(R,R)-Tetrahydrochrysene

(R,R)-Tetrahydrochrysene
Systematic (IUPAC) name

(5R,11R)-5,11-Diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol
Identifiers
CAS Number	138090-06-9
PubChem	CID 446849
ChemSpider	394097
Chemical data
Formula	C₂₂H₂₄O₂
Molar mass	320.42476 g/mol
SMILES CCC1CC2=C(C=CC(=C2)O)C3=C1C4=C(CC3CC)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-/m1/s1 Key:MASYAWHPJCQLSW-ZIAGYGMSSA-N

(R,R)-Tetrahydrochrysene ((R,R)-THC) is a drug used to study the estrogen receptors (ERs) in scientific research. It is an ERβ antagonist and an ERα agonist with 10-fold higher affinity for ERβ relative to ERα.^[1]^[2] (R,R)-THC is a silent antagonist of ERβ,^[3] and, uniquely relative to other known ERβ antagonists, a passive antagonist of the receptor.^[2]

(S,S)-Tetrahydrochrysene ((S,S)-THC) also binds to the ERs, but in contrast to (R,R)-THC, (S,S)-THC is an agonist of both ERα and ERβ and has 20-fold lower affinity for ERβ relative to (R,R)-THC.^[3]

References

↑ Ying Chen (2008). The Role of Steroids in the Regulation of Oocyte Cyst Breakdown and Primordial Follicle Assembly in the Neonatal Mouse Ovary. ProQuest. pp. 101–. ISBN 978-0-549-74620-1.
1 2 Shiau AK, Barstad D, Radek JT, Meyers MJ, Nettles KW, Katzenellenbogen BS, Katzenellenbogen JA, Agard DA, Greene GL (2002). "Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism". Nat. Struct. Biol. 9 (5): 359–64. doi:10.1038/nsb787. PMID 11953755.
1 2 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.

Estrogenics

Receptor
(ligands)

ER (α, β)

Agonists	(R)-DPN (S)-DPN (R,R)-THC (S,S)-THC 2,8-DHHHC 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8β-VE₂ 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-IE₂ 16α-LE₂ (Cpd1471) Δ⁴-Androstenedione Δ⁵-Androstenediol 17α-Estradiol (alfatradiol) 17β-Estradiol (estradiol) Alestramustine Almestrone Anabolic steroids (prodrugs; e.g., testosterone, metandienone (methandrostenolone), others) Anethole Anol Atrimustine Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Cloxestradiol Conjugated equine estrogens (e.g., sodium equilin sulfate, sodium equilenin sulfate) Coumestans (e.g., coumestrol, psoralidin) DHEA DHEA-S Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol dipropionate Diosgenin Doisynoestrol (fenocycline) Doisynolic acid DY-131 (GSK-9089) Endosulfan Epiestriol Epimestrol ERB-196 (WAY-202196) Esterified estrogens (e.g., estrone sulfate, equilin sulfate, equilenin sulfate) Estetrol Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol stearate Estradiol succinate Estradiol undecylate Estradiol valerate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol succinate Estriol tripropionate Estrobin (DBE) Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Estropronicate Etamestrol (eptamestrol) Ethinyl estradiol Ethinyl estradiol 3-isopropylsulfonate Etynodiol diacetate Fenarimol Fenestrel FERb 033 Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol Furostilbestrol GSK-4716 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Hydroxyestrone diacetate Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestranol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methylestradiol Miroestrol Moxestrol Nilestriol Noretynodrel Orestrate Paroxypropione Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Promestriene Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol)) Quadrosilan Quinestradol Quinestrol SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) WAY-166818 WAY-200070

Mixed (SERMs)	2-Hydroxyestrone 27-Hydroxycholesterol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Broparestrol Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW5638 Idoxifene Lasofoxifene Levormeloxifene Menerba Mepitiostane Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Sivifene Tamoxifen TAS-108 Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC Fulvestrant ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 XCT-790 ZK-164015 ZK-191703

GPER

Agonists	7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Fulvestrant (ICI-182,780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCB (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalenone

Antagonists	Estriol G-15 G-36 MIBE

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, aromatase, and 27-hydroxylase).

Others

Precursors	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate 16-Hydroxy-DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione 16-Hydroxyandrostenedione Testosterone

Indirect	Antigonadotropins (e.g., androgens, estrogens, progestogens, prolactin) Calcitriol (vitamin D) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Glucocorticoids • Mineralocorticoids • Progestogenics

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