1.0 2011-09-21 00:07:08 UTC 2015-07-21 06:56:56 UTC FDB022022 16-Ketoestradiol 16-Ketoestradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy. [HMDB] 1,3,5(10)-Estratriene-3,17b-diol-16-one 16-keto-17b-Estradiol 16-Ketoestradiol 16-Oxo-17b-estradiol 16-oxo-17beta-Estradiol 16-oxo-17β-estradiol 16-Oxoestradiol 16-Oxoestradiol-17b 3,17b-Dihydroxyestra-1,3,5(10)-trien-16-one C18H22O3 286.3655 286.15689457 (1S,10R,11S,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-one 16-ketoestradiol 566-75-6 [H][C@@]12CC(=O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 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 KJDGFQJCHFJTRH-YONAWACDSA-N belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Estrogens and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Estrane steroids Aromatic homopolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 16-oxosteroids 17-hydroxysteroids 3-hydroxysteroids Cyclic alcohols and derivatives Cyclic ketones Hydrocarbon derivatives Organic oxides Phenanthrenes and derivatives Secondary alcohols Tetralins 1-hydroxy-2-unsubstituted benzenoid 16-oxosteroid 17-hydroxysteroid 3-hydroxysteroid Alcohol Aromatic homopolycyclic compound Benzenoid Carbonyl group Cyclic alcohol Cyclic ketone Estrogen-skeleton Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Phenanthrene Secondary alcohol Tetralin 16-oxo steroid C18 steroids (estrogens) and derivatives Solid logp 2.40 ALOGPS logs -3.79 ALOGPS solubility 4.61e-02 g/l ALOGPS logp 3.08 ChemAxon pka_strongest_acidic 10.33 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (1S,10R,11S,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-one ChemAxon average_mass 286.3655 ChemAxon mono_mass 286.15689457 ChemAxon smiles [H][C@@]12CC(=O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 ChemAxon formula C18H22O3 ChemAxon inchi 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 ChemAxon inchikey KJDGFQJCHFJTRH-YONAWACDSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 80.37 ChemAxon polarizability 32.35 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 301141 Specdb::MsMs 301142 Specdb::MsMs 301143 Specdb::MsMs 343594 Specdb::MsMs 343595 Specdb::MsMs 343596 Specdb::MsMs 2775002 Specdb::MsMs 2775003 Specdb::MsMs 2775004 Specdb::MsMs 2906820 Specdb::MsMs 2906821 Specdb::MsMs 2906822 Specdb::CMs 15867 Specdb::CMs 37506 Specdb::CMs 154314 Specdb::CMs 1060790 Specdb::CMs 1060792 Specdb::CMs 1060794 Specdb::CMs 1060795 Specdb::CMs 1060797 Specdb::CMs 1060799 Specdb::CMs 1060801 Specdb::CMs 1060803 Specdb::CMs 1060805 Specdb::CMs 1060806 Specdb::CMs 1060808 Specdb::CMs 1060810 Specdb::CMs 1060812 Specdb::CMs 1060814 Specdb::CMs 1060816 Specdb::CMs 1060818 Specdb::CMs 1060820 HMDB00406 #<Reference:0x000055ce3269eb90> #<Reference:0x000055ce3269e938> #<Reference:0x000055ce3269e668> #<Reference:0x000055ce3269e348> #<Reference:0x000055ce3269e0f0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823