LIPID MAPS

Structure Database (LMSD)

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Common Name

5beta,6beta-epoxy-cholesterol

Systematic Name

5β,6β-epoxy-cholestan-3β-ol

Synonyms

5beta,6beta-epoxy-cholestanol

LM ID

LMST01010010

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

5β,6β-epoxy Cholestanol is an oxidative metabolite of cholesterol that is formed via radical and non-radical oxidation of cholesterol at the 5,6-double bond.^1,2 It induces release of lactate dehydrogenase (LDH) and apoptosis in macrophage-differentiated U937 cells.³ 5β,6β-epoxy Cholestanol has been found in human fatty streaks and advanced atherosclerotic lesions but is not present in normal aortic tissue.⁴

This information has been provided by Cayman Chemical

References

1. Pulfer, M.K., and Murphy, R.C. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. J. Biol. Chem. 279(25), 26331-26338 (2004).

2. Lordan, S., O'Brien, N.M., and Mackrill, J.J. The role of calcium in apoptosis induced by 7β-hydroxycholesterol and cholesterol-5β,6β-epoxide. J. Biochem. Mol. Toxicol. 23(5), 324-332 (2009).

3. Garcia-Cruset, S., Carpenter, K.L., Guardiola, F., et al. Oxysterol profiles of normal human arteries, fatty streaks and advanced lesions. Free Radic. Res. 35(1), 31-41 (2001).

4. Aringer, L., and Eneroth, P. Formation and metabolism in vitro of 5,6-epoxides of cholesterol and β-sitosterol. J. Lipid Res. 15(4), 389-398 (1974).

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-DTLXENBRSA-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)

CC(C)CCC[C@](C)([H])[C@]1([H])[C@]2(C)[C@@]([H])(CC1)[C@@]1(C[C@H]3O[C@@]43C[C@@H](O)CC[C@]4(C)[C@@]1([H])CC2)[H]