3-Phenylpropyl isothiocyanate (3-PPITC) is a naturally occurring isothiocyanate found in cruciferous vegetables such as broccoli, cauliflower, and Brussels sprouts. It is formed upon enzymatic hydrolysis of the glucosinolate glucobrassicin by the enzyme myrosinase. 3-PPITC has been shown to possess a wide range of biological activities, including anticancer, anti-inflammatory, and antioxidant effects. It has also been studied for its potential to protect against neurodegenerative diseases and cardiovascular disease. The anticancer activity of 3-PPITC is attributed to its ability to induce apoptosis, inhibit cell proliferation, and modulate cell cycle progression in cancer cells. Studies have shown that 3-PPITC can inhibit the growth of various cancer cell lines, including breast cancer, colon cancer, and leukemia cells. The anti-inflammatory effects of 3-PPITC are mediated through its ability to inhibit the production of pro-inflammatory cytokines and chemokines. 3-PPITC has also been shown to protect against oxidative stress by scavenging free radicals and activating antioxidant enzymes. The neuroprotective effects of 3-PPITC are attributed to its ability to reduce neuronal damage, improve cognitive function, and protect against neurotoxicity. Studies have shown that 3-PPITC can reduce neuronal cell death in models of Alzheimer's disease and Parkinson's disease. The cardioprotective effects of 3-PPITC are attributed to its ability to lower blood pressure, reduce cholesterol levels, and improve blood flow. 3-PPITC has also been shown to protect against heart attack and stroke. The importance of studying 3-PPITC lies in its potential to develop novel therapeutic agents for the treatment of various diseases. The unique chemical structure of 3-PPITC allows it to interact with various cellular targets and pathways, making it a promising candidate for drug development. Further research is needed to fully elucidate the mechanisms of action and to develop safe and effective 3-PPITC-based therapies.'
3-phenylpropyl isothiocyanate: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 75815 |
| CHEMBL ID | 54380 |
| CHEBI ID | 173819 |
| SCHEMBL ID | 1457110 |
| MeSH ID | M0247361 |
| Synonym |
|---|
| 1-isothiocyanato-3-phenylpropane |
| CHEBI:173819 |
| 3-isothiocyanatopropylbenzene |
| benzene, (3-isothiocyanatopropyl)- |
| (3-isothiocyanatopropyl)benzene |
| 3-phenylpropyl isothiocynate |
| 2627-27-2 |
| ppitc |
| ccris 3147 |
| phenylpropyl isothiocyanate |
| isothiocyanic acid 3-phenylpropyl ester |
| 3-phenylpropyl isothiocyanate |
| einecs 220-094-9 |
| AKOS000101074 |
| CHEMBL54380 , |
| SCHEMBL1457110 |
| phenylpropyl isothiocyanate, 3- |
| 3-phenylpropylisothiocyanate |
| unii-1s20ia5ggo |
| 1s20ia5ggo , |
| BP-11162 |
| FT-0627518 |
| benzene,(3-isothiocyanatopropyl)- |
| isothiocyanic acid, 3-phenylpropyl ester |
| (3-isothiocyanatopropyl)benzene # |
| DTXSID1040241 |
| mfcd00041134 |
| bdbm50073716 |
| (3-isothiocyanatopropyl)-benzene |
| (3-isothiocyanatopropyl)benzene, 9ci |
| J-016359 |
| CS-0255617 |
| Q27252818 |
| HY-115771 |
| CAA62727 |
| PD139352 |
| Class | Description |
|---|---|
| benzenes | Any benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives. |
| [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 | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Macrophage migration inhibitory factor | Homo sapiens (human) | IC50 (µMol) | 1.4000 | 0.0380 | 3.0910 | 9.8000 | AID1198788 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| protease binding | Macrophage migration inhibitory factor | Homo sapiens (human) |
| dopachrome isomerase activity | Macrophage migration inhibitory factor | Homo sapiens (human) |
| cytokine activity | Macrophage migration inhibitory factor | Homo sapiens (human) |
| cytokine receptor binding | Macrophage migration inhibitory factor | Homo sapiens (human) |
| protein binding | Macrophage migration inhibitory factor | Homo sapiens (human) |
| chemoattractant activity | Macrophage migration inhibitory factor | Homo sapiens (human) |
| identical protein binding | Macrophage migration inhibitory factor | Homo sapiens (human) |
| phenylpyruvate tautomerase activity | Macrophage migration inhibitory factor | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID232171 | Ratio of glutathione S-transferase activity in tested (cottonseed oil alone + compound) to that of control (cottonseed oil alone) | 1992 | Journal of medicinal chemistry, Jan, Volume: 35, Issue:1 | Phenylalkyl isothiocyanate-cysteine conjugates as glutathione S-transferase stimulating agents. |
| AID75144 | Induction of increased cytosolic glutathione S-transferase activity in large bowel mucosa of A/J mice treated with 3 doses of 0.04 mM compound (dissolved in 0.3 mL of cottonseed oil) for 2 days | 1992 | Journal of medicinal chemistry, Jan, Volume: 35, Issue:1 | Phenylalkyl isothiocyanate-cysteine conjugates as glutathione S-transferase stimulating agents. |
| AID75149 | Induction of increased cytosolic glutathione S-transferase activity in small bowel mucosa of A/J mice treated with 3 doses of 0.04 mM compound (dissolved in 0.3 mL of cottonseed oil) for 2 days | 1992 | Journal of medicinal chemistry, Jan, Volume: 35, Issue:1 | Phenylalkyl isothiocyanate-cysteine conjugates as glutathione S-transferase stimulating agents. |
| AID692257 | Induction of covalent cysteine modification at p53 G245C mutant in human NCI-H596 cells at 100 uM incubated for 1 hr by monochlorobimane fluorometric assay | 2011 | Journal of medicinal chemistry, Feb-10, Volume: 54, Issue:3 | Selective depletion of mutant p53 by cancer chemopreventive isothiocyanates and their structure-activity relationships. |
| AID75142 | Induction of increased cytosolic glutathione S-transferase activity in forestomach of A/J mice treated with 3 doses of 0.04 mM compound (dissolved in 0.3 mL of cottonseed oil) for 2 days | 1992 | Journal of medicinal chemistry, Jan, Volume: 35, Issue:1 | Phenylalkyl isothiocyanate-cysteine conjugates as glutathione S-transferase stimulating agents. |
| AID692266 | Induction of apoptosis in human MDA-MB-231 cells expressing p53 R280K mutant at 10 uM incubated for 24 hrs by FITC/Annexin-V staining method | 2011 | Journal of medicinal chemistry, Feb-10, Volume: 54, Issue:3 | Selective depletion of mutant p53 by cancer chemopreventive isothiocyanates and their structure-activity relationships. |
| AID75146 | Induction of increased cytosolic glutathione S-transferase activity in liver of A/J mice treated with 3 doses of 0.04 mM compound (dissolved in 0.3 mL of cottonseed oil) for 2 days | 1992 | Journal of medicinal chemistry, Jan, Volume: 35, Issue:1 | Phenylalkyl isothiocyanate-cysteine conjugates as glutathione S-transferase stimulating agents. |
| AID1198788 | Inhibition of macrophage migration inhibitory factor tautomerase activity in human Jurkat T cells using L-dopachrome methyl ester as substrate incubated for 30 mins prior to substrate addition measured for 2 mins by spectrophotometric analysis | 2015 | European journal of medicinal chemistry, Mar-26, Volume: 93 | Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor. |
| AID692255 | Induction of p53 G245C mutant depletion in human NCI-H596 cells at 20 uM by immunoblot analysis | 2011 | Journal of medicinal chemistry, Feb-10, Volume: 54, Issue:3 | Selective depletion of mutant p53 by cancer chemopreventive isothiocyanates and their structure-activity relationships. |
| AID692256 | Induction of p53 R280K mutant depletion in human MDA-MB-231 cells at 10 uM by immunoblot analysis | 2011 | Journal of medicinal chemistry, Feb-10, Volume: 54, Issue:3 | Selective depletion of mutant p53 by cancer chemopreventive isothiocyanates and their structure-activity relationships. |
| AID75147 | Induction of increased cytosolic glutathione S-transferase activity in lung of A/J mice treated with 3 doses of 0.04 mM compound (dissolved in 0.3 mL of cottonseed oil) for 2 days | 1992 | Journal of medicinal chemistry, Jan, Volume: 35, Issue:1 | Phenylalkyl isothiocyanate-cysteine conjugates as glutathione S-transferase stimulating agents. |
| AID75140 | Induction of increased cytosolic glutathione S-transferase activity in bladder of A/J mice treated with 3 doses of 0.04 mM compound (dissolved in 0.3 mL of cottonseed oil) for 2 days | 1992 | Journal of medicinal chemistry, Jan, Volume: 35, Issue:1 | Phenylalkyl isothiocyanate-cysteine conjugates as glutathione S-transferase stimulating agents. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 5 (71.43) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 2 (28.57) | 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] | ||
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 (12.13) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 8 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||