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- Name help_outline 5-epi-5-F2t-IsoP Identifier CHEBI:229787 Charge -1 Formula C20H33O5 InChIKeyhelp_outline RZCPXIZGLPAGEV-NVWAOVOPSA-M SMILEShelp_outline C1[C@H]([C@@H]([C@@H]([C@H]1O)/C=C/[C@@H](CCCC([O-])=O)O)C/C=C\CCCCC)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
- Name help_outline UDP-α-D-glucuronate Identifier CHEBI:58052 Charge -3 Formula C15H19N2O18P2 InChIKeyhelp_outline HDYANYHVCAPMJV-LXQIFKJMSA-K SMILEShelp_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 107 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 5-epi-5-F2t-IsoP-glucuronide Identifier CHEBI:229788 Charge -2 Formula C26H40O11 InChIKeyhelp_outline LKJKBLUIGXHKEY-QQIVJUKFSA-L SMILEShelp_outline C1[C@@H]([C@H]([C@H]([C@@H]1O)C/C=C\CCCCC)/C=C/[C@@H](CCCC([O-])=O)O[C@@H]2O[C@H](C([O-])=O)[C@H]([C@@H]([C@H]2O)O)O)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
- Name help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKeyhelp_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILEShelp_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 637 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 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:79911 | RHEA:79912 | RHEA:79913 | RHEA:79914 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Identification of novel F2-isoprostane metabolites by specific UDP-glucuronosyltransferases.
Milne G.L., Nogueira M.S., Gao B., Sanchez S.C., Amin W., Thomas S., Oger C., Galano J.M., Murff H.J., Yang G., Durand T.
UDP-glucuronosyltransferases (UGTs) catalyze the conjugation of glucuronic acid with endogenous and exogenous lipophilic small molecules to facilitate their inactivation and excretion from the body. This represents approximately 35 % of all phase II metabolic transformations. Fatty acids and their ... >> More
UDP-glucuronosyltransferases (UGTs) catalyze the conjugation of glucuronic acid with endogenous and exogenous lipophilic small molecules to facilitate their inactivation and excretion from the body. This represents approximately 35 % of all phase II metabolic transformations. Fatty acids and their oxidized eicosanoid derivatives can be metabolized by UGTs. F<sub>2</sub>-isoprostanes (F<sub>2</sub>-IsoPs) are eicosanoids formed from the free radical oxidation of arachidonic acid. These molecules are potent vasoconstrictors and are widely used as biomarkers of endogenous oxidative damage. An increasing body of evidence demonstrates the efficacy of measuring the β-oxidation metabolites of F<sub>2</sub>-IsoPs rather than the unmetabolized F<sub>2</sub>-IsoPs to quantify oxidative damage in certain settings. Yet, the metabolism of F<sub>2</sub>-IsoPs is incompletely understood. This study sought to identify and characterize novel phase II metabolites of 15-F<sub>2t</sub>-IsoP and 5-epi-5-F<sub>2t</sub>-IsoP, two abundantly produced F<sub>2</sub>-IsoPs, in human liver microsomes (HLM). Utilizing liquid chromatography-mass spectrometry, we demonstrated that glucuronide conjugates are the major metabolites of these F<sub>2</sub>-IsoPs in HLM. Further, we showed that these molecules are metabolized by specific UGT isoforms. 15-F<sub>2t</sub>-IsoP is metabolized by UGT1A3, 1A9, and 2B7, while 5-epi-5-F<sub>2t</sub>-IsoP is metabolized by UGT1A7, 1A9, and 2B7. We identified, for the first time, the formation of intact glucuronide F<sub>2</sub>-IsoPs in human urine and showed that F<sub>2</sub>-IsoP glucuronidation is reduced in people supplemented with eicosapentaenoic and docosahexaenoic acids for 12 weeks. These studies demonstrate that endogenous F<sub>2</sub>-IsoP levels can be modified by factors other than redox mechanisms. << Less
Redox Biol. 70:103020-103020(2024) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.