Exact Mass: 417.2991264

4-Hydroxytetradecanedioylcarnitine

3-[(13-carboxy-4-hydroxytridecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

4-Hydroxytetradecanedioylcarnitine is an acylcarnitine. More specifically, it is an 4-hydroxytetradecanedioic 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. 4-Hydroxytetradecanedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 4-Hydroxytetradecanedioylcarnitine 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].

6-Hydroxytetradecanedioylcarnitine

3-[(13-carboxy-6-hydroxytridecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

6-Hydroxytetradecanedioylcarnitine is an acylcarnitine. More specifically, it is an 6-hydroxytetradecanedioic 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. 6-Hydroxytetradecanedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 6-Hydroxytetradecanedioylcarnitine 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].

7-Hydroxytetradecanedioylcarnitine

3-[(13-carboxy-7-hydroxytridecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

7-Hydroxytetradecanedioylcarnitine is an acylcarnitine. More specifically, it is an 7-hydroxytetradecanedioic 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. 7-Hydroxytetradecanedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 7-Hydroxytetradecanedioylcarnitine 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].

5-Hydroxytetradecanedioylcarnitine

3-[(13-carboxy-5-hydroxytridecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

5-Hydroxytetradecanedioylcarnitine is an acylcarnitine. More specifically, it is an 5-hydroxytetradecanedioic 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. 5-Hydroxytetradecanedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 5-Hydroxytetradecanedioylcarnitine 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].

3-hydroxytetradecanedioylcarnitine

3-[(13-carboxy-3-hydroxytridecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

3-hydroxytetradecanedioylcarnitine is an acylcarnitine. More specifically, it is an 3-hydroxytetradecanedioic 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. 3-hydroxytetradecanedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 3-hydroxytetradecanedioylcarnitine 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-Linoleoyl Histidine

3-(3H-imidazol-4-yl)-2-(octadeca-9,12-dienamido)propanoic acid

C24H39N3O3 (417.2991264)

N-linoleoyl histidine 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 Linoleic acid amide of Histidine. 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-Linoleoyl Histidine 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-Linoleoyl Histidine is therefore classified as a 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.

N-Arachidonoyl Isoleucine

2-(icosa-5,8,11,14-tetraenamido)-3-methylpentanoic acid

N-arachidonoyl isoleucine 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 an Arachidonic acid amide of Isoleucine. 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-Arachidonoyl Isoleucine 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-Arachidonoyl Isoleucine is therefore classified as a 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.

N-Arachidonoyl Leucine

2-(icosa-5,8,11,14-tetraenamido)-4-methylpentanoic acid

N-arachidonoyl leucine 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 an Arachidonic acid amide of Leucine. 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-Arachidonoyl Leucine 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-Arachidonoyl Leucine is therefore classified as a 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.

N-Eicosapentaenoyl Aspartic acid

2-(icosa-5,8,11,14,17-pentaenamido)butanedioic acid

N-eicosapentaenoyl aspartic acid 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 an Eicosapentaenoic acid amide of Aspartic acid. 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-Eicosapentaenoyl Aspartic acid 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-Eicosapentaenoyl Aspartic acid is therefore classified as a 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.

Decoquinate

ethyl 6-(decyloxy)-7-ethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C258 - Antibiotic > C795 - Quinolone Antibiotic

N-Oleoyldopamine

N-[2-(3,4-Dihydroxyphenyl)ethyl]octadec-9-enimidate

Olvanil

N-[(4-Hydroxy-3-methoxyphenyl)methyl]octadec-9-enimidate

Thalicsiline

Aspochalasin H

Oxaloterpin A

aspochalasin I

(-)-Sphingofungin E

Integramine

C28H35NO2 (417.266765)

KA-6606-IV

12-Acetylnapelline N-oxide

Flavadine

8-Acetylheterophyllisine

DECOQUINATE

D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C258 - Antibiotic > C795 - Quinolone Antibiotic CONFIDENCE standard compound; INTERNAL_ID 1087

N-[2-(3,4-dihydroxyphenyl)ethyl]-9-octadecenamide

CB-52

N-cyclopropyl-11-(2-hydroxy-5-pentylphenoxy)-undecanamide

CB-86

N-cyclopropyl-8-[3-(1,1-dimethylheptyl)-5-hydroxyphenoxy]-octanamide

1-[4-[ethyl-[1-(4-methoxyphenyl)propan-2-yl]amino]butanoyl]-N,N-dimethylpiperidine-4-carboxamide

C24H39N3O3 (417.2991264)

5,6-dihydroxy-9,12,13-trimethyl-14-(2-methylpropyl)-2H,5H,6H,7H,8H,13H,13aH,14H,15H,16H,16bH-oxacyclododeca[3,2-e]isoindole-2,16-dione

B,3HCL-Spergualin|Spergualin

C18H39N7O4 (417.3063374)

Aflavazole

C28H35NO2 (417.266765)

Baimonidine

aspochalasin M

Sannamycin F

cespitulactam B

C28H35NO2 (417.266765)

1H-Cycloundec[d]isoindole-1,12,15-trione, 2,3,3a,4,6a,9,10,11,13,14-decahydro-11,13-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-, (7E)-

NCGC00380405-01_C24H35NO5_1H-Cycloundec[d]isoindole-1,12,15-trione, 2,3,3a,4,6a,9,10,11,13,14-decahydro-11,13-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-, (7E)-

CSL-12L

N-[(4-Hydroxy-3-methoxyphenyl)methyl]-9-octadecenamide

C25H39NO4

hydroxydaphgraciline|methyl (4S,6R,6?S,10aR,11S)-6?-ethyl-2,3,4,5,5?,6,6?,7,8,10-decahydro-6-hydroxy-6?-methoxy-2-methyl-1H,4?H-spiro[4,10a-methanopentaleno[1,6-cd]azonine-11,3?-pyran]-9-carboxylate

trichoderone B

daphmacromine E

sinulasulfone

C23H47NO3S (417.3276472)

daphmacromine H

Oxodaphnigracin|Oxodaphnigracine

daphnezomine R

daphnipaxianine D

Lankacyclinol

Ile Ala Ser Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]propanamido]-3-hydroxypropanamido]hexanoic acid

Thr Val Ala Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-methylbutanamido]propanamido]hexanoic acid

13,14-Dihydro Bimatoprost

Idaverine

C24H39N3O3 (417.2991264)

C78272 - Agent Affecting Nervous System > C29698 - Antispasmodic Agent CONFIDENCE standard compound; INTERNAL_ID 1085

3-hydroxy-2-[[3-(3-hydroxy-6-methylheptanoyl)oxy-8-methylnonanoyl]amino]propanoic acid

NCGC00380970-01!3-hydroxy-2-[[3-(3-hydroxy-6-methylheptanoyl)oxy-8-methylnonanoyl]amino]propanoic acid

C24H35NO5_(1aS,2R,3R,6E,10S,10aR,11S,13aS,14aS)-2,3-Dihydroxy-11-isobutyl-6,9,10-trimethyl-3,4,5,7a,10,10a,11,12-octahydro-1aH-oxireno[9,10]cycloundeca[1,2-d]isoindole-13,14(2H,14aH)-dione

NCGC00380304-01_C24H35NO5_(1aS,2R,3R,6E,10S,10aR,11S,13aS,14aS)-2,3-Dihydroxy-11-isobutyl-6,9,10-trimethyl-3,4,5,7a,10,10a,11,12-octahydro-1aH-oxireno[9,10]cycloundeca[1,2-d]isoindole-13,14(2H,14aH)-dione

C25H39NO4_(7E)-12-Hydroxy-3-isobutyl-13-methoxy-4,5,8-trimethyl-3,3a,4,6a,9,10,11,12,13,14-decahydro-1H-cycloundeca[d]isoindole-1,15(2H)-dione

NCGC00380607-01_C25H39NO4_(7E)-12-Hydroxy-3-isobutyl-13-methoxy-4,5,8-trimethyl-3,3a,4,6a,9,10,11,12,13,14-decahydro-1H-cycloundeca[d]isoindole-1,15(2H)-dione

(Z)-N-(3-hydroxyhexadec-9-enoyl)-L-phenylalanine

3-hydroxy-2-[[3-(3-hydroxy-6-methylheptanoyl)oxy-8-methylnonanoyl]amino]propanoic acid [IIN-based on: CCMSLIB00000848029]

NCGC00380970-01!3-hydroxy-2-[[3-(3-hydroxy-6-methylheptanoyl)oxy-8-methylnonanoyl]amino]propanoic acid [IIN-based on: CCMSLIB00000848029]

3-hydroxy-2-[[3-(3-hydroxy-6-methylheptanoyl)oxy-8-methylnonanoyl]amino]propanoic acid [IIN-based: Match]

NCGC00380970-01!3-hydroxy-2-[[3-(3-hydroxy-6-methylheptanoyl)oxy-8-methylnonanoyl]amino]propanoic acid [IIN-based: Match]

5,6-dihydroxy-9,12,13-trimethyl-14-(2-methylpropyl)-2H,5H,6H,7H,8H,13H,13aH,14H,15H,16H,16bH-oxacyclododeca[3,2-e]isoindole-2,16-dione_major

Ala Ile Lys Ser

(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-aminopropanamido]-3-methylpentanamido]hexanamido]-3-hydroxypropanoic acid

Ala Ile Ser Lys

(2S)-6-amino-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-aminopropanamido]-3-methylpentanamido]-3-hydroxypropanamido]hexanoic acid

Ala Lys Ile Ser

(2S)-2-[(2S,3S)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]-3-methylpentanamido]-3-hydroxypropanoic acid

Ala Lys Leu Ser

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]-4-methylpentanamido]-3-hydroxypropanoic acid

Ala Lys Ser Ile

(2S,3S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]-3-hydroxypropanamido]-3-methylpentanoic acid

Ala Lys Ser Leu

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]-3-hydroxypropanamido]-4-methylpentanoic acid

Ala Lys Thr Val

(2S)-2-[(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]-3-hydroxybutanamido]-3-methylbutanoic acid

Ala Lys Val Thr

(2S,3R)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]-3-methylbutanamido]-3-hydroxybutanoic acid

Ala Leu Lys Ser

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-methylpentanamido]hexanamido]-3-hydroxypropanoic acid

Ala Leu Ser Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-4-methylpentanamido]-3-hydroxypropanamido]hexanoic acid

Ala Ser Ile Lys

(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-hydroxypropanamido]-3-methylpentanamido]hexanoic acid

Ala Ser Lys Ile

(2S,3S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-hydroxypropanamido]hexanamido]-3-methylpentanoic acid

Ala Ser Lys Leu

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-hydroxypropanamido]hexanamido]-4-methylpentanoic acid

Ala Ser Leu Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-hydroxypropanamido]-4-methylpentanamido]hexanoic acid

Ala Thr Lys Val

(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-aminopropanamido]-3-hydroxybutanamido]hexanamido]-3-methylbutanoic acid

Ala Thr Val Lys

(2S)-6-amino-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-aminopropanamido]-3-hydroxybutanamido]-3-methylbutanamido]hexanoic acid

Ala Val Lys Thr

(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-methylbutanamido]hexanamido]-3-hydroxybutanoic acid

Ala Val Thr Lys

(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-methylbutanamido]-3-hydroxybutanamido]hexanoic acid

Gly Ile Lys Thr

(2S,3R)-2-[(2S)-6-amino-2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]hexanamido]-3-hydroxybutanoic acid

Gly Ile Thr Lys

(2S)-6-amino-2-[(2S,3R)-2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]-3-hydroxybutanamido]hexanoic acid

Gly Lys Ile Thr

(2S,3R)-2-[(2S,3S)-2-[(2S)-6-amino-2-(2-aminoacetamido)hexanamido]-3-methylpentanamido]-3-hydroxybutanoic acid

Gly Lys Leu Thr

(2S,3R)-2-[(2S)-2-[(2S)-6-amino-2-(2-aminoacetamido)hexanamido]-4-methylpentanamido]-3-hydroxybutanoic acid

Gly Lys Thr Ile

(2S,3S)-2-[(2S,3R)-2-[(2S)-6-amino-2-(2-aminoacetamido)hexanamido]-3-hydroxybutanamido]-3-methylpentanoic acid

Gly Lys Thr Leu

(2S)-2-[(2S,3R)-2-[(2S)-6-amino-2-(2-aminoacetamido)hexanamido]-3-hydroxybutanamido]-4-methylpentanoic acid

Gly Leu Lys Thr

(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-4-methylpentanamido]hexanamido]-3-hydroxybutanoic acid

Gly Leu Thr Lys

(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-(2-aminoacetamido)-4-methylpentanamido]-3-hydroxybutanamido]hexanoic acid

Gly Thr Ile Lys

(2S)-6-amino-2-[(2S,3S)-2-[(2S,3R)-2-(2-aminoacetamido)-3-hydroxybutanamido]-3-methylpentanamido]hexanoic acid

Gly Thr Lys Ile

(2S,3S)-2-[(2S)-6-amino-2-[(2S,3R)-2-(2-aminoacetamido)-3-hydroxybutanamido]hexanamido]-3-methylpentanoic acid

Gly Thr Lys Leu

(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-(2-aminoacetamido)-3-hydroxybutanamido]hexanamido]-4-methylpentanoic acid

Gly Thr Leu Lys

(2S)-6-amino-2-[(2S)-2-[(2S,3R)-2-(2-aminoacetamido)-3-hydroxybutanamido]-4-methylpentanamido]hexanoic acid

Ile Ala Lys Ser

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]propanamido]hexanamido]-3-hydroxypropanoic acid

Ile Gly Lys Thr

(2S,3R)-2-[(2S)-6-amino-2-{2-[(2S,3S)-2-amino-3-methylpentanamido]acetamido}hexanamido]-3-hydroxybutanoic acid

Ile Gly Thr Lys

(2S)-6-amino-2-[(2S,3R)-2-{2-[(2S,3S)-2-amino-3-methylpentanamido]acetamido}-3-hydroxybutanamido]hexanoic acid

Ile Lys Ala Ser

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-amino-3-methylpentanamido]hexanamido]propanamido]-3-hydroxypropanoic acid

Ile Lys Gly Thr

(2S,3R)-2-{2-[(2S)-6-amino-2-[(2S,3S)-2-amino-3-methylpentanamido]hexanamido]acetamido}-3-hydroxybutanoic acid

Ile Lys Ser Ala

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-amino-3-methylpentanamido]hexanamido]-3-hydroxypropanamido]propanoic acid

Ile Lys Thr Gly

2-[(2S,3R)-2-[(2S)-6-amino-2-[(2S,3S)-2-amino-3-methylpentanamido]hexanamido]-3-hydroxybutanamido]acetic acid

Ile Ser Ala Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-3-hydroxypropanamido]propanamido]hexanoic acid

Ile Ser Lys Ala

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-3-hydroxypropanamido]hexanamido]propanoic acid

Ile Thr Gly Lys

(2S)-6-amino-2-{2-[(2S,3R)-2-[(2S,3S)-2-amino-3-methylpentanamido]-3-hydroxybutanamido]acetamido}hexanoic acid

Ile Thr Lys Gly

2-[(2S)-6-amino-2-[(2S,3R)-2-[(2S,3S)-2-amino-3-methylpentanamido]-3-hydroxybutanamido]hexanamido]acetic acid

Lys Ala Ile Ser

(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]-3-methylpentanamido]-3-hydroxypropanoic acid

Lys Ala Leu Ser

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]-4-methylpentanamido]-3-hydroxypropanoic acid

Lys Ala Ser Ile

(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]-3-hydroxypropanamido]-3-methylpentanoic acid

Lys Ala Ser Leu

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]-3-hydroxypropanamido]-4-methylpentanoic acid

Lys Ala Thr Val

(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]-3-hydroxybutanamido]-3-methylbutanoic acid

Lys Ala Val Thr

(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]-3-methylbutanamido]-3-hydroxybutanoic acid

Lys Gly Ile Thr

(2S,3R)-2-[(2S,3S)-2-{2-[(2S)-2,6-diaminohexanamido]acetamido}-3-methylpentanamido]-3-hydroxybutanoic acid

Lys Gly Leu Thr

(2S,3R)-2-[(2S)-2-{2-[(2S)-2,6-diaminohexanamido]acetamido}-4-methylpentanamido]-3-hydroxybutanoic acid

Lys Gly Thr Ile

(2S,3S)-2-[(2S,3R)-2-{2-[(2S)-2,6-diaminohexanamido]acetamido}-3-hydroxybutanamido]-3-methylpentanoic acid

Lys Gly Thr Leu

(2S)-2-[(2S,3R)-2-{2-[(2S)-2,6-diaminohexanamido]acetamido}-3-hydroxybutanamido]-4-methylpentanoic acid

Lys Ile Ala Ser

(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2,6-diaminohexanamido]-3-methylpentanamido]propanamido]-3-hydroxypropanoic acid

Lys Ile Gly Thr

(2S,3R)-2-{2-[(2S,3S)-2-[(2S)-2,6-diaminohexanamido]-3-methylpentanamido]acetamido}-3-hydroxybutanoic acid

Lys Ile Ser Ala

(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2,6-diaminohexanamido]-3-methylpentanamido]-3-hydroxypropanamido]propanoic acid

Lys Ile Thr Gly

2-[(2S,3R)-2-[(2S,3S)-2-[(2S)-2,6-diaminohexanamido]-3-methylpentanamido]-3-hydroxybutanamido]acetic acid

Lys Leu Ala Ser

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-4-methylpentanamido]propanamido]-3-hydroxypropanoic acid

Lys Leu Gly Thr

(2S,3R)-2-{2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-4-methylpentanamido]acetamido}-3-hydroxybutanoic acid

Lys Leu Ser Ala

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-4-methylpentanamido]-3-hydroxypropanamido]propanoic acid

Lys Leu Thr Gly

2-[(2S,3R)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-4-methylpentanamido]-3-hydroxybutanamido]acetic acid

Lys Ser Ala Ile

(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxypropanamido]propanamido]-3-methylpentanoic acid

Lys Ser Ala Leu

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxypropanamido]propanamido]-4-methylpentanoic acid

Lys Ser Ile Ala

(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxypropanamido]-3-methylpentanamido]propanoic acid

Lys Ser Leu Ala

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxypropanamido]-4-methylpentanamido]propanoic acid

Lys Thr Ala Val

(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxybutanamido]propanamido]-3-methylbutanoic acid

Lys Thr Gly Ile

(2S,3S)-2-{2-[(2S,3R)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxybutanamido]acetamido}-3-methylpentanoic acid

Lys Thr Gly Leu

(2S)-2-{2-[(2S,3R)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxybutanamido]acetamido}-4-methylpentanoic acid

Lys Thr Ile Gly

2-[(2S,3S)-2-[(2S,3R)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxybutanamido]-3-methylpentanamido]acetic acid

Lys Thr Leu Gly

2-[(2S)-2-[(2S,3R)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxybutanamido]-4-methylpentanamido]acetic acid

Lys Thr Val Ala

(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2,6-diaminohexanamido]-3-hydroxybutanamido]-3-methylbutanamido]propanoic acid

Lys Val Ala Thr

(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-methylbutanamido]propanamido]-3-hydroxybutanoic acid

Lys Val Thr Ala

(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-methylbutanamido]-3-hydroxybutanamido]propanoic acid

Leu Ala Lys Ser

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]propanamido]hexanamido]-3-hydroxypropanoic acid

Leu Ala Ser Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]propanamido]-3-hydroxypropanamido]hexanoic acid

Leu Gly Lys Thr

(2S,3R)-2-[(2S)-6-amino-2-{2-[(2S)-2-amino-4-methylpentanamido]acetamido}hexanamido]-3-hydroxybutanoic acid

Leu Gly Thr Lys

(2S)-6-amino-2-[(2S,3R)-2-{2-[(2S)-2-amino-4-methylpentanamido]acetamido}-3-hydroxybutanamido]hexanoic acid

Leu Lys Ala Ser

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-4-methylpentanamido]hexanamido]propanamido]-3-hydroxypropanoic acid

Leu Lys Gly Thr

(2S,3R)-2-{2-[(2S)-6-amino-2-[(2S)-2-amino-4-methylpentanamido]hexanamido]acetamido}-3-hydroxybutanoic acid

Leu Lys Ser Ala

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-4-methylpentanamido]hexanamido]-3-hydroxypropanamido]propanoic acid

Leu Lys Thr Gly

2-[(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-amino-4-methylpentanamido]hexanamido]-3-hydroxybutanamido]acetic acid

Leu Ser Ala Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-hydroxypropanamido]propanamido]hexanoic acid

Leu Ser Lys Ala

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-hydroxypropanamido]hexanamido]propanoic acid

Leu Thr Gly Lys

(2S)-6-amino-2-{2-[(2S,3R)-2-[(2S)-2-amino-4-methylpentanamido]-3-hydroxybutanamido]acetamido}hexanoic acid

Leu Thr Lys Gly

2-[(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-amino-4-methylpentanamido]-3-hydroxybutanamido]hexanamido]acetic acid

Ser Ala Ile Lys

(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]propanamido]-3-methylpentanamido]hexanoic acid

Ser Ala Lys Ile

(2S,3S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]propanamido]hexanamido]-3-methylpentanoic acid

Ser Ala Lys Leu

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]propanamido]hexanamido]-4-methylpentanoic acid

Ser Ala Leu Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]propanamido]-4-methylpentanamido]hexanoic acid

Ser Ile Ala Lys

(2S)-6-amino-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-methylpentanamido]propanamido]hexanoic acid

Ser Ile Lys Ala

(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-methylpentanamido]hexanamido]propanoic acid

Ser Lys Ala Ile

(2S,3S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-hydroxypropanamido]hexanamido]propanamido]-3-methylpentanoic acid

Ser Lys Ala Leu

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-hydroxypropanamido]hexanamido]propanamido]-4-methylpentanoic acid

Ser Lys Ile Ala

(2S)-2-[(2S,3S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-hydroxypropanamido]hexanamido]-3-methylpentanamido]propanoic acid

Ser Lys Leu Ala

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-hydroxypropanamido]hexanamido]-4-methylpentanamido]propanoic acid

Ser Leu Ala Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-4-methylpentanamido]propanamido]hexanoic acid

Ser Leu Lys Ala

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-4-methylpentanamido]hexanamido]propanoic acid

Thr Ala Lys Val

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]propanamido]hexanamido]-3-methylbutanoic acid

Thr Ala Val Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]propanamido]-3-methylbutanamido]hexanoic acid

Thr Gly Ile Lys

(2S)-6-amino-2-[(2S,3S)-2-{2-[(2S,3R)-2-amino-3-hydroxybutanamido]acetamido}-3-methylpentanamido]hexanoic acid

Thr Gly Lys Ile

(2S,3S)-2-[(2S)-6-amino-2-{2-[(2S,3R)-2-amino-3-hydroxybutanamido]acetamido}hexanamido]-3-methylpentanoic acid

Thr Gly Lys Leu

(2S)-2-[(2S)-6-amino-2-{2-[(2S,3R)-2-amino-3-hydroxybutanamido]acetamido}hexanamido]-4-methylpentanoic acid

Thr Gly Leu Lys

(2S)-6-amino-2-[(2S)-2-{2-[(2S,3R)-2-amino-3-hydroxybutanamido]acetamido}-4-methylpentanamido]hexanoic acid

Thr Ile Gly Lys

(2S)-6-amino-2-{2-[(2S,3S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-methylpentanamido]acetamido}hexanoic acid

Thr Ile Lys Gly

2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-methylpentanamido]hexanamido]acetic acid

Thr Lys Ala Val

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanamido]propanamido]-3-methylbutanoic acid

Thr Lys Gly Ile

(2S,3S)-2-{2-[(2S)-6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanamido]acetamido}-3-methylpentanoic acid

Thr Lys Gly Leu

(2S)-2-{2-[(2S)-6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanamido]acetamido}-4-methylpentanoic acid

Thr Lys Ile Gly

2-[(2S,3S)-2-[(2S)-6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanamido]-3-methylpentanamido]acetic acid

Thr Lys Leu Gly

2-[(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanamido]-4-methylpentanamido]acetic acid

Thr Lys Val Ala

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanamido]-3-methylbutanamido]propanoic acid

Thr Leu Gly Lys

(2S)-6-amino-2-{2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-4-methylpentanamido]acetamido}hexanoic acid

Thr Leu Lys Gly

2-[(2S)-6-amino-2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-4-methylpentanamido]hexanamido]acetic acid

Thr Val Lys Ala

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-methylbutanamido]hexanamido]propanoic acid

Val Ala Lys Thr

(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]propanamido]hexanamido]-3-hydroxybutanoic acid

Val Ala Thr Lys

(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]propanamido]-3-hydroxybutanamido]hexanoic acid

Val Lys Ala Thr

(2S,3R)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-methylbutanamido]hexanamido]propanamido]-3-hydroxybutanoic acid

Val Lys Thr Ala

(2S)-2-[(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-methylbutanamido]hexanamido]-3-hydroxybutanamido]propanoic acid

Val Thr Ala Lys

(2S)-6-amino-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-amino-3-methylbutanamido]-3-hydroxybutanamido]propanamido]hexanoic acid

Val Thr Lys Ala

(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-amino-3-methylbutanamido]-3-hydroxybutanamido]hexanamido]propanoic acid

(-)-Batrachotoxinin A

1α,25-dihydroxy-23-azavitamin D3 / 1α,25-dihydroxy-23-azacholecalciferol

Latanoprost ethyl amide

N-ethyl-9α,11α,15R-trihydroxy-17-phenyl-18,19,20-trinor-prost-5Z-en-1-amide

Sphingofungin E

2S-amino-3R,4R,5S-trihydroxy-2-(hydroxymethyl)-14-oxo-eicos-6E-enoic acid

Olvanil

N-[(4-hydroxy-3-methoxyphenyl)methyl]-9Z-octadecenamide