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Structure Database (LMSD)

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Common Name

5,6alpha-epoxy-cholesterol

Systematic Name

5α,6α-epoxy-5α-cholestan-3β-ol

Synonyms

5,6alpha-epoxy-cholestanol

LM ID

LMST01010011

Formula

C₂₇H₄₆O₂

Exact Mass

Calculate m/z

402.34978

Sum Composition

ST 27:1;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

5α,6α-epoxy Cholestanol is an oxysterol and a metabolite of cholesterol produced by oxidation.¹ 5α,6α-epoxy Cholestanol accumulates in MCF-7 breast cancer cells in a reactive oxygen species-dependent manner following tamoxifen and PBPE application and induces triacylglycerol biosynthesis by binding to liver x receptor β (LXRβ).² 5α,6α-epoxy Cholestanol levels are increased in rat aorta and mesenteric artery following orchidectomy, an effect that can be prevented by a DHA-supplemented diet.¹ Levels are also increased in post-mortem frontal and occipital cortex of patients with Alzheimer’s disease.³

This information has been provided by Cayman Chemical

References

1. Villalpando, D.M., Rojas, M.M., García, H.S., et al. Dietary docosahexaenoic acid supplementation prevents the formation of cholesterol oxidation products in arteries from orchidectomized rats. PLoS One 12(10), e0185805 (2017).

2. Segala, G., de Medina, P., Iuliano, L., et al. 5,6-Epoxy-cholesterols contribute to the anticancer pharmacology of tamoxifen in breast cancer cells. Biochem. Pharmacol. 86(1), 175-189 (2013).

3. Testa, G., Staurenghi, E., Zerbinati, C., et al. Changes in brain oxysterols at different stages of Alzheimer’s disease: Their involvement in neuroinflammation. Redox Biol. 10, 24-33 (2016).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Formation and metabolism in vitro of 5,6-epoxides of cholesterol and beta-sitosterol.,
J Lipid Res, 1974

Pubmed ID: 4152888

String Representations

InChiKey (Click to copy)

PRYIJAGAEJZDBO-ZEQHCUNVSA-N

InChi (Click to copy)

InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24+,25-,26-,27+/m1/s1

SMILES (Click to copy)

[C@]12(C[C@@H]3O[C@]43C[C@@H](O)CC[C@]4(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C)C)CC[C@@]21[H])[H]