1-Keto-1,2,3,4-tetrahydrophenanthrene (original) (raw)
1-Keto-1,2,3,4-tetrahydrophenanthrene (THP-1), or 1,2,3,4-tetrahydrophenanthren-1-one, is a synthetic steroid-like compound which was reported to be the first synthetic estrogen, or the first synthetic compound identified with estrogenic activity. It was first synthesized in 1933 by Cook et al. and was tested due to its similarity to the presumed chemical structure of estrone. Upon reassessment many decades later, the compound was found to bind only weakly to the estrogen receptors, and, unexpectedly, did not actually have functional activity as an estrogen or antiestrogen in vitro or in vivo. It did, however, show some androgenic and antiandrogenic activity in vitro.
| Property | Value |
|---|---|
| dbo:abstract | 1-Keto-1,2,3,4-tetrahydrophenanthrene (THP-1), or 1,2,3,4-tetrahydrophenanthren-1-one, is a synthetic steroid-like compound which was reported to be the first synthetic estrogen, or the first synthetic compound identified with estrogenic activity. It was first synthesized in 1933 by Cook et al. and was tested due to its similarity to the presumed chemical structure of estrone. Upon reassessment many decades later, the compound was found to bind only weakly to the estrogen receptors, and, unexpectedly, did not actually have functional activity as an estrogen or antiestrogen in vitro or in vivo. It did, however, show some androgenic and antiandrogenic activity in vitro. (en) |
| dbo:casNumber | 573-22-8 |
| dbo:chEMBL | 88130 |
| dbo:fdaUniiCode | RAN6R458LN |
| dbo:pubchem | 225683 |
| dbo:thumbnail | wiki-commons:Special:FilePath/THP-1.svg?width=300 |
| dbo:wikiPageID | 51811965 (xsd:integer) |
| dbo:wikiPageLength | 3378 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1108878375 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Androgen dbr:Antiestrogen dbr:In_vitro dbr:In_vivo dbr:Intrinsic_activity dbc:Ketones dbc:Phenanthrenes dbc:Substances_discovered_in_the_1930s dbc:Synthetic_estrogens dbr:Chemical_compound dbr:Chemical_structure dbr:Antiandrogen dbr:Steroid dbr:Estrin_(compound) dbr:Estrogen_receptor dbr:Estrone dbr:Synthetic_compound |
| dbp:c | 14 (xsd:integer) |
| dbp:casNumber | 573 (xsd:integer) |
| dbp:chembl | 88130 (xsd:integer) |
| dbp:chemspiderid | 196209 (xsd:integer) |
| dbp:h | 12 (xsd:integer) |
| dbp:iupacName | 34 (xsd:integer) |
| dbp:o | 1 (xsd:integer) |
| dbp:pubchem | 225683 (xsd:integer) |
| dbp:smiles | C1CC2=CCC1 (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | KBARGPSSEIXDQU-UHFFFAOYSA-N (en) |
| dbp:synonyms | THP-1; 1,2,3,4-Tetrahydrophenanthren-1-one (en) |
| dbp:unii | RAN6R458LN (en) |
| dbp:width | 225 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Drugbox dbt:Estrogen_receptor_modulators dbt:Genito-urinary-drug-stub dbt:Reflist dbt:Short_description dbt:Steroid-stub dbt:Cascite dbt:Fdacite |
| dcterms:subject | dbc:Ketones dbc:Phenanthrenes dbc:Substances_discovered_in_the_1930s dbc:Synthetic_estrogens |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:Drug |
| rdfs:comment | 1-Keto-1,2,3,4-tetrahydrophenanthrene (THP-1), or 1,2,3,4-tetrahydrophenanthren-1-one, is a synthetic steroid-like compound which was reported to be the first synthetic estrogen, or the first synthetic compound identified with estrogenic activity. It was first synthesized in 1933 by Cook et al. and was tested due to its similarity to the presumed chemical structure of estrone. Upon reassessment many decades later, the compound was found to bind only weakly to the estrogen receptors, and, unexpectedly, did not actually have functional activity as an estrogen or antiestrogen in vitro or in vivo. It did, however, show some androgenic and antiandrogenic activity in vitro. (en) |
| rdfs:label | 1-Keto-1,2,3,4-tetrahydrophenanthrene (en) |
| owl:sameAs | yago-res:1-Keto-1,2,3,4-tetrahydrophenanthrene wikidata:1-Keto-1,2,3,4-tetrahydrophenanthrene https://global.dbpedia.org/id/2cyDw |
| prov:wasDerivedFrom | wikipedia-en:1-Keto-1,2,3,4-tetrahydrophenanthrene?oldid=1108878375&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/THP-1.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:1-Keto-1,2,3,4-tetrahydrophenanthrene |
| is dbo:wikiPageRedirects of | dbr:C14H12O dbr:1-keto-1,2,3,4-tetrahydrophenanthrene dbr:1,2,3,4-Tetrahydrophenanthren-1-one dbr:1,2,3,4-tetrahydrophenanthren-1-one |
| is dbo:wikiPageWikiLink of | dbr:C14H12O dbr:C14H12O2 dbr:1-keto-1,2,3,4-tetrahydrophenanthrene dbr:THP-1 dbr:Estrin_(compound) dbr:1,2,3,4-Tetrahydrophenanthren-1-one dbr:1,2,3,4-tetrahydrophenanthren-1-one |
| is foaf:primaryTopic of | wikipedia-en:1-Keto-1,2,3,4-tetrahydrophenanthrene |
