LIPID MAPS

Structure Database (LMSD)

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Common Name

18:2 Cholesterol ester

Systematic Name

cholest-5-en-3β-yl (9Z,12Z-octadecadienoate)

Synonyms

CE(18:2)
Cholesteryl linoleate

LM ID

LMST01020008

Formula

C₄₅H₇₆O₂

Exact Mass

Calculate m/z

648.58453

Sum Composition

CE 18:2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

Cholesteryl linoleate is a pro-atherogenic cholesterol ester.^1,2 It has been found in the plasma membrane of macrophages as a component of LDL, where it undergoes oxidation to form cholesteryl linoleate hydroperoxides .¹ Cholesteryl linoleate levels are increased in apoB-lipoproteins and positively correlated with hepatic cholesterol levels and the number of atherosclerotic lesions in transgenic mice overexpressing human ABCA1.2 Lipoprotein levels of cholesteryl linoleate are increased and associated with lipid radical formation in patients with β-thalassemia.³

This information has been provided by Cayman Chemical

References

1. Takahashi, Y., Zhu, H., Xu, W., et al. Selective uptake and efflux of cholesteryl linoleate in LDL by macrophages expressing 12/15-lipoxygenase. Biochem. Biophys. Res. Commun. 338(1), 128-135 (2005).

2. Joyce, C.W., Wagner, E.M., Basso, F., et al. ABCA1 overexpression in the liver of LDLr-KO mice leads to accumulation of pro-atherogenic lipoproteins and enhanced atherosclerosis. J. Biol. Chem. 281(44), 33053-33065 (2006).

3. Lerksaipheng, P., Paiboonsukwong, K., Sanvarinda, P., et al. Kinetics of lipid radical formation in lipoproteins from β-thalassemia: Implication of cholesteryl esters and α-tocopherol. Biomed. Pharmacother. 154, 113624 (2022).

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

String Representations

InChiKey (Click to copy)

NAACPBBQTFFYQB-LJAITQKLSA-N

InChi (Click to copy)

InChI=1S/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1

SMILES (Click to copy)

[C@]12(CC=C3C[C@@H](OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C)C)CC[C@@]21[H])[H]