LIPID MAPS

Structure Database (LMSD)

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Common Name

7-oxo-cholesterol

Systematic Name

7-oxo-cholest-5-en-3β-ol

Synonyms

7-keto-cholesterol
7-kChol

LM ID

LMST01010049

Formula

C₂₇H₄₄O₂

Exact Mass

Calculate m/z

400.33413

Sum Composition

ST 27:2;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

7-keto Cholesterol is a bioactive sterol and a major oxysterol component of oxidized LDL.^1,2 It is produced by oxidation of cholesterol via ethanol-mediated lipid peroxidation or photodamage as well as oxidation of 7-dehydro cholesterol by the cytochrome P450 (CYP) isoform CYP7A1.3,4,5 7-keto Cholesterol inhibits CYP7A1 (IC50 = ~1 μM).⁴ It induces activation and chemotaxis of retinal microglia as well as polarization to a pro-inflammatory state via NLRP3 inflammasome activation in vitro.⁶ Intraocular implantation of 7-keto cholesterol coated wafers increases ocular levels of VEGF, IL-1β, and GRO/KC, macrophage infiltration, and neovascularization in rat eye.⁷ Levels of 7-keto cholesterol in lipid deposits are increased in a variety of chronic diseases, including atherosclerosis, Alzheimer's disease, and age-related macular degeneration.

This information has been provided by Cayman Chemical

References

1. Amaral, J., Lee, J.W., Chou, J., et al. 7-Ketocholesterol induces inflammation and angiogenesis in vivo: A novel rat model. PLoS One 8(2), e56099 (2013).

2. Indaram, M., Ma, W., Zhao, L., et al. 7-Ketocholesterol increases retinal microglial migration, activation, and angiogenicity: A potential pathogenic mechanism underlying age-related macular degeneration. Sci. Rep. 5:9144, (2015).

3. Shentu, T.P., Titushkin, I., Singh, D.K., et al. oxLDL-induced decrease in lipid order of membrane domains is inversely correlated with endothelial stiffness and network formation. Am. J. Physiol. Cell Physiol. 299(2), C218-C229 (2010).

4. Shinkyo, R., Xu, L., Tallman, K.A., et al. Conversion of 7-dehydrocholesterol to 7-ketocholesterol is catalyzed by human cytochrome P450 7A1 and occurs by direct oxidation without an epoxide intermediate. J. Biol. Chem. 286(38), 33021-33028 (2011).

5. Rodriguez, I.R., and Fliesler, S.J. Photodamage generates 7-keto- and 7-hydroxycholesterol in the rat retina via a free radical-mediated mechanism. Photochem. Photobiol. 85(5), 1116-1125 (2009).

6. Mitic, T., Shave, S., Semjonous, N., et al. 11β-Hydroxysteroid dehydrogenase type 1 contributes to the balance between 7-keto- and 7-hydroxy-oxysterols in vivo. Biochem. Pharmacol. 86(1), 146-153 (2013).

7. Brown, A.J., Leong, S.l., Dean, R.T., et al. 7-Hydroperoxycholesterol and its products in oxidized low density lipoprotein and human atherosclerotic plaque. J. Lipid Res. 38, 1730-1745 (1997).

Reactions

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

Mus musculus (#10090)

Mammalia (#40674)

Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010

Pubmed ID: 20574076

DOI: 10.1194/jlr.M008748

String Representations

InChiKey (Click to copy)

YIKKMWSQVKJCOP-ABXCMAEBSA-N

InChi (Click to copy)

InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]4([H])[C@]3([H])C(=O)C=C2C[C@@H](O)C1