1.0 2011-09-21 00:27:25 UTC 2015-07-21 06:57:37 UTC FDB023281 21-Hydroxypregnenolone 21-hydroxypregnenolone is an essential intermediate in corticosterone synthesis. The hydrolysis of 21-hydroxypregnenolone of fetal origin by steryl-sulfatase (SOS, EC 3.1.6.2), may be important in the biosynthesis of deoxycorticosterone, which is present in the plasma of pregnant women in high concentration. 21-hydroxypregnenolone has been identified in follicular fluid from follicles of women. Pregnenolone is transformed to 21-hydroxypregnenolone by human adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in human. (PMID 974176, 3347051, 3495701, 7382480, 6247575) [HMDB] (3b)-3,21-dihydroxy-Pregn-5-en-20-one (3b)-3,21-Dihydroxypregn-5-en-20-one (3beta)-3,21-Dihydroxypregn-5-en-20-one (3β)-3,21-dihydroxypregn-5-en-20-one 21-hydroxypregnenolone 3b,21-Dihydroxy-5-pregnen-20-one 3b,21-dihydroxy-Pregn-5-en-20-one 5-Pregnen-3.beta.,21-diol-20-one 5-Pregnen-3b,21-diol-20-one 5-Pregnen-3beta,21-diol-20-one Oprea1_642453 Pregn-5-ene-3b,21-diol-20-one C21H32O3 332.477 332.23514489 2-hydroxy-1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one 21-hydroxypregnenolone 1164-98-3 [H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1 MOIQRAOBRXUWGN-WPWXJNKXSA-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 20-oxosteroids 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Alpha-hydroxy ketones Cyclic alcohols and derivatives Delta-5-steroids Gluco/mineralocorticoids, progestogins and derivatives Hydrocarbon derivatives Organic oxides Primary alcohols Secondary alcohols 20-oxosteroid 21-hydroxysteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alpha-hydroxy ketone Carbonyl group Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Pregnane-skeleton Primary alcohol Progestogin-skeleton Secondary alcohol 21-hydroxy steroid 3beta-hydroxy steroid C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives hydroxypregnenolone Solid logp 3.22 ALOGPS logs -3.87 ALOGPS solubility 4.50e-02 g/l ALOGPS logp 2.76 ChemAxon pka_strongest_acidic 13.86 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 2-hydroxy-1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one ChemAxon average_mass 332.477 ChemAxon mono_mass 332.23514489 ChemAxon smiles [H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C ChemAxon formula C21H32O3 ChemAxon inchi InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1 ChemAxon inchikey MOIQRAOBRXUWGN-WPWXJNKXSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 95.46 ChemAxon polarizability 38.84 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Steroidogenesis SMP00130 map00140 Specdb::CMs 2230 Specdb::CMs 25901 Specdb::CMs 31495 Specdb::CMs 38685 Specdb::CMs 137335 Specdb::CMs 145069 Specdb::MsMs 87903 Specdb::MsMs 87904 Specdb::MsMs 87905 Specdb::MsMs 150513 Specdb::MsMs 150514 Specdb::MsMs 150515 Specdb::MsMs 2770241 Specdb::MsMs 2770242 Specdb::MsMs 2770243 Specdb::MsMs 2908470 Specdb::MsMs 2908471 Specdb::MsMs 2908472 HMDB04026 28043 #<Reference:0x000055ce31ec1828> #<Reference:0x000055ce31ec15a8> #<Reference:0x000055ce31ec13c8> #<Reference:0x000055ce31ec1210> #<Reference:0x000055ce31ec1058> #<Reference:0x000055ce31ec0dd8> 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 Cytochrome P450 21-hydroxylase Q16874 P450-CYP21B Cytochrome P450, family 21, subfamily A, polypeptide 2 Q08AG9 CYP21A2