1.0 2011-09-21 00:08:01 UTC 2015-10-09 22:31:14 UTC FDB022072 Etiocholanolone Etiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness). [HMDB] (3a,5b)-3-Hydroxyandrostan-17-one (3alpha,5beta)-3-Hydroxyandrostan-17-one (3α,5β)-3-hydroxyandrostan-17-one 3a-Etiocholanolone 3a-Hydroxy-5b-androstan-17-one 3a-Hydroxy-5b-androstane-17-one 3a-Hydroxyetiocholan-17-one 3alpha-Etiocholanolone 3alpha-Hydroxy-5beta-androstan-17-one 3alpha-Hydroxyetiocholan-17-one 3α-etiocholanolone 3α-hydroxy-5β-androstan-17-one 3α-hydroxyetiocholan-17-one 5 beta Androsterone 5-Isoandrosterone 5b-Androstan-3a-ol-17-one 5b-Androstane-3a-ol-17-one 5b-Androsterone 5beta-Androstan-3alpha-ol-17-one 5beta-Androsterone 5β-androstan-3α-ol-17-one 5β-androsterone a-Etiocholanolone Aetiocholanolone alpha-Etiocholanolone Etiocholan-3a-ol-17-one Etiocholan-3alpha-ol-17-one Etiocholan-3α-ol-17-one C19H30O2 290.4403 290.224580204 (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one 53-42-9 [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[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+/m1/s1 QGXBDMJGAMFCBF-BNSUEQOYSA-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-alpha-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Ketones Organic oxides Secondary alcohols 17-oxosteroid 3-alpha-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 17-oxo steroid 3alpha-hydroxy steroid Androstane and derivatives C19 steroids (androgens) and derivatives C19 steroids (androgens) and derivatives androstanoid 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,5R,7R,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])C[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+/m1/s1 ChemAxon inchikey QGXBDMJGAMFCBF-BNSUEQOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 83.81 ChemAxon polarizability 34.36 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1335 Specdb::NmrOneD 1391 Specdb::CMs 15352 Specdb::CMs 29612 Specdb::CMs 37565 Specdb::CMs 99575 Specdb::CMs 163748 Specdb::CMs 1063853 Specdb::CMs 1063854 Specdb::CMs 1063856 Specdb::MsMs 707 Specdb::MsMs 708 Specdb::MsMs 709 Specdb::MsMs 4106 Specdb::MsMs 250533 Specdb::MsMs 250534 Specdb::MsMs 250535 Specdb::MsMs 270471 Specdb::MsMs 270472 Specdb::MsMs 270473 Specdb::MsMs 2351233 Specdb::MsMs 2351234 Specdb::MsMs 2351235 Specdb::MsMs 2584127 Specdb::MsMs 2584128 Specdb::MsMs 2584129 HMDB00490 28195 AE2 #<Reference:0x000055ce317f1c50> #<Reference:0x000055ce317f1a98> #<Reference:0x000055ce317f18e0> #<Reference:0x000055ce317f1728> 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 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