Natural Products

Phytohemagglutinin (PHA, Phaseolus vulgaris agglutinin) is expressed in Pichia pastoris using native signal peptides, or the Saccharomyces alpha-factor preprosequence, to direct proteins into the secretory pathway. Phytohemagglutinin induces apoptosis in human HEp-2 carcinoma cells via increasing proapoptotic protein Bax and activating caspases-3.

Deoxycholic acid sodium salt (Sodium Deoxycholate, Sodium Desoxycholate, Cholanoic Acid, ATX-101, Kythera, Belkyra, DCA) is specifically responsible for activating the TGR5 receptor (GPCR19) that stimulates brown adipose tissue (BAT) thermogenic activity.

2'-Deoxyadenosine 5'-monophosphate (5'-dAMP), an endogenous metabolite, is only photosensitized degraded under acidic conditions.

2'-Deoxycytidine-5'-monophosphoric acid (dCMP) is an endogenous metabolite that can be used as a model to describe mechanisms of DNA-strand breaks induced by secondary electrons and decomposes primarily by dissociation of the C-O phosphoester bond.

N-Acetyl-L-arginine (Ac-Arg-OH) dihydrate is an endogenous metabolite.

Levoglucosan (LG, LEV, Leucoglucosan, Glucosan, 1,6-anhydro-b-D-Glucose) is an endogenous metabolite.

Sodium 2-(1H-indol-3-yl)acetate (3-Indoleacetic acid sodium, Indole-3-acetic acid sodium, 3-IAA sodium) is an endogenous metabolite.

Phytic acid dipotassium salt (Phytic acid potassium, IP6 (PS)), an endogenous metabolite in rice grain extract and digest, inhibits β-secretase 1 (BACE1) with IC50 of approximately 0.25 μM.

2-Aminoethylphosphonic acid (2-AEP, (2-Aminoethyl)phosphonic acid) is a type of abundant and ubiquitous naturally occurring phosphonate used as sources of phosphorus by many prokaryotic lineages.

Phospho(enol)pyruvic acid monopotassium salt (Potassium 1-carboxyvinyl hydrogenphosphate) is an endogenous metabolite.

Methyl β-D-Galactopyranoside (Methyl beta-D-galactoside, Methylgalactoside) is an endogenous metabolite.

3-Methoxytyramine (3-O-methyl Dopamine, 3MT) hydrochloride, a major extracellular metabolite of dopamine, is a neuromodulator that in certain situations may be involved in movement control.

D-(+)-Galacturonic acid monohydrate (D-Galacturonic acid hydrate, d-GalA, D-galUA) is an endogenous metabolite that can be used in engineering Saccharomyces cerevisiae.

2-Hydroxyhexanoic acid (2-Hydroxyhexanoic acid) is an endogenous metabolite.

DL-Tartaric Acid (2,3-Dihydroxysuccinic acid) is a white, crystalline organic acid isolated from many plants, particularly tamarinds and grapes and is used as an antioxidant and an additive agent to give a sour taste.

N-Acetyl-DL-methionine is an active endogenous metabolite that decreases the hepatic glutathione level in male Bom:NMRI mice.

Glyoxylic acid monohydrate (2,2-Dihydroxyacetic acid) is an atmospherically relevant ketoacid.

Pyrazole (1H-pyrazole) is a five membered heteroaromatic ring with two nitrogen atoms is of immense significance. Pyrazole is an indispensable anchor for design and development of new pharmacological agents.

N-Acetyl-L-alanine (NAAL, Ac-Ala-OH) is an active endogenous metabolite.

3-Hydroxybenzaldehyde (3-HBA), one of the benzaldehydes commonly found in nature, is produced by 3-hydroxybenzyl-alcohol dehydrogenase, and is a substrate of aldehyde dehydrogenase (ALDH) in rats and humans (ALDH2). 3-Hydroxybenzaldehyde exhibits vasculoprotective effects.

6-Hydroxyindole (1H-indol-6-ol) is an endogenous potent and long-lasting OATP1B1 inhibitor with IC50 of ~10 μM.

Glycolaldehyde dimer (2,5-Dihydroxy-1,4-dioxane, 1,4-Dioxane-2,5-diol, DD) is an active endogenous metabolite that appears moderate absorbent and fluorescent, when it reacts with glycine (Gly)/ammonium sulfate (AS).

Heptadecanoic acid (C17:0), an odd chain saturated fatty acid, significantly inhibits cell proliferation, and migration, while promoting apoptosis in PC‑9 and PC‑9/GR cells. Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis.

L-Histidinol dihydrochloride, a structural analogue of the essential amino acid L-histidine, is a reversible inhibitor of protein biosynthesis which evokes disparate responses from non-tumorigenic and tumorigenic cells in culture.

D-(-)-Lyxose (D-Lyxose) is an active endogenous metabolite.

Nα-Acetyl-L-lysine (Ac-Lys-OH, N(alpha)-Acetyllysine) is an active endogenous metabolite.

3-Methylglutaric acid (MGA, 3MG acid) is a conspicuous C6 dicarboxylic organic acid that can be used as a single solid-state NMR standard compound to perform all calibration steps except for magnet shimming.

O-Acetyl-L-serine (OAS, O-Acetylserine, O-Acetyl-L-serine) hydrochloride (HCl) is an intermediate in the biosynthesis of the amino acid cysteine in bacteria and plants that displays a signalling function leading to changes in transcript levels of a specific gene set irrespective of the sulfur status of the plant.

4-Acetamidobutanoic acid (N-acetyl GABA) is a derivative of Gamma-aminobutyric acid (GABA) resulting from the monoacetylation of the nitrogen of GABA.

Bis(2-ethylhexyl) phthalate (Dioctyl phthalate, DOP, Diplast O, ESBO-D 82, Ergoplast FDO, Ergoplast FDO-S, Etalon) induces DNA strand breaks and gene expression alterations in larval zebrafish Danio rerio.

Itaconic acid, a macrophage-specific (Mϕ-specific) metabolite, mediates crosstalk between macrophage metabolism and peritoneal tumors. Itaconic acid is also a precursor of polymers, chemicals, and fuels that can be synthesized by many fungi.

L-Histidine monohydrochloride monohydrate (L-Histidine hydrochloride hydrate, H-His-OH.HCl.H2O), a structural analogue of the essential amino acid L-histidine, is a reversible inhibitor of protein biosynthesis which evokes disparate responses from non-tumorigenic and tumorigenic cells in culture.

N-Acetylglycine (NAGly, Aceturic acid, Acetamidoacetic acid), a minor constituent of numerous foods, is not genotoxic or acutely toxic.

5,6-Dimethylbenzimidazole (5,6-DMB, Dimezol, Dimedazol, 5,6-Dimethyl-1H-benzo[d]imidazole, 5,6-Dimethyl-1H-benzimidazole) is a vitamin B12 precursor.

D-Pyroglutamic acid (D-5-Oxoproline, D-Pyr-OH, 5-oxo-D-proline, (R)-5-Oxopyrrolidine-2-carboxylic acid) is an active endogenous metabolite that antagonizes the disruption of passive avoidance behaviour induced by the N-methyl-D-aspartate receptor antagonist AP-5.

N-acetyl-L-leucine is an active endogenous metabolite that accelerates vestibular compensation after unilateral labyrinthectomy by action in the cerebellum and thalamus.

Pyridoxal hydrochloride (HQ) is an active endogenous metabolite.

(S)-(-)-1-Phenylethanol ((S)-1-Phenylethanol, (S)-(-)-Phenylethanol) is an enantiomer of 1-Phenylethanol with flavor properties.

Monoethyl malonic acid (Ethyl hydrogen malonate, Monoethyl malonate, 3-Ethoxy-3-oxopropanoic acid) is the major urinary metabolites of ethyl 3-ethoxypropionate (EEP).

(R)-3-Hydroxybutanoic acid (R-3HB, D-3-hydroxybutyric acid) is a monomer of PHB (poly[(R)-3-hydroxybutyrate]) with wide industrial and medical applications. (R)-3-hydroxybutyric acid can also serve as chiral precursor for synthesis of pure biodegradable PHB and its copolyesters.

Calcium 2-hydroxy-4-(methylthio)butanoate is an active endogenous metabolite.

2-Amino-1-phenylethanol (2-APE) is a noradrenaline analogue.

Thymidine-5'-monophosphate (5'-Thymidylic acid) disodium salt is an active endogenous metabolite.

Myosmine is not only one of the minor tobacco alkaloids but is also present in various foods. Myosmine has low affinity against a4b2 nicotinic acetylcholinergic receptors (nAChR) with Ki of 3300 nM.

N-Methylnicotinamide (MNA, Nicotinyl Methylamide, N-Methyl-3-pyridinecarboxamide) is an active endogenous metabolite that improves endothelial dysfunction and attenuates atherogenesis via the modulation of ADMA-DDAH axis.

L-Cysteic acid monohydrate (CAM) is an active endogenous metabolite.

(L)-Dehydroascorbic acid (DHA) is an oxidized form of l-Ascorbic acid (AsA) that efficiently scavenges non-thermal plasma-induced hydroxyl radicals in the presence of thiols and fails to scavenge hydroxyl radicals by itself.

Petroselinic acid (PSA) is a positional isomer of oleic acid isolated from the vegetable oil of Coriandrum sativum fruits. Petroselinic acid can be used for the fermentation of new sophorolipids.

Serotonin (5-Hydroxytryptamine) creatinine sulfate monohydrate is an active endogenous metabolite.

1-Methylnicotinamide (1-MNA, 3-Carbamoyl-1-methylpyridin-1-ium, Trigonellamide) chloride is an active endogenous metabolite of nicotinamide that exhibits anti-inflammatory and anti-thrombotic activities. 1-Methylnicotinamide enhances tumor vasculature formation and markedly increases prostacyclin (PGI2) generation.

Phosphocholine (Phosphorylcholine) chloride calcium salt tetrahydrate is an active endogenous metabolite.

Cholesteryl linoleate is less polar lipid in human nasal fluid that contributes to the inherent antibacterial activity.

Tricosanoic acid is an aliphatic carboxylic acid that exhibits a strong hair-growing effect.

DL-2,3-Diaminopropionic acid monohydrochloride (2,3-Diaminopropanoic acid hydrochloride) is an active endogenous metabolite.

3-Hydroxyanthranilic Acid (3-HAA, 3-HANA), a tryptophan metabolite, has an immunomodulatory effect that may result from inhibition of PI3K/Akt/mTOR and NF-κB activity, thereby decreasing the production of pro-inflammatory mediators.

Phosphonoacetic acid (PAA) is an active endogenous metabolite that possesses a restricted potential to block DNA biosynthesis. Phosphonoacetic acid exhibits anti-viral activities.

Elaidic acid is a major trans fatty acid that inhibits cell viability, elevates cell apoptosis by enhancing oxidative stress. Elaidic acid can be used as a pharmaceutical solvent.

Isomaltulose (Palatinose) hydrate is a disaccharide carbohydrate widely used during exercise to maintain glycaemia and hydration.

(3-Carboxypropyl)trimethylammonium chloride (γ-Butyrobetaine, γBB hydrochloride) is an intermediary metabolite by gut microbes from dietary L-carnitine in mice.

DL-Mandelic acid (MA, 2-Hydroxy-2-phenylacetic acid, Amygdalic acid, Almond acid) can be intercalated into Zn-Al layered double hydroxide (LDH) by an anion-exchange reaction to build a novel antimicrobial layered material.

cis-4-Hydroxy-D-proline (H-D-cis-Hyp-OH) is an endogenous metabolite that can be used to study the specificity and kinetics of D-alanine dehydrogenase.

Uridine-5'-diphosphate (UDP) disodium salt is a potent, selective and natural agonist of P2Y₆ receptor with EC50 = 300 nM and pEC50 of 6.52, respectively. Uridine-5'-diphosphate (UDP) disodium salt is also an antagonist of P2Y₁₄ receptor with pEC50 of 7.28.

N-Acetyl-D-mannosamine (ManNAc, N-acetyl-beta-mannosamine), a precursor of a sialic acid, improves the age-dependent attenuation of synaptic transmission and long-term potentiation (LTP). N-Acetyl-D-mannosamine treatment is a potential therapeutic application for cognitive dysfunction.

(±)-Methyl Jasmonate (MeJA, Methyl jasmonate, Methyl 2-(3-oxo-2-(pent-2-en-1-yl)cyclopentyl)acetate), a phytohormone that acts as a vital cell regulator in plants, is a new candidate for the treatment of Inflammatory bowel diseases (IBDs), modulating the expression of the major classes of caspase-type protease families.

2'-Deoxyuridine 5'-monophosphate disodium salt (dUMP) is a substrate for thymidylate synthase and is converted to deoxythymidine monophosphate (dTMP). The inhibition of dUMP to dTMP at the methylation step is a key in controlling bacterial and eukaryotic cell growth.

Nicotinuric acid (NUA) is the major detoxification product of nicotinic acid and may serve as a simple quantitative index of hepatic biotransformation of nicotinic acid.

D-Mannosamine hydrochloride ((2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride) is an active endogenous metabolite.

3-Hydroxyphenylacetic acid (3-HPAA) is a phenolic acid mostly found in olive oil wastewater and an intestinal metabolite of the dietary flavonoid quercetin. 3-Hydroxyphenylacetic acid exhibits antimicrobial properties.

Isocitric acid (DL-Isocitric acid) trisodium salt is an active endogenous metabolite.

12-Hydroxydodecanoic acid (G12) is an active endogenous metabolite.

Palmitoleic acid (POA, Palmitoleate) stimulates the uptake of glucose in liver through activation of AMPK and FGF-21, dependent on PPARα.

Nα-Acetyl-L-asparagine (N-Acetylasparagine, (S)-2-acetamido-4-amino-4-oxobutanoic acid) is an endogenous metabolite that exists in human brain.

Thiamine monophosphate chloride dihydrate (Vitamin B1 Monophosphate Chloride, Sineurina, Phosphothiamine) is an endogenous metabolite.

Sodium mesoxalate monohydrate (sodium 2,2-dihydroxymalonate) is an endogenous metabolite.

D-Saccharic acid potassium salt (D-Glucaric acid potassium, Potassium bisaccharate) is an endogenous metabolite.

Acetic acid octyl ester (Octyl acetate) is one of the major components of essential oils in the vittae, or oil tubes, of the wild parsnip (Pastinaca sativa). Acetic acid octyl ester exhibits antioxidant activity.

Methyl isoeugenol (Methylisoeugenol) is an eugenol analogue isoeugenol isolated from Acori Tatarinowii Rhizoma. Methyl isoeugenol is a highly attractive lure for Z. diversus and would be a valuable inclusion as an attractant in monitoring and male annihilation programs.

Menthone is one of the main volatile components of the essential oil of peppermint (Mentha piperita L.). Menthone is used as antioxidant agent and has a good compensatory effect with significant reduction in DNA damages in sperm cells.

Methyl acetylacetate (MAA, Acetoacetate methyl ester, Methyl 3-oxobutanoate, Methyl 3-oxobutyrate, Methyl acetoacetate, Methyl acetylacetate), an endogenous metabolite, is used as a chemical reagent used in the synthesis of pharmaceuticals.

Isophorone (IPHO), an α,β-unsaturated cyclic ketone, is a clear liquid with a camphor-like odor. Isophorone is used as a precursor to polymers.

Nudifloric acid (1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid), isolated from Cordyceps bassiana, which is one of Cordyceps species with anti-oxidative, anti-cancer, anti-inflammatory, anti-diabetic, anti-obesity, anti-angiogenic, and anti-nociceptive activities.

Cis-3-Hexenyl hexanoate ((Z)-3-hexenyl hexanoate) is a kind of plant volatile that brings tropical and pulpy profile with citrus and green nuances to all kinds of fruit flavors.

Disodium 5'-inosinate monohydrate (Inosine 5'-monophosphate disodium salt hydrate) is an endogenous metabolite.

(2R,3R)-(-)-2,3-Butanediol ((2R,3R)-Butane-2,3-diol) is an endogenous metabolite.

Dihydroxyfumaric acid hydrate (DHF) is an endogenous metabolite. The diester derivative of dihydroxyfumaric acid hydrate (DHF) has been used exclusively as an electrophile in organic synthesis.

DL-5-Hydroxylysine hydrochloride, an endogenous metabolite, is a racemic mixture of D- and L- enantiomers of 5-hydroxylysine which may be used as potential target markers for radical-induced protein oxidation.

DL-Homocysteine is a weak neurotoxin that affects the production of kynurenic acid (KYNA) in the brain. DL-Homocysteine inhibits the activity of both KYNA biosynthetic enzymes, kynurenine aminotransferases (KATs) I and II.

δ-Valerolactone (Tetrahydro-2H-pyran-2-one, 5-Valerolactone, oxan-2-one) is an endogenous metabolite.

N-Formyl-L-methionine (For-Met-OH) is an endogenous metabolite.

9-Methoxycanthin-6-one is present in intact plant parts and in callus tissues of different explants with anti-tumour activity.

2,5-Dimethylpyrazine (NSC 49139) is an endogenous metabolite.

L-DAB HBR (L-Dab Hydrobromide, L-2,4-Diaminobutyric acid hydrobromide) is an inhibitor of GABA (Gamma-aminobutyric acid) transaminase with IC50 of >500 μM. L-DAB HBR exhibits antitumor activity.

Malonic acid (MOA), one of the major dicarboxylic acids (DCAs) in aerosols, has been identified experimentally and computationally to be a strong acid. Malonic acid (MOA) acts as a mediate bridge for the formation of pure SA-A-based clusters.

Maleic acid inhibits glutamate decarboxylase (GAD) activity, thus enhances acid sensitivity of Listeria monocytogenes. Maleic acid affects the extracellular GABA levels.

trans-Aconitic acid (TAA) is an abundant constituent in the leaves of Echinodorus grandiflorus, a medicinal plant used to treat rheumatoid arthritis in Brazil.

2-Deoxy-D-ribose (Thyminose, Deoxyribose) is an endogenous metabolite.

L-Homoserine (L-Hse) is an important biosynthetic intermediate of threonine, methionine and lysine.

3-Methyl-2-buten-1-ol (Prenol, Prenyl alcohol, Dimethylallyl alcohol) is an endogenous metabolite.

Pyruvic acid (Acetylformic acid) is an important organic chemical intermediate that plays a role in cardiomyocyte pathophysiology and therapy. Pyruvic acid markedly increases the level of lactate dehydrogenase (LDH) and creatine kinase (CK) and reduces the level of Ca²⁺Mg²⁺-ATPase and Na⁺K⁺-ATPase.

Guanosine 5'-triphosphate (5'-GTP, Guanosine triphosphate, H4GTP) trisodium salt is an enhancer of myogenic cell differentiation in a murine cells. Guanosine 5'-triphosphate trisodium salt up-regulates miRNA (specifically miR133a and miR133b) and myogenic regulator factor and induces human myogenic precursor cells to release exosomes stuffed with guanosine based molecules (mainly guanosine) in the extracellular milieu.

N-Formylglycine (2-formamidoacetic acid, For-Gly-OH, FGly) is an endogenous metabolite.

Sodium 2-hydroxybutanoate (Sodium 2-hydroxybutyrate, Sodium DL-2-hydroxybutyrate), converted from 2-Aminobutyric acid, is an intermediate metabolite.

2,4-Dihydroxypyrimidine-5-carboxylic Acid (Uracil 5-carboxylic acid, Isoorotic acid, 5-Carboxyuracil) is an endogenous metabolite.

N-Acetyl-D-galactosamine (D-N-Acetylgalactosamine) is an endogenous metabolite.

L-Glucose (L-(-)-Glucose) is an enantiomer of D-glucose. L-Glucose promotes food intake while cannot be used by cells as an energy source because it cannot be phosphorylated by hexokinase.

D-(-)-Tartaric acid is the unnatural isomer of Tartaric acid which is an important chiral chemical building block with broad industrial and scientific applications.

Potassium sorbate (Sorbic acid potassium) is a nonpoisonous food preservative isolated from Sorbus aucuparia. Potassium sorbate is an effective inhibitor of most molds and yeasts and some bacteria.

Pimelic acid (Heptanedioic acid, 1,5-Pentanedicarboxylic acid, 1,7-Heptanedioic acid) originating from fatty acid synthesis pathway is a bona fide precursor of biotin in B. subtilis.

Glutaric acid (GA) is an attractive C5 dicarboxylic acid with wide applications in the biochemical industry.

Citraconic acid (CA) is a kind of methyl-branched fatty acids that exists in wild soybean.

5-hydroxy-1-tetralone is a fluorescent labeling reagent for the determination of glycosphingolipid from small amounts of biological samples.

Maleamic acid ((Z)-4-Amino-4-oxobut-2-enoic acid) is an endogenous metabolite.

3-(2-Hydroxyphenyl)propanoic acid (Melilotic acid, Melilotate, 2-hydroxybenzenepropanoic acid) is an endogenous metabolite.

L-Anserine nitrate salt, a dipeptide found in most animal tissues, exhibits antioxidant properties, anti-crosslinking, and anti-glycation activities. L-Anserine protects against neurotoxicity induced by ER-stress inducers.

Amarogentin (AG), a secoiridoid glycoside mainly extracted from Swertia and Gentiana roots, exhibits anti-oxidative, anti-tumour, and anti-diabetic activities. Amarogentin is an agonist for the bitter taste receptor TAS2R1 and inhibits in LAD-2 cells substance P-induced production of newly synthesized TNF-α. Amarogentin induces apoptosis in human gastric cancer cells (SNU-16) through G2/M cell cycle arrest and PI3K/Akt signalling pathway. Amarogentin (AG) interacts with the α2 subunit of AMP-activated protein kinase (AMPK) and activates the trimeric kinase with EC50 of 277 pM.

Adamantane is a colorless, crystalline chemical compound first isolated from petroleum with a camphor-like odor. Adamantane is used to treat influenza A virus infections.