1.0 2011-09-21 00:34:55 UTC 2015-07-21 06:57:52 UTC FDB023802 7a,17-Dimethyl-5b-androstane-3a,17b-diol 7a,17-dimethyl-5b-Androstane-3a,17b-diol is a urinary metabolite of the anabolic androgenic steroid (AAS) bolasterone. Androgenic anabolic steroids are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. The use of anabolic steroids was banned by the International Olympic Committee for the first time at the Olympic Games in Montreal in 1976. Since that time the misuse of anabolic steroids by athletes has been controlled by analysis of urine of the excreted steroids or their metabolites, or both. (PMID: 10932808, 14976846, 15042372, 15231229, 16195040, 16292586, 1663826, 16799097, 16888758, 16923823, 17667636, 17723876, 17723877, 2079979, 3308301, 8456050, 8674183, 8725393, 9216475) [HMDB] (3a,5b,7a,17b)-7,17-dimethyl-Androstane-3,17-diol 7a,17a-Dimethyl-5b-androstane-3a,17b-diol C21H36O2 320.5093 320.271530396 (1S,2S,5R,7R,9R,10R,11S,14S,15S)-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol (1S,2S,5R,7R,9R,10R,11S,14S,15S)-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol 13611-10-4 [H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)C[C@]2([H])C[C@H](O)CC[C@]12C InChI=1S/C21H36O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h13-18,22-23H,5-12H2,1-4H3/t13-,14-,15-,16+,17+,18-,19+,20+,21+/m1/s1 ZWQUPIDNCOVROC-HEEAJRSSSA-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-hydroxysteroids 3-alpha-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Tertiary alcohols 17-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol Tertiary alcohol Solid logp 4.23 ALOGPS logs -5.16 ALOGPS solubility 2.20e-03 g/l ALOGPS logp 3.77 ChemAxon pka_strongest_acidic 18.3 ChemAxon pka_strongest_basic -0.47 ChemAxon iupac (1S,2S,5R,7R,9R,10R,11S,14S,15S)-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol ChemAxon average_mass 320.5093 ChemAxon mono_mass 320.271530396 ChemAxon smiles [H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)C[C@]2([H])C[C@H](O)CC[C@]12C ChemAxon formula C21H36O2 ChemAxon inchi InChI=1S/C21H36O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h13-18,22-23H,5-12H2,1-4H3/t13-,14-,15-,16+,17+,18-,19+,20+,21+/m1/s1 ChemAxon inchikey ZWQUPIDNCOVROC-HEEAJRSSSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 93.82 ChemAxon polarizability 38.64 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 11131 Specdb::CMs 38934 Specdb::CMs 167214 Specdb::MsMs 290548 Specdb::MsMs 290549 Specdb::MsMs 290550 Specdb::MsMs 330244 Specdb::MsMs 330245 Specdb::MsMs 330246 Specdb::MsMs 2462419 Specdb::MsMs 2462420 Specdb::MsMs 2462421 Specdb::MsMs 2500520 Specdb::MsMs 2500521 Specdb::MsMs 2500522 HMDB06013 #<Reference:0x000055ce32a63938> #<Reference:0x000055ce32a63780> #<Reference:0x000055ce32a635c8> #<Reference:0x000055ce32a63348> #<Reference:0x000055ce32a63190> #<Reference:0x000055ce32a62fd8> #<Reference:0x000055ce32a62e20> #<Reference:0x000055ce32a62c40> #<Reference:0x000055ce32a62a88> #<Reference:0x000055ce32a628a8> #<Reference:0x000055ce32a626f0> #<Reference:0x000055ce32a62538> #<Reference:0x000055ce32a62380> #<Reference:0x000055ce32a621c8> #<Reference:0x000055ce32a62010> #<Reference:0x000055ce32a61e58> #<Reference:0x000055ce32a61ca0> #<Reference:0x000055ce32a61ae8> #<Reference:0x000055ce32a61930> 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