Classification Term: 2180

Glutamine and derivatives (ontology term: CHEMONTID:0004315)

Compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom." []

found 64 associated metabolites at no_class-level_7 metabolite taxonomy ontology rank level.

Ancestor: Alpha amino acids and derivatives

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

L-Theanine

(2S)-2-amino-5-(ethylamino)-5-oxopentanoic acid

C7H14N2O3 (174.1004)


L-Theanine, also known as L-gamma-glutamylethylamide or N-gamma-ethyl-L-glutamine, is a member of the class of compounds known as glutamine and derivatives. These compounds contain glutamine or a derivative thereof resulting from a reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Theanine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-Theanine can be found in saliva. The regulatory status of theanine varies by country. In Japan, L-theanine has been approved for use in all foods, including herb teas, soft drinks, and desserts. Restrictions apply to infant foods. In the United States, the Food and Drug Administration (FDA) considers it to be generally recognized as safe (GRAS) and allows its sale as a dietary supplement. The German Federal Institute for Risk Assessment, an agency of their Federal Ministry of Food and Agriculture, objects to the addition of L-theanine to beverages. The European Food Safety Authority EFSA advised negatively on health claims related to L-theanine and cognitive function, alleviation of psychological stress, maintenance of normal sleep, and reduction of menstrual discomfort. Therefore, health claims for L-theanine are prohibited in the European Union (Wikipedia). L-Theanine is found in mushrooms and is a constituent of tea (Thea sinensis) and of the fungus Imleria badia. L-Theanine has been shown to exhibit neuroprotectant and neuroprotective functions (PMID: 20416364, 20416364). N(5)-ethyl-L-glutamine is a N(5)-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea. It has a role as a neuroprotective agent, a plant metabolite and a geroprotector. It is a tautomer of a N(5)-ethyl-L-glutamine zwitterion. Theanine, a precursor of ethylamine, is found in green tea. It is under investigation in clinical trial NCT00291070 (Effects of L-Theanine in Boys With ADHD). See also: Green tea leaf (part of). Constituent of tea (Thea sinensis) and of the fungus Xerocomus badius (kostanjevka). L-Theanine is found in tea and mushrooms. A N(5)-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea. KEIO_ID E005 L-Theanine (L-Glutamic Acid γ-ethyl amide) is a non-protein amino acid contained in green tea leaves, which blocks the binding of L-glutamic acid to glutamate receptors in the brain, and with neuroprotective, anticancer and anti-oxidative activities. L-Theanine can pass through the blood–brain barrier and is orally active[1][2][3]. L-Theanine (L-Glutamic Acid γ-ethyl amide) is a non-protein amino acid contained in green tea leaves, which blocks the binding of L-glutamic acid to glutamate receptors in the brain, and with neuroprotective, anticancer and anti-oxidative activities. L-Theanine can pass through the blood–brain barrier and is orally active[1][2][3].

   

L-Agaritine

2-Amino-4-{[4-(hydroxymethyl)phenyl]-C-hydroxycarbonohydrazonoyl}butanoate

C12H17N3O4 (267.1219)


L-Agaritine is found in mushrooms. L-Agaritine is a constituent of some members of the family Agaricaceae, notably Agaricus bisporus (button mushroom). Constituent of some members of the family Agaricaceae, notably Agaricus bisporus (button mushroom). L-Agaritine is found in mushrooms.

   

5-L-Glutamyl-taurine

(2S)-2-amino-5-oxo-5-(2-sulfoethylamino)pentanoic acid

C7H14N2O6S (254.0573)


5-L-Glutamyl-taurine is an intermediate in Taurine and hypotaurine metabolism. 5-L-Glutamyl-taurine is produced from Taurine via the enzyme gamma-glutamyltranspeptidase (EC 2.3.2.2). [HMDB] 5-L-Glutamyl-taurine is an intermediate in Taurine and hypotaurine metabolism. 5-L-Glutamyl-taurine is produced from Taurine via the enzyme gamma-glutamyltranspeptidase (EC 2.3.2.2).

   

Linatine

1-[(4-Amino-4-carboxy-1-hydroxybutylidene)amino]pyrrolidine-2-carboxylate

C10H17N3O5 (259.1168)


Linatine is found in fats and oils. Linatine is isolated from Linum usitatissimum (flax). Isolated from Linum usitatissimum (flax). Linatine is found in tea and fats and oils.

   

gamma-Glutamyl-beta-aminopropiononitrile

(2S)-2-amino-4-[(2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

C8H13N3O3 (199.0957)


This compound belongs to the family of Alpha Amino Acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

   

L-Coprine

2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid

C8H14N2O4 (202.0954)


L-Coprine is found in mushrooms. L-Coprine is present in the moderately toxic ink cap mushroom Coprinus atramentarius (common ink cap). Produces an oversensitivity to ethanol in some people Present in the mod. toxic ink cap mushroom Coprinus atramentarius (common ink cap). Produces an oversensitivity to ethanol in some people. L-Coprine is found in mushrooms.

   

Vulgaxanthin I

(4Z)-4-[(2E)-2-{[1-carboxy-3-(C-hydroxycarbonimidoyl)propyl]imino}ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylate

C14H17N3O7 (339.1066)


Vulgaxanthin I is found in common beet. Vulgaxanthin I is a yellow pigment from Beta species Vulgaxanthin I is a food colouran Yellow pigment from Beta subspecies Food colourant. Vulgaxanthin I is found in red beetroot, common beet, and root vegetables. D004396 - Coloring Agents > D050858 - Betalains

   

Gamma-glutamyl-L-putrescine

(2S)-2-amino-4-[(4-aminobutyl)carbamoyl]butanoic acid

C9H19N3O3 (217.1426)


Gamma-glutamyl-L-putrescine is involved in the putrescine II degradation pathway. γ-glutamyl-L-putrescine reacts with H2O and O2 to produce γ-glutamyl-γ-aminobutyraldehyde, H2O2, and NH4+. γ-glutamyl-L-putrescine is formed from an ATP-driven reaction between putrescine, L-glutamate. Gamma-glutamyl-L-putrescine is involved in the putrescine II degradation pathway.

   

4-(Glutamylamino) butanoate

(2S)-2-amino-4-[(3-carboxypropyl)carbamoyl]butanoic acid

C9H16N2O5 (232.1059)


4-(Glutamylamino) butanoate is a polyamine that is an intermediate in putrescine degradation II. Polyamines (the most common of which are putrescine , spermidine , and spermine ), a group of positively charged small molecules present in virtually all living organisms, have been implicated in many biological processes, including binding to nucleic acids, stabilizing membranes, and stimulating several enzymes. Although polyamines are clearly necessary for optimal cell growth, a surplus of polyamines can cause inhibition of growth and protein synthesis, and thus a balance is desired between the production and breakdown of polyamines. In putrescine degradation II, 4-(Glutamylamino) butanoate is a substrate for gamma-glutamyl-gamma-aminobutyrate hydrolase (puuD) and can be generated from the hydrolysis of gamma-glutamyl-gamma-aminobutyraldehyde. [HMDB] 4-(Glutamylamino) butanoate is a polyamine that is an intermediate in putrescine degradation II. Polyamines (the most common of which are putrescine , spermidine , and spermine ), a group of positively charged small molecules present in virtually all living organisms, have been implicated in many biological processes, including binding to nucleic acids, stabilizing membranes, and stimulating several enzymes. Although polyamines are clearly necessary for optimal cell growth, a surplus of polyamines can cause inhibition of growth and protein synthesis, and thus a balance is desired between the production and breakdown of polyamines. In putrescine degradation II, 4-(Glutamylamino) butanoate is a substrate for gamma-glutamyl-gamma-aminobutyrate hydrolase (puuD) and can be generated from the hydrolysis of gamma-glutamyl-gamma-aminobutyraldehyde.

   

epsilon-(gamma-Glutamyl)lysine

(2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid

C11H21N3O5 (275.1481)


In non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688). In Parkinsons disease (PD), conformational changes in the alpha-synuclein monomer precede the formation of Lewy bodies. Both tTG and its substrate-characteristic N(epsilon)-(gamma-glutamyl)-lysine crosslink are increased in PD nigral dopamine neurons. (PMID 15001552). Expression of tissue transglutaminase (tTgase) and epsilon-(gamma-glutamyl)-lysine was present in all scarring of the blebs sites, being the main cause of failure in glaucoma filtration surgery. Transglutaminases are calcium-dependent enzymes that catalyze the posttranslational modification of proteins through an acyl transfer reaction between the gamma-carboxamide group of a peptide-bound glutaminyl residue and various amines. Covalent cross-linking using epsilon-(gamma-glutamyl)-lysine bonds is stable and resistant to enzymatic, chemical, and mechanical disruption. (PMID: 16936095). In non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688)

   

N(2)-phenylacetyl-L-glutaminate

2-[(1-hydroxy-2-phenylethylidene)amino]-4-(C-hydroxycarbonimidoyl)butanoic acid

C13H16N2O4 (264.111)


N(2)-phenylacetyl-L-glutaminate is considered to be practically insoluble (in water) and acidic

   

N-Acetylglutamine

(2S)-2-Acetamido-5-amino-5-oxopentanoic acid

C7H12N2O4 (188.0797)


N-Acetyl-L-glutamine (NAcGln) or N-Acetylglutamine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylglutamine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylglutamine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-glutamine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618). About 85\\\% of all human proteins and 68\\\% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT‚Äôs (PMID: 30054468). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylglutamine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free glutamine can also occur. In particular, N-Acetylglutamine can be biosynthesized from L-glutamine and acetyl-CoA by the enzyme glutamine N-acyltransferase (EC 2.3.1.68). Excessive amounts N-acetyl amino acids including N-acetylglutamine (as well as N-acetylglycine, N-acetylserine, N-acetylmethionine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylthreonine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylglutamine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986; PMID: 20613759). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557). N-acetylglutamine can be used for parenteral nutrition as a source of glutamine since glutamine is too unstable whereas N-acetylglutamine is very stable. In patients treated with aminoglycosides and/or glycopeptides, an elevation of N-acetylglutamine in urine suggests renal tubular injury. N-Acetylglutamine (GIcNAc) is a modified amino acid (an acetylated analogue of glutamine), a metabolite present in normal human urine. The decomposition products of GIcNAc have been identified by NMR and HPLC-MS as N-acetyl-L-glutamic acid, N-(2,6-dioxo-3-piperidinyl) acetamide, pyroglutamic acid, glutamic acid, and glutamine. GIcNAc is used for parenteral nutrition as a source of glutamine, since glutamine is too unstable, but GIcNAc is very stable. In patients treated with aminoglycosides and/or glycopeptides, elevation GIcNAc in urine suggests renal tubular injury. High amounts of N-acetylated amino acids (i.e.: N-Acetylglutamine) were detected patient with aminoacylase I deficiency (EC 3.5.1.14, a homodimeric zinc-binding metalloenzyme located in the cytosol), a novel inborn error of metabolism. (PMID: 15331932, 11312773, 7952062, 2569664, 16274666) [HMDB] C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant Aceglutamide (α-N-Acetyl-L-glutamine) is a psychostimulant and nootropic, used to improve memory and concentration[1].

   

Phenylbutyrylglutamine

2-[(1-Hydroxy-4-phenylbutylidene)amino]-4-(C-hydroxycarbonimidoyl)butanoate

C15H20N2O4 (292.1423)


Phenylbutyrylglutamine has been identified as a new metabolite of phenylbutyrate in human plasma and urine. Phenylbutyrate is used in humans for treating inborn errors of ureagenesis, certain forms of cancer, cystic fibrosis and thalassemia. After administration of phenylbutyrate to normal humans, the cumulative urinary excretion of phenylacetate, phenylbutyrate, phenylacetylglutamine and phenylbutyrylglutamine amounts to about half of the dose of phenylbutyrate. [HMDB] Phenylbutyrylglutamine has been identified as a new metabolite of phenylbutyrate in human plasma and urine. Phenylbutyrate is used in humans for treating inborn errors of ureagenesis, certain forms of cancer, cystic fibrosis and thalassemia. After administration of phenylbutyrate to normal humans, the cumulative urinary excretion of phenylacetate, phenylbutyrate, phenylacetylglutamine and phenylbutyrylglutamine amounts to about half of the dose of phenylbutyrate.

   

(2S,4S)-Pinnatanine

2-amino-4-[(Z)-[(1E)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-C-hydroxycarbonimidoyl]-4-hydroxybutanoic acid

C10H16N2O5 (244.1059)


(2S,4S)-Pinnatanine is found in root vegetables. (2S,4S)-Pinnatanine is a constituent of Hemerocallis fulva (day lily)

   

L-4-Hydroxyglutamine

2-amino-4-hydroxy-4-(C-hydroxycarbonimidoyl)butanoic acid

C5H10N2O4 (162.0641)


L-4-Hydroxyglutamine is found in root vegetables. L-4-Hydroxyglutamine is present in Hemerocallis fulva (day lily Present in Hemerocallis fulva (day lily). L-4-Hydroxyglutamine is found in root vegetables.

   

L-gamma-Glutamyl-beta-phenyl-beta-L-alanine

2-Amino-4-[(2-carboxy-1-phenylethyl)-C-hydroxycarbonimidoyl]butanoate

C14H18N2O5 (294.1216)


L-gamma-Glutamyl-beta-phenyl-beta-L-alanine is found in pulses. L-gamma-Glutamyl-beta-phenyl-beta-L-alanine is isolated from Phaseolus angularis (Azuki bean). Isolated from Phaseolus angularis (Azuki bean). L-gamma-Glutamyl-beta-phenyl-beta-L-alanine is found in pulses.

   

Agaritinal

2-Amino-4-[(4-formylphenyl)-C-hydroxycarbonohydrazonoyl]butanoate

C12H15N3O4 (265.1063)


Agaritinal is found in mushrooms. Agaritinal is isolated from Agaricus campestris (field mushroom). Isolated from Agaricus campestris (field mushroom). Agaritinal is found in mushrooms.

   

Oxypinnatanine

2-amino-4-hydroxy-4-[(Z)-[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-C-hydroxycarbonimidoyl]butanoic acid

C10H16N2O6 (260.1008)


Oxypinnatanine is found in root vegetables. Oxypinnatanine is a constituent of Hemerocallis fulva (day lily)

   

N-(gamma-Glutamyl)ethanolamine

2-Amino-4-[(2-hydroxyethyl)-C-hydroxycarbonimidoyl]butanoate

C7H14N2O4 (190.0954)


N-(gamma-Glutamyl)ethanolamine is found in mushrooms. N-(gamma-Glutamyl)ethanolamine is a constituent of the fruiting body of Agaricus bisporus (button mushroom). Constituent of the fruiting body of Agaricus bisporus (button mushroom). N-(gamma-Glutamyl)ethanolamine is found in mushrooms.

   

Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol

{[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-5-{[(2S,3S,4S,5R,6R)-6-({[(2S,3S,4S,5R,6R)-4-{[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-({[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxyoxan-2-yl]oxy}methyl)-4-{[(2R,3S,4S,5S,6R)-3-{[(2R,3S,4S,5S,6R)-3-{[(2R,3S,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

C156H260N2O67P2 (3295.6474)


Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolicholis involved in the dolichyl-diphosphooligosaccharide biosynthesis pathway. Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolicholreversibly reacts with dolichyl β-D-glucosyl phosphate to produce (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol and dolichyl-phosphate. Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolicholis produced from a reaction between (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol and dolichyl β-D-glucosyl phosphate, with dolichyl-phosphate as a by product. Glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolicholis involved in the dolichyl-diphosphooligosaccharide biosynthesis pathway.

   

Indoleacetyl glutamine

4-carbamoyl-2-[2-(1H-indol-3-yl)acetamido]butanoic acid

C15H17N3O4 (303.1219)


Indoleacetyl glutamine is indolic derivative of tryptophan. It is generated from indoleacetic acid. Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. Indoleacetyl glutamine frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with hartnup disease, the characteristic symptoms of the disease are mental retardation and pellagra like skin rash. [HMDB] Indoleacetyl glutamine is indolic derivative of tryptophan. It is generated from indoleacetic acid. Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. Indoleacetyl glutamine frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with hartnup disease, the characteristic symptoms of the disease are mental retardation and pellagra like skin rash.

   

Hexaglutamyl folate

(2S,7R,11S)-2,11-Diamino-6-[(4S)-4-amino-4-carboxybutanoyl]-7-{n-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-(carboxymethyl)-5,8-dioxododecanedioate

C44H54N12O21 (1086.3526)


Hexaglutamyl folate is a naturally occurring form of folic acid. The bioavailability of dietary folate may be hampered by the need of the glutamate moieties to be deconjugated before absorption. Folate deficiency in humans leads to anemia, neural tube defects and, possibly, chronic diseases such as cardiovascular disease, colon cancer, and neurocognitive dysfunction. Folate status is ascertained not only by the intake of folate but also by its bioavailability. Bioavailability is defined as the proportion of ingested folate that is absorbed and available for metabolic processes and storage. In humans, the bioavailability of folate from the diet is assumed to be {approx}50\\%, whereas the bioavailability of synthetic folic acid used in supplements and as a food fortificant is estimated to range from 76\\% to 97\\%. (PMID: 17093166). Patients with pernicious anemia in relapse and postgastrectomy macrocytic anemia cannot readily utilize for hematopoiesis a naturally occurring conjugate of pteroylglutamic acid although they respond promptly to administration of the free vitamin. This effect varies in different patients. Inability to utilize the conjugated vitamin appears to depend at least in part upon a conjugase-inhibiting substance present in natural sources of conjugate. (PMID: 1082804). Hexaglutamyl folate is a naturally occurring form of folic acid. The bioavailability of dietary folate may be hampered by the need of the glutamate moieties to be deconjugated before absorption. Folate deficiency in humans leads to anemia, neural tube defects and, possibly, chronic diseases such as cardiovascular disease, colon cancer, and neurocognitive dysfunction. Folate status is ascertained not only by the intake of folate but also by its bioavailability. Bioavailability is defined as the proportion of ingested folate that is absorbed and available for metabolic processes and storage. In humans, the bioavailability of folate from the diet is assumed to be {approx}50\\%, whereas the bioavailability of synthetic folic acid used in supplements and as a food fortificant is estimated to range from 76\\% to 97\\%. (PMID: 17093166)

   

Sialyl-Lewis X

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R)-1,2-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-oxo-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C31H52N2O23 (820.2961)


Carbohydrate antigen which is accumulated in various human cancer tissues and secreted into the blood stream. The carbohydrate moiety can be further modified with fucose or sialic acid. Monoclonal antibodies have been determined which can discriminate each subgroup of this antigen in the sera of cancer patients. Sialyl SSEA-1 antigen is particularly elevated in the sera of patients with a variety of tumors. [HMDB] Carbohydrate antigen which is accumulated in various human cancer tissues and secreted into the blood stream. The carbohydrate moiety can be further modified with fucose or sialic acid. Monoclonal antibodies have been determined which can discriminate each subgroup of this antigen in the sera of cancer patients. Sialyl SSEA-1 antigen is particularly elevated in the sera of patients with a variety of tumors.

   

5beta-Cholestanone

(1S,2S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

C27H46O (386.3548)


5beta-Cholestanone is an oxidation product of coprosterol. It is a substrate of cholestenone 5beta-reductase [EC 1.3.1.3] (KEGG). 5beta-cholestanone belongs to the family of Cholesterols and Derivatives. These are compounds containing an hydroxylated chloestane moeity.

   

Alanyl-Gamma-glutamate

2-Amino-4-[(2-aminopropanoyl)-C-hydroxycarbonimidoyl]butanoate

C8H15N3O4 (217.1063)


Alanyl-Gamma-glutamate is a dipeptide composed of alanine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Asparaginyl-Gamma-glutamate

2-Amino-4-{[2-amino-3-(C-hydroxycarbonimidoyl)propanoyl]-C-hydroxycarbonimidoyl}butanoate

C9H16N4O5 (260.1121)


Asparaginyl-Gamma-glutamate is a dipeptide composed of asparagine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Aspartyl-Gamma-glutamate

2-Amino-4-[(2-amino-3-carboxypropanoyl)-C-hydroxycarbonimidoyl]butanoate

C9H15N3O6 (261.0961)


Aspartyl-Gamma-glutamate is a dipeptide composed of aspartate and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Cysteinyl-Gamma-glutamate

2-Amino-4-[(2-amino-3-sulphanylpropanoyl)-C-hydroxycarbonimidoyl]butanoic acid

C8H15N3O4S (249.0783)


Cysteinyl-Gamma-glutamate is a dipeptide composed of cysteine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Glutaminyl-Gamma-glutamate

2-Amino-4-{[2-amino-4-(C-hydroxycarbonimidoyl)butanoyl]-C-hydroxycarbonimidoyl}butanoate

C10H18N4O5 (274.1277)


Glutaminyl-Gamma-glutamate is a dipeptide composed of glutamine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Glutamyl-Gamma-glutamate

2-Amino-4-[(2-amino-4-carboxybutanoyl)-C-hydroxycarbonimidoyl]butanoate

C10H17N3O6 (275.1117)


Glutamyl-Gamma-glutamate is a dipeptide composed of glutamate and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Glycyl-Gamma-glutamate

2-Amino-4-[(2-aminoacetyl)-C-hydroxycarbonimidoyl]butanoate

C7H13N3O4 (203.0906)


Glycyl-Gamma-glutamate is a dipeptide composed of glycine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Hydroxyprolyl-Gamma-glutamate

2-Amino-4-[(4-hydroxypyrrolidine-2-carbonyl)-C-hydroxycarbonimidoyl]butanoate

C10H17N3O5 (259.1168)


Hydroxyprolyl-Gamma-glutamate is a dipeptide composed of hydroxyproline and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Isoleucyl-Gamma-glutamate

2-Amino-4-[(2-amino-3-methylpentanoyl)-C-hydroxycarbonimidoyl]butanoate

C11H21N3O4 (259.1532)


Isoleucyl-Gamma-glutamate is a dipeptide composed of isoleucine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Leucyl-Gamma-glutamate

2-Amino-4-[(2-amino-4-methylpentanoyl)-C-hydroxycarbonimidoyl]butanoate

C11H21N3O4 (259.1532)


Leucyl-Gamma-glutamate is a dipeptide composed of leucine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Lysyl-Gamma-glutamate

2-Amino-4-[(2,6-diaminohexanoyl)-C-hydroxycarbonimidoyl]butanoate

C11H22N4O4 (274.1641)


Lysyl-Gamma-glutamate is a dipeptide composed of lysine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Methionyl-Gamma-glutamate

2-Amino-4-{[2-amino-4-(methylsulphanyl)butanoyl]-C-hydroxycarbonimidoyl}butanoic acid

C10H19N3O4S (277.1096)


Methionyl-Gamma-glutamate is a dipeptide composed of methionine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Serinyl-Gamma-glutamate

2-Amino-4-[(2-amino-3-hydroxypropanoyl)-C-hydroxycarbonimidoyl]butanoate

C8H15N3O5 (233.1012)


Serinyl-Gamma-glutamate is a dipeptide composed of serine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Threoninyl-Gamma-glutamate

2-Amino-4-[(2-amino-3-hydroxybutanoyl)-C-hydroxycarbonimidoyl]butanoate

C9H17N3O5 (247.1168)


Threoninyl-Gamma-glutamate is a dipeptide composed of threonine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Tryptophyl-Gamma-glutamate

2-Amino-4-{[2-amino-3-(1H-indol-3-yl)propanoyl]-C-hydroxycarbonimidoyl}butanoate

C16H20N4O4 (332.1484)


Tryptophyl-Gamma-glutamate is a dipeptide composed of tryptophan and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

Valyl-Gamma-glutamate

2-Amino-4-[(2-amino-3-methylbutanoyl)-C-hydroxycarbonimidoyl]butanoate

C10H19N3O4 (245.1375)


Valyl-Gamma-glutamate is a dipeptide composed of valine and gamma-glutamate. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.

   

N-gamma-Glutamylglutamine

(2S)-2-Amino-4-{[(4S)-4-amino-4-carboxybutanoyl]-C-hydroxycarbonimidoyl}butanoate

C10H17N3O6 (275.1117)


N-gamma-Glutamylglutamine is a dipeptide obtained from condensation of the gamma-carboxy group of glutamic acid with the side-chain amide group of glutamine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

   

L-N-(3-Carboxypropyl)glutamine

2-amino-4-[(3-carboxypropyl)-C-hydroxycarbonimidoyl]butanoic acid

C9H16N2O5 (232.1059)


L-N-(3-Carboxypropyl)glutamine is found in root vegetables. L-N-(3-Carboxypropyl)glutamine is a constituent of beet

   

N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine

2-Amino-4-[(3,4-dioxocyclohexa-1,5-dien-1-yl)-C-hydroxycarbonimidoyl]butanoate

C11H12N2O5 (252.0746)


N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine is found in mushrooms. N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine is isolated from the mushroom Agaricus bisporus (button mushroom Isolated from the mushroom Agaricus bisporus (button mushroom). N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine is found in mushrooms.

   

N2-(gamma-Glutamyl)-4-carboxyphenylhydrazine

4-({[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}amino)benzoate

C12H15N3O5 (281.1012)


N2-(gamma-Glutamyl)-4-carboxyphenylhydrazine is found in mushrooms. N2-(gamma-Glutamyl)-4-carboxyphenylhydrazine is isolated from Agaricus bisporus (button mushroom). Isolated from Agaricus bisporus (button mushroom). N2-(gamma-Glutamyl)-4-carboxyphenylhydrazine is found in mushrooms.

   

N-Stearoyl Glutamine

4-(C-Hydroxycarbonimidoyl)-2-[(1-hydroxyoctadecylidene)amino]butanoate

C23H44N2O4 (412.3301)


N-stearoyl glutamine 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 Stearic acid amide of Glutamine. 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-Stearoyl Glutamine 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-Stearoyl Glutamine 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 Glutamine

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

C25H40N2O4 (432.2988)


N-arachidonoyl glutamine 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 Glutamine. 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 Glutamine 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 Glutamine 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-Docosahexaenoyl Glutamine

4-(C-Hydroxycarbonimidoyl)-2-[(1-hydroxydocosa-4,7,10,13,16,19-hexaen-1-ylidene)amino]butanoate

C27H40N2O4 (456.2988)


N-docosahexaenoyl glutamine 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 Glutamine. 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 Glutamine 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 Glutamine 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.

   

N-Lauroyl Glutamine

4-carbamoyl-2-dodecanamidobutanoic acid

C17H32N2O4 (328.2362)


N-lauroyl glutamine 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 Lauric acid amide of Glutamine. 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-Lauroyl Glutamine 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-Lauroyl Glutamine 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-Myristoyl Glutamine

4-carbamoyl-2-tetradecanamidobutanoic acid

C19H36N2O4 (356.2675)


N-myristoyl glutamine 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 Myristic acid amide of Glutamine. 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-Myristoyl Glutamine 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-Myristoyl Glutamine 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.

   

Hexanoylglutamine

(2S)-4-(C-hydroxycarbonimidoyl)-2-[(1-hydroxyhexylidene)amino]butanoic acid

C11H20N2O4 (244.1423)


   

(S)-Methyl 2,5-diamino-5-oxopentanoate

(S)-Methyl 2,5-diamino-5-oxopentanoic acid

C6H12N2O3 (160.0848)


   

(2S)-2,5-Diamino-4-fluoro-5-oxopentanoic acid

2-amino-4-carbamoyl-4-fluorobutanoic acid

C5H9FN2O3 (164.0597)


   

(S)-5-[(4-Amino-4-carboxy-1-oxobutyl)amino]-2-nitrobenzoic acid

5-(4-amino-4-carboxybutanamido)-2-nitrobenzoic acid

C12H13N3O7 (311.0753)


   

(S)-2-Amino-5-((4-nitrophenyl)amino)-5-oxopentanoic acid

2-amino-4-[(4-nitrophenyl)carbamoyl]butanoic acid

C11H13N3O5 (267.0855)


   

(R)N-(5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)phenylalanine

2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid

C20H18ClNO6 (403.0823)


   

N-gamma-Glutamylcysteine ethyl ester

2-Amino-4-[(1-ethoxy-1-oxo-3-sulphanylpropan-2-yl)-C-hydroxycarbonimidoyl]butanoic acid

C10H18N2O5S (278.0936)


   

Glutamamide

2-aminopentanediamide

C5H11N3O2 (145.0851)


   

Glutamine glutamate aspartate

4,12-diamino-3,6,9,13-tetraoxo-1,2,7,8-tetraoxacyclotridecan-4-yl 2-amino-5-[(2-amino-4-carbamoylbutanoyl)peroxy]-5-oxopentanoate

C19H27N5O15 (565.1504)


   

Glutamine hydroxamate

2-Amino-4-(dihydroxycarbonimidoyl)butanoate

C5H10N2O4 (162.0641)


   

Glutamine lactate

2-hydroxypropanoyl 2-amino-4-carbamoylbutaneperoxoate

C8H14N2O6 (234.0852)


   

Glutamine pyruvate

2-oxopropanoyl 2-amino-4-carbamoylbutaneperoxoate

C8H12N2O6 (232.0695)


   

Glutamine-glutamate

4-amino-5-[(2-amino-4-carbamoylbutanoyl)peroxy]-5-oxopentanoic acid

C10H17N3O7 (291.1066)


   

Phenylacetyl glutaminate

4-Amino-5-oxo-5-[(2-phenylacetyl)oxy]pentanimidate

C13H16N2O4 (264.111)


   

indole-3-acetyl-glutamine

4-carbamoyl-2-[2-(1H-indol-3-yl)acetamido]butanoate

C15H16N3O4 (302.1141)


Indole-3-acetyl-glutamine, also known as n(2)-(1h-indol-3-ylacetyl)glutaminate or iaa-gln, belongs to glutamine and derivatives class of compounds. Those are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Indole-3-acetyl-glutamine is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Indole-3-acetyl-glutamine can be found in a number of food items such as yellow wax bean, rapini, borage, and fireweed, which makes indole-3-acetyl-glutamine a potential biomarker for the consumption of these food products.