1-Keto-1,2,3,4-tetrahydrophenanthrene

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 xenoestrogen.^[1][2] It was first synthesized in 1933 by Cook et al. and was tested due to its similarity to the presumed chemical structure of estrone.^[1][2] 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.^[2] It did, however, show some mixed androgenic and antiandrogenic activity in vitro.^[2]

1-Keto-1,2,3,4-tetrahydrophenanthrene

Clinical data
Other names	THP-1; 1,2,3,4-Tetrahydrophenanthren-1-one
Identifiers
IUPAC name 3,4-Dihydro-2H-phenanthren-1-one
CAS Number	573-22-8 Y
PubChem CID	225683
ChemSpider	196209
UNII	RAN6R458LN
ChEMBL	ChEMBL88130
CompTox Dashboard (EPA)	DTXSID50280072
Chemical and physical data
Formula	C14H12O
Molar mass	196.249 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CC2=C(C=CC3=CC=CC=C23)C(=O)C1
InChI InChI=1S/C14H12O/c15-14-7-3-6-12-11-5-2-1-4-10(11)8-9-13(12)14/h1-2,4-5,8-9H,3,6-7H2 Key:KBARGPSSEIXDQU-UHFFFAOYSA-N

See also

• Estrin