Human Metabolome Database: Showing metabocard for CE(16:0) (HMDB0000885)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

enzymes (8) Show 8 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2017-12-07 01:19:49 UTC

HMDB ID

HMDB0000885

Secondary Accession Numbers

HMDB0005188
HMDB00885
HMDB05188

Metabolite Identification

Common Name

CE(16:0)

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). CE(16:0) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism. 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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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
1-hexadecanoyl-cholesterol; cholesteryl 1-palmitoic acid	Lipid Annotator
CE(16:0)	Lipid Annotator
CE(16:0/0:0)	Lipid Annotator
1-hexadecanoyl-cholesterol	Lipid Annotator

Chemical Formula

C₄₃H₇₆O₂

Average Molecular Weight

625.0623

Monoisotopic Molecular Weight

624.584531676

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

Traditional Name

cholesteryl palmitate

CAS Registry Number

601-34-3

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

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

InChI Key

BBJQPKLGPMQWBU-JADYGXMDSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as cholesteryl esters. These are compounds containing an esterified cholestane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Cholesteryl esters

Alternative Parents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholesterol ester (CHEBI:3663 )
Cholesteryl esters (C11251 )
Steryl esters (LMST01020005 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	75 - 77 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.9e-06 g/L	ALOGPS
logP	10.57	ALOGPS
logP	14.03	ChemAxon
logS	-8	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	194.21 m³·mol⁻¹	ChemAxon
Polarizability	84.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004r-1255039000-894288c747d8162be0b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4439030000-3c832b67193915b741ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ar1-4709120000-dc6542884db42b6750ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dr-0024009000-8a55f4904b3c9168d2af	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0049103000-e980336a44ede858695b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ku-2029000000-106443473af958bc3183	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Location

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	405.46 +/- 56.51 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	208 +/- 7.8 uM	Adult (>18 years old)	Both	Normal	8061816	details
Blood	Detected and Quantified	190 +/- 6 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	200 +/- 4.5 uM	Adult (>18 years old)	Both	Normal	8061816	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	857.0 +/- 14.0 uM	Adult (>18 years old)	Both	Hypercholesterolemia	8061816	details

Associated Disorders and Diseases

Disease References

Hypercholesterolemia
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 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022299

KNApSAcK ID

Not Available

Chemspider ID

215725

KEGG Compound ID

C11251

BioCyc ID

Cholesterol-esters

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5844

PubChem Compound

246520

PDB ID

Not Available

ChEBI ID

3663

References

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]

Enzymes

Enzyme Details

1. Phosphatidylcholine-sterol acyltransferase

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

Enzyme Details

2. Lysosomal acid lipase/cholesteryl ester hydrolase

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

Enzyme Details

3. Bile salt-activated lipase

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

Enzyme Details

4. Liver carboxylesterase 1

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

Enzyme Details

5. Sterol O-acyltransferase 2

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

Enzyme Details

6. Sterol O-acyltransferase 1

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

Enzyme Details

7. Scavenger receptor class B member 1

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

Enzyme Details

8. Neutral cholesterol ester hydrolase 1

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

Showing metabocard for CE(16:0) (HMDB0000885)

Structure for HMDB0000885 (CE(16:0))

Enzymes