1.0 2011-09-21 00:24:37 UTC 2015-10-09 22:33:19 UTC FDB023096 Canrenone Canrenone is the major metabolite of spironolactone. Spironolactone is a competitive aldosterone receptor antagonist (ARA), has traditionally been the treatment of first choice in idiopathic hyperaldosteronism (IHA) and for preoperative management of aldosterone producing adenoma (APA), and its therapeutic properties are attributable to active metabolite canrenone. Canrenone and the K+ salt of canrenoate are also in clinical use: they avoid the formation of intermediate products with anti-androgenic and progestational actions, resulting in a decreased incidence of side effects. (PMID: 10790593) [HMDB] 17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid g-lactone 17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid lactone 17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactone 17b-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid 20-Spiroxa-4,6-diene-3,21-dione 3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid g-lactone 3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid lactone 3-(3-Oxo-17b-hydroxy-4,6-androstadien-17a-yl)propionic acid g-lactone 3'-(3-Oxo-17b-hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactone Aldadiene Canrenone Phanurane C22H28O3 340.4559 340.203844762 (1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione (1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione 976-71-6 [H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C InChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1 UJVLDDZCTMKXJK-WNHSNXHDSA-N belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Steroid lactones Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroid lactones Aliphatic heteropolycyclic compounds 3-oxosteroids Carboxylic acid esters Cyclohexenones Gamma butyrolactones Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Tetrahydrofurans 3-oxosteroid Aliphatic heteropolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic ketone Cyclohexenone Gamma butyrolactone Hydrocarbon derivative Ketone Lactone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxosteroid Steroid lactone Tetrahydrofuran Solid logp 2.79 ALOGPS logs -4.91 ALOGPS solubility 4.20e-03 g/l ALOGPS logp 3.6 ChemAxon pka_strongest_acidic 19.94 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac (1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione ChemAxon average_mass 340.4559 ChemAxon mono_mass 340.203844762 ChemAxon smiles [H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C ChemAxon formula C22H28O3 ChemAxon inchi InChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1 ChemAxon inchikey UJVLDDZCTMKXJK-WNHSNXHDSA-N ChemAxon polar_surface_area 43.37 ChemAxon refractivity 97.48 ChemAxon polarizability 38.67 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 25797 Specdb::CMs 148108 Specdb::NmrOneD 1922 Specdb::NmrTwoD 1857 Specdb::MsMs 79212 Specdb::MsMs 79213 Specdb::MsMs 79214 Specdb::MsMs 139761 Specdb::MsMs 139762 Specdb::MsMs 139763 Specdb::MsMs 449111 Specdb::MsMs 449112 Specdb::MsMs 449113 Specdb::MsMs 449114 Specdb::MsMs 2226602 Specdb::MsMs 2228142 Specdb::MsMs 2228919 Specdb::MsMs 2238784 Specdb::MsMs 2238819 Specdb::MsMs 2240760 Specdb::MsMs 2240917 Specdb::MsMs 2242821 Specdb::MsMs 2243038 Specdb::MsMs 2257937 Specdb::MsMs 2365312 Specdb::MsMs 2365313 Specdb::MsMs 2365314 Specdb::MsMs 2596528 Specdb::MsMs 2596529 HMDB03033 #<Reference:0x000055ce32d461a0> #<Reference:0x000055ce32d45fe8> 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