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- Name help_outline 20β-dihydro-11-deoxycortisol Identifier CHEBI:235407 Charge 0 Formula C21H32O4 InChIKeyhelp_outline XNFSGLNHLVHCFT-RMWFXKKMSA-N SMILEShelp_outline [H]C12CCC3=CC(=O)CCC3(C)C2([H])CCC4(C)C1([H])CCC4(O)C(O)CO 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NAD+ Identifier CHEBI:57540 (Beilstein: 3868403) help_outline Charge -1 Formula C21H26N7O14P2 InChIKeyhelp_outline BAWFJGJZGIEFAR-NNYOXOHSSA-M SMILEShelp_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,245 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 11-deoxycortisol Identifier CHEBI:28324 (CAS: 152-58-9) help_outline Charge 0 Formula C21H30O4 InChIKeyhelp_outline WHBHBVVOGNECLV-OBQKJFGGSA-N SMILEShelp_outline [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1(O)C(=O)CO 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADH Identifier CHEBI:57945 (Beilstein: 3869564) help_outline Charge -2 Formula C21H27N7O14P2 InChIKeyhelp_outline BOPGDPNILDQYTO-NNYOXOHSSA-L SMILEShelp_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,172 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 10,232 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:86115 | RHEA:86116 | RHEA:86117 | RHEA:86118 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Identification and characterization of a 20beta-HSDH from the anaerobic gut bacterium pii>Butyricicoccus desmolanspi/i> ATCC 43058.
Devendran S., Mendez-Garcia C., Ridlon J.M.
Members of the gastrointestinal microbiota are known to convert glucocorticoids to androstanes, which are subsequently converted to potent androgens by other members of the gut microbiota or host tissues. <i>Butyricicoccus desmolans</i> and <i>Clostridium cadaveris</i> have previously been reporte ... >> More
Members of the gastrointestinal microbiota are known to convert glucocorticoids to androstanes, which are subsequently converted to potent androgens by other members of the gut microbiota or host tissues. <i>Butyricicoccus desmolans</i> and <i>Clostridium cadaveris</i> have previously been reported for steroid-17,20-desmolase and 20β-hydroxysteroid dehydrogenase (HSDH) activities that are responsible for androstane formation from cortisol; however, the genes encoding these enzymes have yet to be reported. In this work, we identified and located a gene encoding 20β-HSDH in both <i>B. desmolans</i> and <i>C. cadaveris</i> The 20β-HSDH of <i>B. desmolans</i> was heterologously overexpressed and purified from <i>Escherichia coli</i> The enzyme was determined to be a homotetramer with subunit molecular mass of 33.8 ± 3.7 kDa. The r20β-HSDH displayed pH optimum in the reductive direction at pH 9.0 and in the oxidative direction at pH 7.0-7.5 with (20β-dihydro)cortisol and NAD(H) as substrates. Cortisol is the preferred substrate with <i>K<sub>m</sub></i> , 0.80 ± 0.06 μM; <i>V<sub>max</sub></i> , 30.36 ± 1.97 μmol·min<sup>-1</sup>; <i>K<sub>cat</sub></i> , 607 ± 39 μmol·μM<sup>-1</sup>·min<sup>-1</sup>; <i>K<sub>cat</sub></i> /<i>K<sub>m</sub></i> , 760 ± 7.67. Phylogenetic analysis of the 20β-HSDH from <i>B. desmolans</i> suggested that the 20β-HSDH is found in several <i>Bifidobacterium spp</i>, one of which was shown to express 20β-HSDH activity. Notably, we also identified a novel steroid-17,20-desmolase-elaborating bacterium, <i>Propionimicrobium lymphophilum</i>, a normal inhabitant of the urinary tract. << Less
J Lipid Res 58:916-925(2017) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.