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Structure Database (LMSD)

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Common Name

16alpha-hydroxyestrone

Systematic Name

3,16α-dihydroxy-1,3,5(10)-estratrien-17-one

Synonyms

1.16a-Hydroxyestrone

LM ID

LMST02010041

Formula

C₁₈H₂₂O₃

Exact Mass

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286.156895

Sum Composition

ST 18:4;O3

Status

Curated

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Classification

Biological Context

16α-hydroxy Estrone (16α-OHE1) is a hydroxylated metabolite of E1 as well as an interconversion product with E2.1,2 E1 is 16α-hydroxylated by cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A5, CYP3A4, and CYP3A7, with CYP3A5 being breast-specific.³ 16α-OHE1 is sulphatized or glucuronidated before excretion.³ It is increased in rheumatoid arthritis and decreased by physical activity.^1,2 Unlike the parent estrogens and other hydroxylated metabolites of E1, 16α-OHE1 binds covalently and persistently activates estrogen receptors.⁴ In addition, this metabolite increases cell proliferation and does not suppress TNF-α secretion, whereas other estrogen metabolites are not pro-proliferative and have marked effects on TNF-α secretion.^1,3 The levels of 16α-OHE1 are increased in some forms of hormone therapy.⁵ Because hormone therapy increases breast cancer risk, 16α-OHE1 has been implicated as a risk factor for breast cancer, although supportive data remains elusive.^6,3,5

This information has been provided by Cayman Chemical

References

1. Obi, N., Wrieling, A., Heinz, J., et al. Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer? Int. J. Womens Health 3, 37-51 (2011).

2. Okobia, M.N., and Bunker, C.H. Estrogen metabolism and breast cancer risk: A review. Afr. J. Reprod. Health 10(1), 13-25 (2006).

3. Swaneck, G.E., and Fishman, J. Covalent binding of the endogenous estrogen 16α-hydroxyestrone to estradiol receptor in human breast cancer cells: Characterization and intranuclear localization. Proc. Natl. Acad. Sci. USA 85(21), 7831-7835 (1988).

4. Cutolo, M., Sulli, A., and Straub, R.H. Estrogen metabolism and autoimmunity. Autoimmun. Rev. 11(6-7), A460-A464 (2012).

5. Matthews, C.E., Fortner, R.T., Xu, X., et al. Association between physical activity and urinary estrogens and estrogen metabolites in premenopausal women. J. Clin. Endocrinol. Metab. 97(10), 3724-3733 (2012).

6. Mackey, R.H., Fanelli, T.J., Modugno, F., et al. Hormone therapy, estrogen metabolism, and risk of breast cancer in the women’s health initiative hormone therapy trial. Cancer Epidemiol. Biomarkers Prev. 21(11), 2022-2032 (2012).