LIPID MAPS

Structure Database (LMSD)

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Common Name

20:4 Cholesterol ester

Systematic Name

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

Synonyms

CE(20:4)
Cholesterol arachidonate

LM ID

LMST01020014

Formula

C₄₇H₇₆O₂

Exact Mass

Calculate m/z

672.584531

Sum Composition

CE 20:4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Cholesteryl arachidonate is a cholesterol ester that is found in plasma and the adrenal gland.¹ It is a component of low-density lipoprotein (LDL) and oxidiation of the arachidonate moiety contributes to macrophage activation and foam cell formation in atherosclerosis.² Cholesteryl arachidonate undergoes hydrolysis to release arachidonic acid during ACTH-stimulated prostaglandin synthesis in rat adrenocortical cells.³ Levels of cholesteryl arachidonate are increased in the bronchoalveolar lavage fluid (BALF) in pediatric cystic fibrosis patients compared to healthy controls as well as in placentas of women with chorioamnionitis.^4,5

This information has been provided by Cayman Chemical

References

1. Cheng, B., Al-Shammari, F.H., Ghader, I.A., et al. Fundamental studies of adrenal retinoid-X-receptor: Protein isoform, tissue expression, subcellular distribution, and ligand availability. J. Steroid. Biochem. Mol. Biol. 171, 110-120 (2017).

2. Choi, S.-H., Yin, H., Ravandi, A., et al. Polyoxygenated cholesterol ester hydroperoxide activates TLR4 and SYK dependent signaling in macrophages. PLoS One 8(12), e83145 (2013).

3. Vahouny, G.V., Chanderbhan, R., Hodges, V.A., et al. Cholesterol arachidonate as a prostaglandin precursor in adrenocortical cells. Prostaglandins 16(2), 207-220 (1978).

4. Ma, D.C., Yoon, A.J., Faull, K.F., et al. Cholesteryl esters are elevated in the lipid fraction of bronchoalveolar lavage fluid collected from pediatric cystic fibrosis patients. PLoS One 10(4), e0125326 (2015).

5. Delmis, J. Placental lipid contents in preterm labor complicated by chorioamnionitis. J. Perinat. Med. 17(6), 417-422 (1989).

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)

IMXSFYNMSOULQS-BEDFLICRSA-N

InChi (Click to copy)

InChI=1S/C47H76O2/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/h11-12,14-15,17-18,20-21,28,37-38,40-44H,7-10,13,16,19,22-27,29-36H2,1-6H3/b12-11-,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\CCCCC)=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