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3β-Hydroxytibolone Other names ORG-30126; 7α-Methyl-17α-ethynylestr-5(10)-ene-3β,17β-diol
(3S ,7R ,8R ,9S ,13S ,14S ,17R )-17-ethynyl-7,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H -cyclopenta[a ]phenanthrene-3,17-diol
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 21 H 30 O 2 Molar mass 314.469 g·mol−1 3D model (JSmol )
C[C@@H]1CC2=C(CC[C@@H](C2)O)[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C#C)O
InChI=1S/C21H30O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,15,17-19,22-23H,5-12H2,2-3H3/t13-,15+,17-,18+,19-,20+,21+/m1/s1
Key:YLEUWNOTNJZCBN-XAAPQAIWSA-N
3β-Hydroxytibolone (developmental code name ORG-30126 ) is a synthetic steroidal estrogen which was never marketed.[1] [2] Along with 3α-hydroxytibolone and δ4 -tibolone , it is a major active metabolite of tibolone , and 3α-hydroxytibolone and 3β-hydroxytibolone are thought to be responsible for the estrogenic activity of tibolone.[1] [2]
Relative affinities (%) of noretynodrel, tibolone, and metabolites
Compound
Code name
PR Tooltip Progesterone receptor
AR Tooltip Androgen receptor
ER Tooltip Estrogen receptor
GR Tooltip Glucocorticoid receptor
MR Tooltip Mineralocorticoid receptor
SHBG Tooltip Sex hormone-binding globulin
CBG Tooltip Corticosteroid binding globulin
Noretynodrel
–
6
0
2
0
0
0
0
Norethisterone (δ4 -NYD )
–
67–75
15
0
0–1
0–3
16
0
3α-Hydroxynoretynodrel
–
?
?
?
?
?
?
?
3β-Hydroxynoretynodrel
–
?
?
?
?
?
?
?
Ethinylestradiol
–
15–25
1–3
112
1–3
<1
0.18
<0.1
Tibolone (7α-Me-NYD )
ORG-OD-14
6
6
1
?
?
?
?
Δ4 -Tibolone
ORG-OM-38
90
35
1
0
2
1
0
3α-Hydroxytibolone
ORG-4094
0
3
4–6
0
?
?
?
3β-Hydroxytibolone
ORG-301260
0
4
3–29
0
?
?
?
7α-Methylethinylestradiol
–
?
?
?
?
?
?
?
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PR Tooltip progesterone receptor , metribolone for the AR Tooltip androgen receptor , E2 for the ER Tooltip estrogen receptor , DEXA Tooltip dexamethasone for the GR Tooltip glucocorticoid receptor , aldosterone for the MR Tooltip mineralocorticoid receptor , DHT Tooltip dihydrotestosterone for SHBG Tooltip sex hormone-binding globulin , and cortisol for CBG Tooltip Corticosteroid-binding globulin . Sources: See template.
Template:Absolute activities of tibolone and metabolites
References
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )
Lavender oil
Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g., cadmium )
Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )
Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )
Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )
Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )
Others (e.g., agnuside , rotundifuran )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown