1.0 2011-09-21 00:05:34 UTC 2015-07-21 06:56:54 UTC FDB021941 3b-Allotetrahydrocortisol 3b-Allotetrahydrocortisol is one of the tetrahydrometabolites of cortisol. The 11-beta-hydroxysteroid dehydrogenase (11beta-HSD) is responsible for the interconversion of both the hormonally inactive cortisone and the active cortisol, which has implications in the pathogenesis of numerous diseases, as reflected in the ratio of tetrahydrometabolites of cortisol. (PMID: 16310418) The daily excretion of allotetrahydrocortisol is above normal in hyperthyroid patients; In contrast, in hyperthyroidism the excretion is diminished below normal levels to approximately half that of normal subjects. (PMID 13906284) A decreased activity of the enzyme 11beta-HSD produces a pattern of urinary steroid metabolites with an abnormal elevation of tetrahydrocortisol and allo-tetrahydrocortisol compared to tetrahydrocortisone; this pattern of steroid excretion is essential for the diagnosis of the syndrome of apparent mineralocorticoid excess type 1. (PMID: 8834992) [HMDB] 3b-Allotetrahydrocortisol 3b,5a-Tetrahydrocortisol allo-3-beta-tetrahydrocortisol Reichstein's substance V C21H34O5 366.4917 366.240624198 2-hydroxy-1-[(1S,2S,5S,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one reichstein substance V 651-43-4 [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18+,19-,20-,21-/m0/s1 AODPIQQILQLWGS-VSJLKEFSSA-N belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. 21-hydroxysteroids Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Hydroxysteroids Aliphatic homopolycyclic compounds 11-beta-hydroxysteroids 17-hydroxysteroids 20-oxosteroids 3-beta-hydroxysteroids Alpha-hydroxy ketones Cyclic alcohols and derivatives Gluco/mineralocorticoids, progestogins and derivatives Hydrocarbon derivatives Organic oxides Polyols Primary alcohols Secondary alcohols Tertiary alcohols 11-beta-hydroxysteroid 11-hydroxysteroid 17-hydroxysteroid 20-oxosteroid 21-hydroxysteroid 3-beta-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alpha-hydroxy ketone Carbonyl group Cyclic alcohol Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Polyol Pregnane-skeleton Primary alcohol Progestogin-skeleton Secondary alcohol Tertiary alcohol Solid logp 1.38 ALOGPS logs -2.90 ALOGPS solubility 4.66e-01 g/l ALOGPS logp 1.11 ChemAxon pka_strongest_acidic 12.58 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 2-hydroxy-1-[(1S,2S,5S,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one ChemAxon average_mass 366.4917 ChemAxon mono_mass 366.240624198 ChemAxon smiles [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C ChemAxon formula C21H34O5 ChemAxon inchi InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18+,19-,20-,21-/m0/s1 ChemAxon inchikey AODPIQQILQLWGS-VSJLKEFSSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 97.6 ChemAxon polarizability 41.04 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 29501 Specdb::MsMs 29502 Specdb::MsMs 29503 Specdb::MsMs 36059 Specdb::MsMs 36060 Specdb::MsMs 36061 Specdb::MsMs 2370230 Specdb::MsMs 2370231 Specdb::MsMs 2370232 Specdb::MsMs 2568001 Specdb::MsMs 2568002 Specdb::MsMs 2568003 Specdb::CMs 13874 Specdb::CMs 37422 Specdb::CMs 134438 Specdb::CMs 142172 Specdb::CMs 1057859 Specdb::CMs 1057861 Specdb::CMs 1057863 Specdb::CMs 1057865 Specdb::CMs 1057867 Specdb::CMs 1057869 Specdb::CMs 1057871 Specdb::CMs 1057873 Specdb::CMs 1057875 Specdb::CMs 1057877 Specdb::CMs 1057879 Specdb::CMs 1057881 Specdb::CMs 1057883 Specdb::CMs 1057885 Specdb::CMs 1057887 Specdb::CMs 1057889 Specdb::CMs 1057891 Specdb::CMs 1057893 Specdb::CMs 1057895 Specdb::CMs 1057897 Specdb::CMs 1057899 HMDB00314 #<Reference:0x000055ce31c2f038> #<Reference:0x000055ce31c2ee80> #<Reference:0x000055ce31c2ecc8> 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