1.0 2011-09-21 00:27:23 UTC 2015-07-21 06:57:37 UTC FDB023280 Pregnanediol Pregnanediol is an endogenous human testosterone metabolite. It can be detected in adults and newborns urine in variable concentrations. Pregnanediol is abnormally elevated in patients with cytochrome P450 (P450C17, steroid 17alpha-monooxygenase, EC 1.14.99.9) oxidoreductase deficiency (Antley-Bixler syndrome, PORD, OMIM 201750). Antley-Bixler syndrome is a multiple congenital malformation syndrome with craniosynostosis, radiohumeral synostosis, femoral bowing, choanal atresia or stenosis, joint contractures, urogenital abnormalities and, often, early death. An assay of urinary pregnanediol excretion provides an accurate indication of outcome in threatened abortion in 74 - 93% per cent of cases. Pregnanediol is one of the most important markers of pregnenolone administration, which can potentially be abused by athletes to maintain an equilibration of the steroidal environment after sex steroids administrations. Patients with recurrent vulvovaginal candidiasis have significantly lower levels of urinary pregnanediol. (PMID: 126703, 16608896, 16906539, 1191599, 2905284, 15763596, 10360427, 11159778, 16687200) [HMDB] (3a,5b,20S)-Pregnane-3,20-diol 3a,20a-Dihydroxy-5b-pregnane 5b-Pregnane-3a,20a-diol 5beta-Pregnane-3alpha,20 alpha-diol Pregnandiol Pregnanediol C21H36O2 320.5093 320.271530396 (1S,2S,10S,11S,14S,15R)-14-ethyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,5-diol 5b-pregnane-3a,20a-diol 80-92-2 [H][C@@]12CC[C@H](CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)(O)CC[C@]12C InChI=1S/C21H36O2/c1-4-14-6-8-17-16-7-5-15-13-21(22,23)12-11-20(15,3)18(16)9-10-19(14,17)2/h14-18,22-23H,4-13H2,1-3H3/t14-,15?,16-,17-,18-,19+,20-/m0/s1 JBSVQUOGNMYMSF-CIQUAOMQSA-N belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Gluco/mineralocorticoids, progestogins and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Pregnane steroids Aliphatic homopolycyclic compounds 3-alpha-hydroxysteroids 3-beta-hydroxysteroids Carbonyl hydrates Cyclic alcohols and derivatives Hydrocarbon derivatives 3-alpha-hydroxysteroid 3-beta-hydroxysteroid 3-hydroxysteroid Aliphatic homopolycyclic compound Carbonyl hydrate Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Progestogin-skeleton Solid logp 4.79 ALOGPS logs -5.79 ALOGPS solubility 5.23e-04 g/l ALOGPS logp 4.52 ChemAxon pka_strongest_acidic 12.03 ChemAxon pka_strongest_basic -4 ChemAxon iupac (1S,2S,10S,11S,14S,15R)-14-ethyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,5-diol ChemAxon average_mass 320.5093 ChemAxon mono_mass 320.271530396 ChemAxon smiles [H][C@@]12CC[C@H](CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)(O)CC[C@]12C ChemAxon formula C21H36O2 ChemAxon inchi InChI=1S/C21H36O2/c1-4-14-6-8-17-16-7-5-15-13-21(22,23)12-11-20(15,3)18(16)9-10-19(14,17)2/h14-18,22-23H,4-13H2,1-3H3/t14-,15?,16-,17-,18-,19+,20-/m0/s1 ChemAxon inchikey JBSVQUOGNMYMSF-CIQUAOMQSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 93.95 ChemAxon polarizability 39.58 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 12232 Specdb::CMs 38684 Specdb::MsMs 292954 Specdb::MsMs 292955 Specdb::MsMs 292956 Specdb::MsMs 333295 Specdb::MsMs 333296 Specdb::MsMs 333297 HMDB04025 #<Reference:0x000055ce31fc39b0> #<Reference:0x000055ce31fc37f8> #<Reference:0x000055ce31fc3640> #<Reference:0x000055ce31fc3488> #<Reference:0x000055ce31fc32d0> #<Reference:0x000055ce31fc3118> #<Reference:0x000055ce31fc2f60> #<Reference:0x000055ce31fc2da8> #<Reference:0x000055ce31fc2bf0> #<Reference:0x000055ce31fc2a38> #<Reference:0x000055ce31fc2880> #<Reference:0x000055ce31fc26c8> #<Reference:0x000055ce31fc2510> #<Reference:0x000055ce31fc2358> #<Reference:0x000055ce31fc21a0> #<Reference:0x000055ce31fc1fe8> #<Reference:0x000055ce31fc1e30> #<Reference:0x000055ce31fc1c78> #<Reference:0x000055ce31fc1ac0> #<Reference:0x000055ce31fc1908> #<Reference:0x000055ce31fc1750> #<Reference:0x000055ce31fc1598> 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