1.0 2011-09-21 00:04:27 UTC 2015-10-09 22:30:01 UTC FDB021881 Androsterone Androsterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone is also can be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone or androstenedione, and is considered an inactive end product; however, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role uridine-diphospho-glucuronosyltransferase (EC 2.4.1.17, UGT) enzymes for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and is widely recognized that the liver is a major site of glucuronidation; however it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution. (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133) [HMDB] (3alpha,5alpha)-3-hydroxy-Androstan-17-one (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one 3-alpha-Hydroxy-17-androstanone 3-alpha-Hydroxy-5-alpha-androstan-17-one 3-alpha-Hydroxy-5-alpha-androstane-17-one 3-alpha-hydroxy-5alpha-Androstan-17-one 3-alpha-Hydroxyetioallocholan-17-one 3-Epihydroxyetioallocholan-17-one 3-hydroxy-(3-alpha,5-alpha)-Androstan-17-one 3-Hydroxyandrostan-17-one 3a-Hydroxyetioallocholan-17-one 3alpha-Hydroxy-17-androstanone 3alpha-Hydroxy-5alpha-androstan-17-one 3alpha-Hydroxyetioallocholan-17-one 5-alpha-Androstan-3-alpha-ol-17-one 5-alpha-Androstane-3alpha-ol-17-one 5-alpha-Androsterone 5a-Androstan-3a-ol-17-one 5a-Androstane-3a-ol-17-one 5a-Androsterone 5alpha-Androstane-3alpha-ol-17-one 5alpha-Androsterone Androkinine Androstanon-3-alpha-ol-17-one Androsterone Androtine Atromide ICI cis-Androsterone C19H30O2 290.4403 290.224580204 (1S,2S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one (1S,2S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one 53-41-8 [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/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-XYQQMQERSA-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-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Ketones Organic oxides Secondary alcohols 17-oxosteroid 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,7S,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])CC[C@@]2([H])CC(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-XYQQMQERSA-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::CMs 20138 Specdb::CMs 37255 Specdb::MsMs 25247 Specdb::MsMs 25248 Specdb::MsMs 25249 Specdb::MsMs 31805 Specdb::MsMs 31806 Specdb::MsMs 31807 Specdb::NmrOneD 269458 Specdb::NmrOneD 269459 Specdb::NmrOneD 269460 Specdb::NmrOneD 269461 Specdb::NmrOneD 269462 Specdb::NmrOneD 269463 Specdb::NmrOneD 269464 Specdb::NmrOneD 269465 Specdb::NmrOneD 269466 Specdb::NmrOneD 269467 Specdb::NmrOneD 269468 Specdb::NmrOneD 269469 Specdb::NmrOneD 269470 Specdb::NmrOneD 269471 Specdb::NmrOneD 269472 Specdb::NmrOneD 269473 Specdb::NmrOneD 269474 Specdb::NmrOneD 269475 Specdb::NmrOneD 269476 Specdb::NmrOneD 269477 HMDB00031 16032 #<Reference:0x000055ce300d5670> #<Reference:0x000055ce300d5490> #<Reference:0x000055ce300d52d8> #<Reference:0x000055ce300d5120> #<Reference:0x000055ce300d4f68> #<Reference:0x000055ce300d4db0> #<Reference:0x000055ce300d4bf8> #<Reference:0x000055ce300d4a40> #<Reference:0x000055ce300d4888> #<Reference:0x000055ce300d46d0> #<Reference:0x000055ce300d4518> #<Reference:0x000055ce300d4360> #<Reference:0x000055ce300d41a8> #<Reference:0x000055ce300d55a8> #<Reference:0x000055ce300cfe00> #<Reference:0x000055ce300cfc48> #<Reference:0x000055ce300cfa90> #<Reference:0x000055ce300cf8d8> 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 Androgen receptor P10275 AR Bile salt sulfotransferase Q06520 SULT2A1 Dehydrogenase/reductase SDR family member 9 Q9BPW9 DHRS9 UDP-glucuronosyltransferase 1-1 P22309 UGT1A1 UDP-glucuronosyltransferase 1-10 Q9HAW8 UGT1A10 UDP-glucuronosyltransferase 1-3 P35503 UGT1A3 UDP-glucuronosyltransferase 1-4 P22310 UGT1A4 UDP-glucuronosyltransferase 1-5 P35504 UGT1A5 UDP-glucuronosyltransferase 1-6 P19224 UGT1A6 UDP-glucuronosyltransferase 1-7 Q9HAW7 UGT1A7 UDP-glucuronosyltransferase 1-8 Q9HAW9 UGT1A8 UDP-glucuronosyltransferase 1-9 O60656 UGT1A9 UDP-glucuronosyltransferase 2A1 Q9Y4X1 UGT2A1 UDP-glucuronosyltransferase 2A3 Q6UWM9 UGT2A3 UDP-glucuronosyltransferase 2B10 P36537 UGT2B10 UDP-glucuronosyltransferase 2B11 O75310 UGT2B11 UDP-glucuronosyltransferase 2B15 P54855 UGT2B15 UDP-glucuronosyltransferase 2B17 O75795 UGT2B17 UDP-glucuronosyltransferase 2B28 Q9BY64 UGT2B28 UDP-glucuronosyltransferase 2B4 P06133 UGT2B4 UDP-glucuronosyltransferase 2B7 P16662 UGT2B7