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| 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 | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
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| Properties | |
| C18H24O3 | |
| Molar mass | 288.38136 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
17α-Epiestriol, or simply17-epiestriol, also known as16α-hydroxy-17α-estradiol orestra-1,3,5(10)-triene-3,16α,17α-triol, is a minor and weakendogenousestrogen, and the 17α-epimer ofestriol (which is 16α-hydroxy-17β-estradiol).[1][2][3] It is formed from16α-hydroxyestrone.[4][5] In contrast to other endogenous estrogens likeestradiol, 17α-epiestriol is a selectiveagonist of theERβ.[6] It is described as a relatively weak estrogen, which is in accordance with its relatively lowaffinity for theERα.[7] 17α-Epiestriol has been found to be approximately 400-fold more potent than estradiol in inhibitingtumor necrosis factor α (TNFα)-inducedvascular cell adhesion molecule 1 (VCAM-1)expressionin vitro.[8]
| Compound | PRTooltip Progesterone receptor | ARTooltip Androgen receptor | ERTooltip Estrogen receptor | GRTooltip Glucocorticoid receptor | MRTooltip Mineralocorticoid receptor | SHBGTooltip Sex hormone-binding globulin | CBGTooltip 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 (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,E2 for theERTooltip estrogen receptor,DEXATooltip dexamethasone for theGRTooltip glucocorticoid receptor,aldosterone for theMRTooltip mineralocorticoid receptor,DHTTooltip dihydrotestosterone forSHBGTooltip sex hormone-binding globulin, andcortisol forCBGTooltip Corticosteroid-binding globulin. | |||||||||
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