1.0 2011-09-21 00:27:30 UTC 2025-11-19 02:43:40 UTC FDB023284 11beta-Hydroxyprogesterone 11beta-Hydroxyprogesterone is a normal human metabolite. Plasma 11beta-Hydroxyprogesterone concentrations does not vary significantly as a function of age, sex, or phase of the menstrual cycle, in contrast to 17-hydroxyprogesterone. Increased plasma 11beta-Hydroxyprogesterone levels in late-onset adrenal 21-hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway. 21-hydroxylase deficiency (OMIM 201910) is probably the most frequent (if not the most frequent) autosomal recessive genetic disease, occurring in almost 1% of Caucasians and about 3% of Ashkenazi Jews. 21-hydroxylase deficiency is unusual among genetic diseases in that approximately 95% of the mutant alleles have apparently been generated by recombination between a normally active gene (CYP21) and a closely linked pseudogene (CYP21P). There are 4 recognized clinical forms of congenital adrenal hyperplasia, the majority of cases being associated with 21-hydroxylase deficiency: salt-wasting (SW), simple virilizing (SV), nonclassic (NC) late-onset (also called attenuated and acquired), and cryptic. (PMID: 3546944, 2537337) [HMDB] 11beta-hydroxyprogesterone acts as a mineralocorticoid agonist in stimulating Na+ absorption in mammalian principal cortical collecting duct cells. 11 beta-hydroxyprogesterone (11OHP) activated the transiently expressed hMR in COS-7 cells in a dose-dependent manner (ED(50): 10(-8) M) and, like aldosterone, stimulated Ams I(sc) in mpkCCD(cl4) cells. Docking 11OHP within the hMR-ligand-binding domain homology model revealed that the agonist activity of 11OHP is caused by contacts between its 11 beta-hydroxyl group and Asn770. Furthermore, 11OHP was unable to activate the mutant hMR/N770A, in which Ala is substituted for Asn at position 770. These findings demonstrate that in the absence of the 21-hydroxyl group, the 11 beta-hydroxyl group can produce the contact with the hMR-Asn770 required for the hMR activation leading to stimulated Na(+) absorption. [HMDB] (11beta)-11-hydroxypregn-4-ene-3,20-dione 11-beta-Hydroxypregn-4-ene-3,20-dione 11-beta-Hydroxyprogesterone 11b-Hydroxyprogesterone 11beta-hydroxypregn-4-ene-3,20-dione 21-Deoxycorticosterone C21H30O3 330.4611 330.219494826 (1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one (1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one 600-57-7 [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1 BFZHCUBIASXHPK-ATWVFEABSA-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 11-beta-hydroxysteroids 20-oxosteroids 3-oxo delta-4-steroids Cyclic alcohols and derivatives Cyclohexenones Delta-4-steroids Hydrocarbon derivatives Organic oxides Secondary alcohols 11-beta-hydroxysteroid 11-hydroxysteroid 20-oxosteroid 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 11beta-hydroxy steroid C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives Solid logp 2.65 ALOGPS logs -3.97 ALOGPS solubility 3.56e-02 g/l ALOGPS logp 2.84 ChemAxon pka_strongest_acidic 18.88 ChemAxon pka_strongest_basic -0.26 ChemAxon iupac (1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one ChemAxon average_mass 330.4611 ChemAxon mono_mass 330.219494826 ChemAxon smiles [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C ChemAxon formula C21H30O3 ChemAxon inchi InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1 ChemAxon inchikey BFZHCUBIASXHPK-ATWVFEABSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 94.3 ChemAxon polarizability 38.12 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Steroidogenesis SMP00130 map00140 Specdb::MsMs 2329998 Specdb::MsMs 2329999 Specdb::MsMs 2330000 Specdb::MsMs 2635144 Specdb::MsMs 2635145 Specdb::MsMs 2635146 Specdb::CMs 2247 Specdb::CMs 2252 Specdb::CMs 169081 HMDB04031 28247 #<Reference:0x000055ce322adfb8> #<Reference:0x000055ce322ade00> #<Reference:0x000055ce322adc48> #<Reference:0x000055ce322ada90> #<Reference:0x000055ce322ad8d8> #<Reference:0x000055ce322ad720> #<Reference:0x000055ce322ad568> #<Reference:0x000055ce322ad3b0> #<Reference:0x000055ce322ad1f8> #<Reference:0x000055ce322ad040> #<Reference:0x000055ce322ace88> #<Reference:0x000055ce322accd0> #<Reference:0x000055ce322acb18> #<Reference:0x000055ce322ac960> #<Reference:0x000055ce322ac7a8> #<Reference:0x000055ce322ac5f0> #<Reference:0x000055ce322ac438> #<Reference:0x000055ce322ac280> #<Reference:0x000055ce322ac0c8> #<Reference:0x000055ce322abec0> #<Reference:0x000055ce322abd08> #<Reference:0x000055ce322abb50> Cytochrome P450, family 21, subfamily A, polypeptide 2 Q08AG9 CYP21A2