1.0 2016-09-30 23:01:27 UTC 2020-04-22 15:11:20 UTC BMDB0002726 BMDB02726 Guggulsterone (8XI,9xi,14xi,17E)-20-methoxypregna-4,17-diene-3,16-dione 20-Methoxy-4,17(20)e-pregnadiene-3,16-dione 4,17(20)-Pregnadiene-3,16-dione Guggulsterone-m C22H30O3 342.4718 342.219494826 (1R,2R,10S,11S,14E,15S)-14-(1-methoxyethylidene)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,13-dione (Z)-guggulsterone 95975-55-6 [H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C InChI=1S/C22H30O3/c1-13(25-4)20-19(24)12-18-16-6-5-14-11-15(23)7-9-21(14,2)17(16)8-10-22(18,20)3/h11,16-18H,5-10,12H2,1-4H3/b20-13-/t16-,17+,18-,21-,22-/m0/s1 WOVLRQSWILBDQL-IABMEBKLSA-N belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Androstane steroids Androgens and derivatives 16-oxosteroids 3-oxo delta-4-steroids Cyclohexenones Delta-4-steroids Hydrocarbon derivatives Organic oxides Vinylogous esters 16-oxosteroid 3-oxo-delta-4-steroid 3-oxosteroid Aliphatic homopolycyclic compound Androgen-skeleton Carbonyl group Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Vinylogous ester Aliphatic homopolycyclic compounds Solid logp 3.50 ALOGPS logs -4.54 ALOGPS logp 3.46 ChemAxon pka_strongest_acidic 18.96 ChemAxon pka_strongest_basic -4.5 ChemAxon iupac (1R,2R,10S,11S,14E,15S)-14-(1-methoxyethylidene)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,13-dione ChemAxon average_mass 342.4718 ChemAxon mono_mass 342.219494826 ChemAxon smiles [H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C ChemAxon formula C22H30O3 ChemAxon inchi InChI=1S/C22H30O3/c1-13(25-4)20-19(24)12-18-16-6-5-14-11-15(23)7-9-21(14,2)17(16)8-10-22(18,20)3/h11,16-18H,5-10,12H2,1-4H3/b20-13-/t16-,17+,18-,21-,22-/m0/s1 ChemAxon inchikey WOVLRQSWILBDQL-IABMEBKLSA-N ChemAxon polar_surface_area 43.37 ChemAxon refractivity 100.48 ChemAxon polarizability 39.54 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 300811 Specdb::MsMs 300812 Specdb::MsMs 300813 Specdb::MsMs 343177 Specdb::MsMs 343178 Specdb::MsMs 343179 Specdb::MsMs 2282980 Specdb::MsMs 2282981 Specdb::MsMs 2282982 Specdb::MsMs 3085330 Specdb::MsMs 3085331 Specdb::MsMs 3085332 Specdb::CMs 15707 Specdb::CMs 172468 FDB023055 558777 643658 C00047241 Guggulsterone