1.0 2011-09-21 00:06:31 UTC 2015-10-09 22:30:22 UTC FDB021984 Epiandrosterone Epiandrosterone is a naturally occurring steroid synthesized in the adrenal cortex, gonads, brain, and gastrointestinal tract. It is less active than androsterone and excreted in small amounts in normal human urine. Epiandrosterone is a metabolite of the most abundant adrenal androgenic steroid dehydroepiandrosterone (DHEA) in young adult humans, but is not completely inactive and is considered an effector as well. Epiandrosterone is a precursor or substrate for cytochrome P450 species and enzymes (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase) that produce 7alpha- and 7beta-hydroxylated metabolites in the human brain and other organs. These 7-hydroxylated derivatives exert anti-glucocorticoid and neuroprotective effects. (PMID: 17017935, 12475725, 15650074, 15784286) [HMDB] 3-Epiandrosterone 3b-Androsterone 3b-Hydroxy-17-oxo-5a-androstane 3b-Hydroxy-5a-androstan-17-one 3b-Hydroxy-5a-androstane-17-one 3b-Hydroxyandrostan-17-one 3b-Hydroxyetioallocholan-17-one 3b-OH-5a-Androstane-17-one 5a-Androstan-3b-ol-17-one 5a-Androstane-3b-ol-17-one d-Epiandrosterone epi-andosterone epi-Androsterone iso-Androsterone Isoandrosterone trans-Androsterone C19H30O2 290.4403 290.224580204 (1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one (1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one 481-29-8 [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12?,13-,14-,15-,16-,18-,19-/m0/s1 QGXBDMJGAMFCBF-QRIARFFBSA-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-beta-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Ketones Organic oxides Secondary alcohols 17-oxosteroid 3-beta-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton Carbonyl group Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol Solid logp 3.71 ALOGPS logs -4.66 ALOGPS solubility 6.37e-03 g/l ALOGPS logp 3.77 ChemAxon pka_strongest_acidic 18.3 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one ChemAxon average_mass 290.4403 ChemAxon mono_mass 290.224580204 ChemAxon smiles [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C ChemAxon formula C19H30O2 ChemAxon inchi InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12?,13-,14-,15-,16-,18-,19-/m0/s1 ChemAxon inchikey QGXBDMJGAMFCBF-QRIARFFBSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 83.81 ChemAxon polarizability 34.7 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1289 Specdb::NmrOneD 1347 Specdb::CMs 16342 Specdb::CMs 37468 Specdb::CMs 157142 Specdb::CMs 1059577 Specdb::CMs 1059578 Specdb::CMs 1059579 Specdb::MsMs 582 Specdb::MsMs 583 Specdb::MsMs 584 Specdb::MsMs 302182 Specdb::MsMs 302183 Specdb::MsMs 302184 Specdb::MsMs 344848 Specdb::MsMs 344849 Specdb::MsMs 344850 Specdb::MsMs 2309355 Specdb::MsMs 2309356 Specdb::MsMs 2309357 Specdb::MsMs 2656717 Specdb::MsMs 2656718 Specdb::MsMs 2656719 HMDB00365 #<Reference:0x0000559ad41578a8> #<Reference:0x0000559ad4157678> #<Reference:0x0000559ad41573d0> #<Reference:0x0000559ad4157150> #<Reference:0x0000559ad4156ef8> #<Reference:0x0000559ad4156ae8> #<Reference:0x0000559ad4156930> #<Reference:0x0000559ad4156728> #<Reference:0x0000559ad41564f8> 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