ChemFOnt: Showing chemical card for Hexanoylcarnitine (CFc000000604)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:02 UTC

Chemfont ID

CFc000000604

Molecule Identification

Common Name

Hexanoylcarnitine

Definition

Hexanoylcarnitine (CAS: 6418-78-6), also known as caproylcarnitine, is an acylcarnitine. Acylcarnitines are the product of the conjugation of carnitine with acyl-coenzyme A, that allows the transport of fatty acids across mitochondrial membranes. Long or medium chain fatty acids are then oxidized in the mitochondria for energy production. The ionic nature of L-carnitine causes high water solubility which decreases with increasing chain lengths of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined not only by their function but also by their physicochemical properties. Hexanoylcarnitine is a medium-chain acylcarnitine present in the urine of patients with medium-chain acyl-CoA dehydrogenase deficiency (PMID: 1635814 ). Hexanoylcarnitine is also found to be associated with celiac disease and glutaric aciduria II which are both inborn errors of metabolism. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism, which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. High-performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile (PMID: 17508264 , Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-Caproylcarnitine	ChEBI
(R)-Hexanoylcarnitine	ChEBI
Hexanoyl-L-carnitine	ChEBI
L-Hexanoylcarnitine	ChEBI
O-Hexanoyl-(R)-carnitine	ChEBI
(R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexyl)oxy]-1-propanaminium inner salt	HMDB
Hexanoate	HMDB
Hexanoic acid	HMDB
Hexanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
L-Carnitine hexanoyl ester	HMDB
L-Hexanoate	HMDB
L-Hexanoic acid	HMDB
L-Hexanoic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
C6 Carnitine	HMDB
Hexanoylcarnitine	HMDB

Chemical Formula

C₁₃H₂₅NO₄

Average Molecular Weight

259.3419

Monoisotopic Molecular Weight

259.178358293

IUPAC Name

(3R)-3-(hexanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

L-carnitine hexanoyl ester

CAS Registry Number

22671-29-0

SMILES

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

InChI Identifier

InChI=1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3/t11-/m1/s1

InChI Key

VVPRQWTYSNDTEA-LLVKDONJSA-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

O-acyl-L-carnitine (CHEBI:84834 )
Fatty acyl carnitines (LMFA07070001 )

Functional Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16425363)

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Organ

Placenta (HMDB: HMDB0000756)
Prostate (HMDB: HMDB0000756)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27609529)

Cell

All cells and tissues (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000756)

Source

Endogenous

Endogenous (HMDB: HMDB0000756)

Animal

Animal (HMDB: HMDB0000756)

Exogenous

Food

Food (HMDB: HMDB0000756)

Exogenous (HMDB: HMDB0000756)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000756)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000756)

Lipid metabolism pathway (HMDB: HMDB0000756)

Cellular process

Cell signaling (HMDB: HMDB0000756)

Biochemical process

Lipid transport (HMDB: HMDB0000756)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0043 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.4	ChemAxon
logS	-4.9	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	10	ChemAxon
Refractivity	91.07 m³·mol⁻¹	ChemAxon
Polarizability	28.79 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

HMDB0000756

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022226

KNApSAcK ID

C00052313

Chemspider ID

2497478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3548

PubChem Compound

3246938

PDB ID

Not Available

ChEBI ID

84834

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Nakanishi, Toyofumi; Shimizu, Akira; Arimoto, Masao; Kanai, Michiko. Synthesis of acylcarnitines for differential diagnosis of metabolic disorders. Nippon Iyo Masu Supekutoru Gakkai Koenshu (1993), 18 129-32.

Showing chemical card for Hexanoylcarnitine (CFc000000604)

MOL for CFc000000604 (Hexanoylcarnitine)

3D MOL for CFc000000604 (Hexanoylcarnitine)

3D SDF for CFc000000604 (Hexanoylcarnitine)

3D-SDF for CFc000000604 (Hexanoylcarnitine)

PDB for CFc000000604 (Hexanoylcarnitine)

3D PDB for CFc000000604 (Hexanoylcarnitine)

SMILES for CFc000000604 (Hexanoylcarnitine)

INCHI for CFc000000604 (Hexanoylcarnitine)

Structure for CFc000000604 (Hexanoylcarnitine)

3D Structure for CFc000000604 (Hexanoylcarnitine)