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17α-Epiestriol
Names
IUPAC name
Estra-1,3,5(10)-triene-3,16α,17α-triol
Systematic IUPAC name
(1S ,2R ,3aS ,3bR ,9bS ,11aS )-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H -cyclopenta[a ]phenanthrene-1,2,7-triol
Other names
17-Epiestriol; 16α-Hydroxy-17α-estradiol; 3,16α,17α-Trihydroxy-1,3,5(10)-estratriene
Identifiers
ChEBI
ChEMBL
ChemSpider
DrugBank
UNII
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17-,18+/m1/s1
Key: PROQIPRRNZUXQM-PNVOZDDCSA-N
CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
Properties
C 18 H 24 O 3
Molar mass
288.38136 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
17α-Epiestriol , or simply 17-epiestriol , also known as 16α-hydroxy-17α-estradiol or estra-1,3,5(10)-triene-3,16α,17α-triol , is a minor and weak endogenous estrogen , and the 17α-epimer of estriol (which is 16α-hydroxy-17β-estradiol).[ 1] [ 2] [ 3] It is formed from 16α-hydroxyestrone .[ 4] [ 5] In contrast to other endogenous estrogens like estradiol , 17α-epiestriol is a selective agonist of the ERβ .[ 6] It is described as a relatively weak estrogen, which is in accordance with its relatively low affinity for the ERα .[ 7] 17α-Epiestriol has been found to be approximately 400-fold more potent than estradiol in inhibiting tumor necrosis factor α (TNFα)-induced vascular cell adhesion molecule 1 (VCAM-1) expression in vitro .[ 8]
Relative affinities (%) of 17α-epiestriol and related steroids[ 9] [ 10] [ 11] [ 12]
Compound
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
Estradiol
2.6
7.9
100
0.6
0.13
8.7
<0.1
Alfatradiol
<1
<1
15
<1
<1
?
?
Estriol
<1
<1
15
<1
<1
?
?
16β-Epiestriol
<1
<1
20
<1
<1
?
?
17α-Epiestriol
<1
<1
31
<1
<1
?
?
Values are percentages (%). Reference ligands (100%) were progesterone for the PR Tooltip progesterone receptor , testosterone 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 .
^ Tewari AK (5 April 2013). Prostate Cancer: A Comprehensive Perspective . Springer Science & Business Media. pp. 373–. ISBN 978-1-4471-2864-9 .
^ Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice . Springer Science & Business Media. pp. 522–. ISBN 978-3-642-96158-8 .
^ Assali NS (3 September 2013). The Maternal Organism . Elsevier. pp. 341–. ISBN 978-1-4832-6380-9 .
^ Von Euler US (2 December 2012). Comparative Endocrinology . Elsevier Science. pp. 135–. ISBN 978-0-323-14609-8 .
^ Tietz NW (1 August 1976). Fundamentals of clinical chemistry . Saunders. p. 773. ISBN 978-0-7216-8866-4 .
^ Sherbet GV (26 July 2013). Therapeutic Strategies in Cancer Biology and Pathology . Elsevier. pp. 83–. ISBN 978-0-12-416590-8 .
^ Dorfman RI (22 October 2013). Steroidal Activity in Experimental Animals and Man . Elsevier Science. pp. 13–. ISBN 978-1-4832-7299-3 .
^ Mukherjee TK, Nathan L, Dinh H, Reddy ST, Chaudhuri G (April 2003). "17-epiestriol, an estrogen metabolite, is more potent than estradiol in inhibiting vascular cell adhesion molecule 1 (VCAM-1) mRNA expression" . The Journal of Biological Chemistry . 278 (14): 11746–52. doi :10.1074/jbc.M207800200 . PMID 12547825 .
^ Raynaud, J.P.; Ojasoo, T.; Bouton, M.M.; Philibert, D. (1979). "Receptor Binding as a Tool in the Development of New Bioactive Steroids" . Drug Design . pp. 169–214. doi :10.1016/B978-0-12-060308-4.50010-X . ISBN 9780120603084 .
^ Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies" . Cancer Research . 38 (11 Pt 2): 4186–98. PMID 359134 .
^ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry . 27 (1–3): 255–69. doi :10.1016/0022-4731(87)90317-7 . PMID 3695484 .
^ Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP (January 1980). "Steroid hormone receptors and pharmacology". Journal of Steroid Biochemistry . 12 : 143–57. doi :10.1016/0022-4731(80)90264-2 . PMID 7421203 .
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