Reaction participants Show >> << Hide
- Name help_outline digitoxin Identifier CHEBI:145796 Charge -1 Formula C41H63O13 InChIKeyhelp_outline YQICPRLGRXWDHI-XUDUSOBPSA-N SMILEShelp_outline C1C[C@@H](C[C@@]2([C@]1([C@@]3([C@@](CC2)([C@@]4([C@](CC3)([C@](CC4)(C=5[CH-]OC(C5)=O)[H])C)O)[H])[H])C)[H])O[C@H]6C[C@@H]([C@@H]([C@H](O6)C)O[C@@H]7O[C@@H]([C@H]([C@H](C7)O)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O)O)C)O 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
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Namehelp_outline
Fe(II)-[cytochrome c]
Identifier
RHEA-COMP:10350
Reactive part
help_outline
- Name help_outline Fe2+ Identifier CHEBI:29033 (CAS: 15438-31-0) help_outline Charge 2 Formula Fe InChIKeyhelp_outline CWYNVVGOOAEACU-UHFFFAOYSA-N SMILEShelp_outline [Fe++] 2D coordinates Mol file for the small molecule Search links Involved in 263 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 9,431 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline dihydrodigitoxin Identifier CHEBI:282234 (CAS: 3786-76-3) help_outline Charge 0 Formula C41H66O13 InChIKeyhelp_outline WWCGMGNIMDOEGK-XWQQVMAMSA-N SMILEShelp_outline [H][C@]1(COC(=O)C1)[C@@]1([H])CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@H](O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1 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
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Namehelp_outline
Fe(III)-[cytochrome c]
Identifier
RHEA-COMP:14399
Reactive part
help_outline
- Name help_outline Fe3+ Identifier CHEBI:29034 (CAS: 20074-52-6) help_outline Charge 3 Formula Fe InChIKeyhelp_outline VTLYFUHAOXGGBS-UHFFFAOYSA-N SMILEShelp_outline [Fe+3] 2D coordinates Mol file for the small molecule Search links Involved in 248 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:62532 | RHEA:62533 | RHEA:62534 | RHEA:62535 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Discovery and characterization of a prevalent human gut bacterial enzyme sufficient for the inactivation of a family of plant toxins.
Koppel N., Bisanz J.E., Pandelia M.E., Turnbaugh P.J., Balskus E.P.
Although the human gut microbiome plays a prominent role in xenobiotic transformation, most of the genes and enzymes responsible for this metabolism are unknown. Recently, we linked the two-gene 'cardiac glycoside reductase' (<i>cgr</i>) operon encoded by the gut Actinobacterium <i>Eggerthella len ... >> More
Although the human gut microbiome plays a prominent role in xenobiotic transformation, most of the genes and enzymes responsible for this metabolism are unknown. Recently, we linked the two-gene 'cardiac glycoside reductase' (<i>cgr</i>) operon encoded by the gut Actinobacterium <i>Eggerthella lenta</i> to inactivation of the cardiac medication and plant natural product digoxin. Here, we compared the genomes of 25 <i>E. lenta</i> strains and close relatives, revealing an expanded 8-gene <i>cgr</i>-associated gene cluster present in all digoxin metabolizers and absent in non-metabolizers. Using heterologous expression and in vitro biochemical characterization, we discovered that a single flavin- and [4Fe-4S] cluster-dependent reductase, Cgr2, is sufficient for digoxin inactivation. Unexpectedly, Cgr2 displayed strict specificity for digoxin and other cardenolides. Quantification of <i>cgr2</i> in gut microbiomes revealed that this gene is widespread and conserved in the human population. Together, these results demonstrate that human-associated gut bacteria maintain specialized enzymes that protect against ingested plant toxins. << Less
Elife 7:E33953-E33953(2018) [PubMed] [EuropePMC]
This publication is cited by 4 other entries.