1,1-dimethylallyl caffeic acid ester
Description
1,1-Dimethylallyl caffeic acid ester, also known as **caffeic acid 1,1-dimethylallyl ester** or **CAPE**, is a natural compound found in propolis, a resinous substance produced by honeybees.
Here's why it's important for research:
**Pharmacological Properties:**
* **Antioxidant:** CAPE exhibits strong antioxidant activity, which can help protect cells from damage caused by free radicals.
* **Anti-inflammatory:** CAPE has been shown to suppress inflammation by inhibiting the production of inflammatory mediators like prostaglandins and cytokines.
* **Anti-cancer:** CAPE is being investigated for its potential anti-cancer properties. It has shown promise in laboratory studies against a range of cancer cell lines, including breast, colon, and prostate cancer.
* **Anti-viral:** CAPE has demonstrated antiviral activity against various viruses, including herpes simplex virus and HIV.
* **Neuroprotective:** CAPE has been shown to protect nerve cells from damage caused by oxidative stress and inflammation.
* **Cardioprotective:** CAPE may offer protection against heart disease by improving blood vessel function and reducing inflammation.
**Research Focus:**
* **Mechanisms of Action:** Researchers are actively investigating the specific mechanisms by which CAPE exerts its various pharmacological effects.
* **Therapeutic Potential:** CAPE is being explored as a potential therapeutic agent for a wide range of diseases, including cancer, inflammatory disorders, viral infections, and neurodegenerative diseases.
* **Drug Development:** Studies are underway to develop CAPE-based drugs for clinical use.
* **Safety and Toxicity:** While CAPE is generally considered safe, research is ongoing to assess its long-term safety and potential toxicity.
**Current Research:**
* **Cancer Therapy:** Clinical trials are investigating the use of CAPE in combination with conventional cancer therapies, such as chemotherapy and radiation.
* **Neurodegenerative Diseases:** Research is exploring the potential of CAPE to prevent or delay the progression of Alzheimer's disease, Parkinson's disease, and other neurodegenerative conditions.
* **Inflammatory Bowel Disease (IBD):** CAPE is being studied for its potential to treat IBD, a chronic inflammatory condition affecting the digestive tract.
**Overall:** 1,1-Dimethylallyl caffeic acid ester (CAPE) is a promising natural compound with a diverse range of pharmacological properties. Its potent antioxidant, anti-inflammatory, and anti-cancer activities have made it a target of intense research, with potential for the development of novel therapeutic agents.
1,1-dimethylallyl caffeic acid ester: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 5281790 |
| CHEMBL ID | 471184 |
| CHEBI ID | 8393 |
| SCHEMBL ID | 14461142 |
| MeSH ID | M0153028 |
Synonyms (22)
| Synonym |
|---|
| 3-methyl-2-butenyl caffeate |
| isoprenyl caffeate |
| 1,1-dimethylallyl caffeic acid ester |
| cinnamic acid, 3,4-dihydroxy-, 3-methyl-2-butenyl ester |
| 1,1-dacae |
| 118971-61-2 |
| prenyl caffeate |
| CHEMBL471184 |
| chebi:8393 , |
| 3-methylbut-2-enyl (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
| 100884-13-7 |
| 3-methylbut-2-enyl caffeate |
| caffeic acid 1,1-dimethylallyl ester |
| SCHEMBL14461142 |
| 3-methylbut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
| 2-propenoic acid,3-(3,4-dihydroxyphenyl)-,3-methyl-2-buten-1-yl ester,(2e)- |
| prenyl cis-caffeate |
| bdbm50030893 |
| J-003986 |
| caffeic acid 1,1-dimethylallyl ester, analytical standard |
| prenyl cafeate |
| Q27108066 |
Drug Classes (1)
| Class | Description |
|---|---|
| hydroxycinnamic acid | Any member of the class of cinnamic acids carrying one or more hydroxy substituents. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
Protein Targets (1)
Activation Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Transthyretin | Homo sapiens (human) | EC50 (µMol) | 21.0000 | 5.6000 | 7.5429 | 8.6000 | AID1169291 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (2)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| signal transduction | Transthyretin | Homo sapiens (human) |
| purine nucleobase metabolic process | Transthyretin | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Molecular Functions (4)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| hormone activity | Transthyretin | Homo sapiens (human) |
| protein binding | Transthyretin | Homo sapiens (human) |
| identical protein binding | Transthyretin | Homo sapiens (human) |
| thyroid hormone binding | Transthyretin | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Ceullar Components (4)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| extracellular region | Transthyretin | Homo sapiens (human) |
| extracellular space | Transthyretin | Homo sapiens (human) |
| azurophil granule lumen | Transthyretin | Homo sapiens (human) |
| extracellular exosome | Transthyretin | Homo sapiens (human) |
| extracellular space | Transthyretin | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Bioassays (17)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1169291 | Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation by fluorescence assay | 2014 | Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21 | Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin. |
| AID332490 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 0.001 multiple round of replication at 12.5 ug/ml after 72 hrs | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID332494 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as reduction in viral DNA synthesis after 1 multiple round of replication at 60 ug/ml after 18 hrs by agarose gel electrophoresis relative to control | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID362056 | Cytotoxicity against mouse RAW264.7 cells assessed as cell survival after 24 hrs by MTT assay | 2008 | Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16 | Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages. |
| AID332486 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 1 multiple round of replication at 12.5 ug/ml after 72 hrs | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID332485 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 1 multiple round of replication at 6.25 ug/ml after 72 hrs | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID380004 | Cytotoxicity against mouse P388 cells after 72 hrs by MTT assay | 2000 | Journal of natural products, Apr, Volume: 63, Issue:4 | A cytotoxic sesquiterpene caffeate from the liverwort Bazzanianovae-zelandiae. |
| AID332492 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 0.001 multiple round of replication at 50 ug/ml after 72 hrs | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID332488 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 1 multiple round of replication at 50 ug/ml after 72 hrs | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID332487 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 1 multiple round of replication at 25 ug/ml after 72 hrs | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID1169294 | Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation at 20 uM by fluorescence assay | 2014 | Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21 | Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin. |
| AID332491 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 0.001 multiple round of replication at 25 ug/ml after 72 hrs | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID362058 | Ratio of EC50 for mouse RAW264.7 cells to EC50 for inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells | 2008 | Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16 | Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages. |
| AID332493 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as reduction in viral DNA synthesis after 1 multiple round of replication at 30 ug/ml after 18 hrs by agarose gel electrophoresis relative to control | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID362057 | Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assessed as nitrite accumulation administered 1 hr before LPS challenge and measured after 24 hrs by Griess reagent assay | 2008 | Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16 | Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages. |
| AID332489 | Antiviral activity against HSV1 H29S in african green monkey Vero cells assessed as log reduction in viral titers after 0.001 multiple round of replication at 6.25 ug/ml after 72 hrs | 1994 | Journal of natural products, May, Volume: 57, Issue:5 | Comparison of the anti-herpes simplex virus activities of propolis and 3-methyl-but-2-enyl caffeate. |
| AID1169299 | Competitive binding to TTR V30M mutant (unknown origin) expressed in Escherichia coli at 1 to 80 uM by fluorescence assay | 2014 | Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21 | Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (8)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 2 (25.00) | 18.7374 |
| 1990's | 2 (25.00) | 18.2507 |
| 2000's | 2 (25.00) | 29.6817 |
| 2010's | 2 (25.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 12.41
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.41) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 1 (11.11%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 8 (88.89%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||