1.0 2011-09-21 01:38:17 UTC 2015-07-21 06:59:23 UTC FDB028343 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid 11b-hydroxy-3,20-dioxopregn-4-en-21-oic acid or HDOPA is a major metabolite of corticosterone that is typically elevated in the liver. The in vivo conversion of corticosterone to DHOPA and then to HDOPA is thought to proceed via the aldehyde intermediate 11b-hydroxy-3,20-dioxopregn-4-en-21-al. Cytochrome P450 3A4 (CYP3A4), is known to convert corticosterone to the gem-diol form of the aldehyde. Because CYP3A4 is highly abundant in the liver, the conversion of corticosterone to its aldehyde presumably occurs readily, and the formation of DHOPA by isomerization of the aldehyde. Subsequent dehydrogenation of DHOPA to HDOPA may be done by one of several liver specfici dehydrogenases. Possible candidates include aldehyde dehydrogenase type 3, lactate dehydrogenase A4, or 11b-hydroxysteroid dehydrogenase I. HDOPA has also been identified as a biomarker that is elevated (3700 X) in animals that have been treated with PPARalpha agonists. Peroxisome proliferator-activated receptor alpha (PPARalpha) is a nuclear receptor with manifold effects on intermediary metabolism (PMID: 17550978). [HMDB] 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oate 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid HDOPA C22H32O5 376.4865 376.224974134 3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoic acid 3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoic acid C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O InChI=1S/C22H32O5/c1-21-8-7-13(23)9-12(21)3-4-14-15-5-6-16(17(24)10-19(26)27)22(15,2)11-18(25)20(14)21/h9,14-18,20,24-25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,17?,18-,20?,21-,22-/m0/s1 MSUMOHDXPKCNSB-ZUNXIJJCSA-N belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Androgens and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Androstane steroids Aliphatic homopolycyclic compounds 11-beta-hydroxysteroids 3-oxo delta-4-steroids Beta hydroxy acids and derivatives Carboxylic acids Cyclic alcohols and derivatives Cyclohexenones Delta-4-steroids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Steroid acids 11-beta-hydroxysteroid 11-hydroxysteroid 20-hydroxysteroid 3-oxo-delta-4-steroid 3-oxosteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Hydroxy acid Hydroxysteroid Ketone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol Steroid acid Solid logp 1.67 ALOGPS logs -3.80 ALOGPS solubility 6.03e-02 g/l ALOGPS logp 1.99 ChemAxon pka_strongest_acidic 4.37 ChemAxon pka_strongest_basic -0.28 ChemAxon iupac 3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]propanoic acid ChemAxon average_mass 376.4865 ChemAxon mono_mass 376.224974134 ChemAxon smiles C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O ChemAxon formula C22H32O5 ChemAxon inchi InChI=1S/C22H32O5/c1-21-8-7-13(23)9-12(21)3-4-14-15-5-6-16(17(24)10-19(26)27)22(15,2)11-18(25)20(14)21/h9,14-18,20,24-25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,17?,18-,20?,21-,22-/m0/s1 ChemAxon inchikey MSUMOHDXPKCNSB-ZUNXIJJCSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 101.36 ChemAxon polarizability 41.66 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19312 Specdb::CMs 39743 Specdb::CMs 132036 Specdb::CMs 139770 Specdb::MsMs 308911 Specdb::MsMs 308912 Specdb::MsMs 308913 Specdb::MsMs 353209 Specdb::MsMs 353210 Specdb::MsMs 353211 Specdb::MsMs 2470122 Specdb::MsMs 2470123 Specdb::MsMs 2470124 Specdb::MsMs 2492831 Specdb::MsMs 2492832 Specdb::MsMs 2492833 HMDB11652 #<Reference:0x000055ce31985ad0> 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