1.0 2011-09-21 00:26:34 UTC 2015-07-21 06:57:35 UTC FDB023225 Etiocholanedione Etiocholanedione is a 5-beta metabolite product of the catabolism of androgens. Etiocholanedione has been identified as a ketosteroid and isolated from the urine of healthy and diseased persons. Etiocholanedione has been identified as a metabolite of an altered androgen metabolism that eventually leads hepatocellular carcinoma to impaired hormone responsiveness in human. Etiocholanedione has been identified as a metabolite of 17alpha-hydroxyprogesterone in some patients affected by congenital adrenal hyperplasia, although it doesn't appear to account for the masculinization observed in congenital hyperplasia. Etiocholanedione can be the product of microbial contamination of urine since a few organisms are able to synthesize it using endogenous steroids as substrates. Human axillary bacteria are able to produce small amounts of etiocholanedione from testosterone. (PMID: 12161001, 13795320, 11161304, 2026727) [HMDB] (5b)-Androstane-3,17-dione 5b-Androstane-3,17-dione 5b-Androstanedione 5beta-Androstane-3,17-dione 5β-androstane-3,17-dione Etiochola-3,17-dione Etiocholane-3,17-dione C19H28O2 288.4244 288.20893014 (1S,2S,7R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-dione 5-β-androstane-3,17-dione 1229-12-5 [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1 RAJWOBJTTGJROA-QJISAEMRSA-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 17-oxosteroids 3-oxo-5-beta-steroids Cyclic ketones Hydrocarbon derivatives Organic oxides 17-oxosteroid 3-oxo-5-beta-steroid 3-oxosteroid Aliphatic homopolycyclic compound Androgen-skeleton Carbonyl group Cyclic ketone Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Androstane and derivatives C19 steroids (androgens) and derivatives C19 steroids (androgens) and derivatives androstane-3,17-dione Solid logp 3.40 ALOGPS logs -4.59 ALOGPS solubility 7.39e-03 g/l ALOGPS logp 3.97 ChemAxon pka_strongest_acidic 19.78 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac (1S,2S,7R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-dione ChemAxon average_mass 288.4244 ChemAxon mono_mass 288.20893014 ChemAxon smiles [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C ChemAxon formula C19H28O2 ChemAxon inchi InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1 ChemAxon inchikey RAJWOBJTTGJROA-QJISAEMRSA-N ChemAxon polar_surface_area 34.14 ChemAxon refractivity 82.78 ChemAxon polarizability 33.79 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19594 Specdb::CMs 29860 Specdb::CMs 31921 Specdb::CMs 99826 Specdb::CMs 99827 Specdb::CMs 153131 Specdb::MsMs 23117 Specdb::MsMs 23118 Specdb::MsMs 23119 Specdb::MsMs 29915 Specdb::MsMs 29916 Specdb::MsMs 29917 Specdb::MsMs 2456004 Specdb::MsMs 2456005 Specdb::MsMs 2456006 Specdb::MsMs 2478856 Specdb::MsMs 2478857 Specdb::MsMs 2478858 HMDB03769 16985 ANO #<Reference:0x000055ce31701c00> #<Reference:0x000055ce31701a20> #<Reference:0x000055ce31701868> #<Reference:0x000055ce317016b0> 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