Subcellular Location: Endosome membrane

2-Phenylglycine, also known as a-amino-a-toluate or L-PHG amino acid, belongs to the class of organic compounds known as 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). Outside of the human body, 2-Phenylglycine has been detected, but not quantified in cow milk. This could make 2-phenylglycine a potential biomarker for the consumption of these foods. 2-Phenylglycine is a metabolite described in normal human urine (PMID 14473597) and plasma (PMID 5888801). 2-Phenylglycine is a metabolite described in normal human urine (PMID 14473597) and plasma (PMID 5888801) [HMDB]

1-Methyluric acid

1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

C6H6N4O3 (182.044)

1-Methyluric acid is one of the three main theophylline metabolites in man. 1-Methyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316, 15833286, 3506820, 15013152, 4039734, 9890610) [HMDB] 1-Methyluric acid is one of the three main theophylline metabolites in man. 1-Methyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline, and theobromine). Methyluric acids can be distinguished from uric acid via simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase, or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 superfamily, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis (PMID:11712316, 15833286, 3506820, 15013152, 4039734, 9890610).

1-Methylxanthine

2-hydroxy-1-methyl-6,9-dihydro-1H-purin-6-one

C6H6N4O2 (166.0491)

1-Methylxanthine is one of the major metabolites of caffeine in humans. The oxidation of 1-methylxanthine to 1-methyluric acid occurs so rapidly that the parent compound could not be detected in plasma, and only low concentrations could be detected in the brain (PMID: 28863020). 1-methylxanthine is the major metabolites of caffeine in the human. The oxidation of 1-methylxanthine to 1-methyluric acid occurred so rapidly that the parent compound could not be detected in plasma, and only low concentrations could be detected in brain. (PMID: 28863020 [HMDB] 1-Methylxanthine, a caffeine derivative, is an essential human urinary metabolite of caffeine and theophylline (1,3-dimethylxanthine, TP)[1]. 1-Methylxanthine enhances the radiosensitivity of tumor cells[2]. 1-Methylxanthine, a caffeine derivative, is an essential human urinary metabolite of caffeine and theophylline (1,3-dimethylxanthine, TP)[1]. 1-Methylxanthine enhances the radiosensitivity of tumor cells[2].

2-hydroxyphenylacetate

ortho-Hydroxyphenylacetic acid

ortho-Hydroxyphenylacetic acid, also known as (o-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(Hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. ortho-Hydroxyphenylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). ortho-Hydroxyphenylacetic acid can be found in a number of food items such as natal plum, lemon verbena, half-highbush blueberry, and parsley, which makes ortho-hydroxyphenylacetic acid a potential biomarker for the consumption of these food products. ortho-Hydroxyphenylacetic acid can be found primarily in blood, feces, and urine. Moreover, ortho-hydroxyphenylacetic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism. ortho-Hydroxyphenylacetic acid is a substrate of the enzyme oxidoreductases (EC 1.14.13.-) in the pathway styrene degradation (KEGG). ortho-Hydroxyphenylacetic acid is also a microbial metabolite. ortho-Hydroxyphenylacetic acid is a substrate of the enzyme oxidoreductases [EC 1.14.13.-] in the pathway styrene degradation. (KEGG) [HMDB]. 2-Hydroxyphenylacetic acid is found in many foods, some of which are rambutan, common oregano, burbot, and wild leek. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 155 INTERNAL_ID 155; CONFIDENCE standard compound CONFIDENCE standard compound; INTERNAL_ID 46 COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2-Hydroxyphenylacetic acid is a potential biomarker for the food products, and found to be associated with phenylketonuria (PKU). 2-Hydroxyphenylacetic acid is a potential biomarker for the food products, and found to be associated with phenylketonuria (PKU).

2,3-Diaminopropionic acid

2,3-Diaminopropionic acid, (DL)-isomer, monohydrochloride

C3H8N2O2 (104.0586)

2,3-Diaminopropionic acid, also known as L-2,3-diaminopropanoate or Dpr, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 2,3-Diaminopropionic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2,3-Diaminopropionic acid (2,3-diaminopropionate) is a non-proteinogenic amino acid found in certain secondary metabolites, including zwittermicin A and tuberactinomycin.2,3-Diaminopropionate is formed by the pyridoxal phosphate (PLP) mediated amination of serine. 2,3-Diaminopropionic acid exists in all living organisms, ranging from bacteria to humans. 2,3-Diaminopropionic acid is a metabolite of b-oxalyl-L-a,b-diaminopropionic acid a neurotoxic amino acid (ODAP). (PMID 5774501) COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

4-Nitrocatechol

4-nitro-Pyrocatechol4-nitropyrocatechol NSC 80651

C6H5NO4 (155.0219)

4-Nitrocatechol is the by-product of the hydroxylation of 4-Nitrophenol by the human cytochrome P450 (CYP) 2E1. This reaction is a useful metabolic marker for the presence of functional cytochrome P450 2E1 in mammalian cell microsomes. Hepatic and extrahepatic microsomal cytochrome P450 isozymes further catalyze the reduction of p-nitrocatechol to p-aminophenol. (PMID: 8267647, 8214571, 8267647) [HMDB] 4-Nitrocatechol is the by-product of the hydroxylation of 4-nitrophenol by the human cytochrome P450 (CYP) 2E1. This reaction is a useful metabolic marker for the presence of functional cytochrome P450 2E1 in mammalian cell microsomes. Hepatic and extrahepatic microsomal cytochrome P450 isozymes further catalyze the reduction of p-nitrocatechol into p-aminophenol (PMID: 8267647, 8214571, 8267647). 4-Nitrocatechol is a potent lipoxygenase inhibitor[1]. 4-Nitrocatechol is a potent lipoxygenase inhibitor[1].

5-Hydroxymethyluracil

5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

C5H6N2O3 (142.0378)

5-Hydroxymethyluracil (5hmU), also known as alpha-hydroxythymine, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. 5hmU has been identified as a thymine base modification found in the genomes of a diverse range of organisms (PMID: 28137275). 5-hydroxymethyluracil has been detected in bacteriophages, dinoflagellates, leishmania, and in eukaryotic genomes where its level appears to be cell type-specific. 5-Hydroxymethyluracil arises from the oxidation of thymine. 5-Hydroxymethyluracil is produced by the enzyme thymine dioxygenase (EC 1.14.11.6) which catalyzes the chemical reaction thymine + 2-oxoglutarate + O2 <-> 5-hydroxymethyluracil + succinate + CO2. The 3 substrates of this enzyme are thymine, 2-oxoglutarate, and O2, whereas its 3 products are 5-hydroxymethyluracil, succinate, and CO2. The 5hmU base can also be generated by oxidation/hydroxylation of thymine by the Ten-Eleven-Translocation (TET) proteins or result from deamination of 5hmC (PMID: 29184924). DNA containing 5hmU has been reported to be more flexible and hydrophilic (PMID: 29184924). 5-Hydroxymethyluracil is an oxidation damage product derived from thymine or 5-methylcytosine. It is a product of thymine dioxygenase [EC 1.14.11.6]. (KEGG) D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents D007155 - Immunologic Factors 5-Hydroxymethyluracil is a product of oxidative DNA damage. 5-Hydroxymethyluracil can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase. 5-Hydroxymethyluracil is a product of oxidative DNA damage. 5-Hydroxymethyluracil can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase.

6-HYDROXYMELATONIN

3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindole

C13H16N2O3 (248.1161)

A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D020011 - Protective Agents > D002316 - Cardiotonic Agents D002317 - Cardiovascular Agents 6-Hydroxymelatonin is a primary metabolic of Melatonin, which is metabolized by cytochrome P450 (CYP) 1A2.

Indolepyruvate

3-(1H-Indol-3-yl)-2-oxopropionic acid

C11H9NO3 (203.0582)

The thiamin diphosphate (ThDP)-dependent enzyme indolepyruvate decarboxylase (IPDC) is involved in the biosynthetic pathway of the phytohormone 3-indoleacetic acid and catalyzes the nonoxidative decarboxylation of 3-indolepyruvate to 3-indoleacetaldehyde and carbon dioxide. (PMID:15835904)¬† In addition, the enzyme was compared with the phenylpyruvate decarboxylase from Azospirillum brasilense and the indolepyruvate decarboxylase from Enterobacter cloacae. (PMID:21501384) Indole-3-pyruvate is a microbial metabolite, urinary indole-3-pyruvate is produced by Clostridium sporogenes (PMID:29168502) and Trypanasoma brucei (PMID:27856732). Indolepyruvate, also known as indolepyruvic acid or (indol-3-yl)pyruvate, belongs to indolyl carboxylic acids and derivatives class of compounds. Those are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indolepyruvate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Indolepyruvate can be found in a number of food items such as spelt, strawberry, gram bean, and oregon yampah, which makes indolepyruvate a potential biomarker for the consumption of these food products. Indolepyruvate exists in all eukaryotes, ranging from yeast to humans. D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D000975 - Antioxidants > D016166 - Free Radical Scavengers D020011 - Protective Agents > D000975 - Antioxidants KEIO_ID I002

L-Histidinol

(2S)-2-amino-3-(1H-imidazol-5-yl)propan-1-ol

L-Histidinol, a structural analogue of the essential amino acid L-histidine, enhances the toxicity of a variety of anticancer drugs for many tumour cells of animal origin (PMID:8297120). L-Histidinol inhibits human myristoyl-CoA:protein-myristoyltransferase (hNMT), an essential eukaryotic enzyme that catalyzes the cotranslational transfer of myristate into the NH2-terminal glycine residue of a number of important proteins of diverse function (PMID:9778369). L-Histidinol, a structural analogue of the essential amino acid L-histidine, enhances the toxicity of a variety of anticancer drugs for many tumor cells of animal origin. (PMID 8297120)

L-Lysine

(2S)-2,6-diaminohexanoic acid

C6H14N2O2 (146.1055)

Lysine (Lys), also known as L-lysine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. Lysine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Lysine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. In humans, lysine is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. Lysine is high in foods such as wheat germ, cottage cheese and chicken. Of meat products, wild game and pork have the highest concentration of lysine. Fruits and vegetables contain little lysine, except avocados. Normal requirements for lysine have been found to be about 8 g per day or 12 mg/kg in adults. Children and infants need more, 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. In organisms that synthesise lysine, it has two main biosynthetic pathways, the diaminopimelate and Œ±-aminoadipate pathways, which employ distinct enzymes and substrates and are found in diverse organisms. Lysine catabolism occurs through one of several pathways, the most common of which is the saccharopine pathway. Lysine plays several roles in humans, most importantly proteinogenesis, but also in the crosslinking of collagen polypeptides, uptake of essential mineral nutrients, and in the production of carnitine, which is key in fatty acid metabolism. Lysine is also often involved in histone modifications, and thus, impacts the epigenome. Lysine is highly concentrated in muscle compared to most other amino acids. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Excess arginine antagonizes lysine. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Lysine also may be a useful adjunct in the treatment of osteoporosis. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine may be an adjunct therapy because it reduces calcium losses in urine. Lysine deficiency also may result in immunodeficiency. Requirements for lysine are probably increased by stress. Lysine toxicity has not occurred with oral doses in humans. Lysine dosages are presently too small and may fail to reach the concentrations necessary to prove potential therapeutic applications. Lysine metabolites, amino caproic acid and carnitine have already shown their therapeutic potential. Thirty grams daily of amino caproic acid has been used as an initial daily dose in treating blood clotting disorders, indicating that the proper doses of lysine, its precursor, have yet to be used in medicine. Low lysine levels have been found in patients with Parkinsons, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize the level and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and those treated with coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) (http://www.dcnutrition.com). Lysine has also been sh... [Spectral] L-Lysine (exact mass = 146.10553) and Carnosine (exact mass = 226.10659) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Dietary supplement, nutrient. Found widely in protein hydrolysates, e.g. casein, egg albumen, fibrin, gelatin, beet molasses. Flavouring agent for a variety of foods L-Lysine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-87-1 (retrieved 2024-07-01) (CAS RN: 56-87-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2]. L-lysine is an essential amino acid[1][2] with important roles in connective tissues and carnitine synthesis, energy production, growth in children, and maintenance of immune functions[2].

Nα-Acetyl-L-lysine

(2S)-6-(Acetylamino)-2-aminohexanoic acid

C8H16N2O3 (188.1161)

N-epsilon-Acetyl-L-lysine also known as Nepsilon-Acetyllysine or N6-Acetyllysine, 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 one of its nitrogen atoms. N-epsilon-Acetyl-L-lysine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-epsilon-Acetyl-L-lysine is a biologically available sidechain, N-capped form of the proteinogenic alpha amino acid L-lysine. Unlike L-lysine, acetylated lysine derivatives such as N-epsilon-Acetyl-L-lysine are zwitterionic compounds. These are molecules that contains an equal number of positively- and negatively-charged functional groups. N-epsilon-Acetyl-L-lysine is found naturally in eukaryotes ranging from yeast to plants to humans. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins (often histones) by specific hydrolases. N-epsilon-Acetyl-L-lysine can be biosynthesized from L-lysine and acetyl-CoA via the enzyme known as Lysine N-acetyltransferase. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins ‚Äì either N-terminal or N-alpha acetylation or N6 (sidechain) acetylation. Side-chain acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. By modifying chromatin proteins and transcription-related factors, these acetylases are believed to regulate the transcription of many genes. The best-characterized mechanism is acetylation, catalyzed by histone acetyltransferase (HAT) enzymes. HATs function enzymatically by transferring an acetyl group from acetyl-coenzyme A (acetyl-CoA) to the amino group of certain lysine side chains within a histones basic N-terminal tail region. Within a histone octamer, these regions extend out from the associated globular domains, and in the context of a nucleosome, they are believed to bind the DNA through charge interactions (positively charged histone tails associated with negatively charged DNA) or mediate interactions between nucleosomes. Lysine acetylation, which neutralizes part of a tail regions positive charge, is postulated to weaken histone-DNA or nucleosome-nucleosome interactions and/or signal a conformational change, thereby destabilizing nucleosome structure or arrangement and giving other nuclear factors, such as the transcription complex, more access to a genetic locus. In agreement with this is the fact that acetylated chromatin has long been associated with states of transcriptional activation. Specific recognition of N6-acetyl-L-lysine is a conserved function of all bromodomains found in different proteins, recognized as an emerging intracellular signalling mechanism that plays critical roles in regulating gene transcription, cell-cycle progression, apoptosis, DNA repair, and cytoskeletal organization (PMID: 9169194 , 10827952 , 17340003 , 16247734 , 9478947 , 10839822 ). N-acetylated amino acids, such as N-epsilon-Acetyl-L-lysine can be released by an N-acylpeptide hydrolase from histones going through proteolytic degradation (PMID: 16465618). Many N-acetylamino acids 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). Isolated from sugarbeet (Beta vulgaris) KEIO_ID A174 Nepsilon-Acetyl-L-lysine is a derivative of the amino acid lysine.

N8-Acetylspermidine

N-[4-[(3-Aminopropyl)amino]butyl]-acetamide

C9H21N3O (187.1685)

N8-Acetylspermidine is a polyamine. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. Acetylation on the terminal nitrogen adjacent to the 4-carbon chain produces N8-acetylspermidine. This reaction is catalyzed by spermidine N8-acetyltransferase and does not result in the conversion of spermidine to putrescine but, instead, the product undergoes deacetylation. This acetyltransferase appears to be associated with chromatin in the cell nucleus and has been reported to be the same as (or related to) the enzyme(s) responsible for histone acetylation. N8-Acetylspermidine does not accumulate in tissues but rather appears to be rapidly deacetylated back to spermidine by a relatively specific cytosolic deacetylase, N8-acetylspermidine deacetylase. The function of this N8-acetylation/deacetylation pathway in cellular processes is not understood clearly, but several observations have suggested a role in cell growth and differentiation. (PMID: 12093478) [HMDB] N8-Acetylspermidine is a polyamine. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. Acetylation on the terminal nitrogen adjacent to the 4-carbon chain produces N8-acetylspermidine. This reaction is catalyzed by spermidine N8-acetyltransferase and does not result in the conversion of spermidine to putrescine. Instead, the product undergoes deacetylation. This acetyltransferase appears to be associated with chromatin in the cell nucleus and has been reported to be the same as (or related to) the enzyme(s) responsible for histone acetylation. N8-Acetylspermidine does not accumulate in tissues but rather appears to be rapidly deacetylated back to spermidine by a relatively specific cytosolic deacetylase, N8-acetylspermidine deacetylase. The function of this N8-acetylation/deacetylation pathway in cellular processes is not understood clearly, but several observations have suggested a role in cell growth and differentiation (PMID: 12093478). KEIO_ID A112

N-Methyltryptamine

[2-(1H-indol-3-yl)ethyl](methyl)amine

C11H14N2 (174.1157)

N-Methyltryptamine (NMT), or monomethyltryptamine, is a tryptamine alkaloid that has been found in the bark, shoots and leaves of numerous plants. (wikipedia). N-Methyltryptamine was detected in urine from all autistic patients with mental retardation and epilepsy and many autistic patients (32/47) with mental retardation (PubMed ID 8747157 ). N-Methyltryptamine (NMT), or monomethyltryptamine, is a tryptamine alkaloid that has been found in the bark, shoots and leaves of numerous plants. (wikipedia)

Prostaglandin B1

7-{2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}heptanoic acid

C20H32O4 (336.23)

Prostaglandin B1 (PGB1) is a metabolite of PGE1. PGE1 is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). PGB1does not inhibit phospholipase activity, but oligomers of PGB1 (PGBx) extracted from human neutrophils inhibit human phospholipases A2 in vitro and in situ in a dose-dependent manner; these oligomers inhibit arachidonic acid mobilization in human neutrophils and endothelial cells. One mechanism for the pharmacological effects of PGBx may be inhibition of cell-associated and extracellular phospholipase A2. PGB1 has the ability to enhance peripheral vascular resistance and elevate blood pressure. The effect is not central in origin and apparently is not the result of changes in cholinergic or alpha-adrenoceptor sensitivity or changes in vascular smooth muscle susceptibility per se. PGB1 blocks S-phase DNA synthesis; inhibition of DNA synthesis does not appear to require elevated levels of cAMP. (PMID: 7667505, 1477202, 2129000, 2597672, 6635328). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Prostaglandin B1 (PGB1) is a metabolite of PGE1. PGE1 is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2).

N-Acetylarylamine

N-Acetylaminobenzene

C8H9NO (135.0684)

N-Acetylarylamine is an odourless solid chemical of leaf or flake-like appearance. It is also known as acetanilide, N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin. N-Acetylarylamine has analgesic and fever-reducing properties; it is in the same class of drugs as acetaminophen (paracetamol). Under the name acetanilid it formerly figured in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately doing damage to the liver and kidneys. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study. Acetanilide has analgesic and fever-reducing properties; it is in the same class of drugs as acetaminophen (paracetamol). Under the name acetanilid it formerly figured in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately doing damage to the liver and kidneys. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study. KEIO_ID A130

Sulfadoxine

4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

C12H14N4O4S (310.0736)

Sulfadoxine is only found in individuals that have used or taken this drug. It is a long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections. [PubChem]Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid. D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent D000890 - Anti-Infective Agents > D013424 - Sulfanilamides CONFIDENCE standard compound; INTERNAL_ID 1010

4-Methylumbelliferone glucuronide

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic acid

C16H16O9 (352.0794)

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D049408 - Luminescent Agents D004396 - Coloring Agents > D005456 - Fluorescent Dyes

3,5-Diiodo-L-tyrosine

(2S)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid

C9H9I2NO3 (432.8672)

3,5-Diiodo-L-tyrosine, also known as diiy or DIT, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 3,5-Diiodo-L-tyrosine exists in all living organisms, ranging from bacteria to humans. In humans, 3,5-diiodo-L-tyrosine is involved in thyroid hormone synthesis. 3,5-Diiodo-L-tyrosine is a product from the iodination of monoiodotyrosine. A product from the iodination of monoiodotyrosine. In the biosynthesis of thyroid hormones, diiodotyrosine residues are coupled with other monoiodotyrosine or diiodotyrosine residues to form T4 or T3 thyroid hormones (thyroxine and triiodothyronine). [HMDB] H - Systemic hormonal preparations, excl. sex hormones and insulins > H03 - Thyroid therapy > H03B - Antithyroid preparations D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones KEIO_ID D056

Aminophenazone

4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one

C13H17N3O (231.1372)

Aminophenazone is only found in individuals that have used or taken this drug. It is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [PubChem]Aminophenazone is metabolized very slowly by normal newborn babies. In older infants, a higher amount of exhaled 13-CO2 is observed. N - Nervous system > N02 - Analgesics > N02B - Other analgesics and antipyretics > N02BB - Pyrazolones C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic CONFIDENCE standard compound; EAWAG_UCHEM_ID 702 KEIO_ID A069; [MS3] KO008857 KEIO_ID A069; [MS2] KO008856 KEIO_ID A069

Eprosartan

4-({2-butyl-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid

C23H24N2O4S (424.1457)

Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure. It acts on the renin-angiotensin system in two ways to decrease total peripheral resistance. First, it blocks the binding of angiotensin II to AT1 receptors in vascular smooth muscle, causing vascular dilatation. Second, it inhibits sympathetic norepinephrine production, further reducing blood pressure. C - Cardiovascular system > C09 - Agents acting on the renin-angiotensin system > C09C - Angiotensin ii receptor blockers (arbs), plain > C09CA - Angiotensin ii receptor blockers (arbs), plain C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent > C66930 - Angiotensin II Receptor Antagonist D057911 - Angiotensin Receptor Antagonists > D057912 - Angiotensin II Type 2 Receptor Blockers COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents CONFIDENCE standard compound; EAWAG_UCHEM_ID 2776 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Eprosartan (SKF-108566J free base) is a selective, competitive, nonpeptid and orally active angiotensin II receptor antagonist, used as an antihypertensive. Eprosartan binds angiotensin II receptor with IC50s of 9.2 nM and 3.9 nM in rat and human adrenal cortical membranes, respectively [1].

dGDP

[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

C10H15N5O10P2 (427.0294)

dGDP is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been removed (hence the deoxy- part of the name). Additionally, the diphosphate of the name indicates that one of the phosphoryl groups of GTP has been removed, most likely by hydrolysis . [HMDB]. dGDP is found in many foods, some of which are tea, black chokeberry, european plum, and roman camomile. dGDP is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been removed (hence the deoxy- part of the name). Additionally, the diphosphate of the name indicates that one of the phosphoryl groups of GTP has been removed, most likely by hydrolysis (Wikipedia). Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Phosphoenolpyruvic acid

Phosphoenolpyruvic Acid Trisodium Salt monohydrate

C3H5O6P (167.9824)

Phosphoenolpyruvate, also known as pep or 2-(phosphonooxy)-2-propenoic acid, is a member of the class of compounds known as phosphate esters. Phosphate esters are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group. Phosphoenolpyruvate is soluble (in water) and an extremely strong acidic compound (based on its pKa). Phosphoenolpyruvate can be found in a number of food items such as okra, endive, chestnut, and dandelion, which makes phosphoenolpyruvate a potential biomarker for the consumption of these food products. Phosphoenolpyruvate can be found primarily in blood, cellular cytoplasm, and saliva, as well as in human prostate tissue. Phosphoenolpyruvate exists in all living species, ranging from bacteria to humans. In humans, phosphoenolpyruvate is involved in several metabolic pathways, some of which include glycolysis, amino sugar metabolism, gluconeogenesis, and glycogenosis, type IC. Phosphoenolpyruvate is also involved in several metabolic disorders, some of which include glycogen storage disease type 1A (GSD1A) or von gierke disease, salla disease/infantile sialic acid storage disease, phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1), and pyruvate dehydrogenase complex deficiency. Phosphoenolpyruvate (2-phosphoenolpyruvate, PEP) as the ester derived from the enol of pyruvate and phosphate. It exists as an anion; the parent acid, which is only of theoretical interest, is phosphoenolpyruvic acid. PEP is an important intermediate in biochemistry. It has the highest-energy phosphate bond found (−61.9 kJ/mol) in living organisms, and is involved in glycolysis and gluconeogenesis. In plants, it is also involved in the biosynthesis of various aromatic compounds, and in carbon fixation; in bacteria, it is also used as the source of energy for the phosphotransferase system . Phosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia). [Spectral] Phosphoenolpyruvate (exact mass = 167.98237) and 6-Phospho-D-gluconate (exact mass = 276.02463) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID P007

Perillic acid

4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acid

C10H14O2 (166.0994)

Perillic acid, also known as perillate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Perillic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Perillic acid is an intermediate in the Limonene and pinene degradation pathway. (KEGG); Its measurement in urine is used to monitor cancer patients receiving oral Limonene (a farnesyl transferase inhibitor that has shown antitumor properties)(PubMed ID 8723738 ). Perillic acid is found in cardamom. C471 - Enzyme Inhibitor > C2020 - Farnesyl Transferase Inhibitor

4-Methylbenzoic acid

4-Toluic acid, potassium salt

C8H8O2 (136.0524)

4-Methylbenzoic acid is found in brassicas. 4-Methylbenzoic acid is isolated from horseradis KEIO_ID M017 p-Toluic acid (4-Methylbenzoic acid) is a substituted?benzoic acid?and can be used as an intermediate for the synthesis of para-aminomethylbenzoic acid (PAMBA), p-tolunitrile, etc. p-Toluic acid (4-Methylbenzoic acid) is a substituted?benzoic acid?and can be used as an intermediate for the synthesis of para-aminomethylbenzoic acid (PAMBA), p-tolunitrile, etc.

2,4,5-Trichlorophenoxyacetic acid

2-(2,4,5-trichlorophenoxy)acetic acid

C8H5Cl3O3 (253.9304)

CONFIDENCE standard compound; INTERNAL_ID 325; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5072; ORIGINAL_PRECURSOR_SCAN_NO 5067 CONFIDENCE standard compound; INTERNAL_ID 325; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5010; ORIGINAL_PRECURSOR_SCAN_NO 5009 CONFIDENCE standard compound; INTERNAL_ID 325; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4998; ORIGINAL_PRECURSOR_SCAN_NO 4994 CONFIDENCE standard compound; INTERNAL_ID 325; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4994; ORIGINAL_PRECURSOR_SCAN_NO 4991 CONFIDENCE standard compound; INTERNAL_ID 325; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4980; ORIGINAL_PRECURSOR_SCAN_NO 4977 CONFIDENCE standard compound; INTERNAL_ID 325; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4981; ORIGINAL_PRECURSOR_SCAN_NO 4979 D010575 - Pesticides > D006540 - Herbicides D016573 - Agrochemicals KEIO_ID T113

resmethrin

5-Benzyl-3-furylmethyl (1Rs,3Rs;1Rs,3Sr)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid

C22H26O3 (338.1882)

DATA_PROCESSING MERGING RMBmix ver. 0.2.7; CONFIDENCE standard compound; INTERNAL_ID 158; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10738; ORIGINAL_PRECURSOR_SCAN_NO 10736 CONFIDENCE standard compound; INTERNAL_ID 158; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10738; ORIGINAL_PRECURSOR_SCAN_NO 10736 CONFIDENCE standard compound; INTERNAL_ID 158; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10701; ORIGINAL_PRECURSOR_SCAN_NO 10696 CONFIDENCE standard compound; INTERNAL_ID 158; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10728; ORIGINAL_PRECURSOR_SCAN_NO 10725 INTERNAL_ID 158; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10689; ORIGINAL_PRECURSOR_SCAN_NO 10685 CONFIDENCE standard compound; INTERNAL_ID 158; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10714; ORIGINAL_PRECURSOR_SCAN_NO 10710 CONFIDENCE standard compound; INTERNAL_ID 158; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10668; ORIGINAL_PRECURSOR_SCAN_NO 10665 CONFIDENCE standard compound; INTERNAL_ID 158; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10689; ORIGINAL_PRECURSOR_SCAN_NO 10685 D010575 - Pesticides > D007306 - Insecticides > D011722 - Pyrethrins D016573 - Agrochemicals

Dicloxacillin

(2S,5R,6R)-6-({[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

C19H17Cl2N3O5S (469.0266)

Dicloxacillin is only found in individuals that have used or taken this drug. It is one of the penicillins which is resistant to penicillinase. [PubChem]Dicloxacillin exerts a bactericidal action against penicillin-susceptible microorganisms during the state of active multiplication. All penicillins inhibit the biosynthesis of the bacterial cell wall. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, dicloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that dicloxacillin interferes with an autolysin inhibitor. J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01C - Beta-lactam antibacterials, penicillins > J01CF - Beta-lactamase resistant penicillins D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D010406 - Penicillins D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic

Beclometasone

beclomethasone

C22H29ClO5 (408.1703)

A - Alimentary tract and metabolism > A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents > A07E - Intestinal antiinflammatory agents > A07EA - Corticosteroids acting locally R - Respiratory system > R03 - Drugs for obstructive airway diseases > R03B - Other drugs for obstructive airway diseases, inhalants > R03BA - Glucocorticoids D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07A - Corticosteroids, plain > D07AC - Corticosteroids, potent (group iii) R - Respiratory system > R01 - Nasal preparations > R01A - Decongestants and other nasal preparations for topical use > R01AD - Corticosteroids D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D005938 - Glucocorticoids C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents D000893 - Anti-Inflammatory Agents

Aristospan

Triamcinolone hexacetonide

C30H41FO7 (532.2836)

Hydroxyzine

2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)ethan-1-ol

C21H27ClN2O2 (374.1761)

A histamine H1 receptor antagonist that is effective in the treatment of chronic urticaria, dermatitis, and histamine-mediated pruritus. Unlike its major metabolite cetirizine, it does cause drowsiness. It is also effective as an antiemetic, for relief of anxiety and tension, and as a sedative. [PubChem] CONFIDENCE standard compound; INTERNAL_ID 1306; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8146; ORIGINAL_PRECURSOR_SCAN_NO 8142 CONFIDENCE standard compound; INTERNAL_ID 1306; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8167; ORIGINAL_PRECURSOR_SCAN_NO 8166 CONFIDENCE standard compound; INTERNAL_ID 1306; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8152; ORIGINAL_PRECURSOR_SCAN_NO 8147 CONFIDENCE standard compound; INTERNAL_ID 1306; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8169; ORIGINAL_PRECURSOR_SCAN_NO 8167 CONFIDENCE standard compound; INTERNAL_ID 1306; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8128; ORIGINAL_PRECURSOR_SCAN_NO 8124 CONFIDENCE standard compound; INTERNAL_ID 1306; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8120; ORIGINAL_PRECURSOR_SCAN_NO 8118 N - Nervous system > N05 - Psycholeptics > N05B - Anxiolytics > N05BB - Diphenylmethane derivatives D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists C308 - Immunotherapeutic Agent > C29578 - Histamine-1 Receptor Antagonist D003879 - Dermatologic Agents > D000982 - Antipruritics Hydroxyzine, a benzodiazepine antihistamine agent, acts as an orally active histamine?H1-receptor and serotonin antagonist. Hydroxyzine has anxiolytic effect and can be used for the research of generalised anxiety disorder[1].

Mepivacaine

N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide

C15H22N2O (246.1732)

A local anesthetic that is chemically related to bupivacaine but pharmacologically related to lidocaine. It is indicated for infiltration, nerve block, and epidural anesthesia. Mepivacaine is effective topically only in large doses and therefore should not be used by this route. (From AMA Drug Evaluations, 1994, p168) D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local > N01BB - Amides D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent CONFIDENCE standard compound; EAWAG_UCHEM_ID 3126

Pyridaben

4-Chloro-2-(1,1-dimethylethyl)-5-(((4-(1,1-dimethylethyl)phenyl)methyl)thio)-3(2H)-pyridazinone

C19H25ClN2OS (364.1376)

CONFIDENCE standard compound; INTERNAL_ID 331; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10598; ORIGINAL_PRECURSOR_SCAN_NO 10596 CONFIDENCE standard compound; INTERNAL_ID 331; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10636; ORIGINAL_PRECURSOR_SCAN_NO 10634 CONFIDENCE standard compound; INTERNAL_ID 331; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10546; ORIGINAL_PRECURSOR_SCAN_NO 10544 CONFIDENCE standard compound; INTERNAL_ID 331; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10660; ORIGINAL_PRECURSOR_SCAN_NO 10659 CONFIDENCE standard compound; INTERNAL_ID 331; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10708; ORIGINAL_PRECURSOR_SCAN_NO 10707 CONFIDENCE standard compound; INTERNAL_ID 331; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10670; ORIGINAL_PRECURSOR_SCAN_NO 10667 CONFIDENCE standard compound; INTERNAL_ID 2632

Orphenadrine

N,N-Dimethyl-2-[(O-methyl-alpha-phenylbenzyl)oxy]ethylamine

C18H23NO (269.178)

Orphenadrine is only found in individuals that have used or taken this drug. It is a muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm. [PubChem]Orphenadrine binds and inhibits both histamine H1 receptors and NMDA receptors. It restores the motor disturbances induced by neuroleptics, in particular the hyperkinesia. The dopamine deficiency in the striatum increases the stimulating effects of the cholinergic system. This stimulation is counteracted by the anticholinergic effect of orphenadrine. It may have a relaxing effect on skeletal muscle spasms and it has a mood elevating effect. D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065686 - Cytochrome P-450 CYP2B6 Inhibitors D002491 - Central Nervous System Agents > D018726 - Anti-Dyskinesia Agents > D000978 - Antiparkinson Agents C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents C78281 - Agent Affecting Musculoskeletal System > C29696 - Muscle Relaxant CONFIDENCE standard compound; EAWAG_UCHEM_ID 3276

Trichlormethiazide

6-chloro-3-(dichloromethyl)-1,1-dioxo-3,4-dihydro-2H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide

C8H8Cl3N3O4S2 (378.9022)

Trichlormethiazide is only found in individuals that have used or taken this drug. It is a thiazide diuretic with properties similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p830)Trichlormethiazide appears to block the active reabsorption of chloride and possibly sodium in the ascending loop of Henle, altering electrolyte transfer in the proximal tubule. This results in excretion of sodium, chloride, and water and, hence, diuresis. As a diuretic, Trichloromethiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like Trichloromethiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of Trichloromethiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle. C - Cardiovascular system > C03 - Diuretics > C03A - Low-ceiling diuretics, thiazides > C03AA - Thiazides, plain D045283 - Natriuretic Agents > D004232 - Diuretics > D049993 - Sodium Chloride Symporter Inhibitors C78275 - Agent Affecting Blood or Body Fluid > C448 - Diuretic > C49185 - Thiazide Diuretic D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D045283 - Natriuretic Agents D049990 - Membrane Transport Modulators

BRODIFACOUM

C31H23BrO3 (522.083)

D006401 - Hematologic Agents > D000925 - Anticoagulants > D015110 - 4-Hydroxycoumarins D010575 - Pesticides > D012378 - Rodenticides D016573 - Agrochemicals

Nilutamide

5,5-Dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)- 2,4-imidazolidinedione

C12H10F3N3O4 (317.0623)

Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration. CONFIDENCE standard compound; INTERNAL_ID 279; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4399; ORIGINAL_PRECURSOR_SCAN_NO 4395 CONFIDENCE standard compound; INTERNAL_ID 279; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4426; ORIGINAL_PRECURSOR_SCAN_NO 4421 CONFIDENCE standard compound; INTERNAL_ID 279; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4395; ORIGINAL_PRECURSOR_SCAN_NO 4393 CONFIDENCE standard compound; INTERNAL_ID 279; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4406; ORIGINAL_PRECURSOR_SCAN_NO 4401 CONFIDENCE standard compound; INTERNAL_ID 279; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4403; ORIGINAL_PRECURSOR_SCAN_NO 4401 CONFIDENCE standard compound; INTERNAL_ID 279; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4490; ORIGINAL_PRECURSOR_SCAN_NO 4487 L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02B - Hormone antagonists and related agents > L02BB - Anti-androgens D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D000726 - Androgen Antagonists C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C146993 - Androgen Receptor Inhibitor C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen D000970 - Antineoplastic Agents

Methomyl

(E)-[(methyl-C-hydroxycarbonimidoyl)oxy][1-(methylsulfanyl)ethylidene]amine

C5H10N2O2S (162.0463)

D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors C471 - Enzyme Inhibitor > C47792 - Acetylcholinesterase Inhibitor Methomyl is an Agricultural insecticide and nematocid CONFIDENCE standard compound; EAWAG_UCHEM_ID 2942 CONFIDENCE standard compound; INTERNAL_ID 2619 D010575 - Pesticides > D007306 - Insecticides D004791 - Enzyme Inhibitors D016573 - Agrochemicals

bendiocarb

2,2-dimethyl-2H-1,3-benzodioxol-4-yl N-methylcarbamate

C11H13NO4 (223.0845)

C471 - Enzyme Inhibitor > C47792 - Acetylcholinesterase Inhibitor CONFIDENCE standard compound; INTERNAL_ID 8476 CONFIDENCE standard compound; INTERNAL_ID 4024 CONFIDENCE standard compound; INTERNAL_ID 2606 D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals

Diethylstilbestrol

4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

C18H20O2 (268.1463)

Diethylstilbestrol is a synthetic estrogen that was developed to supplement a womans natural estrogen production. In 1971, the Food and Drug Administration (FDA) issued a Drug Bulletin advising physicians to stop prescribing DES to pregnant women because it was linked to a rare vaginal cancer in female offspring. Diethylstilbesterol is found in gram bean. Diethylstilbestrol is a synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CC - Estrogens, combinations with other drugs G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CB - Synthetic estrogens, plain L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02A - Hormones and related agents > L02AA - Estrogens D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D009676 - Noxae > D002273 - Carcinogens

Fluocinonide

2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-8-yl]-2-oxoethyl acetate

C26H32F2O7 (494.2116)

Fluocinonide is only found in individuals that have used or taken this drug. It is a topical glucocorticoid used in the treatment of eczema. [PubChem]Fluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort. Fluocinonide binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver. C - Cardiovascular system > C05 - Vasoprotectives > C05A - Agents for treatment of hemorrhoids and anal fissures for topical use > C05AA - Corticosteroids D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07A - Corticosteroids, plain > D07AC - Corticosteroids, potent (group iii) D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D005938 - Glucocorticoids C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid D000893 - Anti-Inflammatory Agents D018926 - Anti-Allergic Agents

Prazepam

7-chloro-1-(cyclopropylmethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

C19H17ClN2O (324.1029)

Prazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine that is used in the treatment of anxiety disorders. It is a schedule IV drug in the U.S. Prazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation. D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents N - Nervous system > N05 - Psycholeptics > N05B - Anxiolytics > N05BA - Benzodiazepine derivatives C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C1012 - Benzodiazepine D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators C78272 - Agent Affecting Nervous System > C28197 - Antianxiety Agent

Trihexyphenidyl

Pharmaceutical associates brand OF trihexyphenidyl hydrochloride

C20H31NO (301.2406)

Trihexyphenidyl is only found in individuals that have used or taken this drug. It is one of the centrally acting muscarinic antagonists used for treatment of parkinsonian disorders and drug-induced extrapyramidal movement disorders and as an antispasmodic. [PubChem]Trihexyphenidyl is a selective M1 muscarinic acetylcholine receptor antagonist. It is able to discriminate between the M1 (cortical or neuronal) and the peripheral muscarinic subtypes (cardiac and glandular). Trihexyphenidyl partially blocks cholinergic activity in the CNS, which is responsible for the symptoms of Parkinsons disease. It is also thought to increase the availability of dopamine, a brain chemical that is critical in the initiation and smooth control of voluntary muscle movement. D002491 - Central Nervous System Agents > D018726 - Anti-Dyskinesia Agents > D000978 - Antiparkinson Agents N - Nervous system > N04 - Anti-parkinson drugs > N04A - Anticholinergic agents > N04AA - Tertiary amines C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists C78272 - Agent Affecting Nervous System > C38149 - Antiparkinsonian Agent

Metaxalone

5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one

C12H15NO3 (221.1052)

Metaxalone (marketed by King Pharmaceuticals under the brand name Skelaxin) is a muscle relaxant used to relax muscles and relieve pain caused by strains, sprains, and other musculoskeletal conditions. Its exact mechanism of action is not known, but it may be due to general central nervous system depression. It is considered to be a moderately strong muscle relaxant, with relatively low incidence of side effects. Skelaxin comes in an 800 mg scored tablet. It previously came in both 400 mg and 800 mg tablets. The 400 mg tablet has been discontinued. Possible side effects include nausea, vomiting, drowsiness and CNS side effects such as dizziness, headache, and irritability. D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents C78281 - Agent Affecting Musculoskeletal System > C29696 - Muscle Relaxant D000890 - Anti-Infective Agents > D023303 - Oxazolidinones CONFIDENCE standard compound; EAWAG_UCHEM_ID 3127

Safrole

4-Allyl-1,2-(methylenedioxy)benzene, 8ci

C10H10O2 (162.0681)

Safrole, also known as shikimol, is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil, or synthesized from other related methylenedioxy compounds. It is the principal component of brown camphor oil, and is found in small amounts in a wide variety of plants, where it functions as a natural pesticide. Safrole is found in anise and nutmeg. Banned by FDA for use in food. Safrole is formerly used as a food flavour It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide and the recreational drug MDMA ("Ecstacy"). Safrole is a natural plant constituent, found in oil of sassafras and certain other essential oils. It is a member of the methylenedioxybenzene group of compounds, many of which (e.g. piperonyl butoxide) are extensively used as insecticide synergists. Safrole is a major source of human exposure to safrole is through consumption of spices, such as nutmeg, cinnamon and black pepper, in which safrole is a constituent. Safrole is also present in root beer, and has been used as an additive in chewing gum, toothpaste, soaps and certain pharmaceutical preparations. Safrole is a weak hepatocarcinogen and it is a matter of considerable interest whether the ally1 moiety or the methylenedioxy group, or both, are involved in the mechanism of its carcinogenesis. Safrole is extensively metabolized, giving rise to a large number of metabolites. Metabolism involves essentially two major routes, oxidation of the ally1 side chain, and oxidation of the methylenedioxy group with subsequent cleavage to form the catechol. Safrole undergoes oxidation of the allylic group to yield the 2, 3-epoxide (safrole epoxide). The dihydrodiol is one of the metabolites of safrole, and presumably arises from the hydration of the 2, 3-epoxide. The principal route of metabolism of safrole is through cleavage of the methylenedioxy group, the major metabolites being allylcatechol and its isomer, propenylcatechol. Eugenol and its isomer I-methoxy- 2-hydroxy-4-allylbenzene have been detected as minor metabolites in rat, mouse and human (PMID:6719936). The Ocotea cymbarum oil made of the Ocotea pretiosa, a plant growing in Brazil, and sassafras oil made of Sassafras albidum, a tree growing in eastern North America, are the main natural sources for safrole. It has a characteristic "candy-shop" aroma Occurs in nutmeg. Banned by FDA for use in food. Formerly used as a food flavour

Roseoflavin

8-Dimethylaminoriboflavin

C18H23N5O6 (405.1648)

A benzopteridine that is riboflavin in which the methyl group at position 8 is substituted by a dimethylamino group.

Zeranol

7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one

C18H26O5 (322.178)

Zeranol is isolated from Fusarium species. It is an anabolic agent and estrogenic agent (mainly veterinary use). Zeranol is used as a growth promoter for food animals. It was banned by the EU in 1989, but is still permitted in the USA and some other countries. It may also arise in livestock by ingestion of Fusarium contaminated pasture or feeds D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens Same as: D06362

Ergocornin

Ergocornine

C31H39N5O5 (561.2951)

Tetrahydrocorticosterone

1-[(1S,2S,5R,7R,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-hydroxyethan-1-one

C21H34O4 (350.2457)

Tetrahydrocorticosterone belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, tetrahydrocorticosterone is considered to be a steroid lipid molecule. Tetrahydrocorticosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tetrahydrocorticosterone is one of the major urinary metabolites from corticosterone. Premenopausal patients with early breast cancer excrete subnormal amounts of tetrahydrocorticosterone as compared with the normal subjects of corresponding ages (PMID: 1133844). D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

2-Hydroxymyristic acid

alpha-Hydroxy-N-tetradecylic acid

C14H28O3 (244.2038)

2-Hydroxymyristic acid is an analog of myristic acid that becomes metabolically activated in cells to form 2-hydroxymyristoyl-CoA, a potent inhibitor of myristoyl-CoA:protein N-myristoyltransferase, the enzyme that catalyzes protein N-myristoylation. Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. (PMID 8103677) [HMDB] 2-Hydroxymyristic acid is an analog of myristic acid that becomes metabolically activated in cells to form 2-hydroxymyristoyl-CoA, a potent inhibitor of myristoyl-CoA:protein N-myristoyltransferase, the enzyme that catalyzes protein N-myristoylation. Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. (PMID 8103677).

Docosatrienoate (22:3n3)

(13E,16E,19E)-Docosa-13,16,19-trienoic acid

C22H38O2 (334.2872)

Docosatrienoic acid, also known as docosatrienoate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Docosatrienoic acid is a very hydrophobic molecule, is practically insoluble (in water), and is relatively neutral. Application of docosatrienoic acid was shown to dose-dependently decrease the peak K+ current amplitude and accelerate the potassium activation and inactivation kinetics at all membrane potentials.

Promazine

N-Dimethylamino-1-methylethyl thiodiphenylamine

C17H20N2S (284.1347)

Promazine is only found in individuals that have used or taken this drug. It is a phenothiazine with actions similar to chlorpromazine but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic. [PubChem]Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazines antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. N - Nervous system > N05 - Psycholeptics > N05A - Antipsychotics > N05AA - Phenothiazines with aliphatic side-chain D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents > D018492 - Dopamine Antagonists C78272 - Agent Affecting Nervous System > C267 - Antiemetic Agent > C740 - Phenothiazine D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents C78272 - Agent Affecting Nervous System > C29710 - Antipsychotic Agent D005765 - Gastrointestinal Agents > D000932 - Antiemetics

Chloroprocaine

4-Amino-2-chlorobenzoic acid 2-(diethylamino)ethyl ester

C13H19ClN2O2 (270.1135)

Chloroprocaine hydrochloride is a local anesthetic given by injection during surgical procedures and labor and delivery. Chloroprocaine, like other local anesthetics, blocks the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse and by reducing the rate of rise of the action potential. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local > N01BA - Esters of aminobenzoic acid D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent

Fenoprofen

calcium(-1) anion; 2-(3-phenoxyphenyl)propanoate

C15H14O3 (242.0943)

Fenoprofen is only found in individuals that have used or taken this drug. It is an anti-inflammatory analgesic and antipyretic highly bound to plasma proteins. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding. [PubChem]Fenoprofens exact mode of action is unknown, but it is thought that prostaglandin synthetase inhibition is involved. Fenoprofen has been shown to inhibit prostaglandin synthetase isolated from bovine seminal vesicles. M - Musculo-skeletal system > M01 - Antiinflammatory and antirheumatic products > M01A - Antiinflammatory and antirheumatic products, non-steroids > M01AE - Propionic acid derivatives D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C471 - Enzyme Inhibitor > C1323 - Cyclooxygenase Inhibitor D000893 - Anti-Inflammatory Agents D004791 - Enzyme Inhibitors

Pemoline

2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one

C9H8N2O2 (176.0586)

N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics > N06BA - Centrally acting sympathomimetics D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant

Sekisanin

8H-[1,3]Dioxolo[6,7][2]benzopyrano[3,4-c]indol-6a(3H)-ol,4,4a,5,6-tetrahydro-3-methoxy-5-methyl-, (3S,4aS,6aS,13bS)-

C18H21NO5 (331.142)

Ciliatine

beta-Aminoethylphosphonic acid

C2H8NO3P (125.0242)

Ciliatine is an organophosphorus compound isolated from human and animal tissues. [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. Ciliatine is an organophosphorus compound isolated from human and animal tissues. KEIO_ID A056 (2-Aminoethyl)phosphonic acid is an endogenous metabolite.

4-Chloro-3-methylphenol

1-Chloro-2-methyl-4-hydroxybenzene

C7H7ClO (142.0185)

C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D016573 - Agrochemicals D010575 - Pesticides Same as: D03468

2,4-Dimethylphenol

2,4-Dimethylphenol titanium (+4)

C8H10O (122.0732)

3-(4-hydroxyphenyl)lactate

2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid

C9H10O4 (182.0579)

Hydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID: 4720815). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358). However, the D-form of hydroxyphenyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produce considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754). Hydroxyphenyllactic acid is a microbial metabolite found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416). Acquisition and generation of the data is financially supported in part by CREST/JST. Hydroxyphenyllactic acid is an antifungal metabolite.

Cysteic acid

2-Amino-3-sulfopropionic acid

C3H7NO5S (169.0045)

Cysteic acid is a crystalline amino acid formed in the oxidation of cysteine; it is a precursor of taurine. A crystalline amino acid formed in the oxidation of cysteine; it is a precursor of taurine. [HMDB]

N-Nitroso-pyrrolidine

tetrahydro-N-nitroso-Pyrrole

C4H8N2O (100.0637)

N-Nitroso-pyrrolidine belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. N-Nitroso-pyrrolidine has been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, pepper (c. annuum), red bell peppers, and yellow bell peppers. This could make N-nitroso-pyrrolidine a potential biomarker for the consumption of these foods. CONFIDENCE standard compound; EAWAG_UCHEM_ID 3450 Found in fried bacon

Propantheline

methylbis(propan-2-yl)[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium

C23H30NO3+ (368.2226)

Propantheline is only found in individuals that have used or taken this drug. It is a muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking. [PubChem]The action of propantheline is achieved via a dual mechanism: (1) a specific anticholinergic effect (antimuscarinic) at the acetylcholine-receptor sites and (2) a direct effect upon smooth muscle (musculotropic). A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03A - Drugs for functional gastrointestinal disorders > A03AB - Synthetic anticholinergics, quaternary ammonium compounds C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents

1-Phenylethylamine

1-Phenethylamine hydrochloride, (+-)-isomer

C8H11N (121.0891)

1-Phenylethylamine, or alpha-phenethylamine, is an amine. Individual enantiomers of this basic compound are useful for performing chiral resolution of acidic compounds by forming diastereomeric salts. -- Wikipedia [HMDB] 1-Phenylethylamine, or alpha-phenethylamine, is an amine. Individual enantiomers of this basic compound are useful for performing chiral resolution of acidic compounds by forming diastereomeric salts. -- Wikipedia.

4-Chloroaniline

4-Chloroaniline, trifluoroboron salt (1:1)

C6H6ClN (127.0189)

CONFIDENCE standard compound; INTERNAL_ID 1361; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3539; ORIGINAL_PRECURSOR_SCAN_NO 3535 CONFIDENCE standard compound; INTERNAL_ID 1361; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3530; ORIGINAL_PRECURSOR_SCAN_NO 3527 CONFIDENCE standard compound; INTERNAL_ID 1361; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3546; ORIGINAL_PRECURSOR_SCAN_NO 3542 CONFIDENCE standard compound; INTERNAL_ID 1361; DATASET 20200303_ENTACT_RP_MIX504; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3544; ORIGINAL_PRECURSOR_SCAN_NO 3541 CONFIDENCE standard compound; INTERNAL_ID 4138 CONFIDENCE standard compound; INTERNAL_ID 8258 CONFIDENCE standard compound; INTERNAL_ID 8115

Benz[c]acridine

12-Azabenz[a]anthracene

C17H11N (229.0891)

CONFIDENCE standard compound; INTERNAL_ID 8306 CONFIDENCE standard compound; INTERNAL_ID 8119

Tetrachlorosalicylanilide

2-Hydroxy-3,4,5,6-tetrachlorobenzanilide

C13H7Cl4NO2 (348.9231)

CONFIDENCE standard compound; INTERNAL_ID 2369 D004791 - Enzyme Inhibitors CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 8640 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 8243

1,4-Cyclohexanedione

C6H8O2 (112.0524)

3,4-Dihydroxymandelic acid

2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid

C8H8O5 (184.0372)

3,4-Dihydroxymandelic acid, also known as DOMA or 3,4-dihydroxyphenylglycolate, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxymandelic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxymandelic acid participates in a number of enzymatic reactions. In particular, 3,4-dihydroxymandelic acid can be biosynthesized from 3,4-dihydroxymandelaldehyde through its interaction with the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, 3,4-dihydroxymandelic acid and guaiacol can be converted into vanillylmandelic acid and pyrocatechol through the action of the enzyme catechol O-methyltransferase. In humans, 3,4-dihydroxymandelic acid is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxymandelic acid has been detected, but not quantified in several different foods, such as yellow wax beans, soy beans, pomegranates, cucurbita (gourd), and daikon radish. 3,4-dihydroxymandelic acid, also known as 3,4-dihydroxyphenylglycolate or (3,4-dihydroxyphenyl)(hydroxy)acetic acid, is a member of the class of compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-dihydroxymandelic acid is soluble (in water) and a moderately acidic compound (based on its pKa). 3,4-dihydroxymandelic acid can be found in a number of food items such as lime, pitanga, sapodilla, and persimmon, which makes 3,4-dihydroxymandelic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxymandelic acid can be found primarily in blood and urine, as well as in human nerve cells tissue. In humans, 3,4-dihydroxymandelic acid is involved in a couple of metabolic pathways, which include disulfiram action pathway and tyrosine metabolism. 3,4-dihydroxymandelic acid is also involved in several metabolic disorders, some of which include hawkinsinuria, alkaptonuria, dopamine beta-hydroxylase deficiency, and tyrosinemia, transient, of the newborn. D000890 - Anti-Infective Agents > D000892 - Anti-Infective Agents, Urinary > D008333 - Mandelic Acids Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID D066 3,4-Dihydroxymandelic acid is a metabolite of norepinephrine.

Quinoline-4-carboxylic acid

C10H7NO2 (173.0477)

NSC 13138 is an endogenous metabolite.

bestatin

(2R)-2-[[(2S,3R)-3-Amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acid

C16H24N2O4 (308.1736)

KEIO_ID B018; [MS2] KO009090 KEIO_ID B018 Bestatin is a natural, broad-spectrum, and competitive CD13 (Aminopeptidase N)/APN and leukotriene A4 hydrolase inhibitor. Bestatin has anticancer effects[1][2].

Fluperlapine

6-fluoro-10-(4-methylpiperazin-1-yl)-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,9,11,13-heptaene

C19H20FN3 (309.1641)

D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants C78272 - Agent Affecting Nervous System > C66885 - Serotonin Antagonist C78272 - Agent Affecting Nervous System > C66883 - Dopamine Antagonist

2-(Methylamino)benzoic acid

N-Methylanthranilic acid, 8ci

2-(Methylamino)benzoic acid is found in citrus. 2-(Methylamino)benzoic acid is isolated from grapefruit peel oi KEIO_ID M127 2-(Methylamino)benzoic acid is the main metabolite of methyl-N-methylanthranilates (MMA) (HY-76705) and is the compound in which the ester group is converted. MMA can be isolated from citrus fruits and has potential analgesic activity. 2-(Methylamino)benzoic acid was used to detect the metabolic levels of MMA in rat liver[1].

TES (buffer)

N-Tris[hydroxymethyl]methyl-2-aminoethanesulfonic acid [TES]

C6H15NO6S (229.062)

Tocainide

AstraZeneca brand OF tocainide hydrochloride

C11H16N2O (192.1263)

Tocainide is only found in individuals that have used or taken this drug. It is an antiarrhythmic agent which exerts a potential- and frequency-dependent block of sodium channels. [PubChem]Tocainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. Tocainide binds preferentially to the inactive state of the sodium channels.The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers. C - Cardiovascular system > C01 - Cardiac therapy > C01B - Antiarrhythmics, class i and iii > C01BB - Antiarrhythmics, class ib D002317 - Cardiovascular Agents > D026941 - Sodium Channel Blockers > D061567 - Voltage-Gated Sodium Channel Blockers C78274 - Agent Affecting Cardiovascular System > C47793 - Antiarrhythmic Agent D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D049990 - Membrane Transport Modulators C93038 - Cation Channel Blocker

3-methyl-2-oxovalerate

alpha-keto-beta-Methyl-n-valeric acid

3-Methyl-2-oxovaleric acid (CAS: 1460-34-0) is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. 3-Methyl-2-oxovaleric acid is a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of 3-methyl-2-oxovaleric acid are associated with maple syrup urine disease. MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465). 3-Methyl-2-oxovaleric 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. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated MSUD. Many affected children with organic acidemias experience intellectual disability or delayed development. (s)-3-methyl-2-oxopentanoate, also known as (3s)-2-oxo-3-methyl-N-valeric acid or (S)-omv, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Thus, (s)-3-methyl-2-oxopentanoate is considered to be a fatty acid lipid molecule (s)-3-methyl-2-oxopentanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). (s)-3-methyl-2-oxopentanoate can be found in a number of food items such as bean, prickly pear, wild leek, and nutmeg, which makes (s)-3-methyl-2-oxopentanoate a potential biomarker for the consumption of these food products (s)-3-methyl-2-oxopentanoate may be a unique S.cerevisiae (yeast) metabolite.

Hydroxyhydroquinone

1,2,4-Trihydroxybenzene

C6H6O3 (126.0317)

1,2,4-Trihydroxybenzene (Hydroxyhydroquinone), a by-product of coffee bean roasting, increases intracellular Ca2+ concentration in rat thymic lymphocytes[1]. 1,2,4-Trihydroxybenzene (Hydroxyhydroquinone), a by-product of coffee bean roasting, increases intracellular Ca2+ concentration in rat thymic lymphocytes[1].

Methyl acetate

Ethyl ester OF monoacetic acid

C3H6O2 (74.0368)

Methyl acetate belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Methyl acetate is present in apple, grape, banana and other fruits. Methyl acetate is a flavouring ingredient and it is an ester that, in the laboratory, is synthesized from acetic acid and methanol in the presence of strong acids such as sulfuric acid in an esterification reaction. In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed back into methanol and acetic acid, especially at elevated temperature. Methyl acetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. Methyl acetate has characteristics very similar to its analog ethyl acetate. Methyl acetate is used as a solvent in glues, paints, and nail polish removers, in chemical reactions, and for extractions. Methyl acetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent. Methyl acetate has a solubility of 25\\% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or acids. The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants Methyl acetate is an ester that is synthesized from acetic acid and methanol in the presence of strong acids such as sulfuric acid in an esterification reaction. In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed back into methanol and acetic acid, especially at elevated temperature.; Methyl acetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. Methyl acetate has characteristics very similar to its analog ethyl acetate. Methyl acetate is used as a solvent in glues, paints, and nail polish removers, in chemical reactions, and for extractions. Methyl acetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent. Methyl acetate has a solubility of 25\\% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or acids. Methyl acetate is VOC exempt.; The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants. Methyl acetate is a flavouring agent and can be found in many foods, some of which are apple, grape, banana, orange mint, and ginger.

p-Toluenesulfonic acid

4-methylbenzenesulfonic acid

C7H8O3S (172.0194)

p-Toluenesulfonic acid, also known as tosylate or para-toluene sulfonate, is a member of the class of compounds known as p-methylbenzenesulfonates. p-Methylbenzenesulfonates are benzenesulfonic acids (or derivative thereof) carrying a methyl group at the para- position. p-Toluenesulfonic acid is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). p-Toluenesulfonic acid (PTSA or pTsOH) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H. It is a white solid that is soluble in water, alcohols, and other polar organic solvents. The CH3C6H4SO2– group is known as the tosyl group and is often abbreviated as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH•H2O. It is a white solid that is soluble in water, alcohols, and other polar organic solvents (Wikipedia). CONFIDENCE standard compound; INTERNAL_ID 337; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2502; ORIGINAL_PRECURSOR_SCAN_NO 2501 CONFIDENCE standard compound; INTERNAL_ID 337; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2509; ORIGINAL_PRECURSOR_SCAN_NO 2508 CONFIDENCE standard compound; INTERNAL_ID 337; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2534; ORIGINAL_PRECURSOR_SCAN_NO 2533 CONFIDENCE standard compound; INTERNAL_ID 337; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2493; ORIGINAL_PRECURSOR_SCAN_NO 2492 CONFIDENCE standard compound; INTERNAL_ID 337; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2571; ORIGINAL_PRECURSOR_SCAN_NO 2570 CONFIDENCE standard compound; INTERNAL_ID 337; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2508; ORIGINAL_PRECURSOR_SCAN_NO 2507

2,2',5,5'-Tetrachlorobiphenyl

1,4-dichloro-2-(2,5-dichlorophenyl)benzene

C12H6Cl4 (289.9224)

D004785 - Environmental Pollutants > D011078 - Polychlorinated Biphenyls

13-HOTE

(9Z,11E,15Z)-(13S)-13-Hydroxyoctadeca-9,11,15-trienoic acid

C18H30O3 (294.2195)

13-HOTE is a biologically active lipid molecule produced due to altered intestinal lipid metabolism indicative of Alox15 activity. (PMID: 18258795) [HMDB] 13-HOTE is a biologically active lipid molecule produced due to altered intestinal lipid metabolism indicative of Alox15 activity. (PMID: 18258795).

Chlorthal-dimethyl

1,4-Dimethyl 2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid

C10H6Cl4O4 (329.902)

CONFIDENCE standard compound; EAWAG_UCHEM_ID 3701

Oxamniquine

(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol

C14H21N3O3 (279.1583)

An anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs. (From Martidale, The Extra Pharmacopoeia, 31st ed, p121) P - Antiparasitic products, insecticides and repellents > P02 - Anthelmintics > P02B - Antitrematodals > P02BA - Quinoline derivatives and related substances D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C250 - Antihelminthic Agent

(2E)-Decenoyl-ACP

1-Amino-1-cyclopentanecarboxylic acid

C6H11NO2 (129.079)

(2E)-Decenoyl-ACP, also known as Cycloleucine or 1-Aminocyclopentanecarboxylic acid, is classified as a member of the L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. (2E)-Decenoyl-ACP is considered to be soluble (in water) and acidic Acquisition and generation of the data is financially supported in part by CREST/JST. C308 - Immunotherapeutic Agent > C574 - Immunosuppressant KEIO_ID A050

D-Arabinose 5-phosphate

{[(2R,3R,4S)-2,3,4-trihydroxy-5-oxopentyl]oxy}phosphonic acid

C5H11O8P (230.0192)

D-Arabinose 5-phosphate is an intermediate in biosynthesis of lipopolysaccharide. It is reversibly converted to D-ribulose 5-phosphate by arabinose-5-phosphate isomerase (EC 5.3.1.13). Acquisition and generation of the data is financially supported in part by CREST/JST. D-Arabinose 5-phosphate is an intermediate in biosynthesis of lipopolysaccharide. KEIO_ID A147

4-Fluorobenzoic acid

4-Fluorobenzoic acid, copper (+2) salt dihydrate

KEIO_ID F023

o-Fluorobenzoate

2-FLUOROBENZOIC ACID

KEIO_ID F024

Methionine sulfoximine

Butanoic acid, 2-amino-4-(S-methylsulfonimidoyl)- (9ci)

C5H12N2O3S (180.0569)

Methionine sulfoximine is found in flours treated with NCl3 as a produced of NCl3 action on wheat protein

Phenoxyacetic acid

Glycollic acid phenyl ether

Phenoxyacetic acid is found in cocoa and cocoa products. Phenoxyacetic acid is a flavouring ingredient. Phenoxyacetic acid is present in cocoa bean Phenoxyacetic acid is a flavouring ingredient. It is found in cocoa and cocoa products. COVID info from PDB, Protein Data Bank KEIO_ID P129 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Phenoxyacetic acid is an endogenous metabolite.

Vistamycin

ribostamycin

C17H34N4O10 (454.2275)

J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01G - Aminoglycoside antibacterials C784 - Protein Synthesis Inhibitor > C2363 - Aminoglycoside Antibiotic D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents C254 - Anti-Infective Agent > C258 - Antibiotic KEIO_ID R016

Thiamine monophosphate

2-[3-[(4-Azanyl-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acid

[C12H18N4O4PS]+ (345.0786)

Thiamine monophosphate, also known as thiamin phosphoric acid or TMP, belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. Thiamine monophosphate is a very strong basic compound (based on its pKa). Thiamine monophosphate is one of the five known natural thiamine phosphate derivatives. Thiamine (vitamin B1) is the transport form of the vitamin while the phosphorylated derivatives are the active forms. Thiamine dihydrogen phosphate ester. The monophosphate ester of thiamine. Synonyms: monophosphothiamine; vitamin B1 monophosphate. -- Pubchem [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. D018977 - Micronutrients > D014815 - Vitamins KEIO_ID T057; [MS3] KO009298 KEIO_ID T057; [MS2] KO009297 KEIO_ID T057

Undecylenic acid

Zinc undecylenate (undecylenic acid)

Undecylenic acid, also known as 10-undecylenate or omega-undecenoic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecylenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Undecylenic acid is found in black elderberry. Undecylenic acid is a flavouring ingredient and is a sweet and woody-tasting compound. Undecylenic acid was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID:31477923). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health. Undecylenic acid is used in the production of the bioplastic Nylon-11, in the treatment of fungal infections in the skin, and as a precursor in the manufacture of a wide assortment of pharmaceuticals, cosmetics, perfumes, and personal hygiene products. D - Dermatologicals > D01 - Antifungals for dermatological use > D01A - Antifungals for topical use Flavouring ingredient. Undecylenic acid is found in black elderberry. C254 - Anti-Infective Agent > C514 - Antifungal Agent Same as: D02159 10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal. 10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal.

Isobutyryl-CoA

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

C25H42N7O17P3S (837.1571)

Isobutyryl-CoA is a substrate for Acyl-CoA dehydrogenase (short-chain specific, mitochondrial), Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial) and Acyl-CoA dehydrogenase (long-chain specific, mitochondrial). [HMDB] Isobutyryl-CoA is a substrate for Acyl-CoA dehydrogenase (short-chain specific, mitochondrial), Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial) and Acyl-CoA dehydrogenase (long-chain specific, mitochondrial). Acquisition and generation of the data is financially supported in part by CREST/JST.

Nicotinic acid mononucleotide

3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium

[C11H15NO9P]+ (336.0484)

Nicotinic acid mononucleotide, also known as nicotinate ribonucleotide, belongs to the class of organic compounds known as nicotinic acid nucleotides. These are pyridine nucleotides in which the pyridine base is nicotinic acid or a derivative thereof. Nicotinic acid mononucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinic acid mononucleotide an intermediate in the cofactor biosynthesis and the nicotinate and nicotinamide metabolism pathways. It is a substrate for nicotinamide riboside kinase, ectonucleotide pyrophosphatase/phosphodiesterase, nicotinamide mononucleotide adenylyltransferase, 5-nucleotidase, nicotinate-nucleotide pyrophosphorylase, and 5(3)-deoxyribonucleotidase. Nicotinic acid mononucleotide is an intermediate in the metabolism of Nicotinate and nicotinamide. It is a substrate for Ectonucleotide pyrophosphatase/phosphodiesterase 2, Ectonucleotide pyrophosphatase/phosphodiesterase 1, Nicotinamide mononucleotide adenylyltransferase 3, Cytosolic 5-nucleotidase IA, Cytosolic 5-nucleotidase IB, Nicotinate-nucleotide pyrophosphorylase, 5(3)-deoxyribonucleotidase (cytosolic type), Cytosolic purine 5-nucleotidase, Nicotinamide mononucleotide adenylyltransferase 2, Ectonucleotide pyrophosphatase/phosphodiesterase 3, 5-nucleotidase, 5(3)-deoxyribonucleotidase (mitochondrial) and Nicotinamide mononucleotide adenylyltransferase 1. [HMDB] NaMN is the most common mononucleotide intermediate (a hub) in NAD biogenesis. For example, in E. coli all three pyridine precursors are converted into NaMN (Table 1 and Figure 3(a)). Qa produced by the de novo Asp–DHAP pathway (genes nadB and nadA) is converted into NaMN by QAPRT (gene nadC). Salvage of both forms of niacin proceeds via NAPRT (gene pncB) either directly upon or after deamidation by NMDSE (gene pncA). Overall, more than 90\% of approximately 680 analyzed bacterial genomes contain at least one of the pathways leading to the formation of NaMN. Most of them (∼480 genomes) have the entire set of nadBAC genes for NaMN de novo synthesis from Asp that are often clustered on the chromosome and/or are co-regulated by the same transcription factors (see Section 7.08.3.1.2). Among the examples provided in Table 1, F. tularensis (Figure 4(c)) has all three genes of this de novo pathway forming a single operon-like cluster and supporting the growth of this organism in the absence of any pyridine precursors in the medium. More than half the genomes with the Asp–DHAP pathway also contain a deamidating niacin salvage pathway (genes pncAB) as do many representatives of the α-, β-, and γ-Proteobacteria, Actinobacteria, and Bacillus/Clostridium group. As already emphasized, the genomic reconstruction approach provides an assessment of the metabolic potential of an organism, which may or may not be realized under given conditions. For example, E. coli and B. subtilis can utilize both de novo and PncAB Nm salvage pathways under the same growth conditions, whereas in M. tuberculosis (having the same gene pattern) the latter pathway was considered nonfunctional, so that the entire NAD pool is generated by the de novo NadABC route. However, a recent study demonstrated the functional activity of the Nm salvage pathway in vivo, under hypoxic conditions in infected macrophages.221 This study also implicated the two downstream enzymes of NAD synthesis (NAMNAT and NADSYN) as attractive chemotherapeutic targets to treat acute and latent forms of tuberculosis. In approximately 100 species, including many Cyanobacteria (e.g., Synechococcus spp.), Bacteroidetes (e.g., Chlorobium spp.) and Proteobacteria (e.g., Caulobacter crescentus, Zymomonas mobilis, Desulfovibrio spp., and Shewanella spp. representing α-, β-, δ-, and γ-groups, respectively) the Asp–DHAP pathway is the only route to NAD biogenesis. Among them, nearly all Helicobacter spp. (except H. hepaticus), contain only the two genes nadA and nadC but lack the first gene of the pathway (nadB), which is a likely subject of nonorthologous gene replacement. One case of NadB (ASPOX) replacement by the ASPDH enzyme in T. maritima (and methanogenic archaea) was discussed in Section 7.08.2.1. However, no orthologues of the established ASPDH could be identified in Helicobacter spp. as well as in approximately 15 other diverse bacterial species that have the nadAC but lack the nadB gene (e.g., all analyzed Corynebacterium spp. except for C. diphtheriae). Therefore, the identity of the ASPOX or ASPDH enzyme in these species is still unknown, representing one of the few remaining cases of ‘locally missing genes’220 in the NAD subsystem. All other bacterial species contain either both the nadA and nadB genes (plus nadC) or none. In a limited number of bacteria (∼20 species), mostly in the two distant groups of Xanthomonadales (within γ-Proteobacteria) and Flavobacteriales (within Bacteroidetes), the Asp–DHAP pathway of Qa synthesis is replaced by the Kyn pathway. As described in Section 7.08.2.1.2, four out of five enzymes (TRDOX, KYNOX, KYNSE, and HADOX) in the bacterial version of this pathway are close homologues of the respective eukaryotic enzymes, whereas the KYNFA gene is a subject of multiple nonorthologous replacements. Although the identity of one alternative form of KYNFA (gene kynB) was established in a group of bacteria that have a partial Kyn pathway for Trp degradation to anthranilate (e.g., in P. aeruginosa or B. cereus57), none of the known KYNFA homologues are present in Xanthomonadales or Flavobacteriales. In a few species (e.g., Salinispora spp.) a complete gene set of the Kyn pathway genes co-occurs with a complete Asp–DHAP pathway. Further experiments would be required to establish to what extent and under what conditions these two pathways contribute to Qa formation. As discussed, the QAPRT enzyme is shared by both de novo pathways, and a respective gene, nadC is always found in the genomes containing one or the other pathway. Similarly, gene nadC always co-occurs with Qa de novo biosynthetic genes with one notable exception of two groups of Streptococci, S. pneumonaie and S. pyogenes. Although all other members of the Lactobacillales group also lack the Qa de novo biosynthetic machinery and rely entirely on niacin salvage, only these two human pathogens contain a nadC gene. The functional significance of this ‘out of context’ gene is unknown, but it is tempting to speculate that it may be involved in a yet-unknown pathway of Qa salvage from the human host. Among approximately 150 bacterial species that lack de novo biosynthesis genes and rely on deamidating salvage of niacin (via NAPRT), the majority (∼100) are from the group of Firmicutes. Such a functional variant (illustrated for Staphylococcus aureus in Figure 4(b)) is characteristic of many bacterial pathogens, both Gram-positive and Gram-negative (e.g., Brucella, Bordetella, and Campylobacter spp. from α-, β-, and δ-Proteobacteria, Borrelia, and Treponema spp. from Spirochaetes). Most of the genomes in this group contain both pncA and pncB genes that are often clustered on the chromosome and/or are co-regulated (see Section 7.08.3.1.2). In some cases (e.g., within Mollicutes and Spirochaetales), only the pncB, but not the pncA gene, can be reliably identified, suggesting that either of these species can utilize only the deamidated form of niacin (Na) or that some of them contain an alternative (yet-unknown) NMASE. Although the nondeamidating conversion of Nm into NMN (via NMPRT) appears to be present in approximately 50 bacterial species (mostly in β- and γ-Proteobacteria), it is hardly ever the only route of NAD biogenesis in these organisms. The only possible exception is observed in Mycoplasma genitalium and M. pneumoniae that contain the nadV gene as the only component of pyridine mononucleotide biosynthetic machinery. In some species (e.g., in Synechocystes spp.), the NMPRT–NMNAT route is committed primarily to the recycling of endogenous Nm. On the other hand, in F. tularensis (Figure 4(c)), NMPRT (gene nadV) together with NMNAT (of the nadM family) constitute the functional nondeamidating Nm salvage pathway as it supports the growth of the nadE′-mutant on Nm but not on Na (L. Sorci et al., unpublished). A similar nondeamidating Nm salvage pathway implemented by NMPRT and NMNAT (of the nadR family) is present in some (but not all) species of Pasteurellaceae in addition to (but never instead of) the RNm salvage pathway (see below), as initially demonstrated for H. ducreyi.128 A two-step conversion of NaMN into NAD via a NaAD intermediate (Route I in Figure 2) is present in the overwhelming majority of bacteria. The signature enzyme of Route I, NAMNAT of the NadD family is present in nearly all approximately 650 bacterial species that are expected to generate NaMN via de novo or salvage pathways (as illustrated by Figures 3(a) and 3(b)). All these species, without a single exception, also contain NADSYN (encoded by either a short or a long form of the nadE gene), which is required for this route. The species that lack the NadD/NadE signature represent several relatively rare functional variants, including: 1. Route I of NAD synthesis (NaMN → NaAD → NAD) variant via a bifunctional NAMNAT/NMNAT enzyme of the NadM family is common for archaea (see Section 7.08.3.2), but it appears to be present in only a handful of bacteria, such as Acinetobacter, Deinococcus, and Thermus groups. Another unusual feature of the latter two groups is the absence of the classical NADKIN, a likely subject of a nonorthologous replacement that remains to be elucidated. 2. Route II of NAD synthesis (NaMN → NMN → NAD). This route is implemented by a combination of the NMNAT of either the NadM family (as in F. tularensis) or the NadR family (as in M. succinoproducens and A. succinogenes) with NMNSYN of the NadE′ family. The case of F. tularensis described in Section 7.08.2.4 is illustrated in Figure 3(b). The rest of the NAD biosynthetic machinery in both species from the Pasteurellaceae group, beyond the shared Route II, is remarkably different from that in F. tularensis. Instead of de novo biosynthesis, they harbor a Na salvage pathway via NAPRT encoded by a pncB gene that is present in a chromosomal cluster with nadE′. Neither of these two genes are present in other Pasteurellaceae that lack the pyridine carboxylate amidation machinery (see below). 3. Salvage of RNm (RNm → NMN → NAD). A genomic signature of this pathway, a combination of the PnuC-like transporter and a bifunctional NMNAT/RNMKIN of the NadR family, is present in many Enterobacteriaceae and in several other diverse species (e.g., in M. tuberculosis). However, in H. influenzae (Figure 3(d)) and related members of Pasteurellaceae, it is the only route of NAD biogenesis. As shown in Table 1, H. influenzae as well as many other members of this group have lost nearly all components of the rich NAD biosynthetic machinery that are present in their close phylogenetic neighbors (such as E. coli and many other Enterobacteriaceae). This pathway is an ultimate route for utilization of the so called V-factors (NADP, NAD, NMN, or RNm) that are required to support growth of H. influenzae. It was established that all other V-factors are degraded to RNm by a combination of periplasmic- and membrane-associated hydrolytic enzymes.222 Although PnuC was initially considered an NMN transporter,223 its recent detailed analysis in both H. influenzae and Salmonella confirmed that its actual physiological function is in the uptake of RNm coupled with the phosphorylation of RNM to NMN by RNMKIN.17,148,224 As already mentioned, H. ducreyi and several other V-factor-independent members of the Pasteurellaceae group (H. somnus, Actinobacillus pleuropneumoniae, and Actinomycetemcomitans) harbor the NMNAT enzyme (NadV) that allows them to grow in the presence of Nm (but not Na) in the medium (Section 7.08.2.2). 4. Uptake of the intact NAD. Several groups of phylogenetically distant intracellular endosymbionts with extremely truncated genomes contain only a single enzyme, NADKIN, from the entire subsystem. Among them are all analyzed species of the Wolbachia, Rickettsia, and Blochmannia groups. These species are expected to uptake and utilize the intact NAD from their host while retaining the ability to convert it into NADP. Among all analyzed bacteria, only the group of Chlamydia does not have NADKIN and depends on the salvage of both NAD and NADP via a unique uptake system.157 A comprehensive genomic reconstruction of the metabolic potential (gene annotations and asserted pathways) across approximately 680 diverse bacterial genomes sets the stage for the accurate cross-genome projection and prediction of regulatory mechanisms that control the realization of this potential in a variety of species and growth conditions. In the next section, we summarize the recent accomplishments in the genomic reconstruction of NAD-related regulons in bacteria. Nicotinic acid mononucleotide. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=321-02-8 (retrieved 2024-06-29) (CAS RN: 321-02-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Himbacine

(+)-Himbacine

C22H35NO2 (345.2668)

A piperidine alkaloid that is decahydronaphtho[2,3-c]furan-1(3H)-one substituted by a methyl group at position 3 and a 2-[(2R,6S)-1,6-dimethylpiperidin-2-yl]ethenyl group at position 4. It has been isolated from the bark of Australian magnolias. D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics relative retention time with respect to 9-anthracene Carboxylic Acid is 0.814 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.809

Neoxanthin

(1R,3S)-6-[(1M,3E,5E,7E,9E,11E,13E,15Z,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,3-diol

C40H56O4 (600.4178)

Neoxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Xanthophylls arise by oxygenation of the carotene backbone. Neoxanthin is an intermediate in the synthesis of abscisic acid from violaxanthin. Neoxanthin has been detected, but not quantified in, several different foods, such as apples, paprikas, Valencia oranges, kiwis, globe artichokes, sparkleberries, hard wheat, and cinnamon. This could make neoxanthin a potential biomarker for the consumption of these foods. Neoxanthin has been shown to exhibit apoptotic and anti-proliferative functions (PMID: 15333710, 15333710). Neoxanthin is a carotenoid and xanthophyll. In plants, it is an intermediate in the biosynthesis of the plant hormone abscisic acid. It is produced from violaxanthin by the action of neoxanthin synthase. It is a major xanthophyll found in green leafy vegetables such as spinach. [Wikipedia] D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

all-trans-Phytofluene

(6E,10E,12E,14E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaene

C40H62 (542.4851)

all-trans-Phytofluene is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds, and crustacea. Animals are unable to synthesize carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048, 15003396). D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids 7,7,8,8,11,12-Hexahydro-Carotene is a carotenoid found in human fluids.

lupinine

Octahydro-2H-quinolizin-1-ylmethanol

C10H19NO (169.1467)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 41 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 55 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 34 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 19 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 11 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 26 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 4

Hexylglutathione

2-Amino-5-((1-((carboxymethyl)amino)-3-(hexylthio)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid

C16H29N3O6S (391.1777)

D004791 - Enzyme Inhibitors

N-hexanoyl-L-Homoserine lactone

N-[(3S)-tetrahydro-2-oxo-3-furanyl]-hexanamide

C10H17NO3 (199.1208)

N-Hexanoyl-L-homoserine lactone (HHSL) is a type of signaling molecule known as an autoinducer, which plays a significant role in bacterial communication and behavior, particularly in processes governed by quorum sensing (QS). Here are some of its key biological functions: Quorum Sensing Signaling: HHSL is involved in quorum sensing, a mechanism by which bacteria communicate with each other to coordinate their behavior based on population density. When the concentration of HHSL reaches a certain threshold, it triggers specific responses in the bacterial population. Regulation of Gene Expression: In many bacteria, HHSL binds to specific transcriptional regulators, leading to the activation or repression of target genes. This regulation can control a variety of biological processes, including bioluminescence, biofilm formation, virulence factor production, and sporulation. Biofilm Formation: HHSL can influence the formation and maintenance of biofilms, which are complex communities of bacteria encased in a self-produced matrix. Biofilms are often associated with increased resistance to antibiotics and host immune responses. Virulence and Pathogenicity: In pathogenic bacteria, HHSL can regulate the expression of virulence factors, contributing to the bacteria’s ability to cause disease. By modulating these factors, HHSL can affect the bacteria’s interaction with the host and its ability to evade the immune system. Symbiotic Interactions: HHSL is not only important in pathogenic bacteria but also in beneficial interactions, such as those found in nitrogen-fixing bacteria or in symbiotic relationships with plants and animals. Understanding the role of HHSL and other autoinducers in bacterial communication and behavior is crucial for developing new strategies to control bacterial infections and manage biofilm-related issues.

N-Octanoyl-DL-homoserine lactone

N-(2-Oxotetrahydrofuran-3-YL)octanamide

C12H21NO3 (227.1521)

1-O-Acetyllycorine

Lycorine, 1-O-acetyl-

C18H19NO5 (329.1263)

1-Hydroxyisoquinoline

1,2-dihydroisoquinolin-1-one

C9H7NO (145.0528)

CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 70 COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Enterodiol

[R-(R*,r*)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediol

C18H22O4 (302.1518)

Enterodiol is one of the most important lignan-type phytoestrogens identified in serum, urine, bile and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have been categorized according to their chemical structures as isoflavones, lignans and coumestans. Enterodiol is formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole-grain cereals (barley, rye and wheat), seeds, nuts, legumes and vegetables. (PMID: 12270221, J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309.) [HMDB]. Enterodiol is a biomarker for the consumption of soy beans and other soy products. Enterodiol is one of the most important lignan-type phytoestrogens identified in serum, urine, bile, and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have been categorized according to their chemical structures as isoflavones, lignans, and coumestans. Enterodiol is formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole-grain cereals (barley, rye, and wheat), seeds, nuts, legumes, and vegetables (PMID: 12270221, J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309.). Enterodiol is a biomarker for the consumption of soy beans and other soy products. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens

Prostaglandin I2

5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

Prostaglandin I2 or prostacyclin (or PGI2) is a member of the family of lipid molecules known as eicosanoids. It is produced in endothelial cells from prostaglandin H2 (PGH2) by the action of the enzyme prostacyclin synthase. It is a powerful vasodilator and inhibits platelet aggregation. Prostaglandin I2 is the main prostaglandin synthesized by the blood vessel wall. This suggests that it may play an important role in limiting platelet-mediated thrombosis. In particular, prostacyclin (PGI2) chiefly prevents formation of the platelet plug involved in primary hemostasis (a part of blood clot formation). The sodium salt (known as epoprostenol) has been used to treat primary pulmonary hypertension. Prostacyclin (PGI2) is released by healthy endothelial cells and performs its function through a paracrine signaling cascade that involves G protein-coupled receptors on nearby platelets and endothelial cells. The platelet Gs protein-coupled receptor (prostacyclin receptor) is activated when it binds to PGI2. This activation, in turn, signals adenylyl cyclase to produce cAMP. cAMP goes on to inhibit any undue platelet activation (in order to promote circulation) and also counteracts any increase in cytosolic calcium levels which would result from thromboxane A2 (TXA2) binding (leading to platelet activation and subsequent coagulation). PGI2 also binds to endothelial prostacyclin receptors and in the same manner raise cAMP levels in the cytosol. This cAMP then goes on to activate protein kinase A (PKA). PKA then continues the cascade by inhibiting myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation. Notably, PGI2 and TXA2 work as antagonists. PGI2 is stable in basic buffers (pH=8), but it is rapidly hydrolyzed to 6-keto PGF1alpha in neutral or acidic solutions. The half-life is short both in vivo and in vitro, ranging from 30 seconds to a few minutes. PGI2 is administered by continuous infusion in humans for the treatment of idiopathic pulmonary hypertension.Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Prostaglandin I2 or prostacyclin (or PGI2) is a member of the family of lipid molecules known as eicosanoids. It is produced in endothelial cells from prostaglandin H2 (PGH2) by the action of the enzyme prostacyclin synthase. It is a powerful vasodilator and inhibits platelet aggregation. Prostaglandin I2 is the main prostaglandin synthesized by the blood vessel wall. This suggests that it may play an important role in limiting platelet-mediated thrombosis. In particular, prostacyclin (PGI2) chiefly prevents formation of the platelet plug involved in primary hemostasis (a part of blood clot formation). The sodium salt (known as epoprostenol) has been used to treat primary pulmonary hypertension. Prostacyclin (PGI2) is released by healthy endothelial cells and performs its function through a paracrine signaling cascade that involves G protein-coupled receptors on nearby platelets and endothelial cells. The platelet Gs protein-coupled receptor (prostacyclin receptor) is activated when it binds to PGI2. This activation, in turn, signals adenylyl cyclase to produce cAMP. cAMP goes on to inhibit any undue platelet activation (in order to promote circulation) and also counteracts any increase in cytosolic calcium levels which would result from thromboxane A2 (TXA2) binding (leading to platelet activation and subsequent coagulation). PGI2 also binds to endothelial prostacyclin receptors and in the same manner raise cAMP levels in the cytosol. This cAMP then goes on to activate protein kinase A (PKA). PKA then continues the cascade by inhibiting myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation. Notably, PGI2 and TXA2 work as antagonists. PGI2 is stable in basic buffers (pH=8), but it is rapidly hydrolyzed to 6-keto PGF1alpha in neutral or acidic solutions. The half-life is short both in vivo and in vitro, ranging from 30 seconds to a few minutes. PGI2 is administered by continuous infusion in humans for the treatment of idiopathic pulmonary hypertension. B - Blood and blood forming organs > B01 - Antithrombotic agents > B01A - Antithrombotic agents > B01AC - Platelet aggregation inhibitors excl. heparin C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents C78568 - Prostaglandin Analogue Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

echinenone

Echinenone/ (Myxoxanthin)

C40H54O (550.4174)

A carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan.

Beta-tocopherol

(2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

C28H48O2 (416.3654)

Brassicasterol

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C28H46O (398.3548)

Brassicasterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, brassicasterol is considered to be a sterol lipid molecule. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Brassicasterol is a potential CSF biomarker for Alzheimer’s disease (PMID: 21585343). C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Constituent of Brassica rapa oil Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].

Dihydroxyindole

2,3-Dihydroxyindole

C8H7NO2 (149.0477)

(E,E)-2,4-Hexadienal

(2Z,4E)-hexa-2,4-dienal

C6H8O (96.0575)

(E,E)-2,4-Hexadienal is found in fishes. (E,E)-2,4-Hexadienal is a flavouring ingredient. (E,E)-2,4-Hexadienal is present in olives, roasted peanuts, tomato, caviar, fish, and te (E,E)-2,4-Hexadienal is a flavouring ingredient. It is found in olives, roasted peanuts, tomato, caviar, fish, and tea.

Aminomalonic acid

2-aminopropanedioic acid

C3H5NO4 (119.0219)

Aminomalonic acid (Ama) is an amino dicarboxylic acid that is an analog of malonic acid in which one of the methylene hydrogens has been replaced by an amino group. It is a strongly acidic compound that is very water soluble. Aminomalonic acid is a natural occurring, largely non-proteogenic amino acid that was first detected in alkaline hydrolysates of proteins in 1984. In particular, aminomalonic acid was isolated from proteins isolated from Escherichia coli cultures and from human atherosclerotic plaques (PMID: 6366787). Aminomalonic acid is a relatively unstable, minor amino acid in complex structures such as bacteria or tissues. The presence of aminomalonic acid has important biological implications because the malonic acid moiety potentially imparts calcium binding properties to proteins. Possible origins of aminomalonic acid in proteins include its introduction via errors in protein synthesis and oxidative damage to amino acid residues in proteins. (PMID: 1621954 , 6366787 ). Aminomalonic acid can be generated naturally via the activity of mammalian and bacterial enzymes on various precursors such as 2-aminomalonamide, diethylaminomalonate and ketomalonic acid (PMID: 35346). Free aminomalonic acid appears to be an oxidation product arising from perturbed serine or threonine metabolism. Aminomalonic acid is produced in animals that have been exposed to Cadmium (a strong pro-oxidant) for extended periods of time and it has been proposed to be a potential biomarker of Cadmium toxicity (PMID: 32193438). Aminomalonic acid has also been found to be elevated in the urine of individuals with anxiety and major depressive disorders (PMID: 30232320). Aminomalonic acid has been reported to be a potential biomarker for hepatocellular carcinoma (PMID: 18767022) and it exhibits strong inhibitory effects on L-asparagine synthase (PMID: 35346). Several metabolomics studies have also found that altered aminomalonic acid levels in serum are associated with neuropsychiatric disorders, melanoma, ketamine overdose and aortic aneurysm, indicating that aminomalonic acid is an important serum indicator for diseases and toxicities (PMID: 32193438). Aminomalonic acid (Ama) was first detected in alkaline hydrolysates of proteins in 1984. Ama has been isolated from proteins of Escherichia coli and human atherosclerotic plaque. The presence of Ama has important biological implications because the malonic acid moiety potentially imparts calcium binding properties to protein. Ama is not formed from any of the 20 major amino acids during the hydrolysis procedure. Furthermore, the amount of Ama found does not depend on the presence of small amounts of O2 during the hydrolysis. No artifactual formation of ama has been demonstrated and may indeed be a constituent of proteins before the hydrolysis procedure. Possible origins of Ama include errors in protein synthesis and oxidative damage to amino acid residues in proteins. (PMID: 1621954, 6366787) [HMDB] Aminomalonic acid is an amino endogenous metabolite, acts as a strong inhibitor of L-asparagine synthetase from Leukemia 5178Y/AR (Ki= 0.0023 M) and mouse pancreas (Ki= 0.0015 M) in vitro. Aminomalonic acid is a potential biomarker to discriminate between different stages of melanoma metastasis[1][2][3].

n-Butyl acetate

Butyl ester OF acetic acid

C6H12O2 (116.0837)

n-Butyl acetate is a flavouring ingredient used in apple flavours. n-Butyl acetate, also known as butyl ethanoate, is an organic compound commonly used as a solvent in the production of lacquers and other products. It is also used as a synthetic fruit flavoring in foods such as candy, ice cream, cheeses, and baked goods. Butyl acetate is found in many types of fruit, where along with other chemicals it imparts characteristic flavors. Apples, especially of the Red Delicious variety, are flavored in part by this chemical. It is a colourless flammable liquid with a sweet smell of banana. Flavouring ingredient used in apple flavours

3-dehydroshikimate

4,5-dihydroxy-3-oxocyclohexene-1-carboxylic acid

C7H8O5 (172.0372)

1-O-Hexadecyl-sn-glycero-3-phosphocholine

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

C24H52NO6P (481.3532)

CDP-ethanolamine

(2-aminoethoxy)[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid

C11H20N4O11P2 (446.0604)

CDP-ethanolamine, also known as cytidine 5’-diphosphoethanolamine, belongs to the class of organic compounds known as CDP-ethanolamines. These are phosphoethanolamines that consist of an ethanolamine having a cytidine 5-diphosphate moiety attached to the oxygen. CDP-ethanolamine is a very strong basic compound (based on its pKa). In humans, CDP-ethanolamine is involved in phosphatidylethanolamine biosynthesis. Outside of the human body, CDP-ethanolamine has been detected, but not quantified in, several different foods, such as Chinese water chestnuts, buffalo currants, red huckleberries, eggplants, and brazil nuts. This could make CDP-ethanolamine a potential biomarker for the consumption of these foods. Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a beta-N1-glycosidic bond. [HMDB]. CDP-Ethanolamine is found in many foods, some of which are allspice, hedge mustard, wasabi, and green vegetables.

Dihydrolipoamide

Dihydrolipoamide, (+-)-isomer

C8H17NOS2 (207.0752)

Dihydrolipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG ID C00579). It is converted to lipoamide via the enzyme dihydrolipoamide dehydrogenase [EC:1.8.1.4]. Dihydrolipoamide is also a substrate of enzyme Acyltransferases [EC 2.3.1.-]. (KEGG) [HMDB]. Dihydrolipoamide is found in many foods, some of which are enokitake, mugwort, welsh onion, and tea. Dihydrolipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG ID C00579). It is converted to lipoamide via the enzyme dihydrolipoamide dehydrogenase [EC:1.8.1.4]. Dihydrolipoamide is also a substrate of enzyme Acyltransferases [EC 2.3.1.-]. (KEGG).

coenzyme F420

SCHEMBL16018850

C29H36N5O18P (773.1793)

3-Mercaptopyruvic acid

beta-3-Mercapto-2-oxo-propanoic acid

C3H4O3S (119.9881)

3-Mercaptopyruvic acid, also known as 3-mercapto-2-oxopropanoate or beta-thiopyruvate, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. 3-Mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3-mercaptopyruvic acid participates in a number of enzymatic reactions. In particular, 3-mercaptopyruvic acid and cyanide can be converted into pyruvic acid and thiocyanate; which is mediated by the enzyme 3-mercaptopyruvate sulfurtransferase. In addition, 3-mercaptopyruvic acid can be biosynthesized from 3-mercaptolactic acid; which is mediated by the enzyme L-lactate dehydrogenase. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. In humans, 3-mercaptopyruvic acid is involved in cystinosis, ocular nonnephropathic. Outside of the human body, 3-mercaptopyruvic acid has been detected, but not quantified in several different foods, such as lima beans, spinachs, shallots, mexican groundcherries, and white lupines. This could make 3-mercaptopyruvic acid a potential biomarker for the consumption of these foods. 3-mercaptopyruvic acid, also known as beta-mercaptopyruvate or beta-thiopyruvic acid, belongs to alpha-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-mercaptopyruvic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 3-mercaptopyruvic acid can be found in a number of food items such as garland chrysanthemum, rubus (blackberry, raspberry), tarragon, and arrowhead, which makes 3-mercaptopyruvic acid a potential biomarker for the consumption of these food products. 3-mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. In humans, 3-mercaptopyruvic acid is involved in a couple of metabolic pathways, which include cysteine metabolism and cystinosis, ocular nonnephropathic. 3-mercaptopyruvic acid is also involved in beta-mercaptolactate-cysteine disulfiduria, which is a metabolic disorder. 3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. Instead, prodrugs, such as sulfanegen, are being evaluated to compensate for the short half-life of 3-mercaptopyruvic acid .

Dihydroxyfumaric acid

2-Butenedioic acid,2,3-dihydroxy-, (2E)-

C4H4O6 (148.0008)

Dihydroxyfumaric acid is a known generator of superoxide anions and by hydroxyl free radicals. Dihydroxyfumarate exposure can cause insulin inhibitory effects. It can spontaneously convert to hydroxypyruvate or to oxaloglycolate. [HMDB] Dihydroxyfumaric acid is a known generator of superoxide anions and by hydroxyl free radicals. Dihydroxyfumarate exposure can cause insulin inhibitory effects. It can spontaneously convert to hydroxypyruvate or to oxaloglycolate.

Protoporphyrinogen IX

3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid

C34H40N4O4 (568.3049)

Protoporphyrinogen IX is an intermediate in heme biosynthesis. It is a porphyrinogen in which two pyrrole rings each have one methyl and one propionate side chain, and the other two pyrrole rings each have one methyl and one vinyl side chain. Fifteen isomers are possible but only one, type IX, occurs naturally. Protoporphyrinogen is produced by oxidative decarboxylation of coproporphyrinogen. Under certain conditions, protoporphyrinogen IX can act as a phototoxin, a neurotoxin, and a metabotoxin. A phototoxin leads to cell damage upon exposure to light. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, and hereditary coproporphyria (HCP). In particular, protoporphyrinogen IX is accumulated and excreted excessively in the feces in acute intermittent porphyria, protoporphyria, and variegate porphyria. There are several types of porphyrias (most are inherited). Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). The neurotoxicity of porphyrins may be due to their selective interactions with tubulin, which disrupt microtubule formation and cause neural malformations (PMID: 3441503). Protoporphyrinogen IX is an intermediate in heme biosynthesis. It is a porphyrinogen in which 2 pyrrole rings each have one methyl and one propionate side chain and the other two pyrrole rings each have one methyl and one vinyl side chain. 15 isomers are possible but only one, type IX, occurs naturally. Protoporphyrinogen is produced by oxidative decarboxylation of coproporphyrinogen. [HMDB]. Protoporphyrinogen IX is found in many foods, some of which are elderberry, grapefruit, green vegetables, and pepper (c. annuum). COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

ADP-Ribosyl-L-arginine

2-amino-5-[(E)-[amino({5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}amino)methylidene]amino]pentanoic acid

C21H35N9O15P2 (715.1728)

ADP-Ribosyl-L-arginine is the substrate of the protein ADP-ribosylarginine hydrolase (EC-Number 3.2.2.19 ), removing ADP-ribose from arginine residues in ADP ribosylated proteins. Arginine residues in proteins act as acceptors, catalyzing the NAD (+)-dependent activation of the enzyme adenylate cyclase (EC 4.6.1.1). (MetaCyc) [HMDB] ADP-Ribosyl-L-arginine is the substrate of the protein ADP-ribosylarginine hydrolase (EC-Number 3.2.2.19 ), removing ADP-ribose from arginine residues in ADP ribosylated proteins. Arginine residues in proteins act as acceptors, catalyzing the NAD (+)-dependent activation of the enzyme adenylate cyclase (EC 4.6.1.1). (MetaCyc).

(+)-Sabinone

(1S,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one

C10H14O (150.1045)

(+)-sabinone is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-sabinone is considered to be an isoprenoid lipid molecule (+)-sabinone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-sabinone can be found in common sage, which makes (+)-sabinone a potential biomarker for the consumption of this food product.

Bleomycin B2

Dehydrophleomycin D1

C55H84N20O21S2 (1424.5561)

C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C259 - Antineoplastic Antibiotic C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent D000970 - Antineoplastic Agents

Linoleoyl-CoA

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

C39H66N7O17P3S (1029.3449)

Linoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long-chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid beta-oxidation. ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates (PMID: 17184976, 16020546).

cis-Sabinol

(1S,3R,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol

C10H16O (152.1201)

(+)-cis-Sabinol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-cis-sabinol is an isoprenoid lipid molecule. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 23746261). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. (+)-cis-Sabinol is very hydrophobic, practically insoluble in water, and relatively neutral. Artemisia annuaand (https://doi.org/10.1007/s11418-006-0112-9) and in herbal plant Dendranthema indicum (PMID: 29510531). (+)-cis-sabinol, also known as sabinol or sabinol, (1alpha,3alpha,5alpha)-isomer, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-cis-sabinol is considered to be an isoprenoid lipid molecule (+)-cis-sabinol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (+)-cis-sabinol can be found in peppermint, which makes (+)-cis-sabinol a potential biomarker for the consumption of this food product.

2-Methylcholine

C6H16NO+ (118.1232)

Arachidonyl-CoA

{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

C41H66N7O17P3S (1053.3449)

Arachidonyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. Arachidonyl-CoA is produced from 8,11,14-Eicosatrienoyl-CoA via the enzyme fatty acid desaturase 1 (EC 1.14.19.-). It is then converted to Arachidonic acid via the enzymepalmitoyl-CoA hydrolase (EC 3.1.2.2).

Glutaconyl-CoA

(3E)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-5-oxopent-3-enoic acid

C26H40N7O19P3S (879.1312)

Glutaconyl-CoA (CAS: 6712-05-6), also known as 4-carboxybut-2-enoyl-CoA, belongs to the class of organic compounds known as 2-enoyl CoAs. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain. Thus, glutaconyl-CoA is considered to be a fatty ester lipid molecule. Glutaconyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Glutaconyl-CoA is a substrate for glutaryl-CoA dehydrogenase. Glutaconyl-CoA is a substrate for Glutaryl-CoA dehydrogenase (mitochondrial). [HMDB]

Dimethyl selenide

Dimethylselenide, 75Se-labeled

C2H6Se (109.9635)

Constituent of Allium subspecies Dimethyl selenide is found in many foods, some of which are breadnut tree seed, buffalo currant, guava, and muskmelon. Dimethyl selenide is found in onion-family vegetables. Dimethyl selenide is a constituent of Allium species.

Isovaleryl-CoA

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid

C26H44N7O17P3S (851.1727)

Isovaleryl-CoA is an intermediate metabolite in the catabolic pathway of leucine. The accumulation of derivatives of isovaleryl-CoA occurs in patients affected with isovaleric acidemia (IVA, OMIM 243500) an autosomal recessive inborn error of leucine metabolism caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD, EC 1.3.99.10, a flavoenzyme that catalyzes the conversion of isovaleryl-CoA to 3-methylcrotonyl-CoA). IVA was the first organic acidemia recognized in humans and can cause significant morbidity and mortality. Early diagnosis and treatment with a protein restricted diet and supplementation with carnitine and glycine are effective in promoting normal development in severely affected individuals. Both intra- and interfamilial variability have been recognized. Initially, two phenotypes with either an acute neonatal or a chronic intermittent presentation were described. More recently, a third group of individuals with mild biochemical abnormalities who can be asymptomatic have been identified through newborn screening of blood spots by tandem mass spectrometry. The majority of patients with IVA today are diagnosed pre-symptomatically through newborn screening by use of MS/MS which reveals elevations of the marker metabolite C5 acylcarnitine in dried blood spots. C5 acylcarnitine represents a mixture of isomers (isovalerylcarnitine, 2-methylbutyrylcarnitine, and pivaloylcarnitine). (PMID: 16602101, Am J Med Genet C Semin Med Genet. 2006 May 15;142(2):95-103.) [HMDB]. Isovaleryl-CoA is found in many foods, some of which are purple laver, alaska wild rhubarb, macadamia nut (m. tetraphylla), and green zucchini. Isovaleryl-CoA is an intermediate metabolite in the catabolic pathway of leucine. The accumulation of derivatives of isovaleryl-CoA occurs in patients affected with isovaleric acidemia (IVA, OMIM: 243500), an autosomal recessive inborn error of leucine metabolism caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD, EC 1.3.99.10), a flavoenzyme that catalyzes the conversion of isovaleryl-CoA into 3-methylcrotonyl-CoA. IVA was the first organic acidemia recognized in humans and can cause significant morbidity and mortality. Early diagnosis and treatment with a protein-restricted diet and supplementation with carnitine and glycine are effective in promoting normal development in severely affected individuals. Both intra- and interfamilial variability have been recognized. Initially, two phenotypes with either an acute neonatal or a chronic intermittent presentation were described. More recently, a third group of individuals with mild biochemical abnormalities who can be asymptomatic have been identified through newborn screening of blood spots by tandem mass spectrometry. The majority of patients with IVA today are diagnosed pre-symptomatically through newborn screening by use of MS/MS which reveals elevations of the marker metabolite C5 acylcarnitine in dried blood spots. C5 Acylcarnitine represents a mixture of isomers (isovalerylcarnitine, 2-methylbutyrylcarnitine, and pivaloylcarnitine) (PMID: 16602101).

5a-Androstan-3b-ol

(1S,2S,5S,7S,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

C19H32O (276.2453)

5a-Androstan-3b-ol is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. 5a-Androstan-3b-ol has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. 5a-Androstan-3b-ol as a pheromone is well suited because of high volatility and lipophilicity. (PMID: 1419890, 8142319, 16415088) [HMDB] 5a-Androstan-3b-ol is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. 5a-Androstan-3b-ol has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. 5a-Androstan-3b-ol as a pheromone is well suited because of high volatility and lipophilicity. (PMID: 1419890, 8142319, 16415088).

Arginine, N2-benzoyl

5-{[amino(imino)methyl]amino}-2-(benzoylamino)pentanoic acid

C13H18N4O3 (278.1379)

DG(10:0/10:0/0:0)

(2S)-1-(decanoyloxy)-3-hydroxypropan-2-yl decanoate

C23H44O5 (400.3189)

DG(10:0/10:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(10:0/10:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.

3,5-Dinitro-Tyr-OH

3,5-Dinitro-DL-tyrosine

C9H9N3O7 (271.044)

A non-proteinogenic L-alpha-amino acid that is L-tyrosine substituted by nitro groups at positions 3 and 5.

Ethyl acetoacetate

Ethyl acetoacetate, 1,3-(14)C-labeled

Ethyl acetoacetate (EAA) is found in coffee and coffee products as well as in strawberry and yellow passion fruit juice. Ethyl acetoacetate is a flavouring agent. The organic compound ethyl acetoacetate is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine, aminopyrine, and vitamin B1, as well as in the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments (Wikipedia). The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.

Histidylleucine

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

C12H20N4O3 (268.1535)

Histidylleucine is a dipeptide composed of histidine and leucine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Debromoaplysiatoxin

Aplysiatoxin, 17-debromo-

C32H48O10 (592.3247)

A member of the class of aplysiatoxins that has the structure of the parent aplysiatoxin, but is lacking the bromo substituent on the benzene ring at the position para to the phenolic hydroxy group. It is a cyanotoxin produced by several species of freshwater and marine cyanobacteria, as well as algae and molluscs. D009676 - Noxae > D011042 - Poisons > D008235 - Lyngbya Toxins D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins D009676 - Noxae > D002273 - Carcinogens

Cholest-5-ene

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

C27H46 (370.3599)

Cholestenes are derivatives of cholestanes which have a double bond. One of the most significant cholestenes is cholecalciferol. If there are two double bonds, the molecule is known as a "cholestadienes". Examples include fusidic acid, lanosterol, and stigmasterol.--Wikipedia. Cholestenes are derivatives of cholestanes which have a double bond. One of the most significant cholestenes is cholecalciferol.

Cholesterol beta-epoxide

(3-beta,5-beta,6-beta)-5,6-Epoxycholestan-3-ol

C27H46O2 (402.3498)

Cortol

(3R,5R,8S,9S,10S,11S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,11,17-triol

C21H36O5 (368.2563)

Involved in C21-Steroid hormone metabolism. [HMDB] Involved in C21-Steroid hormone metabolism.

Indoxyl

1H-Indol-3-ol

C8H7NO (133.0528)

Indoxyl, also known as 1H-indol-3-ol, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Indoxyl is isomeric with oxindol and is obtained as an oily liquid. Indoxyl exists in all living organisms, ranging from bacteria to humans. Indoxyl is obtained from indican, which is a glycoside. Obermayers reagent is a dilute solution FeCl3 in hydrochloric acid. The hydrolysis of indican yields β-D-glucose and indoxyl. Indigo dye is a product of the reaction of indoxyl by a mild oxidizing agent such as atmospheric oxygen. In chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO. Indoxyl can be found in urine and is titrated with Obermayers reagent. Indigo dye is a product of the reaction of indoxyl by a mild oxidizing agent, eg. atmospheric oxygen.

Nudifloramide

1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

C7H8N2O2 (152.0586)

N-methyl-2-pyridone-5-carboxamide (2PY) is one of the end products of nicotinamide-adenine dinucleotide (NAD) degradation. Increased serum 2PY concentrations are observed in chronic renal failure (CRF) patients, which along with the deterioration of kidney function and its toxic properties (significant inhibition of PARP-1), suggests that 2PY is an uremic toxin. (PMID 12694300). 2PY has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). N-methyl-2-pyridone-5-carboxamide (2PY) is one of the end products of nicotinamide-adenine dinucleotide (NAD) degradation. Increased serum 2PY concentrations are observed in chronic renal failure (CRF) patients, which along with the deterioration of kidney function and its toxic properties (significant inhibition of PARP-1), suggests that 2PY is an uremic toxin. (PMID 12694300) [HMDB] Nudifloramide (2PY) is one of the end products of nicotinamide-adenine dinucleotide (NAD) degradation. Nudifloramide significantly inhibits poly(ADP-ribose) polymerase (PARP-1) activity in vitro[1].

Prostaglandin G2

(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid

C20H32O6 (368.2199)

Prostaglandin G2 (PGG2) is synthesized from arachidonic acid on a cyclooxygenase (COX) metabolic pathway as a primary step; the COX biosynthesis of prostaglandin (PG) begins with the highly specific oxygenation of arachidonic acid in the 11R configuration and ends with a 15S oxygenation to form PGG2. The COX site activity that catalyzes the conversion of arachidonic acid to PGG2 is the target for nonsteroidal antiinflammatory drugs (NSAIDs). The peroxidase site activity catalyzes the two-electron reduction of the hydroperoxide bond of PGG2 to yield the corresponding alcohol prostaglandin H2 (PGH2). The formation of a phenoxyl radical on Tyr385 couples the activities of the two sites. The Tyr385 radical is produced via oxidation by compound I, an oxoferryl porphyrin -cation radical, which is generated by reaction of the hemin resting state with PGG2 or other hydroperoxides. The tyrosyl radical homolytically abstracts the 13proS hydrogen atom of arachidonic acid which initiates a radical cascade that ends with the stereoselective formation of PGG2. PGG2 then migrates from the cyclooxygenase (COX) site to the peroxidase (POX) site where it reacts with the hemin group to generate PGH2 and compound I. The heterolytic oxygen-oxygen bond cleavage is assisted by the conserved distal residues His207 and Gln203, mutation of which has been shown to severely impair enzyme activity. Compound I, upon reaction with Tyr385, gives compound II, which in turn is reduced to the hemin resting state by one-electron oxidation of reducing cosubstrates or undergoes reactions that result in enzyme self-inactivation. Prostaglandin endoperoxide H synthase (PGHS) 1 is a bifunctional membrane enzyme of the endoplasmic reticulum that converts arachidonic acid into prostaglandin H2 (PGH2), the precursor of all prostaglandins, thromboxanes, and prostacyclins. These lipid mediators are intricately involved in normal physiology, namely, in mitogenesis, fever generation, pain response, lymphocyte chemotaxis, fertility, and contradictory stimuli such as vasoconstriction and vasodilatation, as well as platelet aggregation and quiescence. PGHS is implicated in numerous pathologies, including inflammation, cancers of the colon, lung, and breast, Alzheimers disease, Parkinsons disease, and numerous cardiovascular diseases including atherosclerosis, thrombosis, myocardial infarction, and stroke. (PMID: 14594816, 16552393, 16411757). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. Prostaglandin G2 (PGG2) is synthesized from arachidonic acid on a cyclooxygenase (COX) metabolic pathway as a primary step; the COX biosynthesis of prostaglandin (PG) begins with the highly specific oxygenation of arachidonic acid in the 11R configuration and ends with a 15S oxygenation to form PGG2. D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

Lipoxin B4

(5S,14R,6E,8Z,10E,12E,15S)-5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acid

Lipoxins (LXs) and aspirin-triggered lipoxin (ATL) are trihydroxytetraene-containing eicosanoids generated from arachidonic acid that are distinct in structure, formation, and function from the many other proinflammatory lipid-derived mediators. These endogenous eicosanoids have now emerged as founding members of the first class of lipid/chemical mediators involved in the resolution of the inflammatory response. Lipoxin A4 (LXA4), ATL, and their metabolic stable analogs elicit cellular responses and regulate leukocyte trafficking in vivo by activating the specific receptor, ALX. Many of the eicosanoids derived from arachidonic acid (AA2), including prostaglandins (PGs) and leukotrienes (LTs), play important roles as local mediators exerting a wide range of actions relevant in immune hypersensitivity and inflammation. However, recent observations indicate that other agents derived from the lipoxygenase (LO) pathways are formed and play a key role in initiating the resolution of acute inflammation. This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. Thus, potent locally released mediators serve as checkpoint controllers of inflammation. In addition to the well-appreciated ability of aspirin to inhibit PGs, aspirin also acetylates cyclooxygenase (COX)-2, triggering the formation of a 15-epimeric form of lipoxins, termed aspirin-triggered LXA4 (ATL). These eicosanoids (i.e. LXA4 and ATL) with a unique trihydroxytetraene structure function as stop signals in inflammation and actively participate in dampening host responses to bring the inflammation to a close, namely, resolution. LXA4 and ATL elicit the multicellular responses via a specific G protein-coupled receptor (GPCR) termed ALX that has been identified in human (PMID: 16968948, 11478982). Lipoxins (LXs) and aspirin-triggered Lipoxin (ATL) are trihydroxytetraene-containing eicosanoids generated from arachidonic acid that are distinct in structure, formation, and function from the many other proinflammatory lipid-derived mediators. These endogenous eicosanoids have now emerged as founding members of the first class of lipid/chemical mediators involved in the resolution of the inflammatory response. Lipoxin A4 (LXA4), ATL, and their metabolic stable analogs elicit cellular responses and regulate leukocyte trafficking in vivo by activating the specific receptor, ALX. Many of the eicosanoids derived from arachidonic acid (AA2), including prostaglandins (PGs) and leukotrienes (LTs), play important roles as local mediators exerting a wide range of actions relevant in immune hypersensitivity and inflammation. However, recent observations indicate that other agents derived from the lipoxygenase (LO) pathways are formed and play a key role in initiating the resolution of acute inflammation. This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. Thus, potent locally released mediators serve as checkpoint controllers of inflammation. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents

1,3-Dichloropropene

1,3-dichloro-1-Propene (acd/name 4.0)

C3H4Cl2 (109.969)

1,3-Dichloropropene, also known as Telone or simply 1,3-D, is a colorless liquid with a sweet smell. It exists as a mixture of the geometric isomers cis-1,3-dichloropropene and trans-1,3-dichloropropene. It dissolves in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It widely used in the US and other countries, but in the process of being phased out in the European Union. [HMDB] 1,3-Dichloropropene, also known as Telone or simply 1,3-D, is a colorless liquid with a sweet smell. It exists as a mixture of the geometric isomers cis-1,3-dichloropropene and trans-1,3-dichloropropene. It dissolves in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It widely used in the US and other countries, but in the process of being phased out in the European Union. D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals

Acetohexamide

4-Acetyl-N-((cyclohexylamino)carbonyl)benzenesulphonamide

C15H20N2O4S (324.1144)

Acetohexamide is only found in individuals that have used or taken this drug. It is a sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide. [PubChem]Sulfonylureas such as acetohexamide bind to an ATP-dependent K⁺ channel on the cell membrane of pancreatic beta cells. This inhibits a tonic, hyperpolarizing outflux of potassium, which causes the electric potential over the membrane to become more positive. This depolarization opens voltage-gated Ca²⁺ channels. The rise in intracellular calcium leads to increased fusion of insulin granulae with the cell membrane, and therefore increased secretion of (pro)insulin. A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins > A10BB - Sulfonylureas C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C97936 - Sulfonylurea Antidiabetic Agent D007004 - Hypoglycemic Agents

Calcitonin

4-{[1-({1-[(5-amino-1-{[1-({1-[(1-{[1-(2-{[4-carbamimidamido-1-({2-hydroxy-1-[(1-{[2-hydroxy-1-({[(2-hydroxy-1-{[({3-hydroxy-1-[2-(C-hydroxycarbonimidoyl)pyrrolidin-1-yl]-1-oxobutan-2-yl}-C-hydroxycarbonimidoyl)methyl]-C-hydroxycarbonimidoyl}ethyl)-C-hydroxycarbonimidoyl]methyl}-C-hydroxycarbonimidoyl)propyl]-C-hydroxycarbonimidoyl}-2-(C-hydroxycarbonimidoyl)ethyl)-C-hydroxycarbonimidoyl]propyl}-C-hydroxycarbonimidoyl)butyl]-C-hydroxycarbonimidoyl}pyrrolidin-1-yl)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-C-hydroxycarbonimidoyl}-2-hydroxypropyl)-C-hydroxycarbonimidoyl]-3-(C-hydroxycarbonimidoyl)propyl}-C-hydroxycarbonimidoyl)-3-methylbutyl]-C-hydroxycarbonimidoyl}pentyl)-C-hydroxycarbonimidoyl]-2-(1H-imidazol-5-yl)ethyl}-C-hydroxycarbonimidoyl)-3-methylbutyl]-C-hydroxycarbonimidoyl}-4-({2-[(2-{[2-({6-amino-2-[(2-{[2-({2-[({22-amino-6,9,12,15,18,21-hexahydroxy-16-[(C-hydroxycarbonimidoyl)methyl]-7-(1-hydroxyethyl)-10,19-bis(hydroxymethyl)-13-(2-methylpropyl)-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosa-5,8,11,14,17,20-hexaen-4-yl}(hydroxy)methylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyhexylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene)amino]-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene}amino)butanoate

C145H240N44O48S2 (3429.7132)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D000077264 - Calcium-Regulating Hormones and Agents D050071 - Bone Density Conservation Agents

Diphenidol

SmithKline beecham brand OF diphenidol hydrochloride

C21H27NO (309.2093)

Diphenidol is only found in individuals that have used or taken this drug. It is an antiemetic agent used in the treatment of vomiting and vertigo. Diphenidol overdose may result in serious toxicity in children.The mechanism by which diphenidol exerts its antiemetic and antivertigo effects is not precisely known. It is thought to diminish vestibular stimulation and depress labyrinthine function and as an antimuscarinic agent. An action on the medullary chemoreceptive trigger zone may also be involved in the antiemetic effect. Diphenidol has no significant sedative, tranquilizing, or antihistaminic action. It has a weak peripheral anticholinergic effect. D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents C78272 - Agent Affecting Nervous System > C267 - Antiemetic Agent D005765 - Gastrointestinal Agents > D000932 - Antiemetics D002491 - Central Nervous System Agents

Echothiophate

diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate

C9H23NO3PS+ (256.1136)

Echothiophate is only found in individuals that have used or taken this drug. It is a potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia.Echothiophate Iodide is a long-acting cholinesterase inhibitor for topical use which enhances the effect of endogenously liberated acetylcholine in iris, ciliary muscle, and other parasympathetically innervated structures of the eye. Echothiophate iodide binds irreversibly to cholinesterase, and is long acting due to the slow rate of hydrolysis by cholinesterase. It causes miosis, increase in facility of outflow of aqueous humor, fall in intraocular pressure, and potentiation of accommodation. S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010277 - Parasympathomimetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D008916 - Miotics C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist D004791 - Enzyme Inhibitors

Acetylhydrazine

Acetylhydrazine, (e)-2-fumarate (1:1)

C2H6N2O (74.048)

The acetylhydrazine metabolite was found to be much less cytotoxic than hydrazine in this hepatocyte inflammation model. (PMID: 18295292) In the pathogenesis of isoniazid-induced hepatic injury, cytochrome P450-dependent metabolic activation of the metabolite, acetylhydrazine (AcHz), is the crucial step. (PMID: 8852701) The mechanism of action of acetylphosphabenzide is likely to involve the formation of acetylhydrazine, capable of producing active electrophiles attacking DNA. (PMID: 9589859) D009676 - Noxae > D002273 - Carcinogens

Remikiren

(2S)-2-{[(2R)-2-benzyl-1-hydroxy-3-(2-methylpropane-2-sulphonyl)propylidene]amino}-N-[(2R,3S,4R)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]-3-(1H-imidazol-5-yl)propanimidic acid

C33H50N4O6S (630.3451)

Remikiren is only found in individuals that have used or taken this drug. It is an orally active, high specificity renin inhibitor. Several in vivo experiments have shown that remikiren is specific for renin and does not decrease arterial pressure by an unrelated mechanism. C - Cardiovascular system > C09 - Agents acting on the renin-angiotensin system > C09X - Other agents acting on the renin-angiotensin system > C09XA - Renin-inhibitors C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors C471 - Enzyme Inhibitor > C783 - Protease Inhibitor

Enalkiren

3-amino-N-[(2S)-1-[[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-(4-methoxyphenyl)-1-oxopropan-2-yl]-3-methylbutanamide

C35H56N6O6 (656.4261)

C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors

Lysergic acid

6-Methyl-9,10-didehydroergoline-8-carboxylic acid

C16H16N2O2 (268.1212)

An ergoline alkaloid comprising 6-methylergoline having additional unsaturation at the 9,10-position and a carboxy group at the 8-position.

Methacycline

(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-5,10,12,12a-tetrahydroxy-6-methylidene-1,3,11-trioxo-1,2,3,4,4a,5,5a,6,11,12a-decahydrotetracene-2-carboxamide

C22H22N2O8 (442.1376)

Methacycline is only found in individuals that have used or taken this drug. It is a broad-spectrum semisynthetic antibiotic related to tetracycline but excreted more slowly and maintaining effective blood levels for a more extended period. [PubChem]Methacycline, a tetracycline antibiotic, is a protein synthesis inhibitors, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex. Methacycline inhibits cell growth by inhibiting translation. It binds to the 16S part of the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Tetracyclines also have been found to inhibit matrix metalloproteinases. This mechanism does not add to their antibiotic effects, but has led to extensive research on chemically modified tetracyclines or CMTs (like incyclinide) for the treatmet of rosacea, acne, and various types of neoplasms. J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01A - Tetracyclines > J01AA - Tetracyclines C784 - Protein Synthesis Inhibitor > C1595 - Tetracycline Antibiotic D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents C254 - Anti-Infective Agent > C258 - Antibiotic

Nisoldipine

3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

C20H24N2O6 (388.1634)

Nisoldipine is a 1,4-dihydropyridine calcium channel blocker. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, nisoldipine prevents calcium-dependent smooth muscle contraction and subsequent vasoconstriction. Nisoldipine may be used in alone or in combination with other agents in the management of hypertension. C - Cardiovascular system > C08 - Calcium channel blockers > C08C - Selective calcium channel blockers with mainly vascular effects > C08CA - Dihydropyridine derivatives C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent > C333 - Calcium Channel Blocker D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents D000077264 - Calcium-Regulating Hormones and Agents D049990 - Membrane Transport Modulators C93038 - Cation Channel Blocker

Dyclonine

1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one

C18H27NO2 (289.2042)

Dyclonine is only found in individuals that have used or taken this drug. It is an oral anaesthetic found in Sucrets, an over the counter throat lozenge. It is also found in some varieties of the Cepacol sore throat spray.Dyclonine blocks both the initiation and conduction of nerve impulses by decreasing the neuronal membranes permeability to sodium ions. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics R - Respiratory system > R02 - Throat preparations > R02A - Throat preparations > R02AD - Anesthetics, local D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent

cefuroxime axetil

C20H22N4O10S (510.1057)

D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D002511 - Cephalosporins D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic

Cortisone acetate

2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-oxoethyl acetate

C23H30O6 (402.2042)

Cortisone acetate is a steroid hormone that has both glucocoriticoid and mineral corticoid activities. Corticosteroids are used to provide relief for inflamed areas of the body. They lessen swelling, redness, itching, and allergic reactions. They are often used as part of the treatment for a number of different diseases, such as severe allergies or skin problems, asthma, or arthritis. Endogenous glucocorticoids and some synthetic corticoids have high affinity to the protein transcortin (also called CBG, corticosteroid-binding protein), whereas all of them bind albumin. Glucocorticoids also bind to the cytosolic glucocorticoid receptor. C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D000893 - Anti-Inflammatory Agents Cortisone acetate (Cortisone 21-acetate), an oxidized metabolite of Cortisol (a Glucocorticoid). Cortisone acetate acts as an immunosuppressant and anti-inflammatory agent. Cortisone acetate can partially intervene in binding of Glucocorticoid to Glucocorticoid-receptor at high concentrations[1][3][4].

Sarmentosin

(Z)-2-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enenitrile

C11H17NO7 (275.1005)

Sarmentosin is found in fruits. Sarmentosin is isolated from Ribes nigrum (blackcurrant

Miserotoxin

ZINC01531158

C9H17NO8 (267.0954)

A beta-D-glucoside having 3-nitropropyl as the anomeric alkyl group.

SCILLIROSIDE

C32H44O12 (620.2833)

D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides

Biflorin

5,7-dihydroxy-2-methyl-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

C16H18O9 (354.0951)

Biflorin is an o-naphthoquinone isolated from Capraria biflora L. (Scrophulariaceae, a perennial shrub widely distributed in several countries of tropical America). Biflorin has cytotoxic and antioxidant potential, strongly inhibiting the growth of five tested tumor cell lines, especially the skin, breast and colon cancer cells with IC50 of 0.40, 0.43 and 0.88 micro/ml for B16, MCF-7 and HCT-8, respectively, while the antioxidant activity was assayed against autoxidation of oleic acid in a water/alcohol system. (PMID: 16042338). Constituent of Eugenia caryophyllata (clove)

Rhazin

methyl (1S,12S,13S,14S,15E)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraene-13-carboxylate

C21H24N2O3 (352.1787)

Akuammidine is a natural product found in Aspidosperma quebracho-blanco, Tabernaemontana citrifolia, and other organisms with data available.

Daphnetoxin

Orthobenzoic acid, cyclic 7,8,10a-ester with 5,6-epoxy-4,5,6,6a,7,8,9,10,10a,10b-decahydro-3a,4,7,8,10a-pentahydroxy-5-(hydroxymethyl)-8-isopropenyl-2,10-dimethylbenz(e)azulen-3(3ah)-one

C27H30O8 (482.1941)

A daphnane-type orthoester diterpene with potential cholesterol-lowering activity, found exclusively in plants of the family Thymelaeaceae.

Gniditrin

Daphne factor P1

C37H42O10 (646.2778)

Simplexin

CID 442086

C30H44O8 (532.3036)

Marckine

1H-Pyrido[3,4-b]indol-6-ol, 1-[[(2S,3R,11bS)-3-ethyl-1,3,4,6,7,11b-hexahydro- 9,10-dimethoxy-2H-benzo[a]quinolizin-2-yl]methyl]- 2,3,4,9-tetrahydro-, (1R)-

C29H37N3O3 (475.2835)

Acerosin

5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-4H-1-benzopyran-4-one, 9ci

C18H16O8 (360.0845)

Acerosin is found in citrus. Acerosin is isolated from fruit peel of mandarin orange (Citrus reticulata

Mesuaxanthone B

1,5,6-Trihydroxyxanthone

C13H8O5 (244.0372)

A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 5 and 6.

chlorophorin

2,4,3,5-tetrahydroxy-4(3,7-di-methyl-2,6-octadienyl)-stilbene

C24H28O4 (380.1987)

2,6-Dinitrotoluene

1-Methyl-2,6-dinitrobenzene

C7H6N2O4 (182.0328)

m-Fluoroaniline

C6H6FN (111.0484)

Proflavine

Hemisulfate, proflavine

C13H11N3 (209.0953)

Proflavine is only found in individuals that have used or taken this drug. It is a topical antiseptic used mainly in wound dressings. [PubChem]Proflavine acts by interchelating DNA (intercalation), thereby disrupting DNA synthesis and leading to high levels of mutation in the copied DNA strands. This prevents bacterial reproduction. C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents

Azidopine

3-{2-[(4-azidophenyl)formamido]ethyl} 5-ethyl 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid

C27H26F3N5O5 (557.1886)

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D000345 - Affinity Labels

TTFB

4,5,6,7-Tetrachloro-2-trifluoromethylbenzimidazole

C8HCl4F3N2 (321.8846)

NAc-AAA-ME

Methyl-N-acetyl-N-L-alanyl-N-L-alanyl alaninate

C12H21N3O5 (287.1481)

BQ 485

N-(N-(N-((Hexahydro-1H-azepin-1-yl)carbonyl)-L-leucyl)-D-tryptophyl)-D-tryptophan

C35H44N6O5 (628.3373)

1,3,5-Trichloro-2-methoxybenzene

Benzene, 1,3,5-trichloro-2-methoxy- (9ci)

C7H5Cl3O (209.9406)

1,3,5-Trichloro-2-methoxybenzene is found in alcoholic beverages. Off-odour component found in foods etc. Responsible for cork taint in wine

R-Soterenol

N-[2-hydroxy-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide

C12H20N2O4S (288.1144)

C78273 - Agent Affecting Respiratory System > C29712 - Anti-asthmatic Agent > C319 - Bronchodilator

FA 7:1

(2E)-2,4-dimethylpent-2-enoic acid

C7H12O2 (128.0837)

3-Amino-2,3-dihydrobenzoic acid

5-Amino-1,3-cyclohexadiene-1-carboxylic acid

C7H9NO2 (139.0633)

D004791 - Enzyme Inhibitors

Crinine

1,2-Didehydrocrinan-3-ol

C16H17NO3 (271.1208)

Powellin

7-Methoxy-1,2-didehydrocrinan-3-ol, (3.alpha.)-

C17H19NO4 (301.1314)

Cyclacillin

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

C15H23N3O4S (341.1409)

Cyclacillin is only found in individuals that have used or taken this drug. It is a cyclohexylamido analog of penicillanic acid. [PubChem]The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases. D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D010406 - Penicillins D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic Same as: D01334

ST 25:5;O8

4-[(11,17-dihydroxy-3,20-dioxopregn-4-en-21-yl)oxy]-4-oxobutanoic acid

C25H34O8 (462.2254)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000893 - Anti-Inflammatory Agents Same as: D01442 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

TG(8:0/8:0/8:0)

Octanoic acid, 1,1,1-(1,2,3-propanetriyl) ester

C27H50O6 (470.3607)

TG(8:0/8:0/8:0) belongs to the family of triradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. Their general formula is [R1]OCC(CO[R2])O[R3]. TG(8:0/8:0/8:0) is made up of one octanoyl(R1), one octanoyl(R2), and one octanoyl(R3). It is used in bakery products. Carrier for essential oils and flavours. Glycerol trioctanoate is found in cereals and cereal products. D010592 - Pharmaceutic Aids > D014677 - Pharmaceutical Vehicles > D005079 - Excipients Same as: D01587 Tricaprilin (Trioctanoin) is used in study for patients with mild to moderate Alzheimer's disease and has a role as an anticonvulsant and a plant metabolite[1][2].

Dipotassium phosphate

Potassium dibasic phosphoric acid trihydric acid

HK2O4P (173.8887)

It is used in foods as a sequestrant, a pH control agent, and a nutrient in fermentation processes. Dipotassium phosphate (K2HPO4) - also phosphoric acid, dipotassium salt; dipotassium hydrogen orthophosphate; potassium phosphate, dibasic - is a highly water-soluble salt which is often used as a fertilizer, food additive and buffering agent. It is a common source of phosphorus and potassium. It is used in foods as a sequestrant, a pH control agent, and a nutrient in fermentation processes C78275 - Agent Affecting Blood or Body Fluid > C29730 - Electrolyte Replacement Agent D020011 - Protective Agents > D002327 - Cariostatic Agents D019995 - Laboratory Chemicals > D002021 - Buffers D001697 - Biomedical and Dental Materials Same as: D02403

FT-0669272

11beta,17alpha,21-trihydroxypregn-4-ene-3,20-dione 17-butyrate, 21-propionate

C28H40O7 (488.2774)

D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07A - Corticosteroids, plain > D07AB - Corticosteroids, moderately potent (group ii) C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D000893 - Anti-Inflammatory Agents Same as: D01886

Argipressin

2-{[(1-{19-amino-13-benzyl-6,9,12,15,18-pentahydroxy-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-[(C-hydroxycarbonimidoyl)methyl]-16-[(4-hydroxyphenyl)methyl]-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaene-4-carbonyl}pyrrolidin-2-yl)(hydroxy)methylidene]amino}-5-carbamimidamido-N-[(C-hydroxycarbonimidoyl)methyl]pentanimidate

C46H65N15O12S2 (1083.4378)

D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents > D014667 - Vasopressins D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D006401 - Hematologic Agents > D003029 - Coagulants > D006490 - Hemostatics D002317 - Cardiovascular Agents > D045283 - Natriuretic Agents D045283 - Natriuretic Agents > D050034 - Antidiuretic Agents Same as: D00101 Argipressin (Arg8-vasopressin) binds to the V1, V2, V3-vascular arginine vasopressin receptor, with a Kd value of 1.31 nM in A7r5 rat aortic smooth muscle cells for V1.

Talampanel

C19H19N3O3 (337.1426)

C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant Same as: D02696 Talampanel (LY300164) is an orally and selective α-amino-3-hydroxy-5-methyl-4-isoxazolepropionate (AMPA) receptor antagonis with anti-seizure activity[1]. Talampanel (IVAX) has neuroprotective effects in rodent stroke models[2]. Talampanel attenuates caspase-3 dependent apoptosis in mouse brain[2].

NS-102

5-Nitro-6,7,8,9-tetrahydrobenzo(G)indole-2,3-dione-3-oxime

C12H11N3O4 (261.075)

NS-102 is a selective kainate (GluK2) receptor antagonist. NS-102 is a potent GluR6/7 receptor antagonist[1][2][3].

FA 11:1

((1S,2R)-2-Hexylcycloprop-1-yl)acetic acid

An undecenoic acid having its double bond in the 10-position. It is derived from castor oil and is used for the treatment of skin problems. D - Dermatologicals > D01 - Antifungals for dermatological use > D01A - Antifungals for topical use C254 - Anti-Infective Agent > C514 - Antifungal Agent Same as: D02159 10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal. 10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal.

Hydroxychlor

alpha,alpha-Bis(4-hydroxyphenyl)-beta,beta,beta-trichloroethane

C14H11Cl3O2 (315.9825)

Mirex

1,2,3,4,5,5,6,7,8,9,10,10-Dodecachloropentacyclo[5.3.0.0(2,6).0(3,9).0(4,8)]decane

C10Cl12 (539.6262)

Mirex is a chlorinated hydrocarbon that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of cyclopentadiene. It was popularized to control fire ants but by virtue of its chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. Ironically, the spread of the red imported fire ant was actually encouraged by the use of Mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976.

Dimethylstilbestrol

(E)-4,4-(1,2-Dimethyl-1,2-ethenediyl)bisphenol

C16H16O2 (240.115)

Androstan-17-ol

5alpha-Androstan-17beta-ol

C19H32O (276.2453)

O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate

Ethoxy-(4-nitrophenoxy)-phenyl-sulphanylidene-$l^{5}-phosphane

C14H14NO4PS (323.0381)

D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors D010575 - Pesticides > D007306 - Insecticides D004791 - Enzyme Inhibitors D016573 - Agrochemicals

5-Diazouracil

5-Diazouracil; 2,6-Dioxo-5-diazopyrimidine

C4H2N4O2 (138.0178)

1,2,4-Trimethylbenzene

1,2,4-Trimethylbenzene (pseudocumene)

C9H12 (120.0939)

1,2,4-trimethylbenzene, also known as pseudocumene or psi-cumene, belongs to benzene and substituted derivatives class of compounds. Those are aromatic compounds containing one monocyclic ring system consisting of benzene. 1,2,4-trimethylbenzene is a plastic tasting compound found in black walnut and corn, which makes 1,2,4-trimethylbenzene a potential biomarker for the consumption of these food products. 1,2,4-trimethylbenzene can be found primarily in urine. 1,2,4-trimethylbenzene exists in all eukaryotes, ranging from yeast to humans. 1,2,4-trimethylbenzene is a non-carcinogenic (not listed by IARC) potentially toxic compound. 1,2,4-Trimethylbenzene is a colorless liquid with chemical formula C9H12. It is a flammable aromatic hydrocarbon with a strong odor. It occurs naturally in coal tar and petroleum (about 3\\%). It is nearly insoluble in water, but well-soluble in ethanol, diethyl ether, and benzene.

2,4-Diphenyl-1-butene

1,1-(1-Methylene-1,3-propanediyl)bisbenzene, 9ci

C16H16 (208.1252)

2,4-Diphenyl-1-butene is a styrene dimer. Present as an impurity in polystyrene food containers and other products - liberated on heatin

Fluprednisolone

Pregna-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6.alpha.,11.beta.)-

C21H27FO5 (378.1842)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D005938 - Glucocorticoids C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid D000893 - Anti-Inflammatory Agents Same as: D04227

2,4-DINITROANILINE

1-Amino-2,4-dinitrobenzene

C6H5N3O4 (183.028)

Moxestrol

Moxestrol; 11beta-Methoxy-17alpha-ethinylestradiol; 17alpha-Ethinyl-11beta-methoxy-1,3,5(10)-estratrien-3,17-diol

C21H26O3 (326.1882)

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CB - Synthetic estrogens, plain D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones ATC code: G03CB04

coelenterazine

8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo-[1,2a]pyrazin-3(7H)-one

C26H21N3O3 (423.1583)

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D049408 - Luminescent Agents

4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine

4-{13-methyl-4,6-dioxa-11,12-diazatricyclo[7.5.0.0³,⁷]tetradeca-1,3(7),8,10,12-pentaen-10-yl}aniline

C17H15N3O2 (293.1164)

D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents

Cgp 52608

1-methyl-3-[(Z)-(4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene)amino]thiourea

C8H12N4OS2 (244.0453)

Barbamide

C20H23Cl3N2O2S (460.0546)

Complestatin

Chloropeptin II

C61H45Cl6N7O15 (1325.1105)

A heterodetic cyclic peptide consisting of N-acylated trytophan, 3,5-dichloro-4-hydroxyphenylglycine, 4-hydroxyphenylglycine, 3,5-dichloro-4-hydroxyphenylglycyl, tyrosine and 4-hydroxyphenylglycine residues joined in sequence and in which the side-chain of the central 4-hydroxyphenylglycine residue is attached to the side-chain of the tryptophan via a C3-C6 bond and to the side-chain of the tyrosine via an ether bond from C5. It is isolated from the culture broth of Streptomyces and has anti-HIV-1 activity.

Lipoyl-AMP

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid

C18H26N5O8PS2 (535.096)

Lipoyl-amp is part of the Protein modification, and Lipoic acid metabolism pathways. It is a substrate for: Lipoyltransferase 1, mitochondrial.

5-(3-Methyl-1-triazeno)imidazole-4-carboxamide

5-(3-Methyl-1-triazeno)imidazole-4-carboxamide monohydrochloride

C5H8N6O (168.076)

D009676 - Noxae > D000477 - Alkylating Agents

Dimethylurea

N,N-Dimethyl-urea

C3H8N2O (88.0637)

Dimethylurea (DMU) (IUPAC systematic name: 1,3-Dimethylurea ) is a urea derivative and used as an intermediate in organic synthesis. It is a colorless crystalline powder with little toxicity.

Chlorophyllide b

C35H32MgN4O6 (628.2172)

Nornitrogen mustard

Nornitrogen mustard, hydrochloride

C4H9Cl2N (141.0112)

Nornitrogen mustard is a metabolite of cyclophosphamide. Cyclophosphamide (trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. It is used to treat various types of cancer and some autoimmune disorders. (Wikipedia) D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds

DG(14:0/14:0/0:0)

(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl tetradecanoate

C31H60O5 (512.4441)

DG(14:0/14:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/14:0/0:0), in particular, consists of two chains of myristic acid at the C-1 and C-2 positions. The myristic acid moieties are derived from nutmeg and butter. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. DG(14:0/14:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(14:0/14:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.

Aplysiatoxin

(1S,3R,4S,9R,13S,14R)-3-[(2S,5S)-5-(2-bromo-5-hydroxyphenyl)-5-methoxypentan-2-yl]-13-hydroxy-9-[(1R)-1-hydroxyethyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione

C32H47BrO10 (670.2352)

The parent member of the class of aplysiatoxins. It is a cyanotoxin produced by several species of freshwater and marine cyanobacteria, as well as algae and molluscs. D009676 - Noxae > D011042 - Poisons > D008235 - Lyngbya Toxins D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins

Isovaltrate

C22H30O8 (422.1941)

Antibiotic PS 5

3-(2-Acetamidoethyl)thio-6-ethyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid

C13H18N2O4S (298.0987)

D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D013845 - Thienamycins D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams

Kuraridinol

(2E) -1- [ 2,4-Dihydroxy-3- [ 5-hydroxy-5-methyl-2- (1-methylethenyl) hexyl ] -6-methoxyphenyl ] -3- (2,4-dihydroxyphenyl) -2-propen-1-one

C26H32O7 (456.2148)

A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2, 4, 2 and 4, a methoxy group at position 6 and a 5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl group at position 3 respectively.

2-(2-Aminoethyl)thiazole

2-(2-Aminoethyl)thiazole dihydrochloride

C5H8N2S (128.0408)

D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D017442 - Histamine Agonists

2-Methylhistamine

2-(2-methyl-1H-imidazol-5-yl)ethan-1-amine

C6H11N3 (125.0953)

DL-Glutamine

C5H10N2O3 (146.0691)

DL-Glutamine is used for biochemical research and drug synthesis.

D-Phenylalanine

alpha-Amino-beta-phenylpropionic acid

C9H11NO2 (165.079)

Flavouring ingredient. (±)-Phenylalanine is found in many foods, some of which are cucumber, green bell pepper, yellow bell pepper, and saskatoon berry.

D-Valine

2-Amino-3-methylbutanoic acid

C5H11NO2 (117.079)

Flavouring ingredient

flumequine

C14H12FNO3 (261.0801)

J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01M - Quinolone antibacterials D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D024841 - Fluoroquinolones C254 - Anti-Infective Agent > C258 - Antibiotic > C795 - Quinolone Antibiotic D004791 - Enzyme Inhibitors CONFIDENCE standard compound; INTERNAL_ID 1030 CONFIDENCE standard compound; INTERNAL_ID 8533 CONFIDENCE standard compound; EAWAG_UCHEM_ID 3642

2-Oxo-3-methylvalerate

(+-)-3-Methyl-2-oxovaleric acid sodium salt

CONFIDENCE standard compound; ML_ID 14 3-Methyl-2-oxovaleric acid is a neurotoxin, an acidogen, and a metabotoxin, and also an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids.

Cedrol

(3R-(3.ALPHA.,3A.BETA.,6.ALPHA.,7.BETA.,8A.ALPHA.))-OCTAHYDRO-3,6,8,8-TETRAMETHYL-1H-3A,7-METHANOAZULEN-6-OL

C15H26O (222.1984)

Cedrol is a cedrane sesquiterpenoid and a tertiary alcohol. Cedrol is a natural product found in Xylopia aromatica, Widdringtonia whytei, and other organisms with data available. Cedrol is a bioactive sesquiterpene, a potent competitive inhibitor of cytochrome P-450 (CYP) enzymes. Cedrol inhibits CYP2B6-mediated bupropion hydroxylase and CYP3A4-mediated midazolam hydroxylation with Ki of 0.9 μM and 3.4 μM, respectively. Cedrol also has weak inhibitory effect on CYP2C8, CYP2C9, and CYP2C19 enzymes[1]. Cedrol is found in cedar essential oil and poetesses anti-septic, anti-inflammatory, anti-spasmodic, tonic, astringent, diuretic, insecticidal, and anti-fungal activities[2]. Cedrol is a bioactive sesquiterpene, a potent competitive inhibitor of cytochrome P-450 (CYP) enzymes. Cedrol inhibits CYP2B6-mediated bupropion hydroxylase and CYP3A4-mediated midazolam hydroxylation with Ki of 0.9 μM and 3.4 μM, respectively. Cedrol also has weak inhibitory effect on CYP2C8, CYP2C9, and CYP2C19 enzymes[1]. Cedrol is found in cedar essential oil and poetesses anti-septic, anti-inflammatory, anti-spasmodic, tonic, astringent, diuretic, insecticidal, and anti-fungal activities[2].

Hydroxyanthraquinone

InChI=1/C14H8O3/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7,15

C14H8O3 (224.0473)

1-hydroxyanthraquinone is a monohydroxyanthraquinone. 1-Hydroxyanthraquinone is a natural product found in Rheum palmatum, Handroanthus impetiginosus, and Morinda citrifolia with data available. D009676 - Noxae > D002273 - Carcinogens 1-Hydroxyanthraquinone, a naturally occurring compound with oral activity from some plants like Tabebuia avellanedae, exhibits carcinogenic effect[1]. 1-Hydroxyanthraquinone, a naturally occurring compound with oral activity from some plants like Tabebuia avellanedae, exhibits carcinogenic effect[1].

6-Hydroxymelatonin

N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

C13H16N2O3 (248.1161)

6-Hydroxymelatonin, also known as lopac-H-0627, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 6-Hydroxymelatonin is considered to be a practically insoluble (in water) and relatively neutral molecule. 6-Hydroxymelatonin has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, 6-hydroxymelatonin is primarily located in the cytoplasm. 6-Hydroxymelatonin is the main primary metabolite that can be biosynthesized from melatonin through its interaction with the enzyme cytochrome P450 (CYP) 1A2 (PMID: 11452239). In humans, 6-hydroxymelatonin is involved in the tryptophan metabolism pathway. Melatonin is a hormone that is metabolized by cytochrome P450 (CYP) 1A2 to its main primary metabolite 6-hydroxymelatonin. (PMID 11452239) [HMDB]. 6-Hydroxymelatonin is found in many foods, some of which are garden onion, millet, peppermint, and apricot. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D020011 - Protective Agents > D002316 - Cardiotonic Agents D002317 - Cardiovascular Agents 6-Hydroxymelatonin is a primary metabolic of Melatonin, which is metabolized by cytochrome P450 (CYP) 1A2.

Flumequine

7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0⁵,¹³]trideca-2,5(13),6,8-tetraene-3-carboxylic acid

C14H12FNO3 (261.0801)

Ciprofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV, enzymes necessary to separate bacterial DNA, thereby inhibiting cell division. Flumequine is a 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. The molecular formula is C14H12FNO3 It is a white powder, odorless, flavorless, insoluble in water but soluble in organic solvent. Flumequine is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class used to treat bacterial infections. It is a first-generation fluoroquinolone antibacterial that has been removed from clinical use and is no longer being marketed. It kills bacteria by interfering with the enzymes that cause DNA to unwind and duplicate. Flumequine was used in veterinarian medicine for the treatment of enteric infections (all infections of the intestinal tract), as well as to treat cattle, swine, chickens, and fish, but only in a limited number of countries. It was occasionally used in France (and a few other European Countries) to treat urinary tract infections under the trade name Apurone. However this was a limited indication because only minimal serum levels were achieved. The first quinolone used was nalidixic acid (was marketed in many countries as Negram) followed by the fluoroquinolone flumequine. The first-generation fluoroquinolone agents, such as flumequine, had poor distribution into the body tissues and limited activity. As such they were used mainly for treatment of urinary tract infections. Flumequine (benzo quinolizine) was first patented in 1973, (German Patent) by Rikker Labs. Flumequine is a known antimicrobial compound described and claimed in U.S. Pat. No. 3,896,131 (Example 3), July 22, 1975. Flumequine is the first quinolone compound with a fluorine atom at the C6-position of the related quinolone basic molecular structure. Even though this was the first fluoroquinolone, it is oftentimes overlooked when classifying the drugs within this class by generations and excluded from such a list. There continues to be considerable debate as to whether or not this DNA damage is to be considered one of the mechanisms of action concerning the severe adverse reactions experienced by some patients following fluoroquinolone therapy. J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01M - Quinolone antibacterials D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D024841 - Fluoroquinolones C254 - Anti-Infective Agent > C258 - Antibiotic > C795 - Quinolone Antibiotic D004791 - Enzyme Inhibitors

Melissic acid A

Melissic acid,synthetic

C30H60O2 (452.4593)

Melissic acid A is found in fats and oils. Melissic acid A is found in some plant waxes, e.g. cotto Found in some plant waxes, e.g. cotton

(+)-Lysergic acid

6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxylic acid

C16H16N2O2 (268.1212)

y,y-Carotene, 7,7',8,8',11,12-hexahydro-, cis-(9CI)

2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaene

C40H62 (542.4851)

N-(N-(N-((Hexahydro-1H-azepin-1-yl)carbonyl)-L-leucyl)-D-tryptophyl)-D-tryptophan

2-({2-[(2-{[(azepan-1-yl)(hydroxy)methylidene]amino}-1-hydroxy-4-methylpentylidene)amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene}amino)-3-(1H-indol-3-yl)propanoate

C35H44N6O5 (628.3373)

N-(3-Chloro-2-oxo-1-(phenylmethyl)propyl)-4-methylbenzenesulfonamide

Benzenesulfonamide,N-[3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-

C17H18ClNO3S (351.0696)

4-(Phosphonomethyl)piperidine-2-carboxylic acid

4-(Phosphonomethyl)-2-piperidinecarboxylic acid

C7H14NO5P (223.061)

5-Diazouracil

5-(diazyn-1-ium-1-yl)-6-oxo-1,6-dihydropyrimidin-2-olate

C4H2N4O2 (138.0178)

Durabolin

15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl 3-phenylpropanoate

C27H34O3 (406.2508)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

cefuroxime axetil

1-{3-[(carbamoyloxy)methyl]-7-[2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy}ethyl acetate

C20H22N4O10S (510.1057)

8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate

8-Methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylic acid

C17H20N2O2 (284.1525)

D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents D005765 - Gastrointestinal Agents > D000932 - Antiemetics D002491 - Central Nervous System Agents Tropisetron (SDZ-ICS-930 free base) is a selective 5-HT3 receptor antagonist and α7-nicotinic receptor agonist with an IC50 of 70.1 ± 0.9 nM for 5-HT3 receptor. IC50 value: 70.1 ± 0.9 nM [1] Target: 5-HT3 receptor in vitro: Tropisetron specifically inhibited both IL-2 gene transcription and IL-2 synthesis in stimulated T cells. tropisetron inhibited both the binding to DNA and the transcriptional activity of NFAT and AP-1. We also observed that tropisetron is a potent inhibitor of PMA plus ionomycin-induced NF-(kappa)B activation but in contrast TNF(alpha)-mediated NF-(kappa)B activation was not affected by this antagonist [2]. Tropisetron prevents the phosphorylation and thus activation of the p38 MAPK, which is involved in post-transcriptional regulation of various cytokines [3]. in vivo: Two different doses of tropisetron (5 and 10 mg/kg) or vehicle were administered intraperitoneally 30 min before pMCAO. Neurological deficit scores, mortality rate and infarct volume were determined 24 h after permanent focal cerebral ischemia [4].

Coelenterazine

2-(4-Hydroxybenzyl)-6-(4-hydroxyphenyl)-8-benzyl-3,7-dihydroimidazo(1,2-a)pyrazin-3-one

C26H21N3O3 (423.1583)

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D049408 - Luminescent Agents

Epi-Lipoxin A4

5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid

Epicholesterol

2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C27H46O (386.3548)

Himbacine

4-[2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3H-naphtho[2,3-c]furan-1-one

C22H35NO2 (345.2668)

Histidinyl-Leucine

2-{[2-amino-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino}-4-methylpentanoate

C12H20N4O3 (268.1535)

Histidinol

2-amino-3-(3H-imidazol-4-yl)propan-1-ol

Iodofiltic Acid

15-(4-iodophenyl)-3-methylpentadecanoic acid

C22H35IO2 (458.1682)

Soterenol monohydrochloride

2-Hydroxy-5-(1-hydroxy-2-(isopropylamino)ethyl)methane sulfonanilide monohydrochloride

C12H20N2O4S (288.1144)

C78273 - Agent Affecting Respiratory System > C29712 - Anti-asthmatic Agent > C319 - Bronchodilator

L-Cysteic acid

(2R)-2-Amino-3-sulphopropanoic acid

C3H7NO5S (169.0045)

Cysteinesulfonic acid, also known as (2r)-2-amino-3-sulfopropanoic acid or 3-sulfoalanine, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Cysteinesulfonic acid is soluble (in water) and an extremely strong acidic compound (based on its pKa). Cysteinesulfonic acid can be found in a number of food items such as roman camomile, pili nut, chicory, and garden tomato, which makes cysteinesulfonic acid a potential biomarker for the consumption of these food products.

vellosimine

15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

C19H20N2O (292.1576)

Vellosimine is a member of the class of compounds known as macroline alkaloids. Macroline alkaloids are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. Vellosimine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Vellosimine can be found in a number of food items such as caraway, italian oregano, star anise, and fox grape, which makes vellosimine a potential biomarker for the consumption of these food products.

Hydroxyphenyllactic acid

2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid

C9H10O4 (182.0579)

Hydroxyphenyllactic acid is an antifungal metabolite.

3-Methyl-2-oxovaleric acid

(3S)-3-Methyl-2-oxopentanoic acid

A 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. Used as a clinical marker for maple syrup urine disease (MSUD). 3-Methyl-2-oxovaleric acid is a neurotoxin, an acidogen, and a metabotoxin, and also an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids.

Acerosin

5,7-Dihydroxy-2- (3-hydroxy-4-methoxyphenyl) -6,8-dimethoxy-4H-1-benzopyran-4-one

C18H16O8 (360.0845)

A trihydroxyflavone that is 5,7,3-trihydroxyflavone with methoxy substituents at positions 6, 8 and 4 respectively.

GLUTARIC ANHYDRIDE

C5H6O3 (114.0317)

Neoxanthin

(1R,3S)-6-[(3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenylidene]-1,5,5-trimethyl-cyclohexane-1,3-diol

C40H56O4 (600.4178)

9-cis-neoxanthin is a neoxanthin in which all of the double bonds have trans geometry except for that at the 9 position, which is cis. It is a 9-cis-epoxycarotenoid and a neoxanthin. Neoxanthin is a natural product found in Hibiscus syriacus, Cladonia rangiferina, and other organisms with data available. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

phytofluene

(12E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,22,26,30-decaene

C40H62 (542.4851)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Phytofluene is a carotenoid pigment with an orange color found naturally in tomatoes and other vegetables. It is the second product of carotenoid biosynthesis. It is formed from phytoene in a desaturation reaction leading to the formation of five conjugated double bonds. In the following step, addition of carbon-carbon conjugated double bonds leads to the formation of z-carotene and appearance of visible color.; Phytofluene is a carotenoid pigment with an orange color found naturally in tomatoes and other vegetables. It is the second product of carotenoid biosynthesis. Phytofluene is found in many foods, some of which are bitter gourd, yellow bell pepper, caraway, and pepper (c. annuum).

Gamma-tocopherol/beta-tocopherol

2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,5,8-TRIMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)-, (2R*(4R*,8R*))- 6-CHROMANOL, 2,5,8-TRIMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)-

C28H48O2 (416.3654)

beta-Tocopherol is an antioxidant which is synthesized by photosynthetic organisms and plays an important role in human and animal nutrition. beta-Tocopherols can be oxidized in dry CH2Cl2 or CH3CN by one electron to form cation radicals that deprotonate to form the neutral phenoxyl radicals, which are then immediately further oxidized by one electron to the phenoxonium cations (an ECE electrochemical mechanism, where E signifies an electron transfer and C represents a chemical step, with the electrochemical mechanism having been determined by in situ spectroscopic analysis). The phenoxonium cation of beta-tocopherol is stable for several minutes (PMID: 16771430). beta-Tocopherol has been identified in the human placenta (PMID: 32033212). Beta-tocopherol is a tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 5 and 8. While it is found in low concentrations in many vegetable oils, only cottonseed oil contains significant amounts. It has a role as a plant metabolite and a food component. It is a vitamin E and a tocopherol. beta-Tocopherol is a natural product found in Trachycarpus fortunei, Crataegus monogyna, and other organisms with data available. A natural tocopherol with less antioxidant activity than alpha-tocopherol. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. As in GAMMA-TOCOPHEROL, it also has three methyl groups on the 6-chromanol nucleus but at different sites. A tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 5 and 8. While it is found in low concentrations in many vegetable oils, only cottonseed oil contains significant amounts. (rel)-β-Tocopherol is a relative configuration of β-Tocopherol.(±)-β-Tocopherol is a lipid-soluble form of vitamin E with antioxidant activity. β-Tocopherol can inhibit tyrosinase activity and melanin synthesis. β-Tocopherol also can prevent the inhibition of cell growth and of PKC activity caused by d-alpha-tocopherol[1]. β-Tocopherol is an analogue of vitamin E, exhibits antioxidant properties. β-Tocopherol can inhibit tyrosinase activity and melanin synthesis. β-Tocopherol also can prevent the inhibition of cell growth and of PKC activity caused by d-alpha-tocopherol[1][2][3]. β-Tocopherol is an analogue of vitamin E, exhibits antioxidant properties. β-Tocopherol can inhibit tyrosinase activity and melanin synthesis. β-Tocopherol also can prevent the inhibition of cell growth and of PKC activity caused by d-alpha-tocopherol[1][2][3].

Mukurozidiol

7H-Furo[3,2-g][1]benzopyran-7-one, 9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-

C17H18O7 (334.1052)

Constituent of Japanese drug byakusi obtained from Angelica subspecies Also from lemon oil and other Citrus subspecies [DFC]. (R)-Byakangelicin is found in lemon, citrus, and herbs and spices. Mukurozidiol is a member of psoralens. (Rac)-Byakangelicin is a natural product found in Ruta graveolens, Angelica, and other organisms with data available. (S)-Byakangelicin is found in herbs and spices. (S)-Byakangelicin is a constituent of common rue (Ruta graveolens). D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins (Rac)-Byakangelicin is a racemate of Byakangelicin mainly isolated from the genus Angelica. Byakangelicin is an aldose-reductase inhibitor with an IC50 value of 6.2 μM[1]. (Rac)-Byakangelicin is a racemate of Byakangelicin mainly isolated from the genus Angelica. Byakangelicin is an aldose-reductase inhibitor with an IC50 value of 6.2 μM[1]. Byakangelicin, one of the active compounds found in the roots of Angelica gigas, can serve as a modulator to improve brain accumulation of diverse active compounds (Umb, Cur, and Dox) and enhance therapeutic effects[1]. Byakangelicin is likely to increase the expression of all PXR target genes (such as MDR1) and induce a wide range of agent-agent interactions. Byakangelicin can inhibit the effects of sex hormones, it may increase the catabolism of endogenous hormones[2]. Byakangelicin, one of the active compounds found in the roots of Angelica gigas, can serve as a modulator to improve brain accumulation of diverse active compounds (Umb, Cur, and Dox) and enhance therapeutic effects[1]. Byakangelicin is likely to increase the expression of all PXR target genes (such as MDR1) and induce a wide range of agent-agent interactions. Byakangelicin can inhibit the effects of sex hormones, it may increase the catabolism of endogenous hormones[2].

13-HoTrE

C18H30O3 (294.2195)

A hydroxyoctadecatrienoic acid that consists of 9Z,11E,15Z-octadecatrienoic acid bearing an additional 13-hydroxy substituent. CONFIDENCE standard compound; NATIVE_RUN_ID STD_neg_MSMS_1min0099.mzML; PROCESSING averaging of repeated ion fragments at 30.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID STD_neg_MSMS_1min0099.mzML; PROCESSING averaging of repeated ion fragments at 20.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID STD_neg_MSMS_1min0099.mzML; PROCESSING averaging of repeated ion fragments at 10.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001341.mzML; PROCESSING averaging of repeated ion fragments at 30.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001341.mzML; PROCESSING averaging of repeated ion fragments at 20.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001341.mzML; PROCESSING averaging of repeated ion fragments at 10.0 eV within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001341.mzML; PROCESSING averaging of repeated ion fragments at 40.0 NCE within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001341.mzML; PROCESSING averaging of repeated ion fragments at 30.0 NCE within 5 ppm window [MS, MS:1000575, mean of spectra, ] CONFIDENCE standard compound; NATIVE_RUN_ID QExHF03_NM_0001341.mzML; PROCESSING averaging of repeated ion fragments at 20.0 NCE within 5 ppm window [MS, MS:1000575, mean of spectra, ]

Dicloxacillin

C19H17Cl2N3O5S (469.0266)

J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01C - Beta-lactam antibacterials, penicillins > J01CF - Beta-lactamase resistant penicillins D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D010406 - Penicillins D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic CONFIDENCE standard compound; EAWAG_UCHEM_ID 3665

oxamniquine

C14H21N3O3 (279.1583)

P - Antiparasitic products, insecticides and repellents > P02 - Anthelmintics > P02B - Antitrematodals > P02BA - Quinoline derivatives and related substances D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C250 - Antihelminthic Agent [Raw Data] CB143_Oxamniquine_pos_50eV_CB000053.txt [Raw Data] CB143_Oxamniquine_pos_40eV_CB000053.txt [Raw Data] CB143_Oxamniquine_pos_30eV_CB000053.txt [Raw Data] CB143_Oxamniquine_pos_20eV_CB000053.txt [Raw Data] CB143_Oxamniquine_pos_10eV_CB000053.txt

4-Methylumbelliferylglucuronide

4-Methylumbelliferone glucuronide

C16H16O9 (352.0794)

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D049408 - Luminescent Agents D004396 - Coloring Agents > D005456 - Fluorescent Dyes relative retention time with respect to 9-anthracene Carboxylic Acid is 0.488 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2121; CONFIDENCE confident structure

undecenoic acid

10c-Undecenoic acid

D - Dermatologicals > D01 - Antifungals for dermatological use > D01A - Antifungals for topical use C254 - Anti-Infective Agent > C514 - Antifungal Agent 10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal. 10-Undecenoic acid is used as a starting agent in the synthesis of Pheromone (11Z)-hexadecenal.

Valine

poly-l-valine

C5H11NO2 (117.079)

A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group. Acquisition and generation of the data is financially supported by the Max-Planck-Society L-Valine (Valine) is a new nonlinear semiorganic material[1]. L-Valine (Valine) is a new nonlinear semiorganic material[1].

Brassicasterol

ergosta-5,22E-dien-3beta-ol

C28H46O (398.3548)

An 3beta-sterol that is (22E)-ergosta-5,22-diene substituted by a hydroxy group at position 3beta. It is a phytosterol found in marine algae, fish, and rapeseed oil. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].

Histidinol

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.044 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.042 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.041 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.040

Justicidin B

C21H16O6 (364.0947)

relative retention time with respect to 9-anthracene Carboxylic Acid is 1.212 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.209

alpha-Ergocryptine

C32H41N5O5 (575.3108)

Ergotaman bearing hydroxy, isopropyl, and 2-methylpropyl groups at the 12, 2 and 5 positions, respectively, and oxo groups at positions 3, 6, and 18. It is a natural ergot alkaloid. Ergocryptine discussed in the literature prior to 1967, when beta-ergocryptine was separated from alpha-ergocryptine, is now referred to as alpha-ergocryptine. D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents > D018491 - Dopamine Agonists relative retention time with respect to 9-anthracene Carboxylic Acid is 1.085 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.083 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.081 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.080

Ergocornine

Ergocorninine

C31H39N5O5 (561.2951)

Ergotaman bearing a hydroxy group at the 12 position, isopropyl groups at the 2 and 5alpha positions, and oxo groups at positions 3, 6, and 18. It is a natural ergot alkaloid. CONFIDENCE Reference Standard (Level 1) relative retention time with respect to 9-anthracene Carboxylic Acid is 1.024 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.021 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.019 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.017

Secoisolariciresinol

(-)-Secoisolariciresinol

C20H26O6 (362.1729)

Annotation level-1 D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens relative retention time with respect to 9-anthracene Carboxylic Acid is 0.816 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.813 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.806 Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids.

Hydrocortisone hemisuccinate

C25H34O8 (462.2254)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000893 - Anti-Inflammatory Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

FLUOCINONIDE

C26H32F2O7 (494.2116)

C - Cardiovascular system > C05 - Vasoprotectives > C05A - Agents for treatment of hemorrhoids and anal fissures for topical use > C05AA - Corticosteroids D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07A - Corticosteroids, plain > D07AC - Corticosteroids, potent (group iii) D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D005938 - Glucocorticoids C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid D000893 - Anti-Inflammatory Agents D018926 - Anti-Allergic Agents

Cortisone acetate

C23H30O6 (402.2042)

C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones D000893 - Anti-Inflammatory Agents Cortisone acetate (Cortisone 21-acetate), an oxidized metabolite of Cortisol (a Glucocorticoid). Cortisone acetate acts as an immunosuppressant and anti-inflammatory agent. Cortisone acetate can partially intervene in binding of Glucocorticoid to Glucocorticoid-receptor at high concentrations[1][3][4].

nisoldipine

Nisoldipine (Sular)

C20H24N2O6 (388.1634)

C - Cardiovascular system > C08 - Calcium channel blockers > C08C - Selective calcium channel blockers with mainly vascular effects > C08CA - Dihydropyridine derivatives C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent > C333 - Calcium Channel Blocker D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents D000077264 - Calcium-Regulating Hormones and Agents D049990 - Membrane Transport Modulators C93038 - Cation Channel Blocker

L-Histidinol

An amino alcohol that is propanol substituted by 1H-imidazol-4-yl group at position 3 and an amino group at position 2 (the 2S stereoisomer).

Indole-3-pyrubate

Indole-3-pyruvic acid

C11H9NO3 (203.0582)

D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D000975 - Antioxidants > D016166 - Free Radical Scavengers D020011 - Protective Agents > D000975 - Antioxidants

5-Hydroxymethyluracil

C5H6N2O3 (142.0378)

A primary alcohol that is uracil bearing a hydroxymethyl substituent at the 5-position. D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents D007155 - Immunologic Factors 5-Hydroxymethyluracil is a product of oxidative DNA damage. 5-Hydroxymethyluracil can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase. 5-Hydroxymethyluracil is a product of oxidative DNA damage. 5-Hydroxymethyluracil can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase.

L-Methionine sulfoximine

L-Methionine-DL-sulfoximine

C5H12N2O3S (180.0569)

A methionine sulfoximine in which the amino group has S-stereochemistry.

Cycloleucine

1-Amino-1-cyclopentanecarboxylic acid

C6H11NO2 (129.079)

C308 - Immunotherapeutic Agent > C574 - Immunosuppressant

6-Hydroxynicotinic Acid

C6H5NO3 (139.0269)

A monohydroxypyridine that is the 6-hydroxy derivative of nicotinic acid. 6-Hydroxynicotinic acid is an endogenous metabolite.

Hydroxyphenyllactic acid

2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid

C9H10O4 (182.0579)

Hydroxyphenyllactic acid is a tyrosine metabolite. It is carcinogenic. The level of hydroxyphenyllactic acid is elevated in patients with deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2). (PMID 4720815) [HMDB] Hydroxyphenyllactic acid is an antifungal metabolite.

2-Hydroxyphenylacetic acid

ortho-Hydroxyphenylacetic acid

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2-Hydroxyphenylacetic acid is a potential biomarker for the food products, and found to be associated with phenylketonuria (PKU). 2-Hydroxyphenylacetic acid is a potential biomarker for the food products, and found to be associated with phenylketonuria (PKU). D-(-)-Mandelic acid is a natural compound isolated from bitter almonds. D-(-)-Mandelic acid is a natural compound isolated from bitter almonds.

ergocryptine

12-hydroxy-2-(1-methylethyl)-5alpha-(2-methylpropyl)ergotaman-3,6,18-trione

C32H41N5O5 (575.3108)

D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents > D018491 - Dopamine Agonists CONFIDENCE Claviceps purpurea sclerotia

N-Methyltryptamine

Nω-methyltryptamine

C11H14N2 (174.1157)

HEXADECANEDIOIC ACID

C16H30O4 (286.2144)

An alpha,omega-dicarboxylic acid that is the 1,14-dicarboxy derivative of tetradecane. Hexadecanedioic acid is covalently linked to Sepharose 4B, shows better performance in terms of specificity than dye-based resins and could be used for depletion of SA from plasma samples. Hexadecanedioic acid is covalently linked to Sepharose 4B, shows better performance in terms of specificity than dye-based resins and could be used for depletion of SA from plasma samples.

Montanic acid

Octacosanoic acid,synthetic

C28H56O2 (424.428)

1-Methyluric acid

C6H6N4O3 (182.044)

An oxopurine that is 7,9-dihydro-1H-purine-2,6,8(3H)-trione substituted by a methyl group at N-1. It is one of the metabolites of caffeine found in human urine.

indoxyl

1H-Indol-3-ol

C8H7NO (133.0528)

Perillic acid

C10H14O2 (166.0994)

C471 - Enzyme Inhibitor > C2020 - Farnesyl Transferase Inhibitor

4-Quinolinecarboxylic acid

Quinoline-4-carboxylic acid

C10H7NO2 (173.0477)

NSC 13138 is an endogenous metabolite.

6-Methylmercaptopurine

C6H6N4S (166.0313)

acetanilide

N-phenylacetamide

C8H9NO (135.0684)

FLUPERLAPINE

C19H20FN3 (309.1641)

mepivacaine

C15H22N2O (246.1732)

D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local > N01BB - Amides D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent

N-Methylanthranilic acid

An aromatic amino acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is substituted by a methyl group. 2-(Methylamino)benzoic acid is the main metabolite of methyl-N-methylanthranilates (MMA) (HY-76705) and is the compound in which the ester group is converted. MMA can be isolated from citrus fruits and has potential analgesic activity. 2-(Methylamino)benzoic acid was used to detect the metabolic levels of MMA in rat liver[1].

N8-Acetylspermidine

C9H21N3O (187.1685)

prazepam

C19H17ClN2O (324.1029)

D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents N - Nervous system > N05 - Psycholeptics > N05B - Anxiolytics > N05BA - Benzodiazepine derivatives C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C1012 - Benzodiazepine D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators C78272 - Agent Affecting Nervous System > C28197 - Antianxiety Agent

tocainide

C11H16N2O (192.1263)

C - Cardiovascular system > C01 - Cardiac therapy > C01B - Antiarrhythmics, class i and iii > C01BB - Antiarrhythmics, class ib D002317 - Cardiovascular Agents > D026941 - Sodium Channel Blockers > D061567 - Voltage-Gated Sodium Channel Blockers C78274 - Agent Affecting Cardiovascular System > C47793 - Antiarrhythmic Agent D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D049990 - Membrane Transport Modulators C93038 - Cation Channel Blocker

4-nitrocatechol

C6H5NO4 (155.0219)

A member of the class of catechols that is benzene-1,2-diol substituted by a nitro group at position 4.It is the by-product of the hydroxylation of p-nitrophenol. 4-Nitrocatechol is a potent lipoxygenase inhibitor[1]. 4-Nitrocatechol is a potent lipoxygenase inhibitor[1].

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens Annotation level-1

(2-Aminoethyl)phosphonic acid

C2H8NO3P (125.0242)

A phosphonic acid in which the hydrogen attached to the phosphorus of phosphonic acid is substituted by a 2-aminoethyl group. (2-Aminoethyl)phosphonic acid is an endogenous metabolite.

L-2,3-Diaminopropionic acid

C3H8N2O2 (104.0586)

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

fenoprofen

calcium(-1) anion; 2-(3-phenoxyphenyl)propanoate

C15H14O3 (242.0943)

M - Musculo-skeletal system > M01 - Antiinflammatory and antirheumatic products > M01A - Antiinflammatory and antirheumatic products, non-steroids > M01AE - Propionic acid derivatives D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C471 - Enzyme Inhibitor > C1323 - Cyclooxygenase Inhibitor D000893 - Anti-Inflammatory Agents D004791 - Enzyme Inhibitors

hydroxyzine

C21H27ClN2O2 (374.1761)

N - Nervous system > N05 - Psycholeptics > N05B - Anxiolytics > N05BB - Diphenylmethane derivatives D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists C308 - Immunotherapeutic Agent > C29578 - Histamine-1 Receptor Antagonist D003879 - Dermatologic Agents > D000982 - Antipruritics Hydroxyzine, a benzodiazepine antihistamine agent, acts as an orally active histamine?H1-receptor and serotonin antagonist. Hydroxyzine has anxiolytic effect and can be used for the research of generalised anxiety disorder[1].

acetohexamide

C15H20N2O4S (324.1144)

A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins > A10BB - Sulfonylureas C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C97936 - Sulfonylurea Antidiabetic Agent D007004 - Hypoglycemic Agents CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4168; ORIGINAL_PRECURSOR_SCAN_NO 4165 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4170; ORIGINAL_PRECURSOR_SCAN_NO 4165 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4125; ORIGINAL_PRECURSOR_SCAN_NO 4121 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4143; ORIGINAL_PRECURSOR_SCAN_NO 4140 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4151; ORIGINAL_PRECURSOR_SCAN_NO 4150 ORIGINAL_PRECURSOR_SCAN_NO 4163; CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4165 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4165; ORIGINAL_PRECURSOR_SCAN_NO 4163 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8394; ORIGINAL_PRECURSOR_SCAN_NO 8389 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8413; ORIGINAL_PRECURSOR_SCAN_NO 8409 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8458; ORIGINAL_PRECURSOR_SCAN_NO 8454 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8489; ORIGINAL_PRECURSOR_SCAN_NO 8485 CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8471; ORIGINAL_PRECURSOR_SCAN_NO 8468

4-Chloro-3-methylphenol

C7H7ClO (142.0185)

CONFIDENCE standard compound; INTERNAL_ID 986; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4527; ORIGINAL_PRECURSOR_SCAN_NO 4526 C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D016573 - Agrochemicals D010575 - Pesticides CONFIDENCE standard compound; INTERNAL_ID 986; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4489; ORIGINAL_PRECURSOR_SCAN_NO 4487 CONFIDENCE standard compound; INTERNAL_ID 986; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4509; ORIGINAL_PRECURSOR_SCAN_NO 4507 CONFIDENCE standard compound; INTERNAL_ID 986; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4544; ORIGINAL_PRECURSOR_SCAN_NO 4540 CONFIDENCE standard compound; INTERNAL_ID 986; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4535; ORIGINAL_PRECURSOR_SCAN_NO 4534

CDP-ethanolamine

C11H20N4O11P2 (446.0604)

A phosphoethanolamine consisting of ethanolamine having a cytidine 5-diphosphate moiety attached to the oxygen.

Thiamine monophosphate

C12H18N4O4PS+ (345.0786)

D018977 - Micronutrients > D014815 - Vitamins

Aminomalonic acid

C3H5NO4 (119.0219)

An amino dicarboxylic acid that is malonic acid in which one of the methylene hydrogens has been replaced by an amino group. Aminomalonic acid is an amino endogenous metabolite, acts as a strong inhibitor of L-asparagine synthetase from Leukemia 5178Y/AR (Ki= 0.0023 M) and mouse pancreas (Ki= 0.0015 M) in vitro. Aminomalonic acid is a potential biomarker to discriminate between different stages of melanoma metastasis[1][2][3].

safrole

C10H10O2 (162.0681)

A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.

5-heptenoic acid

δ-heptenoic acid

C7H12O2 (128.0837)

Montanate

n-octacosanoic acid

C28H56O2 (424.428)

Melissic acid

Melissic acid,synthetic

C30H60O2 (452.4593)

A C30, very long straight-chain, saturated fatty acid.

methacycline

C22H22N2O8 (442.1376)

J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01A - Tetracyclines > J01AA - Tetracyclines A tetracycline that is the 6-methylene analogue of oxytetracycline, obtained by formal dehydration at position 6. C784 - Protein Synthesis Inhibitor > C1595 - Tetracycline Antibiotic D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents C254 - Anti-Infective Agent > C258 - Antibiotic

glutaconyl-CoA

C26H40N7O19P3S (879.1312)

2-Hydroxymyristic acid

2-HYDROXYTETRADECANOIC ACID

C14H28O3 (244.2038)

A derivative of myristic acid having a hydroxy substituent at C-2.

D-D 92

trans-1,3-Dichloropropene

C3H4Cl2 (109.969)

D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals

Catechin C

(2S-cis)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-Benzopyran-3,5,7-triol

C15H14O6 (290.079)

C26170 - Protective Agent > C275 - Antioxidant

C30:0

TRIACONTANOIC ACID

C30H60O2 (452.4593)

FA 14:0;O

Tetradecanoic acid, 3-hydroxy-, D-(-)-

C14H28O3 (244.2038)

Thaspic acid

HEXADECANEDIOIC ACID

C16H30O4 (286.2144)

Hexadecanedioic acid is covalently linked to Sepharose 4B, shows better performance in terms of specificity than dye-based resins and could be used for depletion of SA from plasma samples. Hexadecanedioic acid is covalently linked to Sepharose 4B, shows better performance in terms of specificity than dye-based resins and could be used for depletion of SA from plasma samples.

Prostaglandin G2

9S,11R-epidioxy-15S-hydroperoxy-5Z,13E-prostadienoic acid

C20H32O6 (368.2199)

D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides

Prostaglandin B1

9-oxo-15S-hydroxy-8(12),13E-prostadienoic acid

C20H32O4 (336.23)

A member of the class of prostaglandins B that is prosta-8(12),13-dien-1-oic acid carrying oxo and hydroxy substituents at positions 9 and 15 respectively (the 13E,15S-stereoisomer).

lipoxin B4

5S,14R,15S-trihydroxy-6E,8Z,10E,12E-eicosatetraenoic acid

A C20 hydroxy fatty acid having (5S)-, (14R)- and (15S)-hydroxy groups as well as (6E)- (8Z)-, (10E)- and (12E)-double bonds. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents

FAL 6:2

Sorbic aldehyde

C6H8O (96.0575)

CoA 18:2

S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (9Z,12Z)-octadeca-9,12-dienethioate

C39H66N7O17P3S (1029.3449)

CoA 20:4

(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoyl-CoA;(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoyl-coenzyme A;(5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoyl-coenzyme A;C20:4-CoA;all-cis-5,8,11,14-eicosatetraenoyl-CoA;all-cis-5,8,11,14-eicosatetraenoyl-coenzyme A;arachidonoyl-coenzyme A;arachidonyl-coenzyme A;cis-Delta(5,8,11,14)-eicosatetraenoyl-CoA;cis-Delta(5,8,11,14)-eicosatetraenoyl-coenzyme A

C41H66N7O17P3S (1053.3449)

CoA 5:0

3-methylbutanoyl-coenzyme A;3-methylbutyryl-CoA;3-methylbutyryl-coenzyme A;beta-methylbutanoyl-CoA;beta-methylbutanoyl-coenzyme A;beta-methylbutyryl-CoA;beta-methylbutyryl-coenzyme A;isovaleryl-coenzyme A

C26H44N7O17P3S (851.1727)

CoA 4:0

C25H42N7O17P3S (837.1571)

dihydrolipoamide

6,8-disulfanyloctanimidic acid

C8H17NOS2 (207.0752)

ST 27:1

Cholest-5-ene

C27H46 (370.3599)

ST 21:1;O4

3alpha,11beta,21-5alpha-trihydroxy-pregnane-20-one

C21H34O4 (350.2457)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

ST 23:5;O6

17alpha,21-dihydroxypregn-4-ene-3,11,20-trione acetate

C23H30O6 (402.2042)

Cortol

Pregnane-3,11,17,20,21-pentol,(3a,5b,11b,20S)-

C21H36O5 (368.2563)

(+)-cis-sabinol

(1S,3R,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol

C10H16O (152.1201)

(+)-sabinone

(1S,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one

C10H14O (150.1045)

DL-Lysine

Lysine, DL-

C6H14N2O2 (146.1055)

DL-Lysine is a racemic mixture of the D-Lysine and L-Lysine. Lysine is an α-amino acid that is used in the biosynthesis of proteins[1].

4-CHLOROANILINE

1-Amino-4-chlorobenzene

C6H6ClN (127.0189)

Liquorice

C42H62O16 (822.4038)

resmethrin

C22H26O3 (338.1882)

D010575 - Pesticides > D007306 - Insecticides > D011722 - Pyrethrins D016573 - Agrochemicals

Tricaprilin

Trioctanoylglycerol

C27H50O6 (470.3607)

D010592 - Pharmaceutic Aids > D014677 - Pharmaceutical Vehicles > D005079 - Excipients Same as: D01587 Tricaprilin (Trioctanoin) is used in study for patients with mild to moderate Alzheimer's disease and has a role as an anticonvulsant and a plant metabolite[1][2].

Chlorthal-dimethyl

C10H6Cl4O4 (329.902)

Dipotassium hydrogen phosphate

Di-potassium monohydrogen phosphate

HK2O4P (173.8887)

C78275 - Agent Affecting Blood or Body Fluid > C29730 - Electrolyte Replacement Agent D020011 - Protective Agents > D002327 - Cariostatic Agents D019995 - Laboratory Chemicals > D002021 - Buffers D001697 - Biomedical and Dental Materials

Cyclacillin

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

C15H23N3O4S (341.1409)

D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D010406 - Penicillins D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic

Hydrocortisone probutate

C28H40O7 (488.2774)

AIDS-026330

2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2S-cis)-

C15H14O6 (290.079)

C26170 - Protective Agent > C275 - Antioxidant

Safrol

InChI=1\C10H10O2\c1-2-3-8-4-5-9-10(6-8)12-7-11-9\h2,4-6H,1,3,7H

C10H10O2 (162.0681)

LS-684

4-02-00-00143 (Beilstein Handbook Reference)

C6H12O2 (116.0837)

Arbo 8

(R-(R*,R*))-2,3-Bis((4-hydroxy-3-methoxyphenyl)methyl)butane-1,4-diol

C20H26O6 (362.1729)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids.

Bergaptin

7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-

C21H22O4 (338.1518)

D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins Bergamottin is a potent and competitive CYP1A1 inhibitor with a Ki of 10.703 nM. Bergamottin is a potent and competitive CYP1A1 inhibitor with a Ki of 10.703 nM.

Idryl

InChI=1\C16H10\c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14\h1-10

C16H10 (202.0782)

D004791 - Enzyme Inhibitors

c0264

InChI=1\C6H6O3\c7-4-1-2-5(8)6(9)3-4\h1-3,7-9

C6H6O3 (126.0317)

474-67-9

(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C28H46O (398.3548)

C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].

Cruex

InChI=1\C11H20O2\c1-2-3-4-5-6-7-8-9-10-11(12)13\h2H,1,3-10H2,(H,12,13

AI3-05924

4-14-00-01015 (Beilstein Handbook Reference)

2-(Methylamino)benzoic acid is the main metabolite of methyl-N-methylanthranilates (MMA) (HY-76705) and is the compound in which the ester group is converted. MMA can be isolated from citrus fruits and has potential analgesic activity. 2-(Methylamino)benzoic acid was used to detect the metabolic levels of MMA in rat liver[1].

Pseudocumol

InChI=1\C9H12\c1-7-4-5-8(2)9(3)6-7\h4-6H,1-3H

C9H12 (120.0939)

Byakangelicin

7H-Furo(3,2-g)(1)benzopyran-7-one, 9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-, (R)-

C17H18O7 (334.1052)

Byakangelicin is a member of psoralens. Byakangelicin is a natural product found in Murraya koenigii, Triphasia trifolia, and other organisms with data available. D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins (Rac)-Byakangelicin is a racemate of Byakangelicin mainly isolated from the genus Angelica. Byakangelicin is an aldose-reductase inhibitor with an IC50 value of 6.2 μM[1]. (Rac)-Byakangelicin is a racemate of Byakangelicin mainly isolated from the genus Angelica. Byakangelicin is an aldose-reductase inhibitor with an IC50 value of 6.2 μM[1]. Byakangelicin, one of the active compounds found in the roots of Angelica gigas, can serve as a modulator to improve brain accumulation of diverse active compounds (Umb, Cur, and Dox) and enhance therapeutic effects[1]. Byakangelicin is likely to increase the expression of all PXR target genes (such as MDR1) and induce a wide range of agent-agent interactions. Byakangelicin can inhibit the effects of sex hormones, it may increase the catabolism of endogenous hormones[2]. Byakangelicin, one of the active compounds found in the roots of Angelica gigas, can serve as a modulator to improve brain accumulation of diverse active compounds (Umb, Cur, and Dox) and enhance therapeutic effects[1]. Byakangelicin is likely to increase the expression of all PXR target genes (such as MDR1) and induce a wide range of agent-agent interactions. Byakangelicin can inhibit the effects of sex hormones, it may increase the catabolism of endogenous hormones[2].

Byakangelicol

7H-Furo(3,2-g)(1)benzopyran-7-one, 9-((3,3-dimethyloxiranyl)methoxy)-4-methoxy-, (R)-

C17H16O6 (316.0947)

Byakangelicol, isolated from Angelica dahurica, inhibits interleukin-1beta (IL-1beta) -induced prostaglandin E2 (PGE2) release in A549 cells mediated by suppression of cyclooxygenase-2 (COX-2) expression and the activity of COX-2 enzyme. Byakangelicol has therapeutic potential as an anti-inflammatory agent on airway inflammation[1]. Byakangelicol, isolated from Angelica dahurica, inhibits interleukin-1beta (IL-1beta) -induced prostaglandin E2 (PGE2) release in A549 cells mediated by suppression of cyclooxygenase-2 (COX-2) expression and the activity of COX-2 enzyme. Byakangelicol has therapeutic potential as an anti-inflammatory agent on airway inflammation[1].

Thapsic acid

n-Tetradecane-.omega.,.omega.-dicarboxylic acid

C16H30O4 (286.2144)

614-75-5

InChI=1\C8H8O3\c9-7-4-2-1-3-6(7)5-8(10)11\h1-4,9H,5H2,(H,10,11

Bio1_001201

7-[2-[(E,3S)-3-hydroxyoct-1-enyl]-5-keto-1-cyclopentenyl]enanthic acid

C20H32O4 (336.23)

CHEBI:30918

(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid

C7H8O5 (172.0372)

99-94-5

InChI=1\C8H8O2\c1-6-2-4-7(5-3-6)8(9)10\h2-5H,1H3,(H,9,10

C8H8O2 (136.0524)

p-Toluic acid (4-Methylbenzoic acid) is a substituted?benzoic acid?and can be used as an intermediate for the synthesis of para-aminomethylbenzoic acid (PAMBA), p-tolunitrile, etc. p-Toluic acid (4-Methylbenzoic acid) is a substituted?benzoic acid?and can be used as an intermediate for the synthesis of para-aminomethylbenzoic acid (PAMBA), p-tolunitrile, etc.

129-43-1

InChI=1\C14H8O3\c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16\h1-7,15

C14H8O3 (224.0473)

D009676 - Noxae > D002273 - Carcinogens 1-Hydroxyanthraquinone, a naturally occurring compound with oral activity from some plants like Tabebuia avellanedae, exhibits carcinogenic effect[1]. 1-Hydroxyanthraquinone, a naturally occurring compound with oral activity from some plants like Tabebuia avellanedae, exhibits carcinogenic effect[1].

CHEBI:42717

(2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxy-2-tetrahydropyrancarboxylic acid

C6H10O7 (194.0427)

Biflorin

5,7-dihydroxy-2-methyl-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one

C16H18O9 (354.0951)

E160E

2,4,6,8,10,12,14,16-Heptadecaoctaenal, 2,6,11,15-tetramethyl-17-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (2E,4E,6E,8E,10E,12E,14E,16E)-

C30H40O (416.3079)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids β-Apo-8'-carotenal (Apocarotenal), a provitamin A carotenoid, is an inducer of CYPlA1 and CYPlA2 in rat. β-Apo-8'-carotenal is present in many fruits and vegetables[1]. β-Apo-8'-carotenal (Apocarotenal), a provitamin A carotenoid, is an inducer of CYPlA1 and CYPlA2 in rat. β-Apo-8'-carotenal is present in many fruits and vegetables[1].

2,4-Hexadienal

C6H8O (96.0575)

(e,e)-2,4-hexadienal, also known as fema 3429, is a member of the class of compounds known as medium-chain aldehydes. Medium-chain aldehydes are an aldehyde with a chain length containing between 6 and 12 carbon atoms (e,e)-2,4-hexadienal is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (e,e)-2,4-hexadienal can be found in a number of food items such as fishes, tea, nuts, and fruits, which makes (e,e)-2,4-hexadienal a potential biomarker for the consumption of these food products.

Tetrahydrocorticosterone

3alpha,11beta,21-trihydroxy-5beta-pregnan-20-one

C21H34O4 (350.2457)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones Tetrahydrocorticosterone is one of the major urinary metabolites from corticosterone. Premenopausal patients with early breast cancer excrete subnormal amounts of tetrahydrocorticosterone as compared with the normal subjects of corresponding ages. (PMID 1133844) [HMDB]

Linoleoyl-CoA

C39H66N7O17P3S (1029.3449)

An octadecadienoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of linoleic acid. Linoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of Glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid {beta}-oxidation; ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates. (PMID: 17184976, 16020546) [HMDB]

(1S,3R,4S,9R,13S,14R)-3-[(2S,5S)-5-(2-bromo-5-hydroxyphenyl)-5-methoxypentan-2-yl]-13-hydroxy-9-[(1R)-1-hydroxyethyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione

C32H47BrO10 (670.2352)

D009676 - Noxae > D011042 - Poisons > D008235 - Lyngbya Toxins D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins

(+)-Himbacine

C22H35NO2 (345.2668)

D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics

5alpha-Androstan-17beta-ol

C19H32O (276.2453)

N-Acetyl-ala-ala-ala-methylester

C12H21N3O5 (287.1481)

1-methyl-3-[(Z)-(4-oxo-3-prop-2-enyl-1,3-thiazolidin-2-ylidene)amino]thiourea

C8H12N4OS2 (244.0453)

L-BOAA

N-Oxalyl-L-alpha-beta-diaminopropionic acid (BOAA,ODAP)

C5H8N2O5 (176.0433)

N(3)-oxalyl-L-2,3-diaminopropionic acid is an N(beta)-acyl-L-2,3-diaminopropionic acid in which the acyl group is oxalyl. It is functionally related to a propionic acid. It is a conjugate acid of a N(3)-(carboxylatoformyl)-L-2,3-diaminopropionate(1-). Dencichin is a natural product found in Lathyrus latifolius and Lathyrus sativus with data available. See also: Panax notoginseng root (part of). Dencichin is a non-protein amino acid originally extracted from Panax notoginseng, and can inhibit HIF-prolyl hydroxylase-2 (PHD-2) activity.

Biacangelicol

7H-Furo(3,2-g)(1)benzopyran-7-one, 9-((3,3-dimethyloxiranyl)methoxy)-4-methoxy-, (R)-

C17H16O6 (316.0947)

Byakangelicol is a member of psoralens. Byakangelicol is a natural product found in Murraya koenigii, Ostericum grosseserratum, and other organisms with data available. Byakangelicol, isolated from Angelica dahurica, inhibits interleukin-1beta (IL-1beta) -induced prostaglandin E2 (PGE2) release in A549 cells mediated by suppression of cyclooxygenase-2 (COX-2) expression and the activity of COX-2 enzyme. Byakangelicol has therapeutic potential as an anti-inflammatory agent on airway inflammation[1]. Byakangelicol, isolated from Angelica dahurica, inhibits interleukin-1beta (IL-1beta) -induced prostaglandin E2 (PGE2) release in A549 cells mediated by suppression of cyclooxygenase-2 (COX-2) expression and the activity of COX-2 enzyme. Byakangelicol has therapeutic potential as an anti-inflammatory agent on airway inflammation[1].

Pikrotin

3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR-(1a alpha,2a beta,3beta,6beta,6a beta,8aS*,8b beta,9S*))-

C15H18O7 (310.1052)

Picrotin is an organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. It has a role as a plant metabolite. It is an organic heteropentacyclic compound, an epoxide, a tertiary alcohol, a gamma-lactone, a diol and a picrotoxane sesquiterpenoid. It is functionally related to a picrotoxinin. Picrotin is a natural product found in Dendrobium moniliforme and Anamirta cocculus with data available. An organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant Picrotin is an active compound, also is one of the composition of picrotoxin (an antagonist of GABAA receptors (GABAARs) and glycine receptors (GlyRs)). Picrotin has sensitivity for GlyRs/b> with IC50 values range from 5.2 μM to 106 μM. Picrotin can be used for the research of neurotransmission[1][2]. Picrotin is an active compound, also is one of the composition of picrotoxin (an antagonist of GABAA receptors (GABAARs) and glycine receptors (GlyRs)). Picrotin has sensitivity for GlyRs/b> with IC50 values range from 5.2 μM to 106 μM. Picrotin can be used for the research of neurotransmission[1][2]. Picrotin is an active compound, also is one of the composition of picrotoxin (an antagonist of GABAA receptors (GABAARs) and glycine receptors (GlyRs)). Picrotin has sensitivity for GlyRs/b> with IC50 values range from 5.2 μM to 106 μM. Picrotin can be used for the research of neurotransmission[1][2].

Didrovaltrat

Butanoic acid, 3-methyl-, 6-(acetyloxy)-4a,5,6,7a-tetrahydro-4-((3-methyl-1-oxobutoxy)methyl)spiro(cyclopenta(c)pyran-7(1H),2-oxiran)-1-yl ester, (1S-(1-alpha,4a-alpha,6-alpha,7-beta,7a-alpha))-

C22H32O8 (424.2097)

Apocarotenal

2,4,6,8,10,12,14,16-Heptadecaoctaenal, 2,6,11,15-tetramethyl-17-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (2E,4E,6E,8E,10E,12E,14E,16E)-

C30H40O (416.3079)

trans-1,3-Dichloropropene

C3H4Cl2 (109.969)

D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals

METAXALONE

C12H15NO3 (221.1052)

D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents C78281 - Agent Affecting Musculoskeletal System > C29696 - Muscle Relaxant D000890 - Anti-Infective Agents > D023303 - Oxazolidinones

trichlormethiazide

C8H8Cl3N3O4S2 (378.9022)

C - Cardiovascular system > C03 - Diuretics > C03A - Low-ceiling diuretics, thiazides > C03AA - Thiazides, plain D045283 - Natriuretic Agents > D004232 - Diuretics > D049993 - Sodium Chloride Symporter Inhibitors C78275 - Agent Affecting Blood or Body Fluid > C448 - Diuretic > C49185 - Thiazide Diuretic D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D045283 - Natriuretic Agents D049990 - Membrane Transport Modulators

ethyl acetoacetate

An ethyl ester resulting from the formal condensation of the carboxy group of acetoacetic acid with ethanol.

Pyridaben

C19H25ClN2OS (364.1376)

orphenadrine

C18H23NO (269.178)

D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065686 - Cytochrome P-450 CYP2B6 Inhibitors D002491 - Central Nervous System Agents > D018726 - Anti-Dyskinesia Agents > D000978 - Antiparkinson Agents C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents C78281 - Agent Affecting Musculoskeletal System > C29696 - Muscle Relaxant

N-Nitrosopyrrolidine

C4H8N2O (100.0637)

CHLOROPROCAINE

C13H19ClN2O2 (270.1135)

D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local > N01BA - Esters of aminobenzoic acid D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent

2,4,5-trichlorophenoxyacetic acid

C8H5Cl3O3 (253.9304)

D010575 - Pesticides > D006540 - Herbicides D016573 - Agrochemicals

nilutamide

C12H10F3N3O4 (317.0623)

L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02B - Hormone antagonists and related agents > L02BB - Anti-androgens D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D000726 - Androgen Antagonists C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C146993 - Androgen Receptor Inhibitor C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen D000970 - Antineoplastic Agents

Eprosartan

C23H24N2O4S (424.1457)

C - Cardiovascular system > C09 - Agents acting on the renin-angiotensin system > C09C - Angiotensin ii receptor blockers (arbs), plain > C09CA - Angiotensin ii receptor blockers (arbs), plain C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent > C66930 - Angiotensin II Receptor Antagonist D057911 - Angiotensin Receptor Antagonists > D057912 - Angiotensin II Type 2 Receptor Blockers COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Eprosartan (SKF-108566J free base) is a selective, competitive, nonpeptid and orally active angiotensin II receptor antagonist, used as an antihypertensive. Eprosartan binds angiotensin II receptor with IC50s of 9.2 nM and 3.9 nM in rat and human adrenal cortical membranes, respectively [1].

Acethydrazide

C2H6N2O (74.048)

D009676 - Noxae > D002273 - Carcinogens

SULFADOXINE

C12H14N4O4S (310.0736)

D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent D000890 - Anti-Infective Agents > D013424 - Sulfanilamides

4-Methylbenzoic acid

C8H8O2 (136.0524)

PHENOXYACETIC ACID

A monocarboxylic acid that is the O-phenyl derivative of glycolic acid. A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Phenoxyacetic acid is an endogenous metabolite.

promazine

C17H20N2S (284.1347)

N - Nervous system > N05 - Psycholeptics > N05A - Antipsychotics > N05AA - Phenothiazines with aliphatic side-chain D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents > D018492 - Dopamine Antagonists C78272 - Agent Affecting Nervous System > C267 - Antiemetic Agent > C740 - Phenothiazine D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents C78272 - Agent Affecting Nervous System > C29710 - Antipsychotic Agent D005765 - Gastrointestinal Agents > D000932 - Antiemetics

3,5-Diiodo-L-tyrosine

C9H9I2NO3 (432.8672)

A diiodotyrosine that is L-tyrosine carrying iodo-substituents at positions C-3 and C-5 of the benzyl group. It is an intermediate in the thyroid hormone synthesis. H - Systemic hormonal preparations, excl. sex hormones and insulins > H03 - Thyroid therapy > H03B - Antithyroid preparations D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

1-Phenylethanamine

(S)-(-)-1-Phenylethylamine

C8H11N (121.0891)

A phenylethylamine that is ethylamine substituted by a phenyl group at position 1.

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

C7H8N2O2 (152.0586)

Nudifloramide (2PY) is one of the end products of nicotinamide-adenine dinucleotide (NAD) degradation. Nudifloramide significantly inhibits poly(ADP-ribose) polymerase (PARP-1) activity in vitro[1].

DL-Phenylalanine

l-phenylalanine (2-13c)

C9H11NO2 (165.079)

dyclonine

C18H27NO2 (289.2042)

D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics R - Respiratory system > R02 - Throat preparations > R02A - Throat preparations > R02AD - Anesthetics, local D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent

1,2,4-BENZENETRIOL

1,2,4-Trihydroxybenzene

C6H6O3 (126.0317)

A benzenetriol carrying hydroxy groups at positions 1, 2 and 4. 1,2,4-Trihydroxybenzene (Hydroxyhydroquinone), a by-product of coffee bean roasting, increases intracellular Ca2+ concentration in rat thymic lymphocytes[1]. 1,2,4-Trihydroxybenzene (Hydroxyhydroquinone), a by-product of coffee bean roasting, increases intracellular Ca2+ concentration in rat thymic lymphocytes[1].

Difenidol

DIPHENIDOL

C21H27NO (309.2093)

D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents C78272 - Agent Affecting Nervous System > C267 - Antiemetic Agent D005765 - Gastrointestinal Agents > D000932 - Antiemetics D002491 - Central Nervous System Agents

ribostamycin

C17H34N4O10 (454.2275)

An amino cyclitol glycoside that is 4,6-diaminocyclohexane-1,2,3-triol having a 2,6-diamino-2,6-dideoxy-alpha-D-glucosyl residue attached at position 1 and a beta-D-ribosyl residue attached at position 2. It is an antibiotic produced by Streptomyces ribosidificus (formerly S. thermoflavus). J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01G - Aminoglycoside antibacterials C784 - Protein Synthesis Inhibitor > C2363 - Aminoglycoside Antibiotic D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents C254 - Anti-Infective Agent > C258 - Antibiotic

Triamcinolone hexacetonide

C30H41FO7 (532.2836)

Echothiophate

C9H23NO3PS+ (256.1136)

S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010277 - Parasympathomimetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D008916 - Miotics C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist D004791 - Enzyme Inhibitors

2-FLUOROBENZOIC ACID

Remikiren

C33H50N4O6S (630.3451)

C - Cardiovascular system > C09 - Agents acting on the renin-angiotensin system > C09X - Other agents acting on the renin-angiotensin system > C09XA - Renin-inhibitors C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors C471 - Enzyme Inhibitor > C783 - Protease Inhibitor

Dimethylselenide

Dimethyl selenide

C2H6Se (109.9635)

An organoselenium compound of two methyl groups covalently bound to a selenium.

Methyl β-D-galactopyranoside

Methyl beta-D-galactopyranoside

C7H14O6 (194.079)

Methyl β-D-Galactopyranoside is an endogenous metabolite.

Cholest-5-ene

C27H46 (370.3599)

Isovaleryl-CoA

C26H44N7O17P3S (851.1727)

A methylbutanoyl-CoA is the S-isovaleryl derivative of coenzyme A.

4-FLUOROBENZOIC ACID

A fluorobenzoic acid carrying a fluoro substituent at position 4.

furoic acid

L-Cysteic acid

C3H7NO5S (169.0045)

The L-enantiomer of cysteic acid.

s-Hexylglutathione

C16H29N3O6S (391.1777)

D004791 - Enzyme Inhibitors

Isobutyryl-CoA

C25H42N7O17P3S (837.1571)

A short-chain, methyl-branched fatty acyl-CoA that is the S-isobutyryl derivative of coenzyme A.

D-Arabinose 5-phosphate

aldehydo-D-arabinose 5-phosphate

C5H11O8P (230.0192)

The 5-phospho derivative of D-arabinose. It is an intermediate in the synthesis of lipopolysaccharides.

2-Deoxyguanosine-5-diphosphate

C10H15N5O10P2 (427.0294)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

1-Hydroxyisoquinoline

ISOQUINOLIN-1(2H)-ONE

C9H7NO (145.0528)

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

H-Phg-OH

2-Aminophenylacetic acid