LIPID MAPS

Common Name

7-oxocholesterol(d7)

Systematic Name

7-oxo-cholest-5-en-3β-ol(d7)

Synonyms

LM ID

LMST01010005

Formula

C₂₇H₃₇D₇O₂

Exact Mass

Calculate m/z

407.378068

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Category

Main Class

Sub Class

Sterol Lipids [ST]

Sterols [ST01]

Cholesterol and derivatives [ST0101]

7-keto Cholesterol-d7 is intended for use as an internal standard for the quantification of 7-keto cholesterol by GC- or LC-MS. 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. 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).

2. 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).

3. 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).

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. The Journal of Biological Chemisty 286(38), 33021-33028 (2011).

5. 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).

6. 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).

7. 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).

Comments

Synthetic deuterated standard

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

InChiKey (Click to copy)

YIKKMWSQVKJCOP-KVZGVLACSA-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/i1D3,2D3,17D

SMILES (Click to copy)

[C@]12(C(=O)C=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C([2H])([2H])[2H])(C([2H])([2H])[2H])[2H])CC[C@@]21[H])[H]

HMDB ID

HMDB00501

PubChem CID

3247054

Cayman ID

25972

Created at

-

Updated at

29th Jan 2021