ChemFOnt: Showing chemical card for CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (CFc000002895)

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

CFc000002895

Molecule Identification

Common Name

CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z))

Definition

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₉H₇₆O₂

Average Molecular Weight

697.1265

Monoisotopic Molecular Weight

696.584531676

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

Traditional 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

CAS Registry Number

70110-50-8

SMILES

[H][C@@](C)(CCCC(C)C)C1([H])CCC2([H])C3([H])CC=C4C[C@]([H])(CC[C@]4(C)C3([H])CC[C@]12C)OC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC

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

InChI Key

VOEVEGPMRIYYKC-KNEWWSHNSA-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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Extracellular (HMDB: HMDB0006733)
Membrane (HMDB: HMDB0006733)

Source

Exogenous

Exogenous (HMDB: HMDB0006733)

Food

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)

Vegetable

Root vegetable

Wild carrot (FooDB: FOOD00072)
Carrot (FooDB: FOOD00245)

Fruit vegetable

Olive (FooDB: FOOD00121)

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)
White bread (FooDB: FOOD00987)

Leavened bread

Rye bread (FooDB: FOOD00809)

Nut

Almond (FooDB: FOOD00148)

Fruit

Drupe

Nectarine (FooDB: FOOD00229)

Aquatic origin

Fish

Milk and milk product

Fermented milk product

Herb and spice

Oilseed crop

Coconut oil (FooDB: FOOD00941)

Endogenous

Endogenous (HMDB: HMDB0006733)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.8e-06 g/L	ALOGPS
logP	10.03	ALOGPS
logP	14.53	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	228.51 m³·mol⁻¹	ChemAxon
Polarizability	89.93 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024048

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (CFc000002895)

MOL for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D MOL for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D SDF for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D-SDF for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

PDB for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D PDB for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

SMILES for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

INCHI for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

Structure for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D Structure for CFc000002895 (CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)))