(S,S)-Tetrahydrochrysene

(S,S)-Tetrahydrochrysene ((S,S)-THC) is a steroid-like nonsteroidal estrogen and agonist of both the estrogen receptors, ERα and ERβ.[1] It is an enantiomer of (R,R)-tetrahydrochrysene ((R,R)-THC), which, in contrast, is an ERβ silent antagonist and ERα agonist with 10-fold selectivity (i.e., affinity) for the ERβ over the ERα and with 20-fold greater affinity for the ERβ relative to that of (S,S)-THC.[1]

(S,S)-Tetrahydrochrysene
Clinical data
Other names(S,S)-THC
Identifiers
IUPAC name
  • (S,S)-5,11-Diethyl-5,6,11,12-tetrahydro-2,8-chrysenediol
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC22H24O2
Molar mass320.432 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@H]1CC2=C(C=CC(=C2)O)C3=C1C4=C(C[C@@H]3CC)C=C(C=C4)O
InChI
  • InChI=1S/C22H24O2/c1-3-13-9-15-11-17(23)6-8-20(15)22-14(4-2)10-16-12-18(24)5-7-19(16)21(13)22/h5-8,11-14,23-24H,3-4,9-10H2,1-2H3/t13-,14-/m0/s1
  • Key:MASYAWHPJCQLSW-KBPBESRZSA-N

See also

References
  1. Sun J, Meyers MJ, Fink BE, Rajendran R, Katzenellenbogen JA, Katzenellenbogen BS (1999). "Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-alpha or estrogen receptor-beta". Endocrinology. 140 (2): 800–4. doi:10.1210/endo.140.2.6480. PMID 9927308.


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