1.0 2011-09-21 01:38:16 UTC 2015-07-21 06:59:23 UTC FDB028342 11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid 11b,20-dihydroxy-3-oxopregn-4-en-21-oic acid or DHOPA is a major metabolite of corticosterone that is typically elevated in the liver. The in vivo conversion of corticosterone to DHOPA 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. DHOPA has also been identified as a biomarker that is elevated (50 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] 11b,20-dihydroxy-3-oxopregn-4-en-21-oate 11b,20-dihydroxy-3-oxopregn-4-en-21-oic acid 11beta,20-Dihydroxy-3-oxopregn-4-en-21-oate 11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid DHOPA C22H30O5 374.4706 374.20932407 3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-3-oxopropanoic acid 3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-3-oxopropanoic acid C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(=O)CC(O)=O InChI=1S/C22H30O5/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/h9,14-16,18,20,25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,18-,20?,21-,22-/m0/s1 VUDYWBBYQWVFAG-GKLBWGGBSA-N belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton. 20-oxosteroids Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Oxosteroids Aliphatic homopolycyclic compounds 1,3-dicarbonyl compounds 11-beta-hydroxysteroids 3-oxo delta-4-steroids Androgens and derivatives Beta-hydroxy ketones Beta-keto 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 1,3-dicarbonyl compound 11-beta-hydroxysteroid 11-hydroxysteroid 20-oxosteroid 3-oxo-delta-4-steroid 3-oxosteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton Androstane-skeleton Beta-hydroxy ketone Beta-keto acid Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Hydroxysteroid Keto acid Ketone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Steroid acid Solid logp 2.28 ALOGPS logs -4.07 ALOGPS solubility 3.21e-02 g/l ALOGPS logp 2.73 ChemAxon pka_strongest_acidic 4.21 ChemAxon pka_strongest_basic -0.26 ChemAxon iupac 3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-3-oxopropanoic acid ChemAxon average_mass 374.4706 ChemAxon mono_mass 374.20932407 ChemAxon smiles C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(=O)CC(O)=O ChemAxon formula C22H30O5 ChemAxon inchi InChI=1S/C22H30O5/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/h9,14-16,18,20,25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,18-,20?,21-,22-/m0/s1 ChemAxon inchikey VUDYWBBYQWVFAG-GKLBWGGBSA-N ChemAxon polar_surface_area 91.67 ChemAxon refractivity 100.64 ChemAxon polarizability 41.03 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15561 Specdb::CMs 39742 Specdb::CMs 153978 Specdb::MsMs 300463 Specdb::MsMs 300464 Specdb::MsMs 300465 Specdb::MsMs 342736 Specdb::MsMs 342737 Specdb::MsMs 342738 Specdb::MsMs 2771840 Specdb::MsMs 2771841 Specdb::MsMs 2771842 Specdb::MsMs 2910437 Specdb::MsMs 2910438 Specdb::MsMs 2910439 HMDB11651 #<Reference:0x000055ce3290ed80> 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