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Structure Database (LMSD)

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Common Name

20:5 Cholesterol ester

Systematic Name

cholest-5-en-3β-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoate)

Synonyms

CE(20:5)

LM ID

LMST01020015

Formula

C₄₇H₇₄O₂

Exact Mass

Calculate m/z

670.56888

Sum Composition

CE 20:5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Cholesteryl eicosapentaenoate is a cholesterol ester.¹ It induces cytotoxicity in human monocyte-macrophages in a concentration-dependent manner at concentrations ranging from 88 to 880 μM. Cholesteryl eicosapentaenoate levels are elevated 1.89-fold in the serum of pediatric patients with extrahepatic biliary atresia and decreased in the serum and plasma of patients with Alzheimer’s disease and abetalipoproteinemia, respectively, compared with healthy individuals.^2,3,4

This information has been provided by Cayman Chemical

References

1. Hardwick, S.J., Carpenter, K.L., Law, N.S., et al. Toxicity of polyunsaturated fatty acid esters for human monocyte-macrophages: The anomalous behaviour of cholesteryl linolenate. Free Radic. Res. 26(4), 351-362 (1997).

2. Robberecht, E., Koletzko, B., and Christophe, A. Several mechanisms contribute to the abnormal fatty acid composition of serum phospholipids and cholesterol esters in cholestatic children with extrahepatic biliary atresia. Prostaglandins Leukot. Essent. Fatty Acids 56(3), 199-204 (1997).

3. Tully, A.M., Roche, H.M., Doyle, R., et al. Low serum cholesteryl ester-docosahexaenoic acid levels in Alzheimer’s disease: A case-control study. Br. J. Nutr. 89(4), 483-489 (2003).

4. Subbaiah, P.V., Banerji, B., Gregg, R.E., et al. Molecular species of cholesteryl esters formed in abetalipoproteinemia: Effect of apoprotein B-containing lipoproteins. J. Lipid Res. 31(5), 927-932 (1990).

String Representations

InChiKey (Click to copy)

XZFUGMCJZFRBKF-BDJFIEMMSA-N

InChi (Click to copy)

InChI=1S/C47H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h8-9,11-12,14-15,17-18,20-21,28,37-38,40-44H,7,10,13,16,19,22-27,29-36H2,1-6H3/b9-8-,12-11-,15-14-,18-17-,21-20-/t38-,40+,41+,42-,43+,44+,46+,47-/m1/s1

SMILES (Click to copy)

C(/C/C=C\C/C=C\C/C=C\CC)=C/C/C=C\CCCC(O[C@@H]1CC2=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)CC1)=O