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| Record Information |
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| Version | 3.6 |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2017-03-02 21:26:15 UTC |
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| HMDB ID | HMDB00885 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | CE(16:0) |
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| Description | Cholesteryl palmitic 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). Cholesteryl palmitate is one of the four important lipids found in the tear film. Amniotic fluid cholesteryl palmitate, as measured by thin-layer chromatography, appears to be a very sensitive and specific predictor for the risk of respiratory distress syndrome (RDS) in newborns of normal pregnancies. (PMID: 3405552 , 16922549 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (3beta)-Cholest-5-en-3-ol hexadecanoate | ChEBI | | 16:0 Cholesterol ester | ChEBI | | CE | ChEBI | | Cholesterol palmitate | ChEBI | | Cholesteryl hexadecanoate | ChEBI | | Hexadecanoic acid, cholesteryl ester | ChEBI | | Palmitic acid cholesteryl ester | ChEBI | | (3b)-Cholest-5-en-3-ol hexadecanoate | Generator | | (3b)-Cholest-5-en-3-ol hexadecanoic acid | Generator | | (3beta)-Cholest-5-en-3-ol hexadecanoic acid | Generator | | (3β)-cholest-5-en-3-ol hexadecanoate | Generator | | (3β)-cholest-5-en-3-ol hexadecanoic acid | Generator | | Cholesterol palmitic acid | Generator | | Cholesteryl hexadecanoic acid | Generator | | Hexadecanoate, cholesteryl ester | Generator | | Palmitate cholesteryl ester | Generator | | 1-Palmitoyl-cholesterol | HMDB | | Cholest-5-en-3-yl palmitate | HMDB | | Cholest-5-ene-3-beta-yl palmitate | HMDB | | Cholesterol 1-hexadecanoate | HMDB | | Cholesterol 1-hexadecanoic acid | HMDB | | Cholesterol 1-palmitoate | HMDB | | Cholesterol 1-palmitoic acid | HMDB | | Cholesterol ester(16:0) | HMDB | | Cholesterol ester(16:0/0:0) | HMDB | | Cholesteryl 1-hexadecanoate | HMDB | | Cholesteryl 1-hexadecanoic acid | HMDB | | Cholesteryl 1-palmitoate | HMDB | | Cholesteryl 1-palmitoic acid | HMDB | | Cholesteryl palmitate | HMDB | | Cholesteryl palmitic acid | HMDB | | Hexadecanoate | HMDB | | Hexadecanoic acid | HMDB | | Hexadecanoic acid cholesteryl ester | HMDB |
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| Chemical Formula | C43H76O2 |
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| Average Molecular Weight | 625.0623 |
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| Monoisotopic Molecular Weight | 624.584531676 |
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| IUPAC Name | (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 hexadecanoate |
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| Traditional Name | cholesteryl palmitate |
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| CAS Registry Number | 601-34-3 |
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| SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCCCCCCCCC)[C@H](C)CCCC(C)C |
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| InChI Identifier | InChI=1S/C43H76O2/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/h24,33-34,36-40H,7-23,25-32H2,1-6H3/t34-,36+,37+,38-,39+,40+,42+,43-/m1/s1 |
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| InChI Key | BBJQPKLGPMQWBU-JADYGXMDSA-N |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of chemical entities known as cholesteryl esters. These are compounds containing an esterified cholestane moiety. |
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| Kingdom | Chemical entities |
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| Super Class | Organic compounds |
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| Class | Lipids and lipid-like molecules |
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| Sub Class | Steroids and steroid derivatives |
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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 | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | - Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Hormones, Membrane component
- Membrane integrity/stability
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| Application | - Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 75 - 77 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biofluid Locations | |
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| Tissue Location | Not Available |
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| Pathways | Not Available |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 405.46 +/- 56.51 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 208 +/- 7.8 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 190 +/- 6 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected and Quantified | 200 +/- 4.5 uM | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected and Quantified | 857.0 +/- 14.0 uM | Adult (>18 years old) | Both | Hypercholesterolemia | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Hypercholesterolemia |
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- Kim DH, Lee KJ, Heo GS: Analysis of cholesterol and cholesteryl esters in human serum using capillary supercritical fluid chromatography. J Chromatogr B Biomed Appl. 1994 Apr 22;655(1):1-8. [PubMed:8061816 ]
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| Associated OMIM IDs | None |
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| External Links |
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| DrugBank ID | Not Available |
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| DrugBank Metabolite ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| Phenol Explorer Metabolite ID | Not Available |
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| FoodDB ID | FDB022299 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 215725 |
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| KEGG Compound ID | C11251 |
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| BioCyc ID | Cholesterol-esters |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| NuGOwiki Link | HMDB00885 |
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| Metagene Link | HMDB00885 |
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| METLIN ID | 5844 |
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| PubChem Compound | 246520 |
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| PDB ID | Not Available |
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| ChEBI ID | 3663 |
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| References |
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| Synthesis Reference | Mahadevan, V.; Lundberg, W. O. Preparation of cholesteryl esters of long-chain fatty acids. Journal of the American Oil Chemists' Society (1960), 37 685. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Snow JW, Glick JM, Phillips MC: The phase behavior of cholesteryl esters in intracellular inclusions. J Biol Chem. 1992 Sep 15;267(26):18564-72. [PubMed:1326528 ]
- Mudgil P, Dennis GR, Millar TJ: Interactions of poly(tert-butyl acrylate)-poly(styrene) diblock copolymers with lipids at the air-water interface. Langmuir. 2006 Aug 29;22(18):7672-7. [PubMed:16922549 ]
- Ludmir J, Alvarez JG, Landon MB, Gabbe SG, Mennuti MT, Touchstone JC: Amniotic fluid cholesteryl palmitate in pregnancies complicated by diabetes mellitus. Obstet Gynecol. 1988 Sep;72(3 Pt 1):360-2. [PubMed:3405552 ]
- Van Biervliet JP, Vinaimont N, Vercaemst R, Rosseneu M: Serum cholesterol, cholesteryl ester, and high-density lipoprotein development in newborn infants: response to formulas supplemented with cholesterol and gamma-linolenic acid. J Pediatr. 1992 Apr;120(4 Pt 2):S101-8. [PubMed:1313864 ]
- Rosseneu M, Cambien F, Vinaimont N, Nicaud V, De Backer G: Biomarkers of dietary fat composition in young adults with a parental history of premature coronary heart disease compared with controls. The EARS Study. Atherosclerosis. 1994 Aug;108(2):127-36. [PubMed:7980712 ]
- Alvarez JG, Ludmir J: Semiautomated multisample analysis of amniotic fluid lipids by high-performance thin-layer chromatography-reflectance spectrodensitometry. J Chromatogr. 1993 May 19;615(1):142-7. [PubMed:8340452 ]
- Jachec W, Tomasik A, Ceglarek W, Wos S, Wodniecki J, Wojciechowska C, Skrzep-Poloczek B, Walichiewicz P, Widenka K: Lipid peroxidation and vitamin E in human coronary atherosclerotic lesions. Clin Chim Acta. 2003 Apr;330(1-2):121-9. [PubMed:12636930 ]
- Ludmir J, Alvarez JG, Mennuti MT, Gabbe SG, Touchstone JC: Cholesteryl palmitate as a predictor of fetal lung maturity. Am J Obstet Gynecol. 1987 Jul;157(1):84-8. [PubMed:3605272 ]
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