Contents

3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol

Chemical compound

3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol

Clinical data
Other names	3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
Identifiers
IUPAC name (8R,9S,10S,13S,14S,17S)-10-Ethenyl-3,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-ol
PubChem CID	24896626
ChemSpider	23306322
ChEMBL	ChEMBL398456
CompTox Dashboard (EPA)	DTXSID201250844
Chemical and physical data
Formula	C21H30O
Molar mass	298.470 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(CC1)C=C)C)O
InChI InChI=1S/C21H30O/c1-4-21-12-9-14(2)13-15(21)5-6-16-17-7-8-19(22)20(17,3)11-10-18(16)21/h4-5,13,16-19,22H,1,6-12H2,2-3H3/t16-,17-,18-,19-,20-,21-/m0/s1 Key:PPGVWCDLIZEUNC-PXQJOHHUSA-N

3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol is a synthetic, steroidal estrogen and a selective agonist of the ERβ.^[1] It was discovered serendipitously and was the lead compound among a series of androsta-3,5-dienes as ERβ ligands.^[1][2] Its affinity (IC₅₀) for the ERβ was found to be 9 nM and it showed 62- and 160-fold binding selectivity for this receptor over the ARTooltip androgen receptor and the ERα, respectively.^[1] The EC₅₀ of the compound for the ERβ was found to be 69 nM and its intrinsic activity was 92% (relative to that of estradiol).^[1] As such, it is a potent ERβ agonist with high affinity and selectivity.^[1]

References[edit]

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