1.0 2011-09-21 00:27:26 UTC 2015-07-21 06:57:37 UTC FDB023282 11-Dehydrocorticosterone 11-Dehydrocorticosterone is a mineral corticosteroid. The conversion of inactive 11-ketoglucocorticoids such as 11-dehydrocorticosterone) into active 11b-hydroxyglucocorticoids (such as corticosterone) is catalyzed by 11beta-hydroxysteroid dehydrogenase (11b-HSD1, EC 1.1.1.146), which is expressed in many tissues and plays an important role in metabolically relevant tissues such as the liver, adipose tissue, skeletal muscles and possibly kidney. Chronically elevated local glucocorticoid action as a result of increased 11beta-HSD1 activity rather than elevated systemic glucocorticoid levels has been associated with metabolic syndrome, which is characterized by obesity, insulin resistance, type 2 diabetes and cardiovascular complications. Recent studies indicate that compounds inhibiting 11beta-HSD1 activity ameliorate the adverse effects of excessive glucocorticoid concentrations on metabolic processes, providing promising opportunities for the development of therapeutic interventions. 11-dehydrocorticosterone and corticosterone display antinatriuretic activity, although 11-dehydrocorticosterone is generally a more potent sodium retainer than corticosterone. (PMID: 17584152, Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40.) [HMDB] 11-dehydro-Corticosterone 11-Dehydrocorticosteron 11-Dehydrocorticosterone 11-Oxo-11-deoxycorticosterone 11-Oxocorticosterone 17-(1-keto-2-Hydroxyethyl)-D4-androsten-3,11-dione 17-Deoxycortisone 21-Hydroxypregn-4-ene-3,11-20-trione 21-Hydroxypregn-4-ene-3,11,20-trione 4-Pregnen-21-ol-3,11,20-trione D4-Pregnen-21-ol-3,11,20-trione D4-Pregnene-21-ol-3,11,20-trione Dehydrocorticosterone Dehydrocortocicosterone Kendall's compound A C21H28O4 344.4446 344.198759384 (1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione 11-dehydrocorticosterone 72-23-1 [H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C InChI=1S/C21H28O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1 FUFLCEKSBBHCMO-IWBQTIMDSA-N belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. 21-hydroxysteroids Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Hydroxysteroids Aliphatic homopolycyclic compounds 11-oxosteroids 20-oxosteroids 3-oxo delta-4-steroids Alpha-hydroxy ketones Cyclohexenones Delta-4-steroids Gluco/mineralocorticoids, progestogins and derivatives Hydrocarbon derivatives Organic oxides Primary alcohols 11-oxosteroid 20-oxosteroid 21-hydroxysteroid 3-oxo-delta-4-steroid 3-oxosteroid Alcohol Aliphatic homopolycyclic compound Alpha-hydroxy ketone Carbonyl group Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Pregnane-skeleton Primary alcohol Progestogin-skeleton C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives Solid logp 2.44 ALOGPS logs -3.86 ALOGPS solubility 4.79e-02 g/l ALOGPS logp 2.41 ChemAxon pka_strongest_acidic 13.86 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione ChemAxon average_mass 344.4446 ChemAxon mono_mass 344.198759384 ChemAxon smiles [H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C ChemAxon formula C21H28O4 ChemAxon inchi InChI=1S/C21H28O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1 ChemAxon inchikey FUFLCEKSBBHCMO-IWBQTIMDSA-N ChemAxon polar_surface_area 71.44 ChemAxon refractivity 95.07 ChemAxon polarizability 37.88 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Steroidogenesis SMP00130 map00140 Specdb::CMs 10954 Specdb::CMs 38686 Specdb::CMs 130778 Specdb::CMs 138512 Specdb::MsMs 96855 Specdb::MsMs 96856 Specdb::MsMs 96857 Specdb::MsMs 161445 Specdb::MsMs 161446 Specdb::MsMs 161447 Specdb::MsMs 2674885 Specdb::MsMs 2674886 Specdb::MsMs 2674887 Specdb::MsMs 3034664 Specdb::MsMs 3034665 Specdb::MsMs 3034666 HMDB04029 #<Reference:0x000055ce3233ca38> #<Reference:0x000055ce3233c880> #<Reference:0x000055ce3233c6c8> #<Reference:0x000055ce3233c4e8> #<Reference:0x000055ce3233c330> 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 3-oxo-5-beta-steroid 4-dehydrogenase P51857 AKR1D1 Corticosteroid 11-beta-dehydrogenase isozyme 1 P28845 HSD11B1