16-Ketoestrone

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16-Ketoestrone
16-Ketoestrone.svg
Names
Preferred IUPAC name
(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
Other names
16-Oxoestrone; 16-Keto-E1; 16-Oxo-E1; 3-Hydroxyestra-1,3,5(10)-triene-16,17-dione; NSC-60462
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=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
    Key: ANPHVANSJXDRTP-BSXFFOKHSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC(=O)C2=O)CCC4=C3C=CC(=C4)O
Properties
C18H20O3
Molar mass 284.355 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

16-Ketoestrone (16-keto-E1, or 16-oxoestrone, or 16-oxo-E1) is an endogenous estrogen related to 16α-hydroxyestrone and 16β-hydroxyestrone.[1][2][3] 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.[3] 16-Ketoestrone has been reported to act as an inhibitor of 17β-hydroxysteroid dehydrogenases.[4] 16-Ketoestrone can be converted by 16α-hydroxysteroid dehydrogenase into estriol in the body.[1][5]

References[edit]

  1. ^ a b Breuer, Heinz (1962). "The Metabolism of the Natural Estrogens". Vitamins & Hormones. 20: 285–335. doi:10.1016/S0083-6729(08)60720-7. ISBN 9780127098203. ISSN 0083-6729.
  2. ^ Huffman MN, Lott MH (January 1948). "16-Substituted steroids; 16-keto-alpha-estradiol and 16-ketoestrone". J. Biol. Chem. 172 (1): 325–32. doi:10.1016/S0021-9258(18)35637-0. PMID 18920793.
  3. ^ a b Huggins C, Jensen EV (September 1955). "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. doi:10.1084/jem.102.3.335. PMC 2136510. PMID 13252187.
  4. ^ Inano H, Tamaoki B (January 1983). "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. doi:10.1111/j.1432-1033.1983.tb07104.x. PMID 6572146.
  5. ^ Stimmel BF, Grollman A, Huffman MN (June 1950). "The metabolism of 16-ketoestrone and 16-keto-estradiol in man". J. Biol. Chem. 184 (2): 677–85. doi:10.1016/S0021-9258(19)51001-8. PMID 15428451.