Classification Term: 169001

Acyl carnitines (ontology term: dbf993d8f9241a51a11455d05577aff3)

found 285 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Fatty esters

Child Taxonomies: There is no child term of current ontology term.

trans-2-Tetradecenoylcarnitine

(3R)-3-[(2E)-Tetradec-2-enoyloxy]-4-(trimethylazaniumyl)butanoic acid

C21H40NO4 (370.2957)


trans-2-Tetradecenoylcarnitine is an acylcarnitine. More specifically, it is an trans-2-tetradecenoic 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. trans-2-Tetradecenoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine trans-2-tetradecenoylcarnitine 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 trans-2-tetradecenoylcarnitine is elevated in the blood or plasma of individuals with very long-chain acyl-CoA dehydrogenase (VLACD) deficiency (PMID: 25843429, PMID: 19327992, PMID: 11433098, PMID: 18670371, PMID: 12828998), trifunctional protein (mitochondrial long-chain ketoacyl-coa thiolase) deficiency (PMID: 16423905), mitochondrial dysfunction in diabetes patients (PMID: 28726959), acadvl acyl-coa dehydrogenase very long chain deficiency (PMID: 29491033), nonalcoholic fatty liver disease (NAFLD) (PMID: 27211699), and insulin resistance type 2 diabetes (PMID: 24358186). 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 insulins 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].

   

CAR 6:0

3-(hexanoyloxy)-4-(trimethylazaniumyl)butanoate

C13H25NO4 (259.1783)


   

CAR 4:0

3-[(2-methylpropanoyl)oxy]-4-(trimethylazaniumyl)butanoate

C11H21NO4 (231.1471)


   

CAR 3:0

(3S)-3-(propionyloxy)-4-(trimethylammonio)butanoate

C10H19NO4 (217.1314)


D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D002316 - Cardiotonic Agents D000893 - Anti-Inflammatory Agents D002317 - Cardiovascular Agents D018501 - Antirheumatic Agents

   

CAR 10:0

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

C17H33NO4 (315.2409)


   

CAR 18:0

3-stearoyloxy-4-(trimethylammonio)butyrate

C25H49NO4 (427.3661)


   

Octadecadienoylcarnitine

(9Z,12Z)-octadeca-9,12-dienoylcarnitine;3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoate;9cis,12cis-octadecadienoylcarnitine;linoleylcarnitine

C25H45NO4 (423.3348)


   

CAR 20:1

(11Z)-icoseneoylcarnitine;11-cis-eicoseneoylcarnitine;11-cis-icoseneoylcarnitine;3-[(11Z)-icos-11-enoyloxy]-4-(trimethylammonio)butanoate

C27H51NO4 (453.3818)


   

CAR 20:2

(11Z,14Z)-icosadienoylcarnitine;11-cis,14-cis-eicosadienoylcarnitine;11-cis,14-cis-icosadienoylcarnitine;3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-4-(trimethylammonio)butanoate

C27H49NO4 (451.3661)


   

CAR 22:2

13-cis,16-cis-docosadienoylcarnitine;3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-4-(trimethylammonio)butanoate

C29H53NO4 (479.3974)


   

CAR 8:1

(3S)-3-[(2E)-oct-2-enoyloxy]-4-(trimethylammonio)butanoate;(E)-2-octenoyl-L-carnitine;2-octenoylcarnitine

C15H27NO4 (285.194)


   

CAR 10:2

3-[(2E,4Z)-deca-2,4-dienoyloxy]-4-(trimethylammonio)butanoate;cis-4-trans-2-decadienoylcarnitine

C17H29NO4 (311.2096)


   

CAR 10:3

(2E,5Z,7E)-deca-2,5,7-trienoylcarnitine;2-trans,5-cis,7-trans-decatrienoylcarnitine;3-[(2E,5Z,7E)-deca-2,5,7-trienoyloxy]-4-(trimethylammonio)butanoate

C17H27NO4 (309.194)


   

CAR 10:1

(Z)-dec-4-enoylcarnitine;3-[(4Z)-dec-4-enoyloxy]-4-(trimethylammonio)butanoate;cis-4-decenoylcarnitine

C17H31NO4 (313.2253)


   

CAR 14:2

3-[(5Z,8Z)-tetradeca-5,8-dienoyloxy]-4-(trimethylammonio)butanoate;5-cis,8cis-tetradecadienoylcarnitine

C21H37NO4 (367.2722)


   

Hexadecadienoylcarnitine

3-[(7Z,10Z)-hexadeca-7,10-dienoyloxy]-4-(trimethylammonio)butanoate;7cis,10cis-hexadecadienoylcarnitine

C23H41NO4 (395.3035)


   

CAR 22:4

3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-4-(trimethylammonio)butanoate;all-cis-7,10,13,16-docosatetraenoylcarnitine

C29H49NO4 (475.3661)


   

CAR 22:5

3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-4-(trimethylammonio)butanoate;all-cis-7,10,13,16,19-docosapentaenoylcarnitine

C29H47NO4 (473.3505)


   

CAR 9:0

3-[(2,6-dimethylheptanoyl)oxy]-4-(trimethylazaniumyl)butanoate

C16H31NO4 (301.2253)


   

CAR 5:1

3-{[(2E)-2-methylbut-2-enoyl]oxy}-4-(trimethylazaniumyl)butanoate

C12H21NO4 (243.1471)


   

CAR 6:1

3-[(2E)-hex-2-enoyloxy]-4-(trimethylazaniumyl)butanoate

C13H23NO4 (257.1627)


   

CAR 5:0

3-[(2,2-dimethylpropanoyl)oxy]-4-(trimethylazaniumyl)butanoate

C12H23NO4 (245.1627)


Isovalerylcarnitine is a product of the catabolism of L-leucine. Isovalerylcarnitine is also a selective and reversible calpain activator that induces apoptosis[1][2][3].

   

CAR 11:0

3-[(4,8-dimethylnonanoyl)oxy]-4-(trimethylazaniumyl)butanoate

C18H35NO4 (329.2566)


   

CAR 2:0

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

C9H17NO4 (203.1158)


N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics D002491 - Central Nervous System Agents > D018697 - Nootropic Agents D018977 - Micronutrients > D014815 - Vitamins COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

CAR 20:0

3-(icosanoyloxy)-4-(trimethylazaniumyl)butanoate

C27H53NO4 (455.3974)


   

CAR 4:1

(3S)-3-[(2E)-but-2-enoyloxy]-4-(trimethylazaniumyl)butanoate

C11H19NO4 (229.1314)


   

CAR 22:6

3-[(4E,7E,10E,13E,16E,19E)-docosa-4,7,10,13,16,19-hexaenoyloxy]-4-(trimethylazaniumyl)butanoate

C29H45NO4 (471.3348)


   

CAR 14:1

3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate

C21H39NO4 (369.2879)


   

CAR 12:0

3-(dodecanoyloxy)-4-(trimethylammonio)butanoate;O-lauroylcarnitine;dodecanoylcarnitine;lauroylcarnitine

C19H37NO4 (343.2722)


   

CAR 18:1

(9Z)-octadec-9-enoylcarnitine;3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylammonio)butanoate;acylcarnitine C18:1;oleoylcarnitine

C25H47NO4 (425.3505)


   

CAR 17:0

3-(heptadecanoyloxy)-4-(trimethylazaniumyl)butanoate

C24H47NO4 (413.3505)


   

CAR 7:0

3-(heptanoyloxy)-4-(trimethylazaniumyl)butanoate

C14H27NO4 (273.194)


   

CAR 26:0

3-(hexacosanoyloxy)-4-(trimethylazaniumyl)butanoate

C33H65NO4 (539.4913)


   

CAR 16:0

3-(hexadecanoyloxy)-4-(trimethylammonio)butanoate;O-hexadecanoylcarnitine

C23H45NO4 (399.3348)


   

CAR 22:0

3-(docosyloxy)-4-(trimethylammonio)butanoate;O-docosanoylcarnitine;behenoylcarnitine;docosanoylcarnitine

C29H57NO4 (483.4287)


   

CAR 8:0

3-(octanoyloxy)-4-(trimethylammonio)butanoate;octanoylcarnitine

C15H29NO4 (287.2096)


   

CAR 16:1

(9Z)-hexadec-9-enoylcarnitine;3-[(9Z)-hexadec-9-enoyloxy]-4-(trimethylammonio)butanoate;cis-9-hexadecenoylcarnitine

C23H43NO4 (397.3192)


   

CAR 14:0

3-(tetradecanoyloxy)-4-(trimethylammonio)butanoate;O-myristoylcarnitine;myristoylcarnitine;tetradecanoylcarnitine

C21H41NO4 (371.3035)


COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Tetradecanoylcarnitine is a human carnitine involved in β-oxidation of long-chain fatty acids.

   

CAR 3:1

(3S)-3-(prop-2-enoyloxy)-4-(trimethylazaniumyl)butanoate

C10H17NO4 (215.1158)


   

CAR 18:3

(4S)-4-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-4-(trimethylazaniumyl)butanoate

C25H43NO4 (421.3192)


   

CAR 12:1

3-[(5Z)-dodecenoyloxy]-4-(trimethylazaniumyl)butanoate

C19H35NO4 (341.2566)


   

CAR 16:3

3-[(4Z,7Z,10Z)-hexadecatrienoyloxy]-4-(trimethylazaniumyl)butanoate

C23H39NO4 (393.2879)


   
   

CAR 10:0;6oxo

CAR 10:0;6oxo

C17H31NO5 (329.2202)


   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   

Tridecylcarnitine

(3-carboxy-2-tridecanoyloxypropyl)-trimethylazanium

C20H39NO4 (357.2879)


   
   
   
   
   
   
   
   
   
   
   

CAR 14:2(3,5)

CAR 14:2(3,5)

C21H37NO4 (367.2722)


   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   

CAR 18:1(11E)

CAR 18:1(11E)

C25H47NO4 (425.3505)


   
   
   
   

CAR 18:1(9Z);3OH

CAR 18:1(9Z);3OH

C25H47NO5 (441.3454)


   
   

CAR 18:2(9E,12E)

CAR 18:2(9E,12E)

C25H45NO4 (423.3348)


   
   
   
   
   
   
   
   
   
   
   
   

CAR 20:0;OH/CAR DC18:0/CAR 22:6 [Methyl esters]

CAR 20:0;OH/CAR DC18:0/CAR 22:6 [Methyl esters]

(0)


   
   
   
   
   
   
   
   
   
   
   

CAR 21:0;OH

CAR 21:0;OH

C28H55NO5 (485.408)


   
   
   
   
   
   
   
   
   
   
   

CAR 22:1;OH

CAR 22:1;OH

C29H55NO5 (497.408)


   
   
   
   
   
   
   
   
   

CAR 24:0

(3-carboxy-2-tetracosanoyloxypropyl)-trimethylazanium

C31H62NO4+ (512.4679)


   
   
   
   

CAR 3:0;2COOH

CAR 3:0;2COOH

C21H42O2 (326.3185)


   
   
   
   
   

CAR 4:0;2Me

3-(2-methylbutanoyloxy)-4-(trimethylazaniumyl)butanoate

C12H23NO4 (245.1627)


   

CAR 4:0;2OH,3Me

CAR 4:0;2OH,3Me

C12H23NO5 (261.1576)


   

CAR 4:0;3Me

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

C12H23NO4 (245.1627)


   

CAR 4:0;3OH

CAR 4:0;3OH

C11H21NO5 (247.142)


   
   

CAR 4:0(OH);2Me

CAR 4:0(OH);2Me

C11H21NO5 (247.142)


   

CAR 4:0;OH,Me

CAR 4:0;OH,Me

C12H23NO5 (261.1576)


   
   

CAR 4:1(2Z);3Me

CAR 4:1(2Z);3Me

C12H21NO4 (243.1471)


   
   
   
   
   
   
   

CAR 7:0;2Me,6Me

CAR 7:0;2Me,6Me

C16H31NO4 (301.2253)


   
   
   
   
   
   

CAR 8:1(2)

(3S)-3-[(E)-oct-2-enoyl]oxy-4-(trimethylazaniumyl)butanoate

C15H27NO4 (285.194)


   
   
   
   
   
   

CAR DC10:0/CAR 12:0;OH [Methyl esters]

CAR DC10:0/CAR 12:0;OH [Methyl esters]

(0)


   
   

CAR DC10:1/CAR 12:1;OH [Methyl esters]

CAR DC10:1/CAR 12:1;OH [Methyl esters]

(0)


   
   

CAR DC10:2/CAR 12:2;OH [Methyl esters]

CAR DC10:2/CAR 12:2;OH [Methyl esters]

(0)


   
   
   
   
   
   

CAR DC12:0/CAR 14:0;OH [Methyl esters]

CAR DC12:0/CAR 14:0;OH [Methyl esters]

(0)


   
   

CAR DC12:1/CAR 14:1;OH [Methyl esters]

CAR DC12:1/CAR 14:1;OH [Methyl esters]

(0)


   
   

CAR DC12:2/CAR 14:2;OH [Methyl esters]

CAR DC12:2/CAR 14:2;OH [Methyl esters]

(0)


   
   

CAR DC12:3/CAR 14:3;OH [Methyl esters]

CAR DC12:3/CAR 14:3;OH [Methyl esters]

(0)


   
   
   
   
   
   

CAR DC14:0/CAR 16:0;OH [Methyl esters]

CAR DC14:0/CAR 16:0;OH [Methyl esters]

(0)


   
   

CAR DC14:1/CAR 16:1;OH [Methyl esters]

CAR DC14:1/CAR 16:1;OH [Methyl esters]

(0)


   
   

CAR DC14:2/CAR 16:2;OH [Methyl esters]

CAR DC14:2/CAR 16:2;OH [Methyl esters]

(0)


   
   

CAR DC14:3/CAR 16:3;OH [Methyl esters]

CAR DC14:3/CAR 16:3;OH [Methyl esters]

(0)


   
   
   
   
   
   

CAR DC16:0/CAR 18:0;OH [Methyl esters]

CAR DC16:0/CAR 18:0;OH [Methyl esters]

(0)


   
   

CAR DC16:1/CAR 18:1;OH [Methyl esters]

CAR DC16:1/CAR 18:1;OH [Methyl esters]

(0)


   
   

CAR DC16:2/CAR 18:2;OH [Methyl esters]

CAR DC16:2/CAR 18:2;OH [Methyl esters]

(0)


   
   

CAR DC16:3/CAR 18:3;OH [Methyl esters]

CAR DC16:3/CAR 18:3;OH [Methyl esters]

(0)


   
   
   
   
   
   
   

CAR DC18:1/CAR 20:1;OH [Methyl esters]

CAR DC18:1/CAR 20:1;OH [Methyl esters]

(0)


   
   

CAR DC18:2/CAR 20:2;OH [Methyl esters]

CAR DC18:2/CAR 20:2;OH [Methyl esters]

(0)


   
   

CAR DC18:3/CAR 20:3;OH [Methyl esters]

CAR DC18:3/CAR 20:3;OH [Methyl esters]

(0)


   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   

CAR DC3:0;2Me

CAR DC3:0;2Me

C11H19NO6 (261.1212)


   

CAR DC3:0/CAR 5:0;OH [Methyl esters]

CAR DC3:0/CAR 5:0;OH [Methyl esters]

(0)


   

CAR DC4:0

3-(3-carboxypropanoyloxy)-4-(trimethylazaniumyl)butanoate

C11H19NO6 (261.1212)


   

CAR DC4:0/CAR DC3:0;2Me

CAR DC4:0/CAR DC3:0;2Me

C11H19NO6 (261.1212)


   

CAR DC4:0/CAR DC3:0;2Me [Methyl esters]

CAR DC4:0/CAR DC3:0;2Me [Methyl esters]

(0)


   
   
   

CAR DC5:0;3Me

5-[1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy-3-methyl-5-oxopentanoate

C13H23NO6 (289.1525)


   
   
   
   

CAR DC6:0/CAR 8:0;OH [Methyl esters]

CAR DC6:0/CAR 8:0;OH [Methyl esters]

(0)


   
   

CAR DC6:1/CAR 8:1;OH [Methyl esters]

CAR DC6:1/CAR 8:1;OH [Methyl esters]

(0)


   
   
   
   

CAR DC8:0/CAR 10:0;OH [Methyl esters]

CAR DC8:0/CAR 10:0;OH [Methyl esters]

(0)


   
   

CAR DC8:1/CAR 10:1;OH [Methyl esters]

CAR DC8:1/CAR 10:1;OH [Methyl esters]

(0)


   
   
   

Dehydroxycarnitine

Dehydroxycarnitine

C7H15NO2 (145.1103)


   

Isocaproylcarnitine

Isocaproylcarnitine

C13H25NO4 (259.1783)