1.0 2011-09-21 00:08:25 UTC 2015-07-21 06:56:58 UTC FDB022094 5a-Tetrahydrocortisol 5a-Tetrahydrocortisol is a normal human metabolite. However its increased ratio (5alpha-Tetrahydrocortisol + Tetrahydrocortisol) over Tetrahydrocortisone in urine is the biochemical marker for the syndrome of apparent mineralocorticoid excess (AME). AME is a heritable form of hypertension due to an inborn error of cortisol metabolism and is characterized by hypokalemia and low renin levels despite subnormal or normal levels of aldosterone and other known mineralocorticoids. The syndrome is attributable to congenital deficiency of the enzyme 11 beta-hydroxydehydrogenase (11 beta-HSD), which converts cortisol to biologically inactive cortisone. This results in a prolonged half-life of Cortisol, which acts at the kidney level as a potent mineralocorticoid. (PMID: 8732999) [HMDB] 3,11,17,21-tetrahydroxypregnan-20-one 3a-Allotetrahydrocortisol 3a,11b,17,21-Tetrahydroxy-5a-pregnan-20-one 3a,11b,17a,21-Tetrahydroxy-5a-pregnan-20-one 3a,5a-Tetrahydrocortisol 3alpha, 5alpha-Tetrahydrocortisol 3alpha,5alpha-Tetrahydrocortisol 5a-Pregnane-3a,11b,17a,21-tetraol-20-one 5a-Pregnane-3a,11b,17a,21-tetrol-20-one 5a-Tetrahydrocortisol 5alpha-Tetrahydrocortisol a-THF Allo-3a-tetrahydrocortisol allo-3alpha-Tetrahydrocortisol allo-Tetrahydrocortisol Allopregnane-3a,11b,17a,21-tetrol-20-one Allopregnane-3a,11b,21-tetrol-20-one Allopregnane-3alpha,11beta,17alpha,21-tetrol-20-one allotetrahydro-Compound f allotetrahydro-Cortisol Allotetrahydrocompound f Allotetrahydrocortisol alpha-THF ATHF Kendall's compound c Reichstein's substance C tetrahydro-Allocortisol Tetrahydroallocortisol Wintersteiner's compound d C21H34O5 366.4917 366.240624198 2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one 2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone 302-91-0 [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-FDSHTENPSA-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-alpha-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-alpha-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 C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives 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,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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-FDSHTENPSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 97.6 ChemAxon polarizability 41.32 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9572 Specdb::CMs 37596 Specdb::CMs 150733 Specdb::CMs 1064919 Specdb::CMs 1064921 Specdb::CMs 1064923 Specdb::CMs 1064925 Specdb::CMs 1064927 Specdb::CMs 1064929 Specdb::CMs 1064931 Specdb::CMs 1064933 Specdb::CMs 1064935 Specdb::CMs 1064937 Specdb::CMs 1064939 Specdb::CMs 1064941 Specdb::CMs 1064943 Specdb::CMs 1064945 Specdb::CMs 1064947 Specdb::CMs 1064949 Specdb::CMs 1064951 Specdb::CMs 1064953 Specdb::CMs 1064955 Specdb::CMs 1064956 Specdb::CMs 1064958 Specdb::CMs 1064960 Specdb::MsMs 100689 Specdb::MsMs 100690 Specdb::MsMs 100691 Specdb::MsMs 166110 Specdb::MsMs 166111 Specdb::MsMs 166112 Specdb::MsMs 2464437 Specdb::MsMs 2464438 Specdb::MsMs 2464439 Specdb::MsMs 2500958 Specdb::MsMs 2500959 Specdb::MsMs 2500960 HMDB00526 #<Reference:0x000055ce31679788> #<Reference:0x000055ce316795d0> #<Reference:0x000055ce31679418> #<Reference:0x000055ce316791e8> #<Reference:0x000055ce31679008> #<Reference:0x000055ce31678e00> 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