2,4,3',5'-tetramethoxystilbene: potent inhibitor of human cytochrome P450 1B1; an antihypertensive agent; structure in first source [MeSH]
ID Source | ID |
---|---|
PubMed CID | 5354004 |
CHEMBL ID | 46909 |
SCHEMBL ID | 4366766 |
CHEBI ID | 92804 |
MeSH ID | M0407170 |
Synonym |
---|
BRD-K45988865-001-01-0 |
TMS , |
2,4,3',5'-tetramethoxystilbene |
3,5,2',4'-tetramethoxy-trans-stilbene |
2,3',4,5'-tetramethoxystilbene |
(e)-2,3',4,5'-tetramethoxystilbene |
CHEMBL46909 , |
trans-2,4,3',5'-tetramethoxystilbene |
1-[(e)-2-(3,5-dimethoxyphenyl)vinyl]-2,4-dimethoxybenzene |
trans-2,4,3'',5''-tetramethoxystilbene |
bdbm50108052 |
1-[(e)-2-(2,4-dimethoxyphenyl)ethenyl]-3,5-dimethoxybenzene |
AKOS015967529 |
20578-92-1 |
24144-92-1 |
(e)-1-(3,5-dimethoxystyryl)-2,4-dimethoxybenzene |
SCHEMBL4366766 |
1-[2,(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxybenzene |
AC-35369 |
JDBCWSHYEQUBLW-AATRIKPKSA-N |
oxyresveratrol tetramethyl ether |
HMS3648A21 |
(e)-4,5'-(ethene-1,2-diyl)bis(1,3-dimethoxybenzene) |
trans-2,3',4,5'-tetramethoxystilbene |
HY-19340 |
EX-A1015 |
SR-01000597603-1 |
sr-01000597603 |
CS-5626 |
CHEBI:92804 |
AS-71536 |
1-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxybenzene |
2,4,3',5'-tetramethoxystilbene, >=98% (hplc) |
J-015362 |
BCP21292 |
mfcd03428621 |
HMS3676F17 |
stilbene, 2,3',4,5'-tetramethoxy- |
SR-01000597603-2 |
HMS3412F17 |
3,5,2',4'-tetramethoxystilbene |
benzene, 1-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxy- |
A912947 |
1-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxy-benzene |
3,5,2 inverted exclamation mark ,4 inverted exclamation mark -tetramethoxystilbene |
DTXSID101186212 |
Protein | Taxonomy | Measurement | Average (mM) | Bioassay(s) |
---|---|---|---|---|
Cytochrome P450 1A1 | Homo sapiens (human) | IC50 | 0.3000 | AID1453035; AID1533283; AID54202 |
Cytochrome P450 1A2 | Homo sapiens (human) | IC50 | 3.0667 | AID1453036; AID1533284; AID54221 |
Tyrosinase | Homo sapiens (human) | IC50 | 100.0000 | AID276018 |
Cytochrome P450 1B1 | Homo sapiens (human) | IC50 | 0.0060 | AID1306443; AID1453034; AID1533285; AID54233 |
Cytochrome P450 1B1 | Homo sapiens (human) | Ki | 0.0030 | AID1533725 |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID276025 | Cytotoxicity against human NCI-H187 cells | 2006 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21 ISSN: 0960-894X | Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. |
AID1453034 | Inhibition of recombinant human CYP1B1 expressed in Escherichia coli DH5alpha using ethoxyresorufin as substrate preincubated for 3 mins followed by NADPH addition measured after 10 mins by spectrofluorometric assay | 2017 | European journal of medicinal chemistry, Jul-28, Volume: 135ISSN: 1768-3254 | Inhibitors of cytochrome P450 (CYP) 1B1. |
AID54225 | Selectivity ratio for Cytochrome P450 1B1 compared to Cytochrome P450 1A2 | 2002 | Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1 ISSN: 0022-2623 | Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. |
AID276018 | Inhibition of tyrosinase | 2006 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21 ISSN: 0960-894X | Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. |
AID54233 | Inhibition of ethoxyresorufin O-deethylation (EROD) in bicistronic bacterial membranes expressing human cytochrome P450 1B1 | 2002 | Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1 ISSN: 0022-2623 | Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. |
AID1453035 | Inhibition of recombinant human CYP1A1 expressed in Escherichia coli DH5alpha using ethoxyresorufin as substrate preincubated for 3 mins followed by NADPH addition measured after 10 mins by spectrofluorometric assay | 2017 | European journal of medicinal chemistry, Jul-28, Volume: 135ISSN: 1768-3254 | Inhibitors of cytochrome P450 (CYP) 1B1. |
AID1533287 | Selectivity ratio of IC50 for recombinant human CYP1A1 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1A2 expressed in Escherichia coli membranes | 2018 | ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12 ISSN: 1948-5875 | Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity. |
AID54202 | Inhibition of ethoxyresorufin O-deethylation (EROD) in bicistronic bacterial membranes epressing human cytochrome P450 1A1 | 2002 | Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1 ISSN: 0022-2623 | Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. |
AID54221 | Inhibition of ethoxyresorufin O-deethylation (EROD) in bicistronic bacterial membranes expressing human cytochrome P450 1A2 | 2002 | Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1 ISSN: 0022-2623 | Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. |
AID1533285 | Inhibition of recombinant human CYP1B1 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu | 2018 | ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12 ISSN: 1948-5875 | Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity. |
AID276024 | Cytotoxicity against human BC cells | 2006 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21 ISSN: 0960-894X | Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. |
AID54204 | Selectivity ratio for Cytochrome P450 1B1 compared to Cytochrome P450 1A1 | 2002 | Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1 ISSN: 0022-2623 | Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. |
AID1306443 | Inhibition of recombinant human CYP1B1 expressed in Escherichia coli DH5aplha cells assessed as O-deethylation of ethoxyresorufin in presence of NADPH measured after 2 mins by spectrofluorometric method | 2016 | Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14 ISSN: 1464-3405 | Aryl morpholino triazenes inhibit cytochrome P450 1A1 and 1B1. |
AID1533283 | Inhibition of recombinant human CYP1A1 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu | 2018 | ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12 ISSN: 1948-5875 | Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity. |
AID1533286 | Selectivity ratio of IC50 for recombinant human CYP1A1 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1B1 expressed in Escherichia coli membranes | 2018 | ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12 ISSN: 1948-5875 | Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity. |
AID1533288 | Selectivity ratio of IC50 for recombinant human CYP1A2 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1B1 expressed in Escherichia coli membranes | 2018 | ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12 ISSN: 1948-5875 | Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity. |
AID1533725 | Inhibition of human CYP1B1 using ethoxyresorufin as substrate preincubated for 3 mins followed by NADPH addition measured after 10 mins by EROD assay | 2019 | European journal of medicinal chemistry, Feb-01, Volume: 163ISSN: 1768-3254 | Phytoestrogens and their synthetic analogues as substrate mimic inhibitors of CYP1B1. |
AID1453036 | Inhibition of recombinant human CYP1A2 expressed in Escherichia coli DH5alpha using ethoxyresorufin as substrate preincubated for 3 mins followed by NADPH addition measured after 10 mins by spectrofluorometric assay | 2017 | European journal of medicinal chemistry, Jul-28, Volume: 135ISSN: 1768-3254 | Inhibitors of cytochrome P450 (CYP) 1B1. |
AID1533284 | Inhibition of recombinant human CYP1A2 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu | 2018 | ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12 ISSN: 1948-5875 | Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity. |
AID276017 | Inhibition of tyrosinase at 100 uM | 2006 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21 ISSN: 0960-894X | Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. |
AID276023 | Cytotoxicity against human KB cells | 2006 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21 ISSN: 0960-894X | Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent. |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 8 (29.63) | 29.6817 |
2010's | 19 (70.37) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 2 (7.41%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 25 (92.59%) | 84.16% |
Condition | Indicated | Studies | First Year | Last Year | Average Age | Relationship Strength | Trials | pre-1990 | 1990's | 2000's | 2010's | post-2020 |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Anoxemia | 0 | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Benign Neoplasms | 0 | 2019 | 2019 | 5.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Blood Pressure, High | 0 | 2010 | 2014 | 12.7 | low | 0 | 0 | 0 | 2 | 1 | 0 | |
Breast Cancer | 0 | 2010 | 2010 | 14.0 | low | 0 | 0 | 0 | 1 | 0 | 0 | |
Breast Neoplasms | 0 | 2010 | 2010 | 14.0 | low | 0 | 0 | 0 | 1 | 0 | 0 | |
Cancer of Colon | 0 | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Cancer of Prostate | 0 | 2008 | 2008 | 16.0 | low | 0 | 0 | 0 | 1 | 0 | 0 | |
Cardiac Hypertrophy | 0 | 2010 | 2017 | 11.7 | low | 0 | 0 | 0 | 2 | 1 | 0 | |
Cardiac Toxicity | 0 | 2016 | 2016 | 8.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Cardiomegaly | 0 | 2010 | 2017 | 11.7 | low | 0 | 0 | 0 | 2 | 1 | 0 | |
Cardiotoxicity | 0 | 2016 | 2016 | 8.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Chronic Disease | 0 | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Chronic Illness | 0 | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Cirrhosis | 0 | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Colonic Neoplasms | 0 | 2018 | 2018 | 6.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Disease Models, Animal | 0 | 2010 | 2010 | 14.0 | low | 0 | 0 | 0 | 1 | 0 | 0 | |
Fibrosis | 0 | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Hypertension | 0 | 2010 | 2014 | 12.7 | low | 0 | 0 | 0 | 2 | 1 | 0 | |
Hypertension, Pulmonary | 0 | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Hypertension, Renal | 0 | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Hypertrophy | 0 | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Hypertrophy, Right Ventricular | 0 | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Hypoxia | 0 | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Inflammation | 0 | 2012 | 2018 | 9.0 | low | 0 | 0 | 0 | 0 | 2 | 0 | |
Innate Inflammatory Response | 0 | 2012 | 2018 | 9.0 | low | 0 | 0 | 0 | 0 | 2 | 0 | |
Kidney Diseases | 0 | 2014 | 2014 | 10.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Neoplasms | 0 | 2019 | 2019 | 5.0 | low | 0 | 0 | 0 | 0 | 1 | 0 | |
Prostatic Neoplasms | 0 | 2008 | 2008 | 16.0 | low | 0 | 0 | 0 | 1 | 0 | 0 | |
Proteinuria | 0 | 2010 | 2010 | 14.0 | low | 0 | 0 | 0 | 1 | 0 | 0 | |
Pulmonary Hypertension | 0 | 2012 | 2012 | 12.0 | low | 0 | 0 | 0 | 0 | 1 | 0 |
Article | Year |
---|---|
CYP1B1 inhibition attenuates doxorubicin-induced cardiotoxicity through a mid-chain HETEs-dependent mechanism. Pharmacological research, , Volume: 105 | 2016 |
Article | Year |
---|---|
Quantification of oxyresveratrol analog trans-2,4,3',5'-tetramethoxystilbene in rat plasma by a rapid HPLC method: application in a pre-clinical pharmacokinetic study. Biomedical chromatography : BMC, , Volume: 24, Issue:12 | 2010 |
Article | Year |
---|---|
Tetramethoxystilbene-Loaded Liposomes Restore Reactive-Oxygen-Species-Mediated Attenuation of Dilator Responses in Rat Aortic Vessels Ex vivo. Molecules (Basel, Switzerland), , Nov-29, Volume: 24, Issue:23 | 2019 |
Quantification of oxyresveratrol analog trans-2,4,3',5'-tetramethoxystilbene in rat plasma by a rapid HPLC method: application in a pre-clinical pharmacokinetic study. Biomedical chromatography : BMC, , Volume: 24, Issue:12 | 2010 |
Article | Year |
---|---|
Quantification of oxyresveratrol analog trans-2,4,3',5'-tetramethoxystilbene in rat plasma by a rapid HPLC method: application in a pre-clinical pharmacokinetic study. Biomedical chromatography : BMC, , Volume: 24, Issue:12 | 2010 |