| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:39:02 UTC |
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| Update date | 2015-07-21 06:57:59 UTC |
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| Primary ID | FDB024048 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) |
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| Description | Cholesteryl docosahexaenoic 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 accumulation 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).
Depression has been found weakly related to serum cholesteryl ester arachidonic/docosahexaenoic fatty acid ratio. In healthy human receiving a diet rich in docosahexaenoic acid (DHA), it was incorporated into LDL cholesteryl esters; DHA does not appear to increase the susceptibility of LDL to oxidation. Lower levels of DHA were found in all plasma lipid fractions from infants fed formula compared with those in the human milk-fed infants, irrespective of the source of the formula supplement. (PMID: 16482070, 15262190, 15051839) [HMDB] |
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| CAS Number | 70110-50-8 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C49H76O2 |
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| IUPAC name | (2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl docosa-4,7,10,13,16,19-hexaenoate |
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| InChI Identifier | InChI=1S/C49H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h8-9,11-12,14-15,17-18,20-21,23-24,30,39-40,42-46H,7,10,13,16,19,22,25-29,31-38H2,1-6H3/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1 |
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| InChI Key | VOEVEGPMRIYYKC-KNEWWSHNSA-N |
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| Isomeric SMILES | [H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC |
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| Average Molecular Weight | 697.1265 |
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| Monoisotopic Molecular Weight | 696.584531676 |
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| Classification |
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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
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 29368174 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C02530 |
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| Pubchem Compound ID | 53477890 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB06733 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
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