LIPID MAPS

Structure Database (LMSD)

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Common Name

14:0 Cholesterol ester

Systematic Name

cholest-5-en-3β-yl tetradecanoate

Synonyms

CE(14:0)

LM ID

LMST01020004

Formula

C₄₁H₇₂O₂

Exact Mass

Calculate m/z

596.55323

Sum Composition

CE 14:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

Cholesteryl myristate is a cholesterol ester.¹ Levels of cholesteryl myristate are increased in the serum, liver, and aorta in rabbits fed a high-cholesterol diet and positively correlate with development of non-alcoholic fatty liver disease (NAFLD). Plasma levels of cholesteryl myristate also positively correlate with the presence of unstable atherosclerotic plaques in coronary artery disease.² Cholesterol myristate has been used in the composition of lipid nanoparticles (LNPs) as a drug carrier systems for drugs with low water solubility.³

This information has been provided by Cayman Chemical

References

2. Kim, E.J., Kim, B.H., Seo, H.S., et al. Cholesterol-induced non-alcoholic fatty liver disease and atherosclerosis aggravated by systemic inflammation. PLoS One 5(6), e97841 (2014).

1. Rosenblatt, K.M., and Bunjes, H. Evaluation of the drug loading capacity of different lipid nanoparticle dispersions by passive drug loading. Eur. J. Pharm. Biopharm. 117, 49-59 (2017).

3. Meikle, P.J., Wong, G., Tsorotes, D., et al. Plasma lipidomic analysis of stable and unstable coronary artery disease. Arterioscler. Thromb. Vasc. Biol. 31(11), 2723-2732 (2011).

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)

SJDMTGSQPOFVLR-ZPQCIJQQSA-N

InChi (Click to copy)

InChI=1S/C41H72O2/c1-7-8-9-10-11-12-13-14-15-16-17-21-39(42)43-34-26-28-40(5)33(30-34)22-23-35-37-25-24-36(32(4)20-18-19-31(2)3)41(37,6)29-27-38(35)40/h22,31-32,34-38H,7-21,23-30H2,1-6H3/t32-,34+,35+,36-,37+,38+,40+,41-/m1/s1

SMILES (Click to copy)

C1[C@H](OC(=O)CCCCCCCCCCCCC)CC2=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]4(C)CC[C@]3([H])[C@@]2(C)C1