopamine metabolism | |||
| 9 | Phase 1 - Functionalization of compounds | |||
