ChemFOnt: Showing chemical card for O-butanoyl-carnitine (CFc000042922)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:41 UTC

Chemfont ID

CFc000042922

Molecule Identification

Common Name

O-butanoyl-carnitine

Definition

O-butanoyl-carnitine, also known as (3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoate or L-Carnitine butyryl ester, is classified as a member of the Acyl carnitines. Acyl carnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. O-butanoyl-carnitine is considered to be practically insoluble (in water) and acidic. O-butanoyl-carnitine is a fatty ester lipid molecule

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoate	ChEBI
Butyryl-L-carnitine	ChEBI
L-Carnitine butyryl ester	ChEBI
N-Butyryl-L-(-)-carnitin	ChEBI
O-Butanoyl-(R)-carnitine	ChEBI
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoic acid	Generator
Butylcarnitine	HMDB
O-Butanoyl-carnitine	HMDB
O-Butanoylcarnitine	HMDB
Butyrylcarnitine	ChEBI

Chemical Formula

C₁₁H₂₁NO₄

Average Molecular Weight

231.292

Monoisotopic Molecular Weight

231.14705816

IUPAC Name

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

Traditional Name

O-butanoylcarnitine

CAS Registry Number

25576-40-3

SMILES

CCCC(=O)O[C@H](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/t9-/m1/s1

InChI Key

QWYFHHGCZUCMBN-SECBINFHSA-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-butanoylcarnitine (CHEBI:21949 )
Fatty acyl carnitines (LMFA07070003 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0062510)
Cell membrane (HMDB: HMDB0062510)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0062510)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0062510)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0062510)

Source

Exogenous

Exogenous (HMDB: HMDB0062510)

Food

Food (HMDB: HMDB0062510)

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)

Endogenous

Endogenous (HMDB: HMDB0062510)

Animal

Animal (HMDB: HMDB0062510)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0062510)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0062510)

Lipid metabolism pathway (HMDB: HMDB0062510)

Biochemical process

Lipid transport (HMDB: HMDB0062510)

Role

Biological role

Energy source (HMDB: HMDB0062510)

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	24.8 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