ChemFOnt: Showing chemical card for CE(16:0) (CFc000000706)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:10 UTC

Chemfont ID

CFc000000706

Molecule Identification

Common Name

CE(16:0)

Definition

CE(16:0), also known as 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 of 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
Cholesterol ester(16:0)	HMDB
1-Palmitoyl-cholesterol	HMDB
Cholesteryl 1-hexadecanoic acid	HMDB
Cholesterol ester(16:0/0:0)	HMDB
Cholesterol 1-hexadecanoate	HMDB
CE(16:0/0:0)	HMDB
Cholesterol 1-hexadecanoic acid	HMDB
Cholesterol 1-palmitoic acid	HMDB
Cholesterol 1-palmitoate	HMDB
Cholesteryl 1-palmitoate	HMDB
Cholesteryl 1-hexadecanoate	HMDB
1-Hexadecanoyl-cholesterol	HMDB
Cholesteryl 1-palmitoic acid	HMDB
Cholest-5-en-3-yl palmitate	HMDB
Cholest-5-ene-3-beta-yl palmitate	HMDB
Cholesteryl palmitate	HMDB
Cholesteryl palmitic acid	HMDB
Hexadecanoate	HMDB
Hexadecanoic acid	HMDB
Hexadecanoic acid cholesteryl ester	HMDB
5-Cholesten-3beta-ol stearate	HMDB
5-Cholesten-3β-ol stearate	HMDB
Cholest-5-en-3beta-ol stearate	HMDB
Cholest-5-en-3β-ol stearate	HMDB
Cholesterol hexadecanoate	HMDB
CE(16:0)	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[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl hexadecanoate

Traditional Name

(1S,2R,5S,10S,11S,14R,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 hexadecanoate

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

Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters 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 )

Functional Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8061816)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000885)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000885)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000885)

Source

Endogenous

Endogenous (HMDB: HMDB0000885)

Animal

Animal (HMDB: HMDB0000885)

Exogenous

Food

Food (HMDB: HMDB0000885)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Exogenous (HMDB: HMDB0000885)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000885)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000885)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)

Lipid metabolism pathway (HMDB: HMDB0000885)

Cellular process

Cell signaling (HMDB: HMDB0000885)

Biochemical process

Lipid transport (HMDB: HMDB0000885)

Role

Physical Properties

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	85.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000885

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022299

KNApSAcK ID

Not Available

Chemspider ID

215725

KEGG Compound ID

C11251

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5844

PubChem Compound

246520

PDB ID

Not Available

ChEBI ID

3663

Food Biomarker Ontology

Not Available

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.

Showing chemical card for CE(16:0) (CFc000000706)

MOL for CFc000000706 (CE(16:0))

3D MOL for CFc000000706 (CE(16:0))

3D SDF for CFc000000706 (CE(16:0))

3D-SDF for CFc000000706 (CE(16:0))

PDB for CFc000000706 (CE(16:0))

3D PDB for CFc000000706 (CE(16:0))

SMILES for CFc000000706 (CE(16:0))

INCHI for CFc000000706 (CE(16:0))

Structure for CFc000000706 (CE(16:0))

3D Structure for CFc000000706 (CE(16:0))