1.0 2011-09-21 00:23:52 UTC 2015-07-21 06:57:29 UTC FDB023052 Gestrinone Gestrinone was developed in the early 1970s and was tested clinically as a weekly oral contraceptive in European and North American countries. ]. Without significant advantages over other oral contraceptives and with its high price, gestrinone was no longer used after the Stage II clinical trial. However, from 1982 aroused widespread interest due to substantial therapeutic effects in treating endometriosis. Under different endocrine conditions, gestrinone possesses estrogenic, progestational, androgenic, antiestrogenic and antiprogesterone actions. Starting from gestrinone, chemists can synthesize tetrahydrogestrinone (THG) in one reaction step. THG is a real designer steroid; designer steroids (chemically modified steroids) pose a threat to the integrity of the sport community. These compounds have recently been detected in urine specimens from athletes, resulting in temporary or permanent suspension from amateur and/or professional competition. (PMID: 15934041, 17707720) [HMDB] (17a)-13-ethyl-17-hydroxy-18,19-Dinorpregna-4,9,11-trien-20-yn-3-one 13-ethyl-17-hydroxy-18,19-Dinor-17a-pregna-4,9,11-trien-20-yn-3-one 13-Ethyl-17a-ethynyl-17b-hydroxygona-4,9,11-trien-3-one Dimetriose Ethylnorgestrienone Gestrigone Gestrinona Gestrinone Nemestran Tridomose C21H24O2 308.4141 308.177630012 (10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one gestrinone 16320-04-0 [H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H] InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1 BJJXHLWLUDYTGC-ANULTFPQSA-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 Aliphatic homopolycyclic compounds 17-hydroxysteroids 3-oxosteroids Acetylides Cyclic alcohols and derivatives Cyclohexenones Hydrocarbon derivatives Organic oxides Tertiary alcohols Ynones 17-hydroxysteroid 3-oxosteroid Acetylide Alcohol Aliphatic homopolycyclic compound Carbonyl group Cyclic alcohol Cyclic ketone Cyclohexenone Estrogen-skeleton Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Tertiary alcohol Ynone Solid logp 3.39 ALOGPS logs -4.50 ALOGPS solubility 9.69e-03 g/l ALOGPS logp 2.85 ChemAxon pka_strongest_acidic 17.88 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one ChemAxon average_mass 308.4141 ChemAxon mono_mass 308.177630012 ChemAxon smiles [H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H] ChemAxon formula C21H24O2 ChemAxon inchi InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1 ChemAxon inchikey BJJXHLWLUDYTGC-ANULTFPQSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 93.73 ChemAxon polarizability 35.65 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14780 Specdb::CMs 38468 Specdb::CMs 137550 Specdb::CMs 145284 Specdb::MsMs 65139 Specdb::MsMs 65140 Specdb::MsMs 65141 Specdb::MsMs 122481 Specdb::MsMs 122482 Specdb::MsMs 122483 Specdb::MsMs 2755444 Specdb::MsMs 2755445 Specdb::MsMs 2755446 Specdb::MsMs 2954370 Specdb::MsMs 2954371 Specdb::MsMs 2954372 HMDB02720 #<Reference:0x000055ce3331ebe0> #<Reference:0x000055ce3331ea00>