(6Z,9Z,12Z,15Z,18Z,21Z)-Tetracosa-6,9,12,15,18,21-hexaenoylcarnitine

3-(tetracosa-6,9,12,15,18,21-hexaenoyloxy)-4-(trimethylazaniumyl)butanoate

Formula: C31H49NO4 (499.3661)
Chinese Name:
BioDeep ID: BioDeep_00000170933 ( View LC/MS Profile)
SMILES: CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C



Found 9 Sample Hits

m/z Adducts Species Organ Scanning Sample
500.3671 [M+H]+
PPM:12.6
Homo sapiens esophagus DESI ()
TO42T - MTBLS385
Resolution: 17μm, 69x81

Description

500.379 [M+H]+
PPM:11.2
Mus musculus Liver MALDI (CHCA)
Salmonella_final_pos_recal - MTBLS2671
Resolution: 17μm, 691x430

Description

A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium. [dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671.

500.367 [M+H]+
PPM:12.8
Homo sapiens esophagus DESI ()
TO39T - MTBLS385
Resolution: 17μm, 69x81

Description

500.3688 [M+H]+
PPM:9.2
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

500.3681 [M+H]+
PPM:10.6
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

500.3678 [M+H]+
PPM:11.2
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

500.3696 [M+H]+
PPM:7.6
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

500.3684 [M+H]+
PPM:10
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

500.3675 [M+H]+
PPM:11.8
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description


(6Z,9Z,12Z,15Z,18Z,21Z)-Tetracosa-6,9,12,15,18,21-hexaenoylcarnitine is an acylcarnitine. More specifically, it is an (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic 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. (6Z,9Z,12Z,15Z,18Z,21Z)-Tetracosa-6,9,12,15,18,21-hexaenoylcarnitine is therefore classified as a very-long chain AC. As a very long-chain acylcarnitine (6Z,9Z,12Z,15Z,18Z,21Z)-Tetracosa-6,9,12,15,18,21-hexaenoylcarnitine 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].