Page last updated: 2024-12-08
pinostilbene
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Description
pinostilbene: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
3-methoxy-4',5-dihydroxy-trans-stilbene : A stilbenoid that is trans-resveratrol in which one of the meta-hydroxy groups is converted to the corresponding methyl ether. [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]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 5473050 |
| CHEMBL ID | 498917 |
| CHEBI ID | 63672 |
| SCHEMBL ID | 562335 |
| SCHEMBL ID | 562336 |
| MeSH ID | M0513795 |
Synonyms (49)
| Synonym |
|---|
| 42438-89-1 |
| AC-7026 |
| 3-methoxyresveratrol |
| nsc-723532 |
| nsc723532 |
| CHEMBL498917 , |
| chebi:63672 , |
| 3-[(e)-2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenol |
| 3,4'-dihydroxy-5-methoxy-trans-stilbene |
| P1927 |
| 3-methoxy-4',5-dihydroxy-trans-stilbene |
| resveratrol monomethyl ether |
| pinostilbene |
| C20154 |
| 3-[2-(4-hydroxyphenyl)vinyl]-5-methoxy-phenol;pinostilbene |
| A825900 |
| pinostilbene hydrate |
| AKOS015915100 |
| SCHEMBL562335 |
| SCHEMBL562336 |
| DTXSID50420234 |
| trans-3,4'-dihydroxy-5-methoxystilbene |
| 3-[(e)-2-(4-hydroxyphenyl)vinyl]-5-methoxy-phenol |
| mfcd12407153 |
| KUWZXOMQXYWKBS-NSCUHMNNSA-N |
| bdbm50252422 |
| BCP18618 |
| (e)-3-(4-hydroxystyryl)-5-methoxyphenol |
| 3-[2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenol |
| Q18388690 |
| CS-0023117 |
| HY-N3059 |
| AS-56412 |
| 3-[(1e)-2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenol |
| 871504-87-9 |
| phenol, 3-[2-(4-hydroxyphenyl)ethenyl]-5-methoxy- |
| phenol, 3-[(e)-2-(4-hydroxyphenyl)ethenyl]-5-methoxy- |
| Z3210723812 |
| 3-(2-(4-hydroxyphenyl)ethenyl)-5-methoxyphenol |
| 3-((1e)-2-(4-hydroxyphenyl)ethenyl)-5-methoxyphenol |
| phenol, 3-((1e)-2-(4-hydroxyphenyl)ethenyl)-5-methoxy- |
| 3,4-dihydroxy-5-methoxy-trans-stilbene |
| pinostilbene, trans- |
| 4pak325bem , |
| phenol, 3-(2-(4-hydroxyphenyl)ethenyl)-5-methoxy-, (e)- |
| unii-4pak325bem |
| trans-pinostilbene |
| phenol, 3-(2-(4-hydroxyphenyl)ethenyl)-5-methoxy- |
| 3-[(e)-2-(4-hydroxyphenyl)ethenyl]-5-methoxy-phenol |
Research Excerpts
Pharmacokinetics
| Excerpt | Reference | Relevance |
|---|---|---|
| " Pharmacokinetic comparison among pinostilbene, resveratrol and some resveratrol analogues suggested that stilbenes with meta-hydroxyl group(s) may be associated with metabolic instability and subsequently suffer from rapid clearance and low oral bioavailability." | ( Determination of pinostilbene in rat plasma by LC-MS/MS: Application to a pharmacokinetic study. Chen, W; Chuang, XF; Lin, HS; Yeo, SC, 2016) | 0.43 |
Bioavailability
pinostilbene's bioavailability was limited but highly erratic after oral dosing (50mg/kg) Enhanced bioavailability may thus be a major factor contributing to the neuroprotective activity.
| Excerpt | Reference | Relevance |
|---|---|---|
| " Enhanced bioavailability may thus be a major factor contributing to the neuroprotective activity of pinostilbene." | ( Protective effects of pinostilbene, a resveratrol methylated derivative, against 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y cells. Chang, RC; Chao, J; Cheng, KW; Li, H; Wang, M; Yu, MS, 2010) | 0.36 |
| " However, the methylated resveratrol analogs exhibit better bioavailability as they are more easily transported into the cell and more resistant to degradation." | ( Biosynthesis of methylated resveratrol analogs through the construction of an artificial biosynthetic pathway in E. coli. Choi, O; Hong, YS; Hwang, BY; Jang, JH; Kang, SY; Kim, CY; Lee, JK, 2014) | 0.4 |
| " After oral dosing (50mg/kg), the bioavailability of pinostilbene was limited but highly erratic (F=1." | ( Determination of pinostilbene in rat plasma by LC-MS/MS: Application to a pharmacokinetic study. Chen, W; Chuang, XF; Lin, HS; Yeo, SC, 2016) | 0.43 |
Dosage Studied
| Excerpt | Relevance | Reference |
|---|---|---|
| " After oral dosing (50mg/kg), the bioavailability of pinostilbene was limited but highly erratic (F=1." | ( Determination of pinostilbene in rat plasma by LC-MS/MS: Application to a pharmacokinetic study. Chen, W; Chuang, XF; Lin, HS; Yeo, SC, 2016) | 0.43 |
| " All compounds activated AhR, but their efficacies, potencies and dose-response profiles differed substantially." | ( Hydroxystilbenes and methoxystilbenes activate human aryl hydrocarbon receptor and induce CYP1A genes in human hepatoma cells and human hepatocytes. Bachleda, P; Dvořák, Z; Pastorková, B; Vrzalová, A, 2017) | 0.46 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Drug Classes (1)
| Class | Description |
|---|---|
| stilbenol | Any stilbenoid with at least one phenolic group. |
| [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] | |
Pathways (1)
| Pathway | Proteins | Compounds |
|---|---|---|
| pterostilbene biosynthesis | 1 | 6 |
Protein Targets (2)
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Cytochrome P450 1A1 | Homo sapiens (human) | Ki | 0.1300 | 0.0120 | 0.9469 | 3.8000 | AID1452982 |
| Cytochrome P450 1B1 | Homo sapiens (human) | Ki | 0.9000 | 0.0030 | 0.9741 | 7.4600 | AID1452983 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (88)
Molecular Functions (22)
Ceullar Components (4)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| mitochondrial inner membrane | Cytochrome P450 1A1 | Homo sapiens (human) |
| endoplasmic reticulum membrane | Cytochrome P450 1A1 | Homo sapiens (human) |
| intracellular membrane-bounded organelle | Cytochrome P450 1A1 | Homo sapiens (human) |
| mitochondrion | Cytochrome P450 1B1 | Homo sapiens (human) |
| endoplasmic reticulum membrane | Cytochrome P450 1B1 | Homo sapiens (human) |
| intracellular membrane-bounded organelle | Cytochrome P450 1B1 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Bioassays (23)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID510869 | Cytotoxicity against human Caco-2 cells after 3 days by [3H]thymidine incorporation assay | 2010 | European journal of medicinal chemistry, Sep, Volume: 45, Issue:9 | In vitro and in vivo studies on stilbene analogs as potential treatment agents for colon cancer. |
| AID1183069 | Antifungal activity against Candida lusitaniae CBS 6936 assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID470664 | Cytotoxicity against human HeLa cells after 72 hrs by MTT assay | 2009 | Journal of natural products, Sep, Volume: 72, Issue:9 | Cytotoxic constituents of Soymida febrifuga from Myanmar. |
| AID1183074 | Antifungal activity against Candida tropicalis ATCC MYA-3404/T1 assessed as growth inhibition at 300 ug/ml after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID1452982 | Inhibition of recombinant human CYP1A1 expressed in supersomes coexpressing NADPH-CYP reductase using 7-ethoxyresorufin as substrate after 15 mins in presence of NADP+ by Lineweaver-Burk plot analysis | 2017 | European journal of medicinal chemistry, Jul-28, Volume: 135 | Inhibitors of cytochrome P450 (CYP) 1B1. |
| AID356481 | ABTS radical scavenging activity assessed as trolox equivalent antioxidant capacity after 10 mins | 2003 | Journal of natural products, Sep, Volume: 66, Issue:9 | Resveratrol and two monomethylated stilbenes from Israeli Rumex bucephalophorus and their antioxidant potential. |
| AID1183067 | Antifungal activity against Candida kefyr clinical isolate assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID1183066 | Antifungal activity against Candida inconspicua clinical isolate assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID1183064 | Antifungal activity against Candida glabrata ATCC 90030 assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID470663 | Cytotoxicity against human A549 cells after 72 hrs by MTT assay | 2009 | Journal of natural products, Sep, Volume: 72, Issue:9 | Cytotoxic constituents of Soymida febrifuga from Myanmar. |
| AID1183071 | Antifungal activity against Candida parapsilosis ATCC 22019 assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID1183063 | Antifungal activity against Candida famata VKMY-9 assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID470661 | Cytotoxicity against human PANC1 cells in nutrient-deprived condition after 24 hrs by WST8 assay | 2009 | Journal of natural products, Sep, Volume: 72, Issue:9 | Cytotoxic constituents of Soymida febrifuga from Myanmar. |
| AID1452983 | Inhibition of recombinant human CYP1B1 expressed in supersomes coexpressing NADPH-CYP reductase using 7-ethoxyresorufin as substrate after 15 mins in presence of NADP+ by Lineweaver-Burk plot analysis | 2017 | European journal of medicinal chemistry, Jul-28, Volume: 135 | Inhibitors of cytochrome P450 (CYP) 1B1. |
| AID1183062 | Antifungal activity against Candida dubliniensis ATCC MYA-646 assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID470662 | Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay | 2009 | Journal of natural products, Sep, Volume: 72, Issue:9 | Cytotoxic constituents of Soymida febrifuga from Myanmar. |
| AID1183068 | Antifungal activity against Candida krusei ATCC 6258 assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID470665 | Cytotoxicity against mouse Colon 26-L5 cells after 72 hrs by MTT assay | 2009 | Journal of natural products, Sep, Volume: 72, Issue:9 | Cytotoxic constituents of Soymida febrifuga from Myanmar. |
| AID1183061 | Antifungal activity against Candida albicans SC5314 ATCC MYA-2876 assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID510868 | Cytotoxicity against human HT-29 cells after 3 days by [3H]thymidine incorporation assay | 2010 | European journal of medicinal chemistry, Sep, Volume: 45, Issue:9 | In vitro and in vivo studies on stilbene analogs as potential treatment agents for colon cancer. |
| AID470666 | Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay | 2009 | Journal of natural products, Sep, Volume: 72, Issue:9 | Cytotoxic constituents of Soymida febrifuga from Myanmar. |
| AID1183065 | Antifungal activity against Candida guilliermondii ATCC 6260 assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| AID1183070 | Antifungal activity against Candida norvegensis clinical isolate assessed as growth inhibition after 48 hrs by broth microdilution method | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Antifungal activity of resveratrol derivatives against Candida species. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (30)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 3 (10.00) | 29.6817 |
| 2010's | 20 (66.67) | 24.3611 |
| 2020's | 7 (23.33) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (3.33%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 29 (96.67%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||