ChemFOnt: Showing chemical card for CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)) (CFc000269755)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:10:25 UTC

Chemfont ID

CFc000269755

Molecule Identification

Common Name

CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4))

Definition

CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)) belongs to the family of cholesteryl esters, whose structure is characetized by a cholesterol esterified at the 3-position with a fatty acid. 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(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1S,2R,5S,10S,11S,14R,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl (7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid	HMDB

Chemical Formula

C₄₉H₇₆O₃

Average Molecular Weight

713.144

Monoisotopic Molecular Weight

712.579446307

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 (5Z,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoate

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 (5Z,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoate

CAS Registry Number

Not Available

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)CCC(O)\C=C/C=C\C\C=C/C\C=C/C\C=C/C\C=C/CC)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C49H76O3/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-26-41(50)28-32-47(51)52-42-33-35-48(5)40(37-42)27-29-43-45-31-30-44(39(4)25-23-24-38(2)3)49(45,6)36-34-46(43)48/h8-9,11-12,14-15,17-18,20-22,26-27,38-39,41-46,50H,7,10,13,16,19,23-25,28-37H2,1-6H3/b9-8-,12-11-,15-14-,18-17-,21-20-,26-22-/t39-,41?,42+,43+,44-,45+,46+,48+,49-/m1/s1

InChI Key

INDHWIKAWFBEBY-HEBYEYHISA-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
Long chain fatty alcohol
Fatty alcohol
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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: 5318997)

Source

Endogenous

Endogenous (HMDB: HMDB0290239)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.3e-05 g/L	ALOGPS
logP	9.65	ALOGPS
logP	13.3	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Acidic)	14.87	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	230.03 m³·mol⁻¹	ChemAxon
Polarizability	89.74 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

HMDB0290239

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

156997836

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(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)) (CFc000269755)

MOL for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

3D MOL for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

3D SDF for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

3D-SDF for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

PDB for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

3D PDB for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

SMILES for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

INCHI for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

Structure for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))

3D Structure for CFc000269755 (CE(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)))