Exact Mass: 501.418172

Exact Mass Matches: 501.418172

Found 61 metabolites which its exact mass value is equals to given mass value 501.418172, within given mass tolerance error 0.05 dalton. Try search metabolite list with more accurate mass tolerance error 0.01 dalton.

(9Z,12Z,15Z,18Z,21Z)-Tetracosa-9,12,15,18,21-pentaenoylcarnitine

3-(tetracosa-9,12,15,18,21-pentaenoyloxy)-4-(trimethylazaniumyl)butanoate

C31H51NO4 (501.38178860000005)

(9Z,12Z,15Z,18Z,21Z)-Tetracosa-9,12,15,18,21-pentaenoylcarnitine is an acylcarnitine. More specifically, it is an (9Z,12Z,15Z,18Z,21Z)-tetracosa-9,12,15,18,21-pentaenoic 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. (9Z,12Z,15Z,18Z,21Z)-Tetracosa-9,12,15,18,21-pentaenoylcarnitine is therefore classified as a very-long chain AC. As a very long-chain acylcarnitine (9Z,12Z,15Z,18Z,21Z)-Tetracosa-9,12,15,18,21-pentaenoylcarnitine is generally formed in the cytoplasm from very long acyl groups synthesized by fatty acid synthases or obtained from the diet. Very-long-chain fatty acids are generally too long to be involved in mitochondrial beta-oxidation. As a result peroxisomes are the main organelle where very-long-chain fatty acids are metabolized and their acylcarnitines synthesized (PMID: 18793625). Altered levels of very long-chain acylcarnitines can serve as useful markers for inherited disorders of peroxisomal metabolism. 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].