ChemFOnt: Showing chemical card for Propionylcarnitine (CFc000000658)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:06 UTC

Chemfont ID

CFc000000658

Molecule Identification

Common Name

Propionylcarnitine

Definition

Propionylcarnitine is an acylcarnitine. More specifically, it is an propanoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Propionylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine propionylcarnitine is a member of the most abundant group of carnitines in the body, comprising more than 50% of all acylcarnitines quantified in tissues and biofluids (PMID: 31920980 ). Some short-chain carnitines have been studied as supplements or treatments for a number of diseases, including neurological disorders and inborn errors of metabolism. In particular propionylcarnitine is elevated in the blood or plasma of individuals with methylmalonic academia/methylmalonyl-CoA mutase deficiency (PMID: 26454439 , PMID: 25750861 , PMID: 31622506 , PMID: 30712249 ), propionic academia/mitochondrial propionyl-CoA carboxylase deficiency (PMID: 31715057 , PMID: 28915261 ), obesity and Type 2 Diabetes Mellitus (PMID: 30186675 ), cobalamin C deficiency (PMID: 25367534 ), chronic heart failure (PMID: 22622056 ), diastolic heart failure (PMID: 26010610 ), and systolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with familial Mediterranean fever (PMID: 29900937 ) and type 2 diabetes Mellitus (PMID: 19369366 ). It is also decreased in the urine of individuals with obesity (PMID: 26910390 ). Propionylcarnitine is also found to be associated with propionic acidemia, which is an inborn error of metabolism. Carnitine acetyltransferase (CrAT, EC:2.3.1.7) is responsible for the synthesis of all short-chain and short branched-chain acylcarnitines (PMID: 23485643 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available at [Dambrova et al. 2021, Physiological Reviews].

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Carboxy-N,N,N-trimethyl-2-(1-oxopropoxy)-1-propanaminium inner salt	ChEBI
O-Propionylcarnitine	ChEBI
Propionyl carnitine	ChEBI
(+/-)-propionylcarnitine chloride	HMDB
(3-Carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner salt	HMDB
L-Propionylcarnitine	HMDB
O-Propanoylcarnitine	HMDB
Propionyl-carnitine	HMDB
Propionyl-L-carnitine	HMDB
Propionylcarnitine, (+-)-isomer	HMDB
Propionylcarnitine, (R)-isomer	HMDB

Chemical Formula

C₁₀H₁₉NO₄

Average Molecular Weight

217.2622

Monoisotopic Molecular Weight

217.131408101

IUPAC Name

3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

propionyl-L-carnitine

CAS Registry Number

20064-19-1

SMILES

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

InChI Identifier

InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3

InChI Key

UFAHZIUFPNSHSL-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

O-acylcarnitine (CHEBI:28867 )
Fatty acyl carnitines (C03017 )

Functional Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16425363)
Cerebrospinal Fluid (CSF) (PMID: 22546835)
Saliva (PMID: 22727327)
Cerebrospinal fluid (HMDB: HMDB0000824)

Cellular substructure

Organelle

Organ

Placenta (HMDB: HMDB0000824)

Excreta

Biofluid or Excreta

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

Cell

All cells and tissues (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000824)

Source

Exogenous

Exogenous (HMDB: HMDB0000824)

Food

Food (HMDB: HMDB0000824)

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: HMDB0000824)

Animal

Animal (HMDB: HMDB0000824)

Process

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Analgesic (HMDB: HMDB0000824)
Analgesic (HMDB: HMDB0000824)

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000824)

Pharmaceutical industry

Peripheral nervous system drug (HMDB: HMDB0000824)
Cardiotonic drug (HMDB: HMDB0000824)
Antirheumatic drug (HMDB: HMDB0000824)

Biomarker

Breast cancer ()
Diabetes mellitus type 2 ()
Cardiovascular disease ()
Renal cell carcinoma ()
Heart failure ()
Celiac disease ()
Inflammatory bowel disease ()
Obesity (MarkerDB: MDB00000262)
Propionic acidemia (MarkerDB: MDB00000262)

Biological role

Energy source (HMDB: HMDB0000824)
Energy source (PMID: 35710135)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.7	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.19	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	7	ChemAxon
Refractivity	77.26 m³·mol⁻¹	ChemAxon
Polarizability	22.72 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