Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-08 16:43:49 UTC |
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Update Date | 2022-11-30 19:24:26 UTC |
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HMDB ID | HMDB0112219 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CE(7D6) |
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Description | CE(7D6) is a furan fatty acid ester of cholesterol or simply a cholesteryl ester (CE). Cholesteryl esters are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesteryl esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesteryl esters tend to contain relatively high proportions of C18 fatty acids. Cholesteryl esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesteryl esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesteryl esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesteryl esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesteryl esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesteryl esters from CoA esters of fatty acids and cholesterol. Cholesteryl ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. The shorthand notation for CE(7D6) refers to the furan fatty acid's 7-carbon carboxyalkyl moiety, the dimethyl substitutions in the 3- and 4-positions of its furan moiety, and its 6-carbon alkyl moiety. |
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Structure | CCCCCCC1=C(C)C(C)=C(CCCCCCC(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)O1 InChI=1S/C46H76O3/c1-9-10-11-14-20-42-34(5)35(6)43(49-42)21-15-12-13-16-22-44(47)48-37-27-29-45(7)36(31-37)23-24-38-40-26-25-39(33(4)19-17-18-32(2)3)46(40,8)30-28-41(38)45/h23,32-33,37-41H,9-22,24-31H2,1-8H3 |
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Synonyms | Value | Source |
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2,15-Dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl 7-(5-hexyl-3,4-dimethylfuran-2-yl)heptanoic acid | Generator | CE(DiMe(7,6)) | SMPDB, HMDB | 7D6 cholesteryl ester | SMPDB, HMDB | DiMe(7,6) cholesteryl ester | SMPDB, HMDB | CE(7D6) | SMPDB | 2,15-Dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl 7-(5-hexyl-3,4-dimethylfuran-2-yl)heptanoic acid | Generator, HMDB |
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Chemical Formula | C46H76O3 |
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Average Molecular Weight | 677.111 |
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Monoisotopic Molecular Weight | 676.579446307 |
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IUPAC Name | 2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl 7-(5-hexyl-3,4-dimethylfuran-2-yl)heptanoate |
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Traditional Name | 2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl 7-(5-hexyl-3,4-dimethylfuran-2-yl)heptanoate |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCC1=C(C)C(C)=C(CCCCCCC(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)O1 |
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InChI Identifier | InChI=1S/C46H76O3/c1-9-10-11-14-20-42-34(5)35(6)43(49-42)21-15-12-13-16-22-44(47)48-37-27-29-45(7)36(31-37)23-24-38-40-26-25-39(33(4)19-17-18-32(2)3)46(40,8)30-28-41(38)45/h23,32-33,37-41H,9-22,24-31H2,1-8H3 |
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InChI Key | TWUGSSMJMBCXNC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid esters |
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Direct Parent | Cholesteryl esters |
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Alternative Parents | |
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Substituents | - Cholesteryl ester
- Cholesterol
- Cholestane-skeleton
- Delta-5-steroid
- Furanoid fatty acid
- Fatty acyl
- Furan
- Heteroaromatic compound
- Carboxylic acid ester
- Organoheterocyclic compound
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 10V, Positive-QTOF | splash10-004l-1045019000-a34721693ac7c98dacad | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 20V, Positive-QTOF | splash10-05tu-6139002000-6ff0480793071cd897ab | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 40V, Positive-QTOF | splash10-0690-6119002000-e18676651a15d0055dc9 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 10V, Negative-QTOF | splash10-004r-0015009000-3bdec81f9e8cfeaabfa6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 20V, Negative-QTOF | splash10-000i-0129003000-363a9476852abe7d9043 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 40V, Negative-QTOF | splash10-00kr-1219000000-fb1a8c7793f87fc2d655 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 10V, Negative-QTOF | splash10-004i-0002009000-7cc2236a8303d2df8156 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 20V, Negative-QTOF | splash10-004i-0002019000-ca7dac871029109696c4 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 40V, Negative-QTOF | splash10-05g0-4722409000-28b84f48a37967af98a9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 10V, Positive-QTOF | splash10-016r-1049007000-e4659268dda8636179f6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 20V, Positive-QTOF | splash10-0a4i-9142003000-ac2a54f8604dc7053fbb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - CE(7D6) 40V, Positive-QTOF | splash10-0abc-6932100000-e7f2f953e269f93cc8a9 | 2021-09-24 | Wishart Lab | View Spectrum |
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