CE(18:2(9Z,12Z))
Cholesteryl linoleic acid is a cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumliation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Cholesteryl linoleate is contained in low density lipoprotein and atherosclerotic lesions. The oxidation products of cholesteryl linoleate may cause chronic inflammatory processes. (PMID 9684755 , 11950694 ).
MOLSDFPDBSMILESInChI
Structure for HMDB00610 (CE(18:2(9Z,12Z)))
C45H76O2
649.0837
648.584531676
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z,12Z)-octadeca-9,12-dienoate
cholesteryl linoleate
604-33-1
CCCCCC=C/CC=C/CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]23[H])C1
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
NAACPBBQTFFYQB-LJAITQKLSA-N
This compound belongs to the class of chemical entities known as cholesteryl esters. These are compounds containing an esterified cholestane moiety.
Chemical entities
Organic compounds
Lipids and lipid-like moleclies
Steroids and steroid derivatives
Cholesteryl esters
Aliphatic homopolycyclic compounds
Detected and Quantified
Solid
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0000009000-be0d242fdc5dfce84520View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0000009000-f746df3c4960ff441e25View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-00kb-0380309000-9563a2875a28afc28571View in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Not Available
Not Available
Not Available
None
None
Not Available
Not Available
Not Available
Not Available
FDB022141
Not Available
4450205
C15441
Cholesterol-esters
Not Available
Not Available
HMDB00610
HMDB00610
5584
5287939
CLL
41509
- Lima ES, Di Mascio P, Abdalla DS: Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins. J Lipid Res. 2003 Sep;44(9):1660-6. Epub 2003 Jul 1. [PubMed:12837858 ]
- Saito Y, Shiki Y, Shirai K, Yoshida S: Effect of a new synthetic 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor on cholesterol synthesis and low density lipoprotein uptake by primary cultures of rat hepatocytes. Arzneimittelforschung. 1988 Feb;38(2):251-3. [PubMed:3130840 ]
- Yamakoshi J, Kataoka S, Koga T, Ariga T: Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits. Atherosclerosis. 1999 Jan;142(1):139-49. [PubMed:9920515 ]
- Karten B, Boechzelt H, Abuja PM, Mittelbach M, Oettl K, Sattler W: Femtomole analysis of 9-oxononanoyl cholesterol by high performance liquid chromatography. J Lipid Res. 1998 Jul;39(7):1508-19. [PubMed:9684755 ]
- Huber J, Boechzelt H, Karten B, Surboeck M, Bochkov VN, Binder BR, Sattler W, Leitinger N: Oxidized cholesteryl linoleates stimulate endothelial cells to bind monocytes via the extracellular signal-regulated kinase 1/2 pathway. Arterioscler Thromb Vasc Biol. 2002 Apr 1;22(4):581-6. [PubMed:11950694 ]
Enzymes
- General function:
- Involved in phosphatidylcholine-sterol O-acyltransferase activity
- Specific function:
- Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
- Gene Name:
- LCAT
- Uniprot ID:
- P04180
- Molecular weight:
- 49577.545
- General function:
- Involved in lipid metabolic process
- Specific function:
- Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
- Gene Name:
- LIPA
- Uniprot ID:
- P38571
- Molecular weight:
- 45418.71
- General function:
- Lipid transport and metabolism
- Specific function:
- Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
- Gene Name:
- CEL
- Uniprot ID:
- P19835
- Molecular weight:
- 79666.385
- General function:
- Lipid transport and metabolism
- Specific function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
- Gene Name:
- CES1
- Uniprot ID:
- P23141
- Molecular weight:
- 62520.62
- General function:
- Involved in acyl-CoA binding
- Specific function:
- Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase. May provide cholesteryl esters for lipoprotein secretion from hepatocytes and intestinal mucosa.
- Gene Name:
- SOAT2
- Uniprot ID:
- O75908
- Molecular weight:
- 59895.735
- General function:
- Involved in acyl-CoA binding
- Specific function:
- Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
- Gene Name:
- SOAT1
- Uniprot ID:
- P35610
- Molecular weight:
- 58130.665
- General function:
- Involved in cell adhesion
- Specific function:
- Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma membrane, called caveolae. Facilitates the flux of free and esterified cholesterol between the cell surface and extracellular donors and acceptors, such as HDL and to a lesser extent, apoB-containing lipoproteins and modified lipoproteins. Probably involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity. Receptor for hepatitis C virus glycoprotein E2. Binding between SCARB1 and E2 was found to be independent of the genotype of the viral isolate. Plays an important role in the uptake of HDL cholesteryl ester
- Gene Name:
- SCARB1
- Uniprot ID:
- Q8WTV0
- Molecular weight:
- 60877.4
- General function:
- Involved in hydrolase activity
- Specific function:
- Hydrolyzes 2-acetyl monoalkylglycerol ether, the penultimate precursor of the pathway for de novo synthesis of platelet-activating factor. May be responsible for cholesterol ester hydrolysis in macrophages, thereby contributing to the development of atherosclerosis. Also involved in organ detoxification by hydrolyzing exogenous organophosphorus compounds. May contribute to cancer pathogenesis by promoting tumor cell migration
- Gene Name:
- NCEH1
- Uniprot ID:
- Q6PIU2
- Molecular weight:
- 45807.4