16-Ketoestradiol

16-Ketoestradiol.svg skin-invert-image 200px 3,17β-Dihydroxyestra-1,3,5(10)-trien-16-one (1R,3aS,3bR,9bS,11aS)-1,7-Dihydroxy-11a-methyl-1,3,3a,3b,4,5,9b,10,11,11a-decahydro-2H-cyclopenta[a]phenanthren-2-one 17-Oxoestradiol; 17-Oxo-estradiol; 17-Keto-E2; 17-Oxo-E2; 16-Oxo-estra-1,3,5(10)-trien-3,17β-diol; NSC-51169 566-75-6 34165 1627347 59791 1S/C18H22O3/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/h3,5,8,13-15,17,19,21H,2,4,6-7,9H2,1H3/t13-,14-,15+,17+,18+/m1/s1 KJDGFQJCHFJTRH-YONAWACDSA-N C14383 66417 C[C@]12CC[C@H]3[C@H]([C@@H]1CC(=O)[C@@H]2O)CCC4=C3C=CC(=C4)O 6CE096RR70 18 22 3 16-Ketoestradiol (16-keto-E2, 16-oxoestradiol, or 16-oxo-E2) is an endogenous estrogen related to 16-ketoestrone.https://hmdb.ca/metabolites/HMDB0000406 Human Metabolome Database: Showing metabocard for 16-Ketoestradiol (HMDB0000406)Breuer Heinz The Metabolism of the Natural Estrogens Vitamins & Hormones 20 1962 285–335 0083-6729 10.1016/S0083-6729(08)60720-7 9780127098203 Huggins C, Jensen EV The depression of estrone-induced uterine growth by phenolic estrogens with oxygenated functions at positions 6 or 16: the impeded estrogens J. Exp. Med. 102 3 335–46 September 1955 13252187 2136510 10.1084/jem.102.3.335 16-Ketoestrone is a very weak estrogen with only 1/1000 the estrogenic potency of estradiol in the uterus. It is a so-called "short-acting" or "impeded" estrogen, similarly to estriol and dimethylstilbestrol. Clark JH, Paszko Z, Peck EJ Nuclear binding and retention of the receptor estrogen complex: relation to the agonistic and antagonistic properties of estriol Endocrinology 100 1 91–6 January 1977 830547 10.1210/endo-100-1-91 Clark JH, Hardin JW, McCormack SA Mechanism of action of estrogen agonists and antagonists J. Anim. Sci. 49 46–65 1979 Suppl 2 400777 10.1093/ansci/49.supplement_ii.46 Lunan CB, Klopper A Antioestrogens. A review Clin. Endocrinol. (Oxf) 4 5 551–72 September 1975 170029 10.1111/j.1365-2265.1975.tb01568.x 9628572 free Clark JH, Markaverich BM The agonistic and antagonistic effects of short acting estrogens: a review Pharmacol. Ther. 21 3 429–53 1983 6356176 10.1016/0163-7258(83)90063-3 Clark JH, Markaverich BM The agonistic and antagonistic actions of estriol J. Steroid Biochem. 20 4B 1005–13 April 1984 6202959 10.1016/0022-4731(84)90011-6 See also 16-Ketoestrone References Category:Secondary alcohols Category:Estranes Category:Estrogens Category:Human metabolites Category:Hydroxyarenes