Colupulone, a bitter β-acid, can be isolated from hops [1].

Branchamin is a group of amino acids.

Trichostatin A (TSA) is a natural derivative of diene isohydroxamic acids. Trichostatin A is a histone deacetylase inhibitor (IC50=1.8 nM) that is reversible and specific. Trichostatin A leads to the hyperacetylation of core histones, which regulates chromatin structure.

Oxaloacetic acid, also known as oxosuccinic acid or oxalacetic acid, is a four-carbon dicarboxylic acid appearing as an intermediate of the citric acid cycle. In vivo, oxaloacetate (the ionized form of oxaloacetic acid) is formed by the oxidation of L-mal

3-hydroxybutyric acid is involved in the synthesis and degradation of ketone bodies. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in the blood and urine in ketosis. Beta-hydroxybutyrate is a typical pa

γ-Oryzanol (Gamma-Oryzanol) is a natural nutrient extract isolated from rice bran oil that contains a mixture of sterols and ferulic acids, which may aid in the destruction of free radicals in the skin. It has recently been researched for its ability to slow the progress of melanin pigmentation by intercepting the ultraviolet rays at the skin's surface and hindering their transmission.

Myristic acid (Crodacid) , a 14 carbon saturated fatty acid, is a rare molecule in cells and is a substrate of some fatty acid desaturases. This compound has the ability to acylate proteins by covalently binding to the N-terminal glycine residues, in a process called N-terminal myristoylation. Myristoylation of substrate proteins by this fatty acid has the potential to activate and mediate many physiological pathways. Furthermore, saturated fatty acids have been reported to be essential for biological activities of lipopolysaccharides and have demonstrated the ability to induce expression of COX-2 and NFκB (nuclear factor κB) activation.

Glycerol or glycerin is a colourless, odourless, viscous liquid that is sweet-tasting and mostly non-toxic. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol is an important component of trigl

Increased levels of erucic acid (22:1n9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 ). Erucic acid (13(Z)-Docosenoic Acid) is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid. Erucic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.

Trans-2-butene-1,4-dicarboxylic acid (3-Hexenedioic Acid) is a normal human unsaturated dicarboxylic acid metabolite with increased excretion in patients with Dicarboxylic aciduria caused by fatty acid metabolism disorders The urinary excretion of Trans-2-butene-1,4-dicarboxylic acid is increased in conditions of augmented mobilization of fatty acids or inhibited fatty acid oxidation.

1-Dodecanol is an endogenous metabolite and a saturated fatty alcohol from coconut oil fatty acids. It has a floral odor and is used in detergents, Lepidopteran pheromone/sex attractant, lubricating oils, pesticides and pharmaceuticals.

3,4-Diaminotoluene, an aromatic amine derived from toluene, has been used in the synthesis of a variety of compounds such as polyurethanes, polyureas and polyamides, as well as in the synthesis of amino acids, peptides and proteins. It has also been used in the synthesis of various drugs such as antibiotics and antivirals.

L-Tartaric acid ((2R,3R)-(+)-Tartaric acid) occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine. It is used as an antioxidant. Salts of tartaric acid are known as tartrates. L-Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.

Guanine (2-Aminohypoxanthine) is a purine base that is a constituent of nucleotides occurring in nucleic acids.

D-Pantothenic acid (vitamin B5) is a water-soluble vitamin ubiquitously found in plants and animal tissues with an antioxidant property. D-Pantothenic acid is a component of coenzyme A (CoA) and a part of the vitamin B2 complex. D-Pantothenic acid is a growth factor and is essential for various metabolic functions, including the metabolism of carbohydrates, proteins, and fatty acids. This vitamin is also involved in the synthesis of cholesterol, lipids, neurotransmitters, steroid hormones, and hemoglobin.

Glycoursodeoxycholic acid (Ursodeoxycholylglycine) is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct, therefore, exist in a glycine conjugated form. Bile acids are steroid acids found predominantly in bile of mammals.

Urea (Carbonyldiamide) is formed in the liver from ammonia produced by the deamination of amino acids. It is the principal end metabolite of protein catabolism and accounts for about one-half of the total urinary solids.

L-Cystine (Cystine Acid) is not considered one of the 20 amino acids, L-Cystine (Cystine Acid) is a sulfur-containing derivative obtained from oxidation of cysteine amino acid thiol side chains. It functions as an antioxidant and protects tissues against radiation and pollution, slowing the aging process. It also aids protein synthesis. L-Cystine (Cystine Acid) is abundant in many proteins of skeletal tissues and skin, and found in insulin and digestive enzymes chromotrypsinogen A, papain, and trypsinogen.

DL-Methionine (Acimetion) is an amino acid. Amino acids are the building blocks that our bodies use to make proteins. DL-Methionine is found in meat, fish, and dairy products. It plays an important role in the many functions within the body.

α-Factor Mating Pheromone, yeast acetate (Mating Factor α acetate) is a peptide of 13 amino acids secreted by Saccharomyces cerevisiae α cells.

rel-(2R,3S)-2,3-Dihydroxysuccinic acid hydrate (meso-Tartaric acid monohydrate) occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine. It is used as an antioxidant. Salts of tartaric acid are known as tartrates. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.

Indolicidin is comprised of 13 amino acids, 5 of which are tryptophan residues, and the carboxylterminal arginine is carboxamidated. Indolicidin has the highest tryptophan content of any known protein.

3-Feruloyl-4-caffeoylquinic acid is a chlorogenic acid isomer. Chlorogenic acids are relevant coffee quality markers, taste, and aroma precursors as well as important bioactive compounds.

Forrestiacid K, a terpenoid derived from Pseudotsuga forrestii, functions as an inhibitor of ATP-citrate lyase (ACL) [1].

Forrestiacid J is an inhibitor of ATP-citrate lyase (ACL), exhibiting an IC50 value of 2.6 μM [1].

L-Homoserine ((S)-(-)-2-AMINO-4-HYDROXYBUTYRIC ACID) is a more reactive variant of the amino acid serine. In this variant, the hydroxyl side chain contains an additional CH2 group which brings the hydroxyl group closer to its own carboxyl group, allowing it to chemically react to form a five-membered ring. This occurs at the point that amino acids normally join to their neighbours in a peptide bond. L-Homoserine is therefore unsuitable for forming proteins and has been eliminated from the repertoire of amino acids used by living things. L-Homoserine is the final product on the C-terminal end of the N-terminal fragment following a cyanogen bromide cleavage.

Ribose 5-phosphate is the intermediate product of the oxidative branch of the pentose phosphate pathway (PPP) and the final product of the non-oxidative branch of PPP. Ribose 5-phosphate is used in the synthesis of nucleotides and nucleic acids.

Cholesterol (cholesteryl alcohol) is a natural product that is the major sterol in mammals and an agonist of estrogen-related receptor α (ERRα). Cholesterol is widely found in the cell membranes of animals and is also used in the synthesis of several important hormones and bile acids.

Biotin (Vitamin H) is a water-soluble B-vitamin and is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids.

γ-Glu-Gly (gamma-Glutamylglycine), a γ-glutamyl dipeptide, is a human lipid metabolite with a structure resembling that of GABA (γ-aminobutyric acid). It functions as an antagonist of excitatory amino acids.

2,2-Dihydroxyacetic acid (Formylformic acid) is an intermediate in the glyoxalate cycle, which enables certain organisms to convert fatty acids to carbohydrates.2,2-Dihydroxyacetic acid has been found to be associated with primary hyperoxaluria, an inborn error of metabolism. As an aldehyde, glyoxalate is also highly active and can modify proteins to form advanced glycosylation products (AGEs).

Moronic acid shows oral therapeutic efficacy in HSV-infected mice and possessed novel anti-HSV activity. It also shows significant anti-HIV activity (EC(50) 186) and was modified to develop more potent anti-AIDS agents. Moronic acid is a new structural lead for anti-EBV drug development, can substantially reduce the numbers of EBV particles produced by the cells after lytic induction. Morolic and moronic acids have shown sustained antidiabetic and antihyperglycemic action possibly mediated by an insulin sensitization with consequent changes of glucose, cholesterol and triglycerides, in part mediated by inhibition of 11β-HSD 1 as indicated by in vitro.

Phosphatidylserine is a naturally occurring phospholipid that comprises 2-10% of total phospholipids in mammals and is enriched in the central nervous system, particularly the retina. It is anionic and found mainly on the inner leaflet of the cell membrane. It is biosynthesized from phosphatidylcholine or phosphatidylethanolamine by phosphatidyl synthase 1 (PSS1) or PSS2, respectively, in the endoplasmic reticulum and can be reversibly converted back by the same enzymes. It can also be irreversibly converted to phosphatidylethanolamine by phosphatidylserine decarboxylase in the mitochondria. Phosphatidylserine binds to T cell immunoglobulin mucin type 1 (TIM-1) and TIM-4 receptors as well as brain-specific angiogenesis inhibitor 1 (BAI1), leading to anti-inflammatory and anti-atherosclerotic effects. It is also a cofactor involved in the activation of various signaling pathways through activation of protein kinase C, neutral sphingomyelinase, and c-Raf-1 protein kinase among others. Phosphatidylserine is externalized during apoptosis by scramblases in the plasma membrane as a signal for phagocytes to engulf the cell. Phosphatidylserines (bovine) is a mixture of bovine phosphatidylserines containing fatty acids with variable chain lengths at the sn-1 and sn-2 positions.

9(S),12(S),13(S)-TriHOME is a linoleic acid-derived oxylipin that has diverse biological activities.1,2,3,4It has been found in various plants and is produced in human eosinophils in a 15-lipoxygenase-dependent, soluble epoxide hydrolase-independent manner.1,59(S),12(S)13(S)-TriHOME inhibits antigen-induced β-hexosaminidase release from RBL-2H3 mast cells (IC50= 28.7 μg/ml).2It inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia (IC50= 40.95 μM).3In vivo, 9(S),12(S),13(S)-TriHOME (1 g/animal) enhances the antiviral IgA and IgG antibody responses induced by a nasal influenza hemagglutinin (HA) vaccine by 5.2- and 2-fold, respectively, in mice.4 1.Hamberg, M., and Hamberg, G.Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds: Sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acidPlant Physiol.110(3)807-815(1996) 2.Hong, S.S., and Oh, J.S.Inhibitors of antigen-induced degranulation of RBL-2H3 cells isolated from wheat branJ. Korean Soc. Appl. Biol. Chem.5569-74(2012) 3.Kim, C.S., Kwon, O.W., Kim, S.Y., et al.Five new oxylipins from Chaenomeles sinensisLipids49(11)1151-1159(2014) 4.Shirahata, T., Sunazuka, T., Yoshida, K., et al.Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acidsTetrahedron62(40)9483-9496(2006) 5.Fuchs, D., Tang, X., Johnsson, A.-K., et al.Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent processBiochim. Biophys. Acta Mol. Cell Biol. Lipids1865(4)158611(2020)

Silicon dioxide is a transparent, tasteless crystals found in nature as agate, amethyst, chalcedony, cristobalite, flint, sand, QUARTZ, and tridymite. The compound is insoluble in water or acids except hydrofluoric acid.

(2S,3R,4S)-4-Hydroxyisoleucine (Hydroxyisoleucine) from fenugreek (Trigonella foenum-graecum) seeds is a potential insulinotropic (anti-diabetic) and anti-obesity amino acid. HIL stimulates glucose-dependent insulin secretion from pancreatic cells. HIL activates insulin receptor substrate-associated phosphoinositide 3 (PI3) kinase activity. HIL reduces plasma levels of triglycerides, free fatty acids and cholesterol.

L-Cysteic acid monohydrate (3-Sulfo-L-alanine Monohydrate) is an oxidation product of L-cysteine that may be used as a competitive inhibitor of the bacterial aspartate: alanine antiporter (AspT) exchange of aspartate and in other aspartate biological systems. L-Cysteic acid monohydrate is used in monomeric surfactant development. L-Cysteic acid monohydrate may be used in studies of excitatory amino acids in the brain, such as those that bind to cysteine sulfinic acid receptors. It is a useful agonist at several rat metabotropic glutamate receptors (mGluRs).

Br-Mmc (4-Bromomethyl-7-methoxycoumarin) is used as a new fluorescence label for fatty acids. It is used for the determination of fatty acids by HPLC or TLC.

Mead acid, also known as 5,8,11-Eicosatrienoic acid, is an unsaturated fatty acid belonging to the Omega-9 series. It serves as an indicator of deficiency in essential fatty acids.

Phosphocreatine dipotassium, primarily found in the skeletal muscles of vertebrates and one of organic compounds known as alpha amino acids and derivatives.

2,3-Dihydroxy-olean-12-en-28-oic acids show a low cytotoxicity towards several human tumor cell lines.

Brassicanate A sulfoxide, isolated from Brassica oleracea [1], exhibits herbicidal properties by inhibiting the biosynthesis of essential amino acids in plants. It operates by binding to key enzymes such as dihydroxyacid dehydratase (DHAD), hydroxymethylpyruvate dioxygenase (HPPD), acetolactate synthase (ALS), PYL family proteins, and transport inhibitor response 1 (TIR1), thereby reducing their enzymatic activity.

Vulpinic and gyrophoric acids are known as ultraviolet filters for natural lichen populations, they can effectively prevent cytotoxic, apoptotic and cytoskeleton alterative activities of 2.5 J/cm(2) UVB in a dose-dependent manner, suggest that vulpinic and gyrophoric acids can be promising cosmetic ingredients to photo-protect human skin cells. Gyrophoric acid also has anti-proliferative/cytotoxic effect.

Nucleocidin, an antitrypanosomal antibiotic, inhibits the transfer of labeled amino acids from S-RNA to protein.

Enniatin A1, a cyclic hexadepsipeptide composed of alternating D-α-hydroxyisovaleric acids and N-methyl-L-amino acids isolated from Fusarium mycotoxins, exhibits anticarcinogenic effects through the induction of apoptosis and disruption of the ERK signaling pathway. It also inhibits ACAT in rat liver microsomes with an IC50 of 49 μM.

N-Isovaleroylglycine (Isovaleroylglycine) is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases, the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. N-Isovaleroylglycine is a byproduct of the catabolism of the amino acid leucine. Accumulation of N-Isovaleroylglycine occurs in Isovaleric Acidemia (IVA).

Heptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many odd length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid constitutes 0.61% of milk fat and 0.83% of ruminant me

Tetradecanedioic acid (Tetradecanedicarboxylate) is a long-chain fatty acid that is a type of endogenous metabolite. It can serve as a candidate biomarker for drug-drug interactions mediated by organic anion transporting peptides.

Betonicine can be found in herbs and spices and pulses. Betonicine can be found primarily in the urine. This compound belongs to the class of organic compounds known as l-alpha-amino acids.

7α-Hydroxy-4-cholesten-3-one is a bile acid precursor that crosses the blood-brain barrier and can be used as an indicator of hepatic bile acid synthesis.7α-Hydroxy-4-cholesten-3-one is a pregnane X receptor (PXR) agonist.7α-Hydroxy-4-cholesten-3-one can be used to study the relationship between bile acids and bile acids.7α-Hydroxy-4-cholesten-3-one is an agonist of the pregnane X receptor (PXR). 7α-Hydroxy-4-cholesten-3-one can be used to study diseases associated with defective bile acid biosynthesis.