ChemFOnt: Showing chemical card for DL-Acetylcarnitine (CFc000221026)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:40:34 UTC

Chemfont ID

CFc000221026

Molecule Identification

Common Name

DL-Acetylcarnitine

Definition

DL-Acetylcarnitine is an acylcarnitine. More specifically, it is an acetic 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. DL-Acetylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine DL-Acetylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. In particular DL-Acetylcarnitine is elevated in the blood or plasma of individuals with very long chain acyl-CoA dehydrogenase deficiency (PMID: 9034211 ), colorectal cancer (PMID: 25105552 ), short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (PMID: 11489939 ), paclitaxel induced neuropathy (PMID: 29946863 ), type 2 diabetes Mellitus (PMID: 28726959 ; PMID: 25964024 , PMID: 28726959 , PMID: 19369366 , PMID: 24358186 ), chronic heart failure (PMID: 22622056 ), ornithine transcarbamylase (PMID: 3346778 ), pre-diabetes (PMID: 23010998 , PMID: 24358186 ), type 1 diabetes mellitus (PMID: 16789638 ), methylmalonic acidemia (PMID: 8214594 ), myeloma (PMID: 30096165 ), and diastolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with 3-methyl-crotonyl-glycinuria (PMID: 25732994 ), antiviral drug induced neuropathy (PMID: 9030365 , PMID: 11364244 ), Alzheimer Disease (PMID: 27196316 ), major depressive disorder (PMID: 30061399 ), carnitine palmitoyltransferase 2 deficiency (PMID: 20543534 ), Familial Mediterranean Fever (PMID: 29900937 ), chronic fatigue syndrome (PMID: 9854142 ), methylmalonic acidemia (PMID: 15164354 ), hepatocellular carcinoma (PMID: 26976432 , PMID: 31662827 ), and coronary artery disease (PMID: 20173117 ). DL-Acetylcarnitine is elevated in the urine of individuals with colorectal cancer (25105552 ), uterine fibroids (32590215), heart failure (8070147), diabetes mellitus (10221661), and hepatocellular carcinoma (24923488). It is also decreased in the urine of individuals with carnitine palmitoyltransferase 2 deficiency (20543534 ). Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). 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-(Acetyloxy)-4-(trimethylammonio)butanoate	ChEBI
Acetyl-DL-carnitine	ChEBI
Acetylcarnitine	ChEBI
DL-O-Acetylcarnitine	ChEBI
3-(Acetyloxy)-4-(trimethylammonio)butanoic acid	Generator
(+-)-Acetylcarnitine	HMDB
(-)-Acetylcarnitine	HMDB
(R)-Acetylcarnitine	HMDB
Acetyl-carnitine	HMDB
Acetyl-L-(-)-carnitine	HMDB
Acetyl-L-carnitine	HMDB
ALCAR	HMDB
L-Carnitine acetyl ester	HMDB
L-O-Acetylcarnitine	HMDB
Levocarnitine acetyl	HMDB
Nicetile	HMDB
O-Acetyl-L-carnitine	HMDB
O-Acetylcarnitine	HMDB
Acetylcarnitine, (R)-isomer	HMDB
Carnitine, acetyl	HMDB
Acetyl L carnitine	HMDB
Medosan	HMDB
Sigma-tau brand OF acetyl L-carnitine	HMDB
Acetyl carnitine	HMDB
Branigen	HMDB
Glaxo brand OF acetyl L-carnitine	HMDB
Sigma tau brand OF acetyl L carnitine	HMDB
Glaxo brand OF acetyl L carnitine	HMDB

Chemical Formula

C₉H₁₇NO₄

Average Molecular Weight

203.2356

Monoisotopic Molecular Weight

203.115758037

IUPAC Name

3-(acetyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

alcar

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3

InChI Key

RDHQFKQIGNGIED-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:73024 )
an <i>O</i>-acyl-L-carnitine (O-ACETYLCARNITINE )

Functional Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 26847922)

Cell

All cells and tissues (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0240773)

Endogenous

Endogenous (HMDB: HMDB0240773)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7	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	6	ChemAxon
Refractivity	72.64 m³·mol⁻¹	ChemAxon
Polarizability	20.88 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

HMDB0240773

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021904

KNApSAcK ID

Not Available

Chemspider ID

21243783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

73024

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for DL-Acetylcarnitine (CFc000221026)

MOL for CFc000221026 (DL-Acetylcarnitine)

3D MOL for CFc000221026 (DL-Acetylcarnitine)

3D SDF for CFc000221026 (DL-Acetylcarnitine)

3D-SDF for CFc000221026 (DL-Acetylcarnitine)

PDB for CFc000221026 (DL-Acetylcarnitine)

3D PDB for CFc000221026 (DL-Acetylcarnitine)

SMILES for CFc000221026 (DL-Acetylcarnitine)

INCHI for CFc000221026 (DL-Acetylcarnitine)

Structure for CFc000221026 (DL-Acetylcarnitine)

3D Structure for CFc000221026 (DL-Acetylcarnitine)