ChemFOnt: Showing chemical card for CE(11:1D3) (CFc000092606)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:03:36 UTC

Chemfont ID

CFc000092606

Molecule Identification

Common Name

CE(11:1D3)

Definition

CE(11:1D3) is an unsaturated furan fatty acid ester of cholesterol or simply a cholesteryl ester (CE). Cholesteryl esters are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesteryl esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesteryl esters tend to contain relatively high proportions of C18 fatty acids. Cholesteryl esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesteryl esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesteryl esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesteryl esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesteryl esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesteryl esters from CoA esters of fatty acids and cholesterol. Cholesteryl ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. The shorthand notation for CE(11:1D3) refers to the furan fatty acid's 11-carbon carboxyalkenyl moiety, the dimethyl substitutions in the 3- and 4-positions of its furan moiety, and its 3-carbon alkyl moiety.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,15-Dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl (10E)-11-(3,4-dimethyl-5-propylfuran-2-yl)undec-10-enoic acid	HMDB
CE(dime(11:1,3))	HMDB
11:1D3 Cholesteryl ester	HMDB
DiMe(11:1,3) cholesteryl ester	HMDB
2,15-Dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (10E)-11-(3,4-dimethyl-5-propylfuran-2-yl)undec-10-enoic acid	HMDB
CE(11:1D3)	SMPDB

Chemical Formula

C₄₇H₇₆O₃

Average Molecular Weight

689.122

Monoisotopic Molecular Weight

688.579446307

IUPAC Name

2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (10E)-11-(3,4-dimethyl-5-propylfuran-2-yl)undec-10-enoate

Traditional Name

2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (10E)-11-(3,4-dimethyl-5-propylfuran-2-yl)undec-10-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCCC(C)C)=C(\[H])C1=C(C)C(C)=C(CCC)O1

InChI Identifier

InChI=1S/C47H76O3/c1-9-19-43-35(5)36(6)44(50-43)22-16-14-12-10-11-13-15-17-23-45(48)49-38-28-30-46(7)37(32-38)24-25-39-41-27-26-40(34(4)21-18-20-33(2)3)47(41,8)31-29-42(39)46/h16,22,24,33-34,38-42H,9-15,17-21,23,25-32H2,1-8H3/b22-16+

InChI Key

WCBDUQUDBQTXPU-CJLVFECKSA-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
Furanoid fatty acid
Fatty acyl
Furan
Heteroaromatic compound
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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: HMDB0112197)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	10.1	ALOGPS
logP	14.36	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	213.76 m³·mol⁻¹	ChemAxon
Polarizability	90.88 Å³	ChemAxon
Number of Rings	5	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

HMDB0112197

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

131819640

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CE(11:1D3) (CFc000092606)

MOL for CFc000092606 (CE(11:1D3))

3D MOL for CFc000092606 (CE(11:1D3))

3D SDF for CFc000092606 (CE(11:1D3))

3D-SDF for CFc000092606 (CE(11:1D3))

PDB for CFc000092606 (CE(11:1D3))

3D PDB for CFc000092606 (CE(11:1D3))

SMILES for CFc000092606 (CE(11:1D3))

INCHI for CFc000092606 (CE(11:1D3))

Structure for CFc000092606 (CE(11:1D3))

3D Structure for CFc000092606 (CE(11:1D3))