16-Ketoestrone

{{Chembox

| ImageFile = 16-Ketoestrone.svg

| ImageSize = 200px

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| IUPACName = 3-Hydroxyestra-1,3,5(10)-triene-16,17-dione

| SystematicName = (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

| OtherNames = 16-Oxoestrone; 16-Keto-E1; 16-Oxo-E1; NSC-60462

| Section1 = {{Chembox Identifiers

| CASNo = 1228-73-5

| ChEBI = 34166

| ChEMBL =

| ChemSpiderID = 216072

| 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

| InChIKey = ANPHVANSJXDRTP-BSXFFOKHSA-N

| KEGG = C14441

| PubChem = 246876

| SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC(=O)C2=O)CCC4=C3C=CC(=C4)O

| UNII = 113V416QTU

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| Section2 = {{Chembox Properties

| C=18 | H=20 | O=3

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| Section3 = {{Chembox Hazards

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16-Ketoestrone (16-keto-E1, or 16-oxoestrone, or 16-oxo-E1) is an endogenous estrogen related to 16α-hydroxyestrone and 16β-hydroxyestrone.{{cite journal|last1=Breuer|first1=Heinz|title=The Metabolism of the Natural Estrogens|volume=20|year=1962|pages=285–335|issn=0083-6729|journal=Vitamins & Hormones|doi=10.1016/S0083-6729(08)60720-7|isbn=9780127098203}}{{cite journal | vauthors = Huffman MN, Lott MH | title = 16-Substituted steroids; 16-keto-alpha-estradiol and 16-ketoestrone | journal = J. Biol. Chem. | volume = 172 | issue = 1 | pages = 325–32 | date = January 1948 | doi = 10.1016/S0021-9258(18)35637-0 | pmid = 18920793 | url = https://www.jbc.org/content/172/1/325.short| doi-access = free }}{{cite journal | vauthors = Huggins C, Jensen EV | title = The depression of estrone-induced uterine growth by phenolic estrogens with oxygenated functions at positions 6 or 16: the impeded estrogens | journal = J. Exp. Med. | volume = 102 | issue = 3 | pages = 335–46 | date = September 1955 | pmid = 13252187 | pmc = 2136510 | doi = 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.{{cite journal | vauthors = Inano H, Tamaoki B | title = Affinity labeling of arginyl residues at the catalytic region of estradiol 17 beta-dehydrogenase from human placenta by 16-oxoestrone | journal = Eur. J. Biochem. | volume = 129 | issue = 3 | pages = 691–5 | date = January 1983 | pmid = 6572146 | doi = 10.1111/j.1432-1033.1983.tb07104.x | doi-access = free }} 16-Ketoestrone can be converted by 16α-hydroxysteroid dehydrogenase into estriol in the body.{{cite journal | vauthors = Stimmel BF, Grollman A, Huffman MN | title = The metabolism of 16-ketoestrone and 16-keto-estradiol in man | journal = J. Biol. Chem. | volume = 184 | issue = 2 | pages = 677–85 | date = June 1950 | doi = 10.1016/S0021-9258(19)51001-8 | pmid = 15428451 | doi-access = free }}