ChemFOnt: Showing chemical card for Linoleyl carnitine (CFc000002758)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:43 UTC

Chemfont ID

CFc000002758

Molecule Identification

Common Name

Linoleyl carnitine

Definition

Linoleyl carnitine is a long-chain acyl fatty acid derivative ester of carnitine. Long-chain acyl fatty acid derivatives accumulate in the cytosol and serum of patients suffering of mitochondrial carnitine palmitoyltransferase II (CPT II, EC 2.3.1.12) deficiency, the most common inherited disorder of lipid metabolism in adults. Carnitine palmitoyltransferase II deficiency is an autosomal recessive disorder of fatty acid metabolism presenting as two clinical phenotypes: (i) a severe infantile hepatocardiomuscular form and (ii) a milder adult muscular form. Energy production from long-chain fatty acids (LCFAs) requires the transport of LCFAs into the mitochondrial matrix. This transport is carnitine-dependent and involves translocation machinery. Mitochondrial fatty acid oxidation disorders cause hypoglycaemia, hepatic dysfunction, myopathy, cardiomyopathy and encephalopathy. Patients with end-stage renal disease (ESRD) undergoing long-term haemodialysis exhibit elevated acylcarnitine concentrations (PMID: 11999976 , 10682306 , 15025677 , 16168195 ). Moreover, linoleyl carnitine is found to be associated with glutaric aciduria II, which is an inborn error of metabolism.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₅H₄₅NO₄

Average Molecular Weight

423.6291

Monoisotopic Molecular Weight

423.334858933

IUPAC Name

(3R)-3-(octadeca-9,12-dienoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-(octadeca-9,12-dienoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

36816-10-1

SMILES

[H][C@@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC

InChI Identifier

InChI=1S/C25H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/t23-/m1/s1

InChI Key

MJLXQSQYKZWZCB-HSZRJFAPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Organ

Placenta (HMDB: HMDB0006469)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27543620)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006469)

Source

Exogenous

Exogenous (HMDB: HMDB0006469)

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)

Endogenous

Endogenous (HMDB: HMDB0006469)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Obesity (MarkerDB: MDB00029888)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.6e-06 g/L	ALOGPS
logP	1.46	ALOGPS
logP	2.2	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	148.51 m³·mol⁻¹	ChemAxon
Polarizability	51.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023928

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

3082450

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Linoleyl carnitine (CFc000002758)

MOL for CFc000002758 (Linoleyl carnitine)

3D MOL for CFc000002758 (Linoleyl carnitine)

3D SDF for CFc000002758 (Linoleyl carnitine)

3D-SDF for CFc000002758 (Linoleyl carnitine)

PDB for CFc000002758 (Linoleyl carnitine)

3D PDB for CFc000002758 (Linoleyl carnitine)

SMILES for CFc000002758 (Linoleyl carnitine)

INCHI for CFc000002758 (Linoleyl carnitine)

Structure for CFc000002758 (Linoleyl carnitine)

3D Structure for CFc000002758 (Linoleyl carnitine)