PDCPentadecanoylcarnitine

Formula

C₂₂H₄₃NO₄

Molar mass

385.60 g·mol⁻¹

CAS

-

PubChem CID

123132011

Origin

An endogenous compound. It is the carnitine metabolite of pentadecanoic acid, a saturated fifteen-carbon fatty acid supplied by the diet, mainly by dairy fats and certain seafood products. Its presence in the body therefore depends directly on the dietary intake of that odd-chain fatty acid.

InChIKey

MDDWQHVKSHTZTD-UHFFFAOYSA-N

Editorial estimate, not clinical.

Pentadecanoylcarnitine is the carnitine ester of pentadecanoic acid, a saturated fifteen-carbon fatty acid that the body receives essentially from dairy fats. Its established function is metabolic: carnitine esters constitute the form in which fatty acids cross the inner mitochondrial membrane before their oxidation. Venn-Watson and colleagues attributed to it in 2022 a second, signalling function, at the end of a screen covering 148 biomarkers spread over twelve primary human cell systems and 78 target assays. The compound there behaved as a full agonist of both cannabinoid receptors, with median effective concentrations of 3.7 micromolar at CB1 and 3.2 micromolar at CB2 and maximal effects slightly above those of the positive control, which led the authors to present it as the second full agonist endocannabinoid identified. The same work noted agonist activity at the 5-HT1A and 5-HT1B receptors, antagonist activity at the H1 and H2 receptors, and dose-dependent anti-inflammatory effects marked by falls in interleukin 1 alpha, ITAC, MCP-1 and IP-10. Two caveats accompany the reading of these results. The effective concentrations lie in the micromolar range, far above those of the reference endocannabinoid ligands, and the authors declare interests with the companies that exploit odd-chain fatty acids commercially. Independent confirmation of these activities remains to be established.

The molecule is neither an N-acylethanolamine nor a monoacylglycerol, unlike the classical endocannabinoids: it is a carnitine ester. It forms by transfer of pentadecanoic acid, activated as a coenzyme A thioester, onto the hydroxyl function of L-carnitine, a reaction catalysed by the carnitine acyltransferases. That esterification is the step that allows fatty acids to cross the inner mitochondrial membrane, upstream of their oxidation. The compound is therefore originally an intermediate of fatty acid transport, whose signalling activity constitutes a second function.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Class

Endocannabinoid

Origin

An endogenous compound. It is the carnitine metabolite of pentadecanoic acid, a saturated fifteen-carbon fatty acid supplied by the diet, mainly by dairy fats and certain seafood products. Its presence in the body therefore depends directly on the dietary intake of that odd-chain fatty acid.

Status

Endogenous

1. 1.Venn-Watson et coll. 2022 : la pentadécanoylcarnitine, endocannabinoïde aux activités pléiotropesPMID 35999445
2. 2.Giesbertz et coll. 2015 : méthode LC-MS/MS de quantification des acylcarnitines isomères et à chaîne impairePMID 26239049