1.0 2011-09-21 00:06:29 UTC 2020-04-21 18:02:45 UTC FDB021982 17alpha-Hydroxypregnenolone 17a-Hydroxypregnenolone is a 21-carbon steroid that is converted from pregnenolone by cytochrome P450 17alpha hydroxylase/C17,20 lyase (CYP17, EC 1.14.99.9). 17a-Hydroxypregnenolone is an intermediate in the delta-5 pathway of biosynthesis of gonadal steroid hormones and the adrenal corticosteroids. The first, rate-limiting and hormonally regulated step in the biosynthesis of all steroid hormones is the conversion of cholesterol to pregnenolone. The conversion of cholesterol to pregnenolone is accomplished by the cleavage of the cholesterol side chain, catalyzed by a mitochondrial cytochrome P450 enzyme termed P450scc where scc designates Side Chain Cleavage. All steroid hormones are made from the pregnenolone produced by P450scc; thus, the presence or absence of each of the activities of CYP17 directs this pregnenolone towards its final metabolic pathway. While all cytochrome P450 enzymes can catalyze multiple reactions on a single active site, CYP17 is the only one described to date in which these multiple activities are differentially regulated by a physiologic process. 17a-Hydroxypregnenolone is converted to dehydroepiandrosterone by the 17,20 lyase activity of CYP17. The ratio of the 17,20 lyase to 17 alpha-hydroxylase activity of CYP17 determines the ratio of C21 to C19 steroids produced. This ratio is regulated post-translationally by at least three factors: the abundance of the electron-donating protein P450 oxidoreductase, the presence of cytochrome b5, and the serine phosphorylation of CYP17. (PMID: 12573809) [HMDB] (3b)-3,17-Dihydroxypregn-5-en-20-one (3beta)-3,17-Dihydroxypregn-5-en-20-one (3β)-3,17-dihydroxypregn-5-en-20-one 17-Hydroxy-D5-pregnenolone 17-Hydroxypregnenolone 17-OH-pregnenolone 17a-Hydroxypregnenolone 17a-Hydroxypregnolone 17alpha-Hydroxypregnanolone 17alpha-Hydroxypregnenolone 17α-hydroxypregnenolone 3b,17-Dihydroxy-5-pregnen-20-one 3b,17-Dihydroxy-pregn-5-en-20-one 3b,17a-Dihydroxypregn-5-en-20-one 5-Pregnen-3b,17a-diol-20-one 5-Pregnen-3beta,17alpha-diol-20-one 5-Pregnen-3β,17α-diol-20-one C21H32O3 332.477 332.23514489 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone 387-79-1 [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1 JERGUCIJOXJXHF-TVWVXWENSA-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 17-hydroxysteroids 20-oxosteroids 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Alpha-hydroxy ketones Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Organic oxides Secondary alcohols Tertiary alcohols 17-hydroxysteroid 20-oxosteroid 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 Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Progestogin-skeleton Secondary alcohol Tertiary alcohol 17alpha-hydroxy steroid 3beta-hydroxy steroid C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives hydroxypregnenolone Solid logp 3.15 ALOGPS logs -3.95 ALOGPS solubility 3.77e-02 g/l ALOGPS logp 2.83 ChemAxon pka_strongest_acidic 12.7 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one ChemAxon average_mass 332.477 ChemAxon mono_mass 332.23514489 ChemAxon smiles [H][C@@]12CC[C@](O)(C(C)=O)[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/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1 ChemAxon inchikey JERGUCIJOXJXHF-TVWVXWENSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 95.16 ChemAxon polarizability 38.66 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Androgen and Estrogen Metabolism SMP00068 map00150 Steroidogenesis SMP00130 map00140 Specdb::NmrTwoD 1287 Specdb::NmrOneD 1345 Specdb::MsMs 576 Specdb::MsMs 577 Specdb::MsMs 578 Specdb::MsMs 4035 Specdb::MsMs 322198 Specdb::MsMs 322199 Specdb::MsMs 322200 Specdb::MsMs 370051 Specdb::MsMs 370052 Specdb::MsMs 370053 Specdb::MsMs 2782615 Specdb::MsMs 2782616 Specdb::MsMs 2782617 Specdb::MsMs 2926234 Specdb::MsMs 2926235 Specdb::MsMs 2926236 Specdb::CMs 2177 Specdb::CMs 2199 Specdb::CMs 25380 Specdb::CMs 28723 Specdb::CMs 29899 Specdb::CMs 31133 Specdb::CMs 31134 Specdb::CMs 37466 Specdb::CMs 134191 Specdb::CMs 141925 Specdb::CMs 1059497 Specdb::CMs 1059499 Specdb::CMs 1059501 Specdb::CMs 1059503 Specdb::CMs 1059505 Specdb::CMs 1059507 Specdb::CMs 1059510 Specdb::CMs 1059512 Specdb::CMs 1059514 Specdb::CMs 1059516 Specdb::CMs 1059517 HMDB00363 28750 #<Reference:0x000055ce33324720> #<Reference:0x000055ce33324568> #<Reference:0x000055ce333243b0> #<Reference:0x000055ce333241f8> 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