ChemFOnt: Showing chemical card for CE(19:0) (CFc000002899)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:53 UTC

Chemfont ID

CFc000002899

Molecule Identification

Common Name

CE(19:0)

Definition

Cholesteryl nonadecanoic acid is a cholesteryl ester. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 16458590 , 9420339 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
19:0 Cholesterol ester	ChEBI
19:0 Cholesteryl ester	ChEBI
CE 19:0	ChEBI
Cholest-5-en-3beta-yl nonadecanoate	ChEBI
Nonadecanoylcholesterol	ChEBI
Cholest-5-en-3b-yl nonadecanoate	Generator
Cholest-5-en-3b-yl nonadecanoic acid	Generator
Cholest-5-en-3beta-yl nonadecanoic acid	Generator
Cholest-5-en-3β-yl nonadecanoate	Generator
Cholest-5-en-3β-yl nonadecanoic acid	Generator
Cholesteryl nonadecanoate	HMDB
Cholesteryl nonadecanoic acid	HMDB
Cholesterol ester(19:0)	HMDB
Cholesterol ester(19:0/0:0)	HMDB
Cholesterol 1-nonadecanoic acid	HMDB
1--Cholesterol	HMDB
Cholesteryl 1-nonadecanoate	HMDB
CE(19:0/0:0)	HMDB
Cholesteryl 1-nonadecanoic acid	HMDB
1-Nonadecanoyl-cholesterol	HMDB
Cholesterol 1-nonadecanoate	HMDB
cholesterol 1-	Lipid Annotator
cholesteryl 1-	Lipid Annotator
CE(19:0)	Lipid Annotator, ChEBI

Chemical Formula

C₄₆H₈₂O₂

Average Molecular Weight

667.1421

Monoisotopic Molecular Weight

666.631481868

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 nonadecanoate

Traditional 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 nonadecanoate

CAS Registry Number

25605-90-7

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)CCCCCCCCCCCCCCCCCC)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C46H82O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-26-44(47)48-39-31-33-45(5)38(35-39)27-28-40-42-30-29-41(37(4)25-23-24-36(2)3)46(42,6)34-32-43(40)45/h27,36-37,39-43H,7-26,28-35H2,1-6H3/t37-,39+,40+,41-,42+,43+,45+,46-/m1/s1

InChI Key

VHYWECIJXTVRSG-TVDLSCFRSA-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

Not Available

Functional Ontology

Physiological effect

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 5318997)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006738)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0006738)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006738)

Source

Endogenous

Endogenous (HMDB: HMDB0006738)

Animal

Animal (HMDB: HMDB0006738)

Exogenous

Food

Food (HMDB: HMDB0006738)

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)

Exogenous (HMDB: HMDB0006738)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006738)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006738)

Lipid metabolism pathway (HMDB: HMDB0006738)

Cellular process

Cell signaling (HMDB: HMDB0006738)

Biochemical process

Lipid transport (HMDB: HMDB0006738)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.2e-06 g/L	ALOGPS
logP	10.88	ALOGPS
logP	15.37	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	24	ChemAxon
Refractivity	208.01 m³·mol⁻¹	ChemAxon
Polarizability	91.55 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

HMDB0006738

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024052

KNApSAcK ID

Not Available

Chemspider ID

20118443

KEGG Compound ID

C02530

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14274981

PDB ID

Not Available

ChEBI ID

133745

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Rizvi, T. Z.; Adil, G. A.; Gondal, H. Y.; Sherazi, H. A. Synthesis and characterization of liquid crystalline cholesterol derivatives. Science International (Lahore) (1997), 9(1), 31-32.

Showing chemical card for CE(19:0) (CFc000002899)

MOL for CFc000002899 (CE(19:0))

3D MOL for CFc000002899 (CE(19:0))

3D SDF for CFc000002899 (CE(19:0))

3D-SDF for CFc000002899 (CE(19:0))

PDB for CFc000002899 (CE(19:0))

3D PDB for CFc000002899 (CE(19:0))

SMILES for CFc000002899 (CE(19:0))

INCHI for CFc000002899 (CE(19:0))

Structure for CFc000002899 (CE(19:0))

3D Structure for CFc000002899 (CE(19:0))