Compound: D5KU4JGS7Y
SMILES: Oc1cc2c([C@@H]3[C@](C=C)([C@H]4[C@]([C@@H](O)CC4)(C)CC3)CC2)cc1
InChIKey: NMCRWZRLOOYKTG-SWBPCFCJSA-N
Synonyms: D5KU4JGS7Y, 8beta-VE2, UNII-D5KU4JGS7Y, 8beta-Vinylestra-1,3,5(10)-triene-3,17beta-ol, 367929-02-0, Estra-1,3,5(10)-triene-3,17-diol, 8-ethenyl-, (17beta)-, (17beta)-8-Ethenylestra-1,3,5(10)-triene-3,17-diol, (8S,9S,13S,14S,17S)-8-Ethenyl-13-methyl-7,9,11,12,14,15,16,17-octahydro-6H-cyclopenta(a)phenanthrene-3,17-diol, BAY-257, (8S,9S,13S,14S,17S)-8-ethenyl-13-methyl-7,9,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol, 8.BETA.-VE2, SCHEMBL1826307, CHEMBL5303353, DTXSID801047801, 8-vinylestra-1,3,5(10)-triene-3,17b-diol, 8.BETA.-VINYLESTRA-1,3,5(10)-TRIENE-3,17.BETA.-OL, (17.BETA.)-8-ETHENYLESTRA-1,3,5(10)-TRIENE-3,17-DIOL
Theoretical properties:
molecular_formula: C20H26O2
molecular_weight: 298.4 g/mol
exact_mass: 298.193280068 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 40.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": null, "chebi": null, "chembl": "Unnamed Compound is a unknown type listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "8\u03b2-VE2, or 8\u03b2-vinylestradiol, also known as 8\u03b2-vinylestra-1,3,5(10)-triene-3\u03b2,17\u03b2-diol, is a synthetic estrogen featuring an estradiol core. It is a highly potent and selective agonist of the ER\u03b2 that is used in scientific research to study the function of the ER\u03b2. It has 190-fold higher potency in transactivation assays of the ER\u03b2 relative to the ER\u03b1 and 93- (rat) and 180-fold (human) preference in binding affinity for the ER\u03b2 over the ER\u03b1.\nIn rodents, 8\u03b2-VE2 stimulates follicular growth and to a comparable extent as estradiol, whereas the highly ER\u03b1-selective agonist 16\u03b1-LE2 has no effect on ovarian follicle development, indicating that the ER\u03b2 and not the ER\u03b1 is involved in the effects of estrogen on ovarian follicles. In contrast, 16\u03b1-LE2 stimulates uterine weight, whereas 8\u03b2-VE2 has no effect, indicating that the ER\u03b1 and not the ER\u03b2 is involved in the effects of estrogen on the uterus.\nResearch has determined through experimental rodent studies with estradiol, 16\u03b1-LE2, and 8\u03b2-VE2 that the positive, protective effects of estrogens on bone formation resorption and bone mineral density are mediated via the ER\u03b1, whereas the ER\u03b2 does not appear to be involved. On the other hand, while both ER\u03b1 and ER\u03b2 are expressed in skeletal muscle, it was found that ER\u03b2 is the predominant ER subtype that is responsible for estrogen stimulation of skeletal muscle growth and regeneration. Moreover, similarly to testosterone, 8\u03b2-VE2 has anabolic effects in skeletal muscle and significantly increases muscle mass as well as produces muscle hypertrophy in rats. In contrast to testosterone however, 8\u03b2-VE2 shows no androgenic effects. The effects of 8\u03b2-VE2 and ER\u03b2 may be mediated, in part, by local stimulation of insulin-like growth factor 1 (IGF-1)-induced myogenic protein synthesis, as 8\u03b2-VE2 has been found to strongly induce expression of IGF-1 in the rat levator ani muscle."}