ChemFOnt: Showing chemical card for Vaccenyl carnitine (CFc000002730)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:41 UTC

Chemfont ID

CFc000002730

Molecule Identification

Common Name

Vaccenyl carnitine

Definition

Vaccenyl 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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₅H₄₉NO₃

Average Molecular Weight

411.6615

Monoisotopic Molecular Weight

411.371244439

IUPAC Name

3-(octadec-11-en-1-yloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

3-(octadec-11-en-1-yloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

None

SMILES

CCCCCCC=CCCCCCCCCCCOC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C25H49NO3/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-29-24(22-25(27)28)23-26(2,3)4/h10-11,24H,5-9,12-23H2,1-4H3

InChI Key

FYTSXCMSQVVSOE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Tetraalkylammonium salts

Alternative Parents

Substituents

Tetraalkylammonium salt
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Carbonyl group
Amine
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006351)

Source

Exogenous

Exogenous (HMDB: HMDB0006351)

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: HMDB0006351)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.2e-06 g/L	ALOGPS
logP	3.44	ALOGPS
logP	2.94	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.36 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	147.64 m³·mol⁻¹	ChemAxon
Polarizability	53.68 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

FDB023900

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 Vaccenyl carnitine (CFc000002730)

MOL for CFc000002730 (Vaccenyl carnitine)

3D MOL for CFc000002730 (Vaccenyl carnitine)

3D SDF for CFc000002730 (Vaccenyl carnitine)

3D-SDF for CFc000002730 (Vaccenyl carnitine)

PDB for CFc000002730 (Vaccenyl carnitine)

3D PDB for CFc000002730 (Vaccenyl carnitine)

SMILES for CFc000002730 (Vaccenyl carnitine)

INCHI for CFc000002730 (Vaccenyl carnitine)

Structure for CFc000002730 (Vaccenyl carnitine)

3D Structure for CFc000002730 (Vaccenyl carnitine)