1'-Sulfoxyelemicin is a metabolite of elemicin presumed to be made in mice. No reports are found of it forming in humans. Predictions performed using physiologically based kinetic (PBK) models show that this presumed metabolite is likely to form from elemicin in very small quantities in humans.[1]

1'-Sulfoxyelemicin is created from elemicin's intermediate metabolite 1'-hydroxyelemicin by the action of sulfotransferase (SULT). The SULT enzymes SULT1A1 and SULT1A3 were found to perform this action on the related compound 1'-hydroxyestragole and are assumed to also carry out this action on 1'-hydroxyelemicin.

The action of SULT on 1'-hydroxyelemicin brings the XLogP3 of 1.4 for 1'-hydroxyelemicin up to 1.41 for 1'-sulfoxyelemicin. SULT prevents 1'-hydroxyelemicin from forming 1'-oxoelemicin, thereby preventing alkaloid formation.

Substrate SULT End Product
1'-Hydroxyelemicin 1'-Sulfoxyelemicin
1-Hydroxyelemicin.gif 1-sulfoxyelemicin.png
Cofactor Byproduct
3'-phosphoadenylylsulfate adenosine 3',5'-bisphosphate

Chemical Properties

Molecular Weight: 304.35 [g/mol]
Formula: C12H16O7S
XLogP3: 1.41[2]
Canonical SMILES: C=CC(C1=CC(=C(C(=C1)OC)OC)OC)O[S](=O)(=O)O

1. Physiologically based kinetic models for the alkenylbenzene elemicin in rat and human and possible implications for risk assessment.
van den Berg SJ, Punt A, Soffers AE, Vervoort J, Ngeleja S, Spenkelink B, Rietjens IM. PubMed PMID: 22992039
2. XLogP3 values calculated using the Virtual Computational Chemistry Laboratory's
On-line Lipophilicity(logP), Water Solubility(LogS) & pKa Prediction calculator.
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