ChemFOnt: Showing chemical card for Butyrylcarnitine (CFc000001346)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:57 UTC

Chemfont ID

CFc000001346

Molecule Identification

Common Name

Butyrylcarnitine

Definition

Butyrylcarnitine, also known as (3R)-3-(butyryloxy)-4-(trimethylammonio)butanoate or L-carnitine butyryl ester, is classified as a member of the acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Butyrylcarnitine is considered to be practically insoluble (in water) and acidic. Butyrylcarnitine is elevated in patients with short-chain acyl-CoA dehydrogenase (SCAD) deficiency, in infants with acute acidosis and generalized muscle weakness, and in middle-aged patients with chronic myopathy localized in muscle (OMIM: 201470 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O-Butyrylcarnitine	ChEBI
(3-Carboxy-2-hydroxypropyl)trimethyl-L-butyrate	HMDB
(R)-3-Carboxy-N,N,N-trimethyl-2-(1-oxobutoxy)-1-propanaminium	HMDB
Butyryl-L-carnitine	HMDB
Ester with (3-carboxy-2-hydroxypropyl)trimethylammonium L-butyric acid	HMDB
Ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium butyric acid	HMDB
L-Carnitine butyryl ester	HMDB
N-Butyryl-L(-)-carnitine	HMDB
O-Butanoylcarnitine	HMDB
Butylcarnitine	MeSH

Chemical Formula

C₁₁H₂₁NO₄

Average Molecular Weight

231.2887

Monoisotopic Molecular Weight

231.147058165

IUPAC Name

3-(butanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

L-carnitine butyryl ester

CAS Registry Number

25576-40-3

SMILES

CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3

InChI Key

QWYFHHGCZUCMBN-UHFFFAOYSA-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

butyrate ester (CHEBI:7676 )
C4-acylcarnitine (CHEBI:7676 )
Fatty acyl carnitines (C02862 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16425363)
Cerebrospinal Fluid (CSF) (PMID: 22546835)
Saliva (PMID: 22308371)

Cell

Fibroblasts (HMDB: HMDB0002013)

Organ

Placenta (HMDB: HMDB0002013)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27624970)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002013)

Source

Endogenous

Endogenous (HMDB: HMDB0002013)

Animal

Animal (HMDB: HMDB0002013)

Exogenous

Food

Food (HMDB: HMDB0002013)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Exogenous (HMDB: HMDB0002013)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (HMDB: HMDB0002013)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002013)

Lipid metabolism pathway (HMDB: HMDB0002013)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002013)

Biochemical process

Lipid transport (HMDB: HMDB0002013)

Role

Biological role

Energy source (HMDB: HMDB0002013)

Industrial application

Pharmaceutical industry

Biomarker

Obesity (MarkerDB: MDB00000365)
Eosinophilic esophagitis (MarkerDB: MDB00000365)
Glutaric Acidemia Type 2 (MarkerDB: MDB00000365)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.3	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.27	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	8	ChemAxon
Refractivity	81.86 m³·mol⁻¹	ChemAxon
Polarizability	24.78 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

FDB022795

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02862

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439829

PDB ID

Not Available

ChEBI ID

7676

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Lozano Pedro; Daz Mirta; de Diego Teresa; Iborra Jose L Ester synthesis from trimethylammonium alcohols in dry organic media catalyzed by immobilized Candida antarctica lipase B. Biotechnology and bioengineering (2003), 82(3), 352-8.

Showing chemical card for Butyrylcarnitine (CFc000001346)

MOL for CFc000001346 (Butyrylcarnitine)

3D MOL for CFc000001346 (Butyrylcarnitine)

3D SDF for CFc000001346 (Butyrylcarnitine)

3D-SDF for CFc000001346 (Butyrylcarnitine)

PDB for CFc000001346 (Butyrylcarnitine)

3D PDB for CFc000001346 (Butyrylcarnitine)

SMILES for CFc000001346 (Butyrylcarnitine)

INCHI for CFc000001346 (Butyrylcarnitine)

Structure for CFc000001346 (Butyrylcarnitine)

3D Structure for CFc000001346 (Butyrylcarnitine)