16-Ketoestradiol

16-Ketoestradiol (16-keto-E2), or 16-oxoestradiol (16-oxo-E2), is an endogenous estrogen related to 16-ketoestrone.[1][2][3] 16-Ketoestrone is a very weak estrogen with only 1/1000th the estrogenic potency of estradiol in the uterus.[3] It is a so-called "short-acting" or "impeded" estrogen, similarly to estriol and dimethylstilbestrol.[4][5][6][7][8]

16-Ketoestradiol
Names
IUPAC name
(8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthren-16-one
Other names
17-Oxoestradiol; 17-Oxo-estradiol; 17-Keto-E2; 17-Oxo-E2; 3,17β-Dihydroxyestra-1,3,5(10)-trien-16-one; 16-Oxo-estra-1,3,5(10)-trien-3,17β-diol; NSC-51169
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
Properties
C18H22O3
Molar mass 286.371 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. https://hmdb.ca/metabolites/HMDB0000406
  2. Breuer, Heinz (1962). The Metabolism of the Natural Estrogens. Vitamins and Hormones : Advances in Research and Applications. Vitamins & Hormones. 20. pp. 285–335. doi:10.1016/S0083-6729(08)60720-7. ISBN 9780127098203. ISSN 0083-6729.
  3. 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. Clark JH, Paszko Z, Peck EJ (January 1977). "Nuclear binding and retention of the receptor estrogen complex: relation to the agonistic and antagonistic properties of estriol". Endocrinology. 100 (1): 91–6. doi:10.1210/endo-100-1-91. PMID 830547.
  5. Clark JH, Hardin JW, McCormack SA (1979). "Mechanism of action of estrogen agonists and antagonists". J. Anim. Sci. 49 Suppl 2: 46–65. doi:10.1093/ansci/49.supplement_ii.46. PMID 400777.
  6. Lunan CB, Klopper A (September 1975). "Antioestrogens. A review". Clin. Endocrinol. (Oxf). 4 (5): 551–72. doi:10.1111/j.1365-2265.1975.tb01568.x. PMID 170029. S2CID 9628572.
  7. Clark JH, Markaverich BM (1983). "The agonistic and antagonistic effects of short acting estrogens: a review". Pharmacol. Ther. 21 (3): 429–53. doi:10.1016/0163-7258(83)90063-3. PMID 6356176.
  8. Clark JH, Markaverich BM (April 1984). "The agonistic and antagonistic actions of estriol". J. Steroid Biochem. 20 (4B): 1005–13. doi:10.1016/0022-4731(84)90011-6. PMID 6202959.



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