1.0 2011-09-21 01:38:18 UTC 2015-10-09 22:33:27 UTC FDB028344 17-alpha,20-alpha-Dihydroxypregn-4-en-3-one 17 alpha, 20 alpha-dihydroxy-4-pregnen-3-one (17 alpha, 20 alpha-OHP) is a steroid hormone that is elevated in late pregnancy. In particular, the concentration of plasma 17,20 alpha-OHP is significantly increased during the third trimester of pregnancy, and the increment continues to increase through labor and delivery (PMID: 6874891). 17 alpha, 20 alpha-dihydroxy-4-pregnen-3-one is known to be a substrate for the enzyme 20a-hydroxysteroid dehydrogenase or 20alpha-HSD (EC 1.1.1.149). This enzyme catalyzes the chemical reaction: 17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+. This enzyme is actively involved in the control of progesterone homeostasis in pregnancy of mammals. While 20alpha-HSD expression and activity is downregulated in the corpus luteum of pregnancy, 24 hrs prior to parturition ovarian 20alpha-HSD activity is acutely stimulated. [HMDB] (20S)-17,20-dihydroxypregn-4-en-3-one 17 alpha, 20 alpha-OHP 17 alpha, 20 alpha-P 17,20 alpha-OHP 17a,20a-Dihydroxypregn-4-en-3-one 17alpha,20alpha-Dihydroxypregn-4-en-3-one 17α,20α-dihydroxypregn-4-en-3-one C21H32O3 332.477 332.23514489 (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one 652-69-7 [H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=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/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16+,17-,18-,19-,20-,21-/m0/s1 MASCESDECGBIBB-HNXXTFFGSA-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 1,2-diols 17-hydroxysteroids 3-oxo delta-4-steroids Cyclic alcohols and derivatives Cyclohexenones Delta-4-steroids Hydrocarbon derivatives Organic oxides Secondary alcohols Tertiary alcohols 1,2-diol 17-hydroxysteroid 20-hydroxysteroid 3-oxo-delta-4-steroid 3-oxosteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Cyclic alcohol Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Progestogin-skeleton Secondary alcohol Tertiary alcohol 17,20-dihydroxypregn-4-en-3-one C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives Solid logp 2.84 ALOGPS logs -3.91 ALOGPS solubility 4.12e-02 g/l ALOGPS logp 3.02 ChemAxon pka_strongest_acidic 13.42 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one ChemAxon average_mass 332.477 ChemAxon mono_mass 332.23514489 ChemAxon smiles [H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=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/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16+,17-,18-,19-,20-,21-/m0/s1 ChemAxon inchikey MASCESDECGBIBB-HNXXTFFGSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 95.03 ChemAxon polarizability 38.63 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1986 Specdb::NmrOneD 2053 Specdb::CMs 14242 Specdb::CMs 39744 Specdb::CMs 132539 Specdb::CMs 140273 Specdb::MsMs 297409 Specdb::MsMs 297410 Specdb::MsMs 297411 Specdb::MsMs 338941 Specdb::MsMs 338942 Specdb::MsMs 338943 Specdb::MsMs 2719470 Specdb::MsMs 2719471 Specdb::MsMs 2719472 Specdb::MsMs 2958738 Specdb::MsMs 2958739 Specdb::MsMs 2958740 HMDB11653 16418 #<Reference:0x000055ce306cb278> 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