1.02011-09-21 00:24:37 UTC2015-10-09 22:33:19 UTCFDB023096CanrenoneCanrenone 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-lactone17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid lactone17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactone17b-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid20-Spiroxa-4,6-diene-3,21-dione3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid g-lactone3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid lactone3-(3-Oxo-17b-hydroxy-4,6-androstadien-17a-yl)propionic acid g-lactone3'-(3-Oxo-17b-hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactoneAldadieneCanrenonePhanuraneC22H28O3340.4559340.203844762(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'-dione976-71-6[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12CInChI=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/s1UJVLDDZCTMKXJK-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 lactonesOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesSteroid lactonesAliphatic heteropolycyclic compounds3-oxosteroidsCarboxylic acid estersCyclohexenonesGamma butyrolactonesHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesOxacyclic compoundsTetrahydrofurans3-oxosteroidAliphatic heteropolycyclic compoundCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterCyclic ketoneCyclohexenoneGamma butyrolactoneHydrocarbon derivativeKetoneLactoneMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxosteroidSteroid lactoneTetrahydrofuranSolidlogp2.79logs-4.91solubility4.20e-03 g/llogp3.6pka_strongest_acidic19.94pka_strongest_basic-4.8iupac(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'-dioneaverage_mass340.4559mono_mass340.203844762smiles[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12CformulaC22H28O3inchiInChI=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/s1inchikeyUJVLDDZCTMKXJK-WNHSNXHDSA-Npolar_surface_area43.37refractivity97.48polarizability38.67rotatable_bond_count0acceptor_count2donor_count0physiological_charge0formal_charge0Specdb::NmrOneD1922Specdb::NmrTwoD1857Specdb::CMs25797Specdb::CMs148108Specdb::MsMs79212Specdb::MsMs79213Specdb::MsMs79214Specdb::MsMs139761Specdb::MsMs139762Specdb::MsMs139763Specdb::MsMs449111Specdb::MsMs449112Specdb::MsMs449113Specdb::MsMs449114Specdb::MsMs2226602Specdb::MsMs2228142Specdb::MsMs2228919Specdb::MsMs2238784Specdb::MsMs2238819Specdb::MsMs2240760Specdb::MsMs2240917Specdb::MsMs2242821Specdb::MsMs2243038Specdb::MsMs2257937Specdb::MsMs2365312Specdb::MsMs2365313Specdb::MsMs2365314Specdb::MsMs2596528Specdb::MsMs2596529HMDB03033#<Reference:0x000055567484d170>#<Reference:0x000055567484cfb8>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823