Exact Mass: 459.3266

(5Z)-7-[(1S,5E)-5-[(2E)-Oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoylcarnitine

3-({7-[5-(oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoyl}oxy)-4-(trimethylazaniumyl)butanoate

(5Z)-7-[(1S,5E)-5-[(2E)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoylcarnitine is an acylcarnitine. More specifically, it is an (5Z)-7-[(1S,5E)-5-[(2E)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic 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. (5Z)-7-[(1S,5E)-5-[(2E)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (5Z)-7-[(1S,5E)-5-[(2E)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoylcarnitine 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. 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].

N-Docosahexaenoyl Methionine

2-(docosa-4,7,10,13,16,19-hexaenamido)-4-(methylsulfanyl)butanoic acid

C27H41NO3S (459.2807)

N-docosahexaenoyl methionine belongs to the class of compounds known as N-acylamides. These are molecules characterized by a fatty acyl group linked to a primary amine by an amide bond. More specifically, it is a Docosahexaenoyl amide of Methionine. It is believed that there are more than 800 types of N-acylamides in the human body. N-acylamides fall into several categories: amino acid conjugates (e.g., those acyl amides conjugated with amino acids), neurotransmitter conjugates (e.g., those acylamides conjugated with neurotransmitters), ethanolamine conjugates (e.g., those acylamides conjugated to ethanolamine), and taurine conjugates (e.g., those acyamides conjugated to taurine). N-Docosahexaenoyl Methionine is an amino acid conjugate. N-acylamides can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain N-acylamides; 2) medium-chain N-acylamides; 3) long-chain N-acylamides; and 4) very long-chain N-acylamides; 5) hydroxy N-acylamides; 6) branched chain N-acylamides; 7) unsaturated N-acylamides; 8) dicarboxylic N-acylamides and 9) miscellaneous N-acylamides. N-Docosahexaenoyl Methionine is therefore classified as a very long chain N-acylamide. N-acyl amides have a variety of signaling functions in physiology, including in cardiovascular activity, metabolic homeostasis, memory, cognition, pain, motor control and others (PMID: 15655504). N-acyl amides have also been shown to play a role in cell migration, inflammation and certain pathological conditions such as diabetes, cancer, neurodegenerative disease, and obesity (PMID: 23144998; PMID: 25136293; PMID: 28854168).N-acyl amides can be synthesized both endogenously and by gut microbiota (PMID: 28854168). N-acylamides can be biosynthesized via different routes, depending on the parent amine group. N-acyl ethanolamines (NAEs) are formed via the hydrolysis of an unusual phospholipid precursor, N-acyl-phosphatidylethanolamine (NAPE), by a specific phospholipase D. N-acyl amino acids are synthesized via a circulating peptidase M20 domain containing 1 (PM20D1), which can catalyze the bidirectional the condensation and hydrolysis of a variety of N-acyl amino acids. The degradation of N-acylamides is largely mediated by an enzyme called fatty acid amide hydrolase (FAAH), which catalyzes the hydrolysis of N-acylamides into fatty acids and the biogenic amines. Many N-acylamides are involved in lipid signaling system through interactions with transient receptor potential channels (TRP). TRP channel proteins interact with N-acyl amides such as N-arachidonoyl ethanolamide (Anandamide), N-arachidonoyl dopamine and others in an opportunistic fashion (PMID: 23178153). This signaling system has been shown to play a role in the physiological processes involved in inflammation (PMID: 25136293). Other N-acyl amides, including N-oleoyl-glutamine, have also been characterized as TRP channel antagonists (PMID: 29967167). N-acylamides have also been shown to have G-protein-coupled receptors (GPCRs) binding activity (PMID: 28854168). The study of N-acylamides is an active area of research and it is likely that many novel N-acylamides will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.

Turosteride

1,3-bis(propan-2-yl)-1-{2,6,15-trimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-14-carbonyl}urea

C27H45N3O3 (459.3461)

cristatin A|cycloalanyl-6,7-di(isopent-2-enyl)-2-(1,1-dimethylallyl)-8-(Z)-ene-tryprophan

Dehydroechinulin

(-)-Dehydroechinulin

verdine

Dehydrovariecolorin L

(-)-Dehydrovariecolorin L

3-[2-(1,1-dimethyl-allyl)-5,7-bis-(3-methyl-but-2-enyl)-indol-3-ylmethylene]-6-methyl-piperazine-2,5-dione

didehydroechinulin|didehydroechinulin B

Kimbasine B

N-docosanoylanthranilic acid

C29H49NO3 (459.3712)

(20R,22R)-N-methyl-5,6,12,13-tetrahydro-3beta,13alpha,23beta-trihydroxy-5alpha,12alpha,17beta,25alpha-veratraman-7-en-6-one|puqienine C

(20R*,22R*)-N-methyl-5,6,12,13-tetrahydro-3beta,13alpha,23beta-trihydroxy-5alpha,12alpha,17beta,25alpha-veratraman-7-en-6-one|puqienine C

C28H45NO4 (459.3348)

(20R,22R)-N-methyl-5,6,12,13-tetrahydro-3beta,13alpha,23beta-trihydroxy-5alpha,12alpha,17beta,25alpha-veratraman-14-en-6-one|puqienine D

(20R*,22R*)-N-methyl-5,6,12,13-tetrahydro-3beta,13alpha,23beta-trihydroxy-5alpha,12alpha,17beta,25alpha-veratraman-14-en-6-one|puqienine D

C28H45NO4 (459.3348)

12beta,27-dihydroxysolasodine

(6S)-3-{[2-(1,1-dimethylprop-2-en-1-yl)-4,5-bis(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methylidene}-6-methylpiperazin-2,5-dione|dehydrovariecolorin L

Trp Lys Leu

C24H37N5O4 (459.2845)

Lys Ala Asn Lys

(2S)-6-amino-2-[(2S)-3-carbamoyl-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]propanamido]hexanoic acid

Trp Leu Lys

C24H37N5O4 (459.2845)

Ala Ile Arg Thr

(2S,3R)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-aminopropanamido]-3-methylpentanamido]-5-carbamimidamidopentanamido]-3-hydroxybutanoic acid

Ala Ile Thr Arg

(2S)-2-[(2S,3R)-2-[(2S,3S)-2-[(2S)-2-aminopropanamido]-3-methylpentanamido]-3-hydroxybutanamido]-5-carbamimidamidopentanoic acid

Ala Lys Lys Asn

(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]hexanamido]-3-carbamoylpropanoic acid

Ala Lys Asn Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]-3-carbamoylpropanamido]hexanoic acid

Ala Leu Arg Thr

(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]-3-hydroxybutanoic acid

Ala Leu Thr Arg

(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-methylpentanamido]-3-hydroxybutanamido]-5-carbamimidamidopentanoic acid

Ala Asn Lys Lys

(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-carbamoylpropanamido]hexanamido]hexanoic acid

Ala Arg Ile Thr

(2S,3R)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-5-carbamimidamidopentanamido]-3-methylpentanamido]-3-hydroxybutanoic acid

Ala Arg Leu Thr

(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-3-hydroxybutanoic acid

Ala Arg Thr Ile

(2S,3S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-aminopropanamido]-5-carbamimidamidopentanamido]-3-hydroxybutanamido]-3-methylpentanoic acid

Ala Arg Thr Leu

(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-aminopropanamido]-5-carbamimidamidopentanamido]-3-hydroxybutanamido]-4-methylpentanoic acid

Ala Thr Ile Arg

(2S)-2-[(2S,3S)-2-[(2S,3R)-2-[(2S)-2-aminopropanamido]-3-hydroxybutanamido]-3-methylpentanamido]-5-carbamimidamidopentanoic acid

Ala Thr Leu Arg

(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-aminopropanamido]-3-hydroxybutanamido]-4-methylpentanamido]-5-carbamimidamidopentanoic acid

Ala Thr Arg Ile

(2S,3S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-aminopropanamido]-3-hydroxybutanamido]-5-carbamimidamidopentanamido]-3-methylpentanoic acid

Ala Thr Arg Leu

(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-aminopropanamido]-3-hydroxybutanamido]-5-carbamimidamidopentanamido]-4-methylpentanoic acid

Gly Lys Lys Lys

(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-6-amino-2-(2-aminoacetamido)hexanamido]hexanamido]hexanoic acid

C20H41N7O5 (459.3169)

Gly Lys Lys Gln

(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-(2-aminoacetamido)hexanamido]hexanamido]-4-carbamoylbutanoic acid

Gly Lys Gln Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-(2-aminoacetamido)hexanamido]-4-carbamoylbutanamido]hexanoic acid

Gly Gln Lys Lys

(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-4-carbamoylbutanamido]hexanamido]hexanoic acid

Ile Ala Arg Thr

(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]propanamido]-5-carbamimidamidopentanamido]-3-hydroxybutanoic acid

Ile Ala Thr Arg

(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]propanamido]-3-hydroxybutanamido]-5-carbamimidamidopentanoic acid