16-Ketoestrone

16-Ketoestrone.svg skin-invert-image 200px 3-Hydroxyestra-1,3,5(10)-triene-16,17-dione (3aS,3bR,9bS,11aS)-7-Hydroxy-11a-methyl-3a,3b,4,5,9b,10,11,11a-octahydro-1H-cyclopenta[a]phenanthrene-1,2(3H)-dione 16-Oxoestrone; 16-Keto-E1; 16-Oxo-E1; NSC-60462 1228-73-5 34166 216072 1S/C18H20O3/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/h3,5,8,13-15,19H,2,4,6-7,9H2,1H3/t13-,14-,15+,18+/m1/s1 ANPHVANSJXDRTP-BSXFFOKHSA-N C14441 246876 C[C@]12CC[C@H]3[C@H]([C@@H]1CC(=O)C2=O)CCC4=C3C=CC(=C4)O 113V416QTU 18 20 3 16-Ketoestrone (16-keto-E1, or 16-oxoestrone, or 16-oxo-E1) is an endogenous estrogen related to 16α-hydroxyestrone and 16β-hydroxyestrone.Breuer Heinz The Metabolism of the Natural Estrogens 20 1962 285–335 0083-6729 Vitamins & Hormones 10.1016/S0083-6729(08)60720-7 9780127098203 Huffman MN, Lott MH 16-Substituted steroids; 16-keto-alpha-estradiol and 16-ketoestrone J. Biol. Chem. 172 1 325–32 January 1948 10.1016/S0021-9258(18)35637-0 18920793 https://www.jbc.org/content/172/1/325.short free 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 In contrast to 16α-hydroxyestrone and 16β-hydroxyestrone, but similarly to 16-ketoestradiol, 16-ketoestrone is a very weak estrogen with less than 1/1000 the estrogenic potency of estrone in the uterus. 16-Ketoestrone has been reported to act as an inhibitor of 17β-hydroxysteroid dehydrogenases. Inano H, Tamaoki B Affinity labeling of arginyl residues at the catalytic region of estradiol 17 beta-dehydrogenase from human placenta by 16-oxoestrone Eur. J. Biochem. 129 3 691–5 January 1983 6572146 10.1111/j.1432-1033.1983.tb07104.x free 16-Ketoestrone can be converted by 16α-hydroxysteroid dehydrogenase into estriol in the body. Stimmel BF, Grollman A, Huffman MN The metabolism of 16-ketoestrone and 16-keto-estradiol in man J. Biol. Chem. 184 2 677–85 June 1950 10.1016/S0021-9258(19)51001-8 15428451 free References Category:Diketones Category:Estranes Category:Estrogens Category:Human metabolites Category:Hydroxyarenes