Protein Information

Name FMO3
Synonyms Dimethylaniline monooxygenase [N oxide forming] 3; Dimethylaniline oxidase 3; FMO 3; FMO II; FMO form 2; FMO3; FMOII; Flavin containing monooxygenase 3…

Compound Information

Name sulfoxide
CAS 5-[2-(octylsulfinyl)propyl]-1,3-benzodioxole

Reference List

PubMed Abstract RScore(About this table)
18930712 Krause RJ, Elfarra AA: Reduction of L-methionine selenoxide to seleno-L-methionine by endogenous thiols, ascorbic acid, or methimazole. Biochem Pharmacol. 2009 Jan 1;77(1):134-40. Epub 2008 Sep 27.


Seleno-L-methionine (SeMet) can be oxidized to L-methionine selenoxide (MetSeO) by flavin-containing monooxygenase 3 (FMO3) and rat liver microsomes in the presence of NADPH.
1(0,0,0,1) Details
18681461 Barshteyn N, Elfarra AA: Detection of multiple globin monoadducts and cross-links after in vitro exposure of rat erythrocytes to S-(1,2-dichlorovinyl)-L-cysteine sulfoxide and after in vivo treatment of rats with S-(1,2-dichlorovinyl)-L-cysteine sulfoxide. Chem Res Toxicol. 2008 Sep;21(9):1716-25. Epub 2008 Aug 6.

S-(1,2-dichlorovinyl)- L-cysteine sulfoxide (DCVCS), a Michael acceptor produced by an FMO3-mediated oxidation of the trichloroethylene metabolite S-(1,2-dichlorovinyl)- L-cysteine (DCVC), is a more potent nephrotoxicant than DCVC.
31(0,1,1,1) Details
17892265 Barshteyn N, Elfarra AA: Formation of three N-acetyl-L-cysteine monoadducts and one diadduct by the reaction of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide with N-acetyl-L-cysteine at physiological conditions: chemical mechanisms and toxicological implications. Chem Res Toxicol. 2007 Oct;20(10):1563-9. Epub 2007 Sep 25.

Previously, our laboratory has shown that S-(1,2-dichlorovinyl)-L-cysteine sulfoxide (DCVCS), a Michael acceptor produced by a flavin-containing monooxygenase 3 (FMO3)-mediated oxidation of S-(1,2-dichlorovinyl)-L-cysteine (DCVC), is a more potent nephrotoxicant than DCVC.
31(0,1,1,1) Details
19283698 Hai X, Adams E, Hoogmartens J, Van Schepdael A: Enantioselective in-line and off-line CE methods for the kinetic study on cimetidine and its chiral metabolites with reference to flavin-containing monooxygenase genetic isoforms. Electrophoresis. 2009 Apr;30(7):1248-57.


FMO1 produces more (-)-CSO-enantiomer, while FMO3 generates mainly (+)-CSO-enantiomer.
2(0,0,0,2) Details
18930751 Henderson MC, Siddens LK, Morre JT, Krueger SK, Williams DE: Metabolism of the anti-tuberculosis drug ethionamide by mouse and human FMO1, FMO2 and FMO3 and mouse and human lung microsomes. Toxicol Appl Pharmacol. 2008 Dec 15;233(3):420-7. Epub 2008 Oct 1.

M. tuberculosis possesses a flavin monooxygenase (EtaA) that oxygenates ETA first to the sulfoxide and then to 2-ethyl-4-amidopyridine, presumably through a second oxygenation involving sulfinic acid.
2(0,0,0,2) Details