LIPID MAPS

Structure Database (LMSD)

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Common Name

16:1 Cholesterol ester

Systematic Name

cholest-5-en-3β-yl (9Z-hexadecenoate)

Synonyms

CE(16:1)
Cholesteryl palmitoleate

LM ID

LMST01020006

Formula

C₄₃H₇₄O₂

Exact Mass

Calculate m/z

622.568881

Sum Composition

CE 16:1

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Cholesteryl palmitoleate is a cholesterol ester.^1,2,3 Plasma levels of cholesteryl palmitoleate are increased in ApoE-/- mice exposed to cigarette smoke and in pediatric patients with biliary atresia.^1,2 Cholesteryl palmitoleate has been used as a standard for the identification of cholesterol esters in human meibomian gland secretions.³

This information has been provided by Cayman Chemical

References

1. 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).

2. Butovich, I.A. Fatty acid composition of cholesteryl esters of human meibomian gland secretions. Steroids 75(10), 726-733 (2010).

3. Boué, S., Tarasov, K., Jänis, M., et al. Modulation of atherogenic lipidome by cigarette smoke in apolipoprotein E-deficient mice. Atherosclerosis 225(2), 328-334 (2012).

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)

HODJWNWCVNUPAQ-XDOSKZMUSA-N

InChi (Click to copy)

InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/b13-12-/t34-,36+,37+,38-,39+,40+,42+,43-/m1/s1

SMILES (Click to copy)

C1[C@H](OC(=O)CCCCCCC/C=C\CCCCCC)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