Exact Mass: 425.27803420000004

D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents > D014704 - Veratrum Alkaloids CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2330 Jervine (11-Ketocyclopamine) is a potent Hedgehog (Hh) inhibitor with an IC50 of 500-700 nM[1]. Jervine is a natural teratogenic sterodial alkaloid from rhizomes of Veratrum nigrum. Jervine has anti-inflammatory and antioxidant properties[2]. Jervine (11-Ketocyclopamine) is a potent Hedgehog (Hh) inhibitor with an IC50 of 500-700 nM[1]. Jervine is a natural teratogenic sterodial alkaloid from rhizomes of Veratrum nigrum. Jervine has anti-inflammatory and antioxidant properties[2].

Diprenorphine

D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D009292 - Narcotic Antagonists C78272 - Agent Affecting Nervous System > C681 - Opiate Antagonist Same as: D07863

Nafoxidine

1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine

C29H31NO2 (425.2354666)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator C274 - Antineoplastic Agent > C1742 - Angiogenesis Inhibitor > C1971 - Angiogenesis Activator Inhibitor C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist D000970 - Antineoplastic Agents C1892 - Chemopreventive Agent

LysoPE(14:0/0:0)

(2-aminoethoxy)[(2R)-2-hydroxy-3-(tetradecanoyloxy)propoxy]phosphinic acid

LysoPE(14:0/0:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term lysophospholipid (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix lyso- comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. [HMDB] LysoPE(14:0/0:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term lysophospholipid (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix lyso- comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.

LysoPE(0:0/14:0)

(2-aminoethoxy)[(2R)-3-hydroxy-2-(tetradecanoyloxy)propoxy]phosphinic acid

LysoPE(0:0/14:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term lysophospholipid (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix lyso- comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. [HMDB] LysoPE(0:0/14:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term lysophospholipid (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix lyso- comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.

(6Z,8Z)-Hexadeca-6,8-dienedioylcarnitine

3-[(15-carboxypentadeca-6,8-dienoyl)oxy]-4-(trimethylazaniumyl)butanoate

(6Z,8Z)-Hexadeca-6,8-dienedioylcarnitine is an acylcarnitine. More specifically, it is an (6Z,8Z)-hexadeca-6,8-dienedioic 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,8Z)-Hexadeca-6,8-dienedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (6Z,8Z)-Hexadeca-6,8-dienedioylcarnitine 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].

(4E,6Z)-Hexadeca-4,6-dienedioylcarnitine

3-[(15-carboxypentadeca-4,6-dienoyl)oxy]-4-(trimethylazaniumyl)butanoate

(4E,6Z)-Hexadeca-4,6-dienedioylcarnitine is an acylcarnitine. More specifically, it is an (4E,6Z)-hexadeca-4,6-dienedioic 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. (4E,6Z)-Hexadeca-4,6-dienedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (4E,6Z)-Hexadeca-4,6-dienedioylcarnitine 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].

(6E,9E)-Hexadeca-6,9-dienedioylcarnitine

3-[(15-carboxypentadeca-6,9-dienoyl)oxy]-4-(trimethylazaniumyl)butanoate

(6E,9E)-Hexadeca-6,9-dienedioylcarnitine is an acylcarnitine. More specifically, it is an (6E,9E)-hexadeca-6,9-dienedioic 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. (6E,9E)-Hexadeca-6,9-dienedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (6E,9E)-Hexadeca-6,9-dienedioylcarnitine 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].

(7Z,13Z)-hexadeca-7,13-dienedioylcarnitine

3-[(15-carboxypentadeca-7,13-dienoyl)oxy]-4-(trimethylazaniumyl)butanoate

(7Z,13Z)-Hexadeca-7,13-dienedioylcarnitine is an acylcarnitine. More specifically, it is an (7Z,13Z)-hexadeca-7,13-dienedioic 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. (7Z,13Z)-Hexadeca-7,13-dienedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (7Z,13Z)-Hexadeca-7,13-dienedioylcarnitine 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].

(4Z,7Z)-Hexadeca-4,7-dienedioylcarnitine

3-[(15-carboxypentadeca-4,7-dienoyl)oxy]-4-(trimethylazaniumyl)butanoate

(4Z,7Z)-Hexadeca-4,7-dienedioylcarnitine is an acylcarnitine. More specifically, it is an (4Z,7Z)-hexadeca-4,7-dienedioic 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. (4Z,7Z)-Hexadeca-4,7-dienedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (4Z,7Z)-Hexadeca-4,7-dienedioylcarnitine 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].

(12E,14E)-hexadeca-12,14-dienedioylcarnitine

3-[(15-carboxypentadeca-12,14-dienoyl)oxy]-4-(trimethylazaniumyl)butanoate

(12E,14E)-Hexadeca-12,14-dienedioylcarnitine is an acylcarnitine. More specifically, it is an (12E,14Z)-hexadeca-12,14-dienedioic 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. (12E,14E)-Hexadeca-12,14-dienedioylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (12E,14E)-Hexadeca-12,14-dienedioylcarnitine 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 Proline

1-(docosa-4,7,10,13,16,19-hexaenoyl)pyrrolidine-2-carboxylic acid

N-docosahexaenoyl proline 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 Proline. 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 Proline 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 Proline 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.

2-Azetidinecarboxylic acid, 3-(3-((aminoiminomethyl)amino)propyl)-1-((4-(((1,1-dimethylethyl)amino)carbonyl)-1-piperazinyl)carbonyl)-4-oxo-, (2S,3R)-

Diprenorphine

3-(cyclopropylmethyl)-16-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol

Gly-pro-arg-pro

1-(2-{[1-(2-aminoacetyl)pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoyl)pyrrolidine-2-carboxylic acid

Jervine

5-hydroxy-2,3,6,15-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-spiro[furo[3,2-b]pyridine-2,14-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadecane]-7,15-dien-17-one

Piriprost

5-[5-hydroxy-4-(3-hydroxyoct-1-en-1-yl)-1-phenyl-1H,4H,5H,6H-cyclopenta[b]pyrrol-2-yl]pentanoic acid

Jervine

(2R,3S,3R,3aS,6S,6aS,6bS,7aR,11aS,1 1bR)-2,3,3a,4,4,5,6,6,6a,6b,7,7,7a,8,11a,11b-hexad ecahydro-3-hydroxy-3,6,10,11b-tetramethyl-Spiro[9H -benzo[a]fluorene-9,2(3H)-furo[3,2-b]pyridin]-11(1 H)-one

Jervine is a member of piperidines. Jervine is a natural product found in Veratrum stamineum, Veratrum grandiflorum, and other organisms with data available. Jervine is a steroidal alkaloid with molecular formula C27H39NO3 which is derived from the Veratrum plant genus. Similar to cyclopamine, which also occurs in the Veratrum genus, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation. D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents > D014704 - Veratrum Alkaloids Jervine (11-Ketocyclopamine) is a potent Hedgehog (Hh) inhibitor with an IC50 of 500-700 nM[1]. Jervine is a natural teratogenic sterodial alkaloid from rhizomes of Veratrum nigrum. Jervine has anti-inflammatory and antioxidant properties[2]. Jervine (11-Ketocyclopamine) is a potent Hedgehog (Hh) inhibitor with an IC50 of 500-700 nM[1]. Jervine is a natural teratogenic sterodial alkaloid from rhizomes of Veratrum nigrum. Jervine has anti-inflammatory and antioxidant properties[2].

Brachystamide D|brachystamide-D|N-isobutyl-16-(3,4-methylenedioxyphenyl)-2E,4E,15E-hexadecatrienamide|pergumidiene

hyatelactam

C22H35NO7 (425.24134000000004)

9-(2-amino-3-(4-O-methyl-alpha-rhamnopyranosyloxy)phenyl)nonanoic acid

Tri-Ac-(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol

C24H43NO5 (425.31410680000005)

(23R)-17,23-Epoxy-3beta-hydroxy-(13alphaH(?)-veratra-5,12(14)-dien-11-on|(23R)-17,23-epoxy-3beta-hydroxy-(13alphaH(?)-veratra-5,12(14)-dien-11-one|jervine|jervine sulfate

Ile Phe Phe

Prostaglandin D2 serinol amide

N-[(2-hydroxy-1-hydroxymethyl)ethyl]-11-oxo-9α,15S-dihydroxy-prosta-5Z,13E-dien-1-amide

Prostaglandin E2 serinol amide

N-[(2-hydroxy-1-hydroxymethyl)ethyl]-9-oxo-11α,15S-dihydroxy-prosta-5Z,13E-dien-1-amide

Phe Ile Phe

VERALODINE

NCGC00160229-01!VERALODINE

C27H39NO3_(3beta,9xi,22S,23R)-3-Hydroxy-17,23-epoxyveratraman-11-one

NCGC00380997-01_C27H39NO3_(3beta,9xi,22S,23R)-3-Hydroxy-17,23-epoxyveratraman-11-one

(3S,3R,3aS,6S,6aS,6bS,7aR,9R,11bR)-3-hydroxy-3,6,10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-11-one

1-tetradecanoyl-sn-glycero-3-phosphoethanolamine

1-Myristoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine

Ala Ala His Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]propanamido]-3-(1H-imidazol-4-yl)propanamido]hexanoic acid

Ala Ala Lys His

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]propanamido]hexanamido]-3-(1H-imidazol-4-yl)propanoic acid

Ala His Ala Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]hexanoic acid

Ala His Lys Ala

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-(1H-imidazol-4-yl)propanamido]hexanamido]propanoic acid

Ala Lys Ala His

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]propanamido]-3-(1H-imidazol-4-yl)propanoic acid

Ala Lys His Ala

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-aminopropanamido]hexanamido]-3-(1H-imidazol-4-yl)propanamido]propanoic acid

Gly Pro Pro Arg

(2S)-2-{[(2S)-1-{[(2S)-1-(2-aminoacetyl)pyrrolidin-2-yl]carbonyl}pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

Gly Pro Arg Pro

(2S)-1-[(2S)-2-{[(2S)-1-(2-aminoacetyl)pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoyl]pyrrolidine-2-carboxylic acid

Gly Arg Pro Pro

(2S)-1-{[(2S)-1-[(2S)-2-(2-aminoacetamido)-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]carbonyl}pyrrolidine-2-carboxylic acid

His Ala Ala Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]propanamido]propanamido]hexanoic acid

His Ala Lys Ala

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]propanamido]hexanamido]propanoic acid

His Lys Ala Ala

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]hexanamido]propanamido]propanoic acid

Leu Phe Phe

Lys Ala Ala His

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]propanamido]-3-(1H-imidazol-4-yl)propanoic acid

Lys Ala His Ala

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]propanamido]-3-(1H-imidazol-4-yl)propanamido]propanoic acid

Lys His Ala Ala

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]propanoic acid

Phe Phe Leu

Pro Gly Pro Arg

(2S)-5-carbamimidamido-2-{[(2S)-1-{2-[(2S)-pyrrolidin-2-ylformamido]acetyl}pyrrolidin-2-yl]formamido}pentanoic acid

Pro Gly Arg Pro

(2S)-1-[(2S)-5-carbamimidamido-2-{2-[(2S)-pyrrolidin-2-ylformamido]acetamido}pentanoyl]pyrrolidine-2-carboxylic acid

Pro Pro Gly Arg

(2S)-5-carbamimidamido-2-(2-{[(2S)-1-{[(2S)-pyrrolidin-2-yl]carbonyl}pyrrolidin-2-yl]formamido}acetamido)pentanoic acid

Phe Leu Phe

Pro Pro Arg Gly

2-[(2S)-5-carbamimidamido-2-{[(2S)-1-{[(2S)-pyrrolidin-2-yl]carbonyl}pyrrolidin-2-yl]formamido}pentanamido]acetic acid

Pro Arg Gly Pro

(2S)-1-{2-[(2S)-5-carbamimidamido-2-[(2S)-pyrrolidin-2-ylformamido]pentanamido]acetyl}pyrrolidine-2-carboxylic acid

Pro Arg Pro Gly

2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-pyrrolidin-2-ylformamido]pentanoyl]pyrrolidin-2-yl]formamido}acetic acid

Arg Gly Pro Pro

(2S)-1-{[(2S)-1-{2-[(2S)-2-amino-5-carbamimidamidopentanamido]acetyl}pyrrolidin-2-yl]carbonyl}pyrrolidine-2-carboxylic acid

Arg Pro Gly Pro

(2S)-1-(2-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidine-2-carboxylic acid

Arg Pro Pro Gly

2-{[(2S)-1-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]carbonyl}pyrrolidin-2-yl]formamido}acetic acid

Phe Phe Ile

C20H44NO6P (425.29060940000005)

PC(O-6:0/O-6:0)

3,5,9-Trioxa-4-phosphapentadecan-1-aminium, 7-(hexyloxy)-4-hydroxy-N,N,N-trimethyl-, inner salt, 4-oxide, (R)-

PC(O-6:0/O-6:0)[U]

3,5,9-Trioxa-4-phosphapentadecan-1-aminium, 7-(hexyloxy)-4-hydroxy-N,N,N-trimethyl-, inner salt, 4-oxide

C20H44NO6P (425.29060940000005)

PC(11:0/0:0)

Undecanoin, 1-mono-, 3-(dihydrogen phosphate), monoester with choline hydroxide inner salt, L-

PC(11:0/0:0)[U]

3,5,9-Trioxa-4-phosphaeicosan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide

PC(0:0/11:0)[U]

3,5,8-Trioxa-4-phosphanonadecan-1-aminium, 4-hydroxy-7-(hydroxymethyl)-N,N,N-trimethyl-9-oxo-, inner salt, 4-oxide

C20H44NO6P (425.29060940000005)

PC(O-12:0/0:0)[U]

3,5,9-Trioxa-4-phosphaheneicosan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-, inner salt, 4-oxide

PE(14:0/0:0)

Tetradecanoic acid, 3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester, (R)-

LPE(14:0)

1-Hydroxy-2-myristoyl-sn-glycero-3-phosphoethanolamine

PGD2-dihydroxypropanylamine

N-(1,3-dihydroxypropan-2-yl)-9S,15S-dihydroxy-11-oxo-5Z,13E-prostadienoyl amine

PGE2-dihydroxypropanylamine

N-(1,3-dihydroxypropan-2-yl)-9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoyl amine

NA 27:8;O

(5E,7E)-8-[(3aS,4R,5R,7aR)-4-[(1Z,3E)-5-oxo-5-(2-methyl-butylamino)-penta-1,3-dienyl]-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]octa-5,7-dienoic acid

LPC 11:0

1-undecanoyl-sn-glycero-3-phosphocholine

LPE 14:0

Tetradecanoic acid, 3-[[(2-aminoethoxy)hydroxyphosphinyl]oxy]-2-hydroxypropyl ester, (R)-

C21H40NNaO4S (425.2575600000001)

sodium 2-[methyloleoylamino]ethane-1-sulphonate

Piriprost

5-[5-hydroxy-4-[(E)-3-hydroxyoct-1-enyl]-1-phenyl-5,6-dihydro-4H-cyclopenta[b]pyrrol-2-yl]pentanoic acid