1.0 2011-09-21 00:23:55 UTC 2015-07-21 06:57:29 UTC FDB023055 Guggulsterone Guggulsterone is an ingredient in many nutritional supplements. Guggulsterone is a plant sterol derived from the gum resin (guggulu) of the tree Commiphora mukul. This sterol can inhibit NF-κB activation and downregulate the expression of inflammatory gene products such as COX-2 and MMP-9, which are major players in the development of arthritis. Guggulsterone also can suppress osteoclastogenesis induced by RANKL (receptor activator of NF-κB ligand), a bone-resorbing cytokine. The anti-inflammatory activity of C. mukul (guggul) has been compared with that of NSAIDs, namely phenylbutazone and ibuprofen. Guggulsterone is used to treat obesity, diabetes, hyperlipidemia, atherosclerosis, and osteoarthritis, and has been recently shown to antagonize the farnesoid X receptor and decrease the expression of bile acid-activated genes. It modulates activation of NF-kappaB, which has been closely linked with inflammatory diseases affected by guggulsterone. (PMID: 17475558, 15322087) [HMDB] (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. Androgens and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Androstane steroids Aliphatic homopolycyclic compounds 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 Solid logp 3.50 ALOGPS logs -4.54 ALOGPS solubility 9.91e-03 g/l 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 Specdb::CMs 15707 Specdb::CMs 172468 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 HMDB02726 #<Reference:0x000055ce3003f378> #<Reference:0x000055ce3003f1c0> 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