1.0 2011-09-21 00:29:04 UTC 2015-07-21 06:57:39 UTC FDB023382 7a-Hydroxydehydroepiandrosterone 7a-Hydroxydehydroepiandrosterone is a major metabolite of dehydroepiandrosterone (DHEA), which is is 7alpha-hydroxylated by the cytochrome P450 7B1 (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase, CYP7B1) in the human brain and liver microsomes. Exposure to the proinflammatory cytokines TNFalpha, IL-1alpha, IL-1beta, and IL-17 increases CYP7B activity in synovial tissue. Increased CYP7B activity leads to higher levels of the DHEA metabolite 7alpha-OH-DHEA in synovial fluid, which may contribute to the maintenance of the chronic inflammation observed in rheumatoid arthritis patients. The glucocorticoid dhydrocorticosterone inhibits the conversion of DHEA to 7a-Hydroxydehydroepiandrosterone. The total levels of 7a-Hydroxydehydroepiandrosterone are increased in serum of patients with Alzheimer's disease. (PMID: 17467270, 15751070, 12667489, 9520908) [HMDB] (-)-7a-Hydroxydehydroepiandrosterone (3b,7a)-3,7-dihydroxy-Androst-5-en-17-one 3b,7a-Dihydroxy-5-androsten-17-one 3b,7a-Dihydroxy-5-androstene-17-one 3b,7a-dihydroxy-Androst-5-en-17-one 3beta,7alpha-Dihydroxy-5-androstene-17-one 3β,7α-dihydroxy-5-androstene-17-one 7-a-OH-DHEA 7-alpha-OH-DHEA 7a-Hydroxy-DHEA 7a-Hydroxydehydroisoandrosterone 7a-OH-DHEA 7alpha-OH-DHEA 7α-OH-dhea C19H28O3 304.4238 304.203844762 (1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one 7β-oh-dhea 53-00-9 [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1 OLPSAOWBSPXZEA-JIEICEMKSA-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 17-oxosteroids 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids 7-hydroxysteroids Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Ketones Organic oxides Secondary alcohols 17-oxosteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton Carbonyl group Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol 3-hydroxy steroid C19 steroids (androgens) and derivatives Solid logp 1.84 ALOGPS logs -3.38 ALOGPS solubility 1.27e-01 g/l ALOGPS logp 2.21 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -0.81 ChemAxon iupac (1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one ChemAxon average_mass 304.4238 ChemAxon mono_mass 304.203844762 ChemAxon smiles [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C ChemAxon formula C19H28O3 ChemAxon inchi InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1 ChemAxon inchikey OLPSAOWBSPXZEA-JIEICEMKSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 86.1 ChemAxon polarizability 34.78 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 22478 Specdb::CMs 38769 Specdb::CMs 145809 Specdb::MsMs 315949 Specdb::MsMs 315950 Specdb::MsMs 315951 Specdb::MsMs 362071 Specdb::MsMs 362072 Specdb::MsMs 362073 Specdb::MsMs 3048023 Specdb::MsMs 3048024 Specdb::MsMs 3048025 Specdb::MsMs 3095848 Specdb::MsMs 3095849 Specdb::MsMs 3095850 HMDB04611 #<Reference:0x000055ce32b27a90> #<Reference:0x000055ce32b27860> #<Reference:0x000055ce32b276a8> #<Reference:0x000055ce32b27478> 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 Corticosteroid 11-beta-dehydrogenase isozyme 1 P28845 HSD11B1