5-o-(3'-o-glucosylcaffeoyl)quinic acid

5-O-(3'-O-Glucosylcaffeoyl)quinic acid (compound 19) is a phenolic compound primarily found in the leaves of *Ilex glabra* L. Gray (Aquifoliaceae).

3-Hydroxyisovaleric acid (Beta-Hydroxyisovaleric acid) is an endogenous metabolite excreted in the urine and can serve as an early and sensitive indicator of biotin deficiency.

5-Aminosalicylic Acid (5-ASA) is an anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE.

3-Hydroxybutyric acid (Butanoic acid) (or beta-hydroxybutyrate) is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyrate in blood and urine are raised in ketosis. In humans, 3-hydroxybutyrate is synthesized in the liver from acetyl-CoA and can be used as an energy source by the brain when blood glucose is low. Blood levels of 3-hydroxybutyric acid levels may be monitored in diabetic patients to look for diabetic ketoacidosis. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing mammals. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for the synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies is utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmitoylphosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391 ). 3-Hydroxybutyric acid is found to be associated with fumarase deficiency and medium-chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism.

Indole-3-carboxylic acid (3-Indoleformic acid) is a normal urinary indolic tryptophan metabolite .

4-Hydroxy-5-methyl-3-furanone (4-Hydroxy-5-methylfuran-3(2H)-one) is a natural product isolated from Eurycotis floridana.

5-Aminolevulinic acid hydrochloride (5-ALA) is an intermediate in heme biosynthesis and a universal precursor of tetrapyrroles.

3-Indoleacetic acid sodium (Heteroauxin sodium salt) is a naturally occurring plant hormone of the auxin class. It can stimulate cell elongation and division, promoting plant growth and development. However, at high concentrations, it exhibits growth inhibiting effects, including epinasty and prevention of shoot and root growth. This latter effect formed the basis for which synthetic auxins were developed as herbicides and bioregulators in agriculture.

3-Amino-4-hydroxybenzoic acid (3-amino-4-hydroxybenzenecarboxylic acid) is a useful research chemical.

O-Phospho-L-serine (Phosphoserine) is the phosphoric acid ester of serine.

o-Toluic acid, also 2-methylbenzoic acid, is an aromatic carboxylic acid. It is a human xenobiotic metabolite.

Mono-Methyl glutarate is an endogenous metabolite i with anti-inflammatory and antioxidant activity.

3-Hydroxyphenylacetic acid is a rutin metabolite and an antioxidant. It has a protective biological activity in human. It is a substrate of enzyme 4-hydroxyphenylacetate 3-monooxygenase [EC 1.14.13.3] in the pathway tyrosine metabolism. 3-Hydroxyphenylace

D-(-)-Quinic acid (Kinic acid) is a cellular metal ion chelator, capable of promoting reactions with metal M(II,III) ions under pH-specific conditions. It may possess potent inhibition against alpha-mannosidase and alpha-fucosidase.

Methyl 3-O-methylgallate (M3OMG) is a rare natural product with promising antioxidant activities.

The combination of Valproic acid with Coumarin-3-carboxylic acid (3-Carboxycoumarin) suppresses the proliferation and migration of lung cancer cells via EGFR/VEGFR2/c-Met-Akt-NF-κB signaling pathways; this combination may have a wide therapeutic and/or adjuvant therapeutic application in the treatment of lung cancer.

O-Acetylserine (OASS) is an acylated amino acid derivative. It is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. Its presence in humans arises from either microbial metabolism in the gut or through consumptio

Produced in the gut microflora as one of the three main metabolites formed from the catechin diet. Its use in the production of glycol benzoates for the application of plasticizer in adhesive formulations is increasing. It is also used in the manufacture

O-PHOSPHO-L-SERINE is an ester of serine and phosphate, which are normal metabolites in human biofluids.O-phospho-L-serine is a phagocytosis inhibitor that inhibits glial cell proliferation and cone cell regeneration after photodamage.

(S)-3-Hydroxybutanoic acid (L-(+)-3-Hydroxybutyric acid) is a normal human metabolite that has been found elevated in geriatric patients remitting from depression. (S)-3-Hydroxybutanoic acid is synthesized in the liver from acetyl-CoA in humans, and can be used as an energy source by the brain when blood glucose is low.

3-Bromobenzoic acid (m-Bromobenzoic acid) is a marine derived natural products found in Tubastraea micranthus.

3-(3-Methoxyphenyl)propionic acid (3-Methoxyhydrocinnamic acid) is a naturally occurring human metabolite, It is an organic acid and excreted in human urine.

3-Indoleacetic acid (indolylacetic acid) (IAA) is the most common plant hormone of the auxin class and it regulates various aspects of plant growth and development.

5-Methoxysalicylic acid (5-MeOSA), a natural product, serves as an effective matrix for oligonucleotide analysis in MALDI MS when used alongside spermine.

5-Methoxyindole-3-acetic acid (5-Methoxyindoleacetic acid) is a metabolite of Melatonin and is isolated from pineal tissue.

3-Indolepropionic acid (Indolepropionic acid) is shown to be a powerful antioxidant with potential in the treatment for Alzheimer’s disease.

3-Furanoic acid (3-Carboxyfuran) is an organic acid regularly occurring in the urine of healthy individuals. 3-Furanoic acid (3-Carboxyfuran) is also a compound found in honey and honeydew samples.

5'-Guanylic acid disodium salt (GMP-5) is a purine ribonucleoside monophosphate. L-Glutamic acid and guanosine monophosphate are biosynthesized from xanthylic acid and L-glutamine via GMP synthase [glutamine-hydrolyzing]. Guanosine triphosphate and guanosine monophosphate are biosynthesized from diguanosine tetraphosphate via bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]. In humans, guanosine monophosphate is involved in the kanamycin, telithromycin, tobramycin, and erythromycin action pathways, and several metabolic disorders including AICA-ribosiduria, adenosine deaminase deficiency, adenine phosphoribosyltransferase deficiency (aprt), and 2-hydroxyglutric aciduria (D and L form) pathways. Guanosine monophosphate is also found in foods like onion-family vegetables, millet, Chinese water chestnut, and red rice, serving as a potential biomarker for the consumption of these foods.

3-(Methylthio)propionic acid (4-Thiapentanoic acid) is one of the metabolites of methionine (especially of D-methionine). Cultures of Streptomyces lincolnensis accumulated 3-methylthioacrylic acid in amounts directly related to the concentration of methionine in the medium. The first intermediate in the pathway may be the keto acid, which is then oxidatively decarboxylated to 3-methylthiopropionic acid.

(E)-3-(4-Methoxyphenyl)acrylic acid is a small molecule compound isolated from the rhizome of Etlingera pavieana (Pierre ex Gagnep.) R. M. Sm. It is a novel α-glucosidase inhibitor with hepatoprotective, antiamnesic, and cognitive enhancement activities, and it can be used to lower blood pressure sugar.

(R)-5-Oxopyrrolidine-2-carboxylic acid (D-Pyroglutamic acid) is a cyclic derivative of glutamic acid, physiologically present in mammalian tissues. It releases GABA from the cerebral cortex and exhibits anti-anxiety effects in a simple approach-avoidance conflict situation in rats. In clinical pharmacology experiments, it significantly shortens the plasma half-life of ethanol during acute intoxication.

3-Methoxybenzoic acid (NSC 27014) is a food additive,and has antibacterial activity.

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

3-Indoleacrylic acid is a metabolite of tryptophan produced by Peptostreptococcus species. 3-Indoleacrylic acid has a beneficial effect on intestinal epithelial barrier function and mitigates inflammatory responses by immune cells.

Indole-3-butyric acid (IBA) is a plant hormone in the auxin family and is an ingredient in many commercial plant rooting horticultural products.

3-Methoxyphenylacetic acid belongs to the class of organic compounds known as anisoles. 3-Methoxyphenylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa).3-Methoxyphenylacetic acid (m-Methoxyphenylacetic acid), a m-hydroxyphenylacetic acid (m-OHPAA) derivative, is a phytotoxin in Rhizoctonia solani. 3-Methoxyphenylacetic acid is used to develop a toxin-mediated bioassay for resistance to rhizoctonia root rot

3-(3,4,5-Trimethoxyphenyl)propanoic acid, a constituent of Piper retrofractum and Piper longum, is found in herbs and spices.

5-Acetylsalicylic acid (5-acetyl-2-hydroxybenzoic acid) has anti-inflammatory effects and can be used to treat inflammatory bowel disease, including ulcerative colitis, inflamed anus or rectum, and to maintain remission in Crohn's disease.

Tetrahydroxystilbene-2-O-β-D-glucoside (EH-201) is a low MW inducer of erythropoietin. Tetrahydroxystilbene-2-O-β-D-glucoside induces expression of erythropoietin, PPAR-γ coactivator 1α (PGC-1α) and haemoglobin in astrocytes and PC12 neuronal-like cells. In vivo, Tetrahydroxystilbene-2-O-β-D-glucoside treatment restores memory impairment, as assessed by the passive avoidance test, in SD, Aβ and KA mouse models. In the hippocampus of mice given Tetrahydroxystilbene-2-O-β-D-glucoside in their diet, levels of erythropoietin, PGC-1α and haemoglobin were increased. Treatment with Tetrahydroxystilbene-2-O-β-D-glucoside might be a therapeutic strategy for memory impairment in neurodegenerative disease, physiological ageing or traumatic brain injury.

4-hydroxy-3-methylbenzoic acid (4,3-Cresotic acid) is a organic acid identified in urine specimens from a healthy population.

3-Methyladipic acid is a metabolite of the catabolism of phytanic acid. Patients with adult Refsums disease (ARD) are unable to detoxify phytanic acid by alpha-oxidation, and so the w-oxidation pathway is the only metabolic pathway available for phytanic

3-O-Ethyl-L-ascorbic acid is a cosmetic tyrosinase inhibitor with whitening ability and is a stabilized vitamin C derivative. It also has antioxidant properties.

2-Amino-5-ureidopentanoic acid (Citrulline) exists in the liver, is not a protein component, is an important intermediate in the human urea cycle, can be combined with ornithine, arginine to treat hyperammonemia.

5-aminovalerate (or 5-aminopentanoic acid) is a lysine degradation product. It can be produced both endogenously or through bacterial catabolism of lysine. 5-aminovalerate is formed via the following multi-step reaction: L-lysine leads to cadverine leads

3-Methyl-2-oxobutanoic acid (2-Oxoisovaleric acid) is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. 3-Methyl-2-oxobutanoic acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. 3-Methyl-2-oxobutanoic acid is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis.

(S)-2-Hydroxy-3-phenylpropanoic acid (L-(−)-3-Phenyllactic acid) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via lactate dehydrogenase. The D-form is derived from bacterial sources, while the L-form is endogenous. Phenyllactate levels are normally very low in blood or urine, but high levels indicate phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to a deficiency of phenylalanine hydroxylase (PAH), causing phenylalanine to convert to phenylpyruvic acid rather than tyrosine.

trans-3-Indoleacrylic acid is one of the endogenous metabolites that inhibits RSL3-induced ferroptosis and can be used to study colorectal cancer.

3-Ethoxy-3-oxopropanoic acid (Monoethyl malonic acid) belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. 3-Ethoxy-3-oxopropanoic acid exists as a solid, soluble (in water), and a weakly acidic compound (based on its pKa). 3-Ethoxy-3-oxopropanoic acid has been primarily detected in blood. Within the cell, monoethyl malonic acid is primarily located in the cytoplasm.

3-Methylbut-2-enoic acid (Senecioic acid) appears in the urine of patients with 3-Methylcrotonic aciduria, which is a disorder characterized by urine that contains increased amounts of 3-methylcrotonic acid.

Methylglutaric acid is a leucine metabolite. A large amount of methylglutaric acid is identified in urine of patients with deficiency of 3-methylglutaconyl coenzyme A hydratase (PMID 6181239 ). Methylglutaric acid is also found to be associated with 3-hyd