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- Name help_outline 3-oxochol-4-en-24-oyl-CoA Identifier CHEBI:86412 Charge -4 Formula C45H66N7O18P3S InChIKeyhelp_outline VVQGMUPGBRZRFY-ABDXREKHSA-J SMILEShelp_outline C[C@H](CCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C 2D coordinates Mol file for the small molecule Search links Involved in 3 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 1,186 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 3-oxochol-4,6-dien-24-oyl-CoA Identifier CHEBI:140634 Charge -4 Formula C45H64N7O18P3S InChIKeyhelp_outline IQGCDPWHEHJEGO-ABDXREKHSA-J SMILEShelp_outline [C@@H]1(N2C3=C(C(=NC=N3)N)N=C2)O[C@H](COP(OP(OCC(C)([C@H](C(NCCC(NCCSC(=O)CC[C@@](C)([C@]4(CC[C@@]5([C@@]4(CC[C@@]6([C@]7(CCC(C=C7C=C[C@@]56[H])=O)C)[H])C)[H])[H])[H])=O)=O)O)C)(=O)[O-])(=O)[O-])[C@H]([C@H]1O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 2 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 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 1,116 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:56648 | RHEA:56649 | RHEA:56650 | RHEA:56651 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Identification of a gene encoding a flavoprotein involved in bile acid metabolism by the human gut bacterium Clostridium scindens ATCC 35704.
Harris S.C., Devendran S., Alves J.M.P., Mythen S.M., Hylemon P.B., Ridlon J.M.
<h4>Background</h4>The multi-step bile acid 7α-dehydroxylating pathway by which a few species of Clostridium convert host primary bile acids to toxic secondary bile acids is of great importance to gut microbiome structure and host physiology and disease. While genes in the oxidative arm of the 7α- ... >> More
<h4>Background</h4>The multi-step bile acid 7α-dehydroxylating pathway by which a few species of Clostridium convert host primary bile acids to toxic secondary bile acids is of great importance to gut microbiome structure and host physiology and disease. While genes in the oxidative arm of the 7α-dehydroxylating pathway have been identified, genes in the reductive arm of the pathway are still obscure.<h4>Methods</h4>We identified a candidate flavoprotein-encoding gene predicted to metabolize steroids. This gene was cloned and overexpressed in E. coli and affinity purified. Reaction substrate and product were separated by thin layer chromatography and identified by liquid chromatograph mass spectrometry-ion trap-time of flight (LCMS-IT-TOF). Phylogenetic analysis of the amino acid sequence was performed.<h4>Results</h4>We report the identification of a gene encoding a flavoprotein (EDS08212.1) involved in secondary bile acid metabolism by Clostridium scindens ATCC 35704 and related species. Purified rEDS08212.1 catalyzed formation of a product from 3-dehydro-deoxycholic acid that UPLC-IT-TOF-MS analysis suggests loses 4amu. Our phylogeny identified this gene in other bile acid 7α-dehydroxylating bacteria.<h4>Conclusions</h4>These data suggest formation of a product, 3-dehydro-4,6-deoxycholic acid, a recognized intermediate in the reductive arm of bile acid 7α-dehydroxylation pathway and the first report of a gene in the reductive arm of the bile acid 7α-dehydroxylating pathway. << Less
Biochim. Biophys. Acta 1863:276-283(2018) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.