1.0 2011-09-21 00:26:36 UTC 2015-07-21 06:57:35 UTC FDB023228 Androst-5-ene-3beta,17beta-diol Androstenediol is a term used to refer to two different steroids with molecular weights of 290.44: '4-androstenediol' (4-androstene-3beta,17beta-diol) and '5-androstenediol' (5-androstene-3beta,17beta-diol). 4-Androstenediol is closer to testosterone structurally, and has androgenic effects. 5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Coffey, 1988). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune(HE2100). An intermediate in testosterone biosynthesis, found in the testis or the adrenal. Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-fydroxysteroid dehydrogenaseS), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-fydroxysteroid dehydrogenase). [HMDB] (3b,17b)-Androst-5-ene-3,17-diol (3beta,17beta)-Androst-5-ene-3,17-diol (3β,17β)-androst-5-ene-3,17-diol 3b,17b-Dihydroxy-5-androstene 3b,17b-Dihydroxyandrost-5-ene 3beta,17beta-Dihydroxy-5-androstene 3beta,17beta-Dihydroxyandrost-5-ene 3β,17β-dihydroxy-5-androstene 3β,17β-dihydroxyandrost-5-ene 5-Androstenediol androst-5-ene-3,17-diol Androst-5-ene-3b,17b-diol Androst-5-ene-3beta,17beta-diol Androst-5-ene-3β,17β-diol Androst-5-enediol Androstenediol b,17b-diol delta-5-Androstenediol delta(sup 5)-Androstenediol delta5-Androstenediol Hermaphrodiol Tetrabol C19H30O2 290.4403 290.224580204 (1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol 5-androstenediol 521-17-5 [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 QADHLRWLCPCEKT-LOVVWNRFSA-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-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Secondary alcohols 17-hydroxysteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol 17beta-hydroxy steroid 3beta-hydroxy steroid Androstane and derivatives C19 steroids (androgens) and derivatives C19 steroids (androgens) and derivatives Solid logp 3.42 ALOGPS logs -3.72 ALOGPS solubility 5.50e-02 g/l ALOGPS logp 2.8 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -0.77 ChemAxon iupac (1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol ChemAxon average_mass 290.4403 ChemAxon mono_mass 290.224580204 ChemAxon smiles [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 ChemAxon inchikey QADHLRWLCPCEKT-LOVVWNRFSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 85.48 ChemAxon polarizability 34.68 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2049 Specdb::CMs 17815 Specdb::CMs 31484 Specdb::CMs 38656 Specdb::CMs 133893 Specdb::CMs 141627 Specdb::MsMs 65223 Specdb::MsMs 65224 Specdb::MsMs 65225 Specdb::MsMs 122589 Specdb::MsMs 122590 Specdb::MsMs 122591 Specdb::MsMs 2668495 Specdb::MsMs 2668496 Specdb::MsMs 2668497 Specdb::MsMs 3013361 Specdb::MsMs 3013362 Specdb::MsMs 3013363 HMDB03818 2710 B81 #<Reference:0x000055ce30ad87d0> #<Reference:0x000055ce30ad8618> #<Reference:0x000055ce30ad8230> #<Reference:0x000055ce30ad8028> #<Reference:0x000055ce30ae7ca8> #<Reference:0x000055ce30ae79d8> #<Reference:0x000055ce30ae74b0> #<Reference:0x000055ce30ae7230> #<Reference:0x000055ce30ae6ec0> #<Reference:0x000055ce30ae6bc8> #<Reference:0x000055ce30ae6a10> #<Reference:0x000055ce30ae6858> #<Reference:0x000055ce30ae6628> #<Reference:0x000055ce30ae6290> 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-alpha-steroid 4-dehydrogenase 1 P18405 SRD5A1 3-oxo-5-beta-steroid 4-dehydrogenase P51857 AKR1D1 Testosterone 17-beta-dehydrogenase 3 P37058 HSD17B3