16-Ketoestradiol

16-Ketoestradiol (16-keto-E2, 16-oxoestradiol, or 16-oxo-E2) is an endogenous estrogen related to 16-ketoestrone.[1][2][3] 16-Ketoestrone is a very weak estrogen with only 1/1000 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
3,17β-Dihydroxyestra-1,3,5(10)-trien-16-one
Systematic IUPAC name
(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
Other names
17-Oxoestradiol; 17-Oxo-estradiol; 17-Keto-E2; 17-Oxo-E2; 16-Oxo-estra-1,3,5(10)-trien-3,17β-diol; NSC-51169
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=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
    Key: KJDGFQJCHFJTRH-YONAWACDSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC(=O)[C@@H]2O)CCC4=C3C=CC(=C4)O
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. "Human Metabolome Database: Showing metabocard for 16-Ketoestradiol (HMDB0000406)".
  2. Breuer, Heinz (1962). The Metabolism of the Natural Estrogens. Vitamins & Hormones. Vol. 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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