BMS 189453: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
BMS-453 : A member of the class of dihydronaphthalenes that is 1,2-dihydronaphthalene which is substituted at positions 1, 1, 4, and 6 by methyl, methyl, phenyl, and 2-(p-carboxyphenyl)vinyl groups, respectively (the E isomer). It is a potent retinoic acid receptor gamma (RARbeta) agonist that acts as an antagonist against RARalpha and RARgamma. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 9875424 |
| CHEMBL ID | 2385268 |
| CHEBI ID | 90739 |
| SCHEMBL ID | 6755036 |
| SCHEMBL ID | 6755033 |
| MeSH ID | M0355648 |
| Synonym |
|---|
| bms453 |
| bms-453 |
| bms 453 |
| 4-[(e)-2-(5,5-dimethyl-8-phenyl-6h-naphthalen-2-yl)ethenyl]benzoic acid |
| bms 189453 |
| bms-189453 |
| m531iv9e0v , |
| unii-m531iv9e0v |
| benzoic acid, 4-(2-(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl)-, (e)- |
| 166977-43-1 |
| CHEMBL2385268 , |
| benzoic acid, 4-((1e)-2-(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl)- |
| 164108-16-1 |
| SCHEMBL6755036 |
| SCHEMBL6755033 |
| 4-[(1e)-2-(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl]-benzoic acid |
| AKOS024457612 |
| bms-189453, >=98% (hplc) |
| J-010327 |
| bdbm50178961 |
| (e)-4-(2-(5,5-dimethyl-8-phenyl-5,6-dihydronaphthalen-2-yl)vinyl)benzoic acid , |
| bms 453;bms453;bms 189453;bms-189453;bms189453 |
| AS-16498 |
| (e)-4-[2-(5,5-dimethyl-8-phenyl-5,6-dihydronaphthalen-2-yl)vinyl]benzoic acid |
| benzoic acid, 4-[(1e)-2-(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl]- |
| NCGC00370835-06 |
| EX-A4818 |
| Q27283498 |
| 4-[(e)-2-(5,5-dimethyl-8-phenyl-5,6-dihydronaphthalen-2-yl)vinyl]benzoic acid |
| CHEBI:90739 |
| bms189453 |
| e)-4-[2-(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl]-benzoic acid |
| HY-100608 |
| A899389 |
| CS-0019762 |
| (e)-4-(2-(5,5-dimethyl-8-phenyl-5,6-dihydronaphthalen-2-yl)vinyl)benzoicacid |
| AC-36599 |
| 4-[(1e)-2-(5,6-dihydro-5,5-dimethyl -8-phenyl-2-naphthalenyl)ethenyl]-benzoic acid |
| Excerpt | Relevance | Reference |
|---|---|---|
| "5 to 100 mg/kg for 1 week, only minimal testicular changes occurred at all doses, shortly after the dosing period." | ( BMS-189453, a novel retinoid receptor antagonist, is a potent testicular toxin. Bregman, CL; Buroker, RA; Clay, RJ; Frantz, JD; Mezza, LE; Schulze, GE, 2001) | 0.31 |
| " Enhanced efficacy and a lengthened infertility period with full recovery of spermatogenesis were observed using systematically modified dosing regimens." | ( Oral administration of a retinoic Acid receptor antagonist reversibly inhibits spermatogenesis in mice. Chung, SS; Griffey, SM; Reczek, PR; Roberts, SS; Wang, X; Wolgemuth, DJ, 2011) | 0.37 |
| " Similarly, oral dosing of WIN 18,446, which inhibits testicular retinoic acid biosynthesis, effectively contracepts rabbits." | ( New approaches to male non-hormonal contraception. Amory, JK; Nya-Ngatchou, JJ, 2013) | 0.39 |
| Role | Description |
|---|---|
| retinoic acid receptor beta agonist | Any retinoic acid receptor (RAR) agonist with specificity for RARbeta. |
| retinoic acid receptor gamma antagonist | A retinoic acid receptor antagonist that antagonises retinoic acid receptor gamma. |
| retinoic acid receptor alpha antagonist | A retinoic acid receptor antagonist that antagonises retinoic acid receptor alpha. |
| teratogenic agent | A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. |
| [role 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] | |
| Class | Description |
|---|---|
| dihydronaphthalenes | Any carbobycyclic compound that is a dihydronaphthalene or a compound obtained from a dihydronaphthalene by formal substitution of one or more hydrogens. |
| benzoic acids | Any aromatic carboxylic acid that consists of benzene in which at least a single hydrogen has been substituted by a carboxy group. |
| stilbenoid | Any olefinic compound characterised by a 1,2-diphenylethylene backbone. |
| [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) |
|---|---|---|---|---|---|---|---|
| Retinoic acid receptor alpha | Homo sapiens (human) | Ki | 0.0077 | 0.0010 | 0.9485 | 6.5000 | AID1306247 |
| Retinoic acid receptor beta | Homo sapiens (human) | Ki | 0.0167 | 0.0007 | 1.5673 | 9.9010 | AID1306248 |
| Retinoic acid receptor gamma | Homo sapiens (human) | Ki | 0.0173 | 0.0000 | 1.9975 | 10.0000 | AID1306249 |
| Retinoic acid receptor RXR-alpha | Homo sapiens (human) | Ki | 0.0139 | 0.0004 | 0.5692 | 7.6320 | AID1306247; AID1306248; AID1306249 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Retinoic acid receptor gamma | Homo sapiens (human) | Kb | 0.0185 | 0.0185 | 0.0185 | 0.0185 | AID1306245 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID748277 | Metabolic stability in CD1 mouse liver microsomes assessed as parent compound remaining at 10'-6 M after 60 mins | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID1306247 | Displacement of [3H]-TTNPB from RARalpha/RXRalpha (unknown origin) expressed in baculovirus expression system by scintillation proximity assay | 2016 | Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14 | Identification of potent and selective retinoic acid receptor gamma (RARγ) antagonists for the treatment of osteoarthritis pain using structure based drug design. |
| AID1821793 | Solubility of the compound in DSF buffer in presence of 2% DMSO | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Design of a Potent TLX Agonist by Rational Fragment Fusion. |
| AID1821798 | Agonist activity at human Gal4-fused TLX LBD expressed in human HEK293T cells coexpressing Gal4-VP16 assessed as repressor activity of receptor by measuring decrease in reporter activity at 0.03 to 30 uM measured after 14 hrs by Dual-Glo Luciferase assay | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Design of a Potent TLX Agonist by Rational Fragment Fusion. |
| AID748270 | Effect on spermatogenesis in CD1 mouse assessed as disruptive effect on spermatid alignment at 2 to 10 mg/kg, po for 7 days | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID1821800 | Agonist activity at human full length Gal4-fused TLX transfected in human HEK293T cells coexpressing pFR-TAE-Luc assessed as repressor activity of receptor by measuring decrease in reporter activity at 0.03 to 30 uM by dual-glo luciferase assay | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Design of a Potent TLX Agonist by Rational Fragment Fusion. |
| AID1306249 | Displacement of [3H]-TTNPB from RARgamma/RXRalpha (unknown origin) expressed in baculovirus expression system by scintillation proximity assay | 2016 | Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14 | Identification of potent and selective retinoic acid receptor gamma (RARγ) antagonists for the treatment of osteoarthritis pain using structure based drug design. |
| AID748281 | Permeability from apical to basolateral side in human Caco2 cells assessed as drug recovery at 10'-5 M at pH 6.5 to 7.4 | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID748283 | Drug recovery in CD1 mouse plasma 10'-5 M | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID1821785 | Cytotoxicity against human HEK293T cells assessed as reduction in cell viability at >10 uM incubated for 24 hrs by WST-1 assay | 2022 | Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3 | Design of a Potent TLX Agonist by Rational Fragment Fusion. |
| AID748287 | Aqueous solubility of the compound in PBS at pH 7.4 | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID748269 | Effect on spermatogenesis in CD1 mouse assessed as sperm release into testicular lumen at 2 to 10 mg/kg, po for 7 days | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID1306246 | Antagonist activity at RARgamma-LBD (unknown origin) expressed in HEK-293 cells assessed as inhibition of ATRA induced Gal4/luciferase gene expression after 24 hrs relative to ATRA | 2016 | Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14 | Identification of potent and selective retinoic acid receptor gamma (RARγ) antagonists for the treatment of osteoarthritis pain using structure based drug design. |
| AID748286 | Partition coefficient, log D of the compound in n-octanol-PBS at 10'-4 M at pH 7.4 | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID748288 | Chemical stability of the compound by HPLC-MS analysis | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID748284 | Permeability from apical to basolateral side in human Caco2 cells at 10'-5 M at pH 6.5 to 7.4 | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID1306248 | Displacement of [3H]-TTNPB from RARbeta/RXRalpha (unknown origin) expressed in baculovirus expression system by scintillation proximity assay | 2016 | Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14 | Identification of potent and selective retinoic acid receptor gamma (RARγ) antagonists for the treatment of osteoarthritis pain using structure based drug design. |
| AID1306245 | Antagonist activity at RARgamma-LBD (unknown origin) expressed in HEK-293 cells assessed as inhibition of ATRA induced Gal4/luciferase gene expression after 24 hrs | 2016 | Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14 | Identification of potent and selective retinoic acid receptor gamma (RARγ) antagonists for the treatment of osteoarthritis pain using structure based drug design. |
| AID748285 | Plasma protein binding in CD1 mouse at 10'-5 M | 2013 | ACS medicinal chemistry letters, May-09, Volume: 4, Issue:5 | Pharmacological activity of retinoic acid receptor alpha-selective antagonists |
| AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | 2014 | Journal of biomolecular screening, Jul, Volume: 19, Issue:6 | A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum. |
| AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | |||
| [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 | 1 (4.17) | 18.2507 |
| 2000's | 8 (33.33) | 29.6817 |
| 2010's | 11 (45.83) | 24.3611 |
| 2020's | 4 (16.67) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (19.75) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (3.85%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 25 (96.15%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||