ChemFOnt: Showing chemical card for O-decanoyl-L-carnitine (CFc000043043)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:53 UTC

Chemfont ID

CFc000043043

Molecule Identification

Common Name

O-decanoyl-L-carnitine

Definition

O-Decanoyl-L-carnitine is an acylcarnitine. More specifically, it is an decanoic 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. O-Decanoyl-L-carnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine O-decanoyl-L-carnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. In particular O-decanoyl-L-carnitine is elevated in the blood or plasma of individuals with glutaric aciduria II (PMID: 24453145 ), ulcerative colitis (PMID: 27609529 ), Crohn's disease (PMID: 27609529 ), obesity (PMID: 20111019 ), medium-chain acyl-CoA dehydrogenase deficiency disorders (PMID: 21239873 ), overweight (PMID: 25781947 ), multiple acyl coenzyme A dehydrogenase deficiency (PMID: 8496747 , PMID: 30510944 ), type 2 diabetes Mellitus (PMID: 19369366 ), age-related increase in alanine aminotransferase (PMID: 24874467 ), prostate cancer (PMID: 31842810 ), Yin-deficiency-heat syndrome (PMID: 31909891 ), CVD in type 2 diabetes Mellitus (PMID: 32431666 ), cardioembolic stroke, Its recurrence (PMID: 30026276 ), and diastolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with Celiac disease (PMID: 16425363 ), colorectal cancer (PMID: 23675754 ), esophageal squamous cell carcinoma (PMID: 23397110 ), inflammatory bowel disease (PMID: 21912810 ), phenylketonuria (PMID: 18946205 ), intracerebral hemorrhage (PMID: 29265114 ), and pregnancy (PMID: 24704061 - in serum of pregnant women with fetus with CHD). O-Decanoyl-L-carnitine is elevated in the urine of individuals with overweight (PMID: 21890434 ) and renal cell carcinoma (PMID: 29658093 ). Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). 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
L-Decanoylcarnitine	ChEBI
O-Decanoyl-(R)-carnitine	ChEBI
O-Decanoyl-R-carnitine	ChEBI
Decanoyl-L-carnitine	HMDB

Chemical Formula

C₁₇H₃₃NO₄

Average Molecular Weight

315.454

Monoisotopic Molecular Weight

315.240958547

IUPAC Name

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

Traditional Name

O-decanoyl-L-carnitine

CAS Registry Number

1492-27-9

SMILES

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

InChI Identifier

InChI=1S/C17H33NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h15H,5-14H2,1-4H3/t15-/m1/s1

InChI Key

LZOSYCMHQXPBFU-OAHLLOKOSA-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:28717 )
O-decanoylcarnitine (CHEBI:28717 )
Fatty acyl carnitines (C03299 )
Fatty acyl carnitines (LMFA07070006 )

Functional Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

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: HMDB0062631)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00014 g/L	ALOGPS
logP	-0.85	ALOGPS
logP	-0.63	ChemAxon
logS	-6.4	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	14	ChemAxon
Refractivity	109.47 m³·mol⁻¹	ChemAxon
Polarizability	37.53 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