NCBI Taxonomy: 8417

Bufalin

C24H34O4 (386.24569640000004)

Bufalin is a cardiotonic steroid toxin[1] originally isolated from Chinese toad venom, which is a component of some traditional Chinese medicines.[2][3] Bufalin has in vitro antitumor effects against various malignant cell lines, including hepatocellular[4] and lung carcinoma.[5] However, as with other bufadienolides, its potential use is hampered by its cardiotoxicity.[6] Bufalin is a 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo. It has a role as an antineoplastic agent, a cardiotonic drug, an anti-inflammatory agent and an animal metabolite. It is a 3beta-hydroxy steroid and a 14beta-hydroxy steroid. It is functionally related to a bufanolide. Bufalin is a natural product found in Cunninghamella blakesleeana, Bufo gargarizans, and other organisms with data available. Bufalin is an active ingredient and one of the glycosides in the traditional Chinese medicine ChanSu; it is also a bufadienolide toxin originally isolated from the venom of the Chinese toad Bufo gargarizans, with potential cardiotonic and antineoplastic activity. Although the mechanism of action of bufalin is still under investigation, this agent is a specific Na+/K+-ATPase inhibitor and can induce apoptosis in cancer cell lines through the activation of the transcription factor AP-1 via a mitogen activated protein kinase (MAPK) pathway. A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo. Bufalin is an active component isolated from Chan Su, acts as a potent Na+/K+-ATPase inhibitor, binds to the subunit α1, α2 and α3, with Kd of 42.5, 45 and 40 nM, respectively[1][2]. Anti-cancer activity[2]. Bufalin is an active component isolated from Chan Su, acts as a potent Na+/K+-ATPase inhibitor, binds to the subunit α1, α2 and α3, with Kd of 42.5, 45 and 40 nM, respectively[1][2]. Anti-cancer activity[2].

Arenobufagin

C24H32O6 (416.2198772)

Arenobufagin is a natural product found in Bufo gargarizans, Bufotes viridis, and other organisms with data available. D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides Arenobufagin is a natural bufadienolide from toad venom; has potent antineoplastic activity against HCC HepG2 cells as well as corresponding multidrug-resistant HepG2/ADM cells. IC50 value: Target: in vitro: arenobufagin induced mitochondria-mediated apoptosis in HCC cells, with decreasing mitochondrial potential, as well as increasing Bax/Bcl-2 expression ratio, Bax translocation from cytosol to mitochondria. Arenobufagin also induced autophagy in HepG2/ADM cells. Autophagy-specific inhibitors (3-methyladenine, chloroquine and bafilomycin A1) or Beclin1 and Atg 5 small interfering RNAs (siRNAs) enhanced arenobufagin-induced apoptosis, indicating that arenobufagin-mediated autophagy may protect HepG2/ADM cells from undergoing apoptotic cell death [1]. arenobufagin inhibited vascular endothelial growth factor (VEGF)-induced viability, migration, invasion and tube formation in human umbilical vein endothelial cells (HUVECs) in vitro [2]. Arenobufagin blocked the Na+/K+ pump current in a dose-dependent manner with a half-maximal concentration of 0.29 microM and a Hill coefficient of 1.1 [3]. in vivo: arenobufagin inhibited the growth of HepG2/ADM xenograft tumors, which were associated with poly (ADP-ribose) polymerase cleavage, light chain 3-II activation and mTOR inhibition [1]. Arenobufagin also suppressed sprouting formation from VEGF-treated aortic rings in an ex vivo model [2]. Arenobufagin is a natural bufadienolide from toad venom; has potent antineoplastic activity against HCC HepG2 cells as well as corresponding multidrug-resistant HepG2/ADM cells. IC50 value: Target: in vitro: arenobufagin induced mitochondria-mediated apoptosis in HCC cells, with decreasing mitochondrial potential, as well as increasing Bax/Bcl-2 expression ratio, Bax translocation from cytosol to mitochondria. Arenobufagin also induced autophagy in HepG2/ADM cells. Autophagy-specific inhibitors (3-methyladenine, chloroquine and bafilomycin A1) or Beclin1 and Atg 5 small interfering RNAs (siRNAs) enhanced arenobufagin-induced apoptosis, indicating that arenobufagin-mediated autophagy may protect HepG2/ADM cells from undergoing apoptotic cell death [1]. arenobufagin inhibited vascular endothelial growth factor (VEGF)-induced viability, migration, invasion and tube formation in human umbilical vein endothelial cells (HUVECs) in vitro [2]. Arenobufagin blocked the Na+/K+ pump current in a dose-dependent manner with a half-maximal concentration of 0.29 microM and a Hill coefficient of 1.1 [3]. in vivo: arenobufagin inhibited the growth of HepG2/ADM xenograft tumors, which were associated with poly (ADP-ribose) polymerase cleavage, light chain 3-II activation and mTOR inhibition [1]. Arenobufagin also suppressed sprouting formation from VEGF-treated aortic rings in an ex vivo model [2].

Bufotalin

C26H36O6 (444.2511756)

Bufotalin is a steroid lactone. It is functionally related to a bufanolide. Bufotalin is a natural product found in Bufo gargarizans, Duttaphrynus melanostictus Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species.[2][3] Bufotalin can be extracted from the skin parotoid glands of several types of toad. Rhinella marina (Cane toad), Rhaebo guttatus (Smooth-sided toad), Bufo melanostictus (Asian toad), and Bufo bufo (common European toad) are sources of bufotalin. Traditional medicine Bufotalin is part of Ch'an Su, a traditional Chinese medicine used for cancer. It is also known as Venenum Bufonis or senso (Japanese).[5] Toxicity Specifically, in cats the lethal median dose is 0.13 mg/kg.[1] and in dogs is 0.36 mg/kg (intravenous).[6] Knowing this it is advisable to monitor those functions continuously using an EKG. As there is no antidote against bufotalin all occurring symptoms need to be treated separately or if possible in combination with others. To increase the clearance theoretically, due to the similarities with digitoxin, cholestyramine, a bile salt, might help.[6] Recent animal studies have shown that taurine restores cardiac functions.[7] Symptomatic measures include lignocaine, atropine and phenytoin for cardiac toxicity and intravenous potassium compounds to correct hyperkalaemia from its effect on the Na+/K+ ATPase pump.[6] Pharmacology and mechanism of action After a single intravenous injection, bufotalin gets quickly distributed and eliminated from the blood plasma with a half-time of 28.6 minutes and a MRT of 14.7 min. After 30 minutes after an administration of bufotalin, the concentrations within the brain and lungs are significantly higher than those in blood and other tissues.[8] It also increases cancer cell's susceptibility to apoptosis via TNF-α signalling by the BH3 interacting domain death agonist and STAT proteins.[9] Bufotalin induces apoptosis in vitro in human hepatocellular carcinoma Hep 3B cells and might involve caspases and apoptosis inducing factor (AIF).[10] The use of bufotalin as a cancer treating compound is still in the experimental phase. It also arrests cell cycle at G(2)/M, by up- and down- regulation of several enzymes. Bufotalin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=471-95-4 (retrieved 2024-06-29) (CAS RN: 471-95-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Bufotalin is a steroid lactone isolated from Venenum Bufonis with potently antitumor activities. Bufotalin induces cancer cell apoptosis and also induces endoplasmic reticulum (ER) stress activation[1][2]. Bufotalin is a steroid lactone isolated from Venenum Bufonis with potently antitumor activities. Bufotalin induces cancer cell apoptosis and also induces endoplasmic reticulum (ER) stress activation[1][2].

Adenosine

C10H13N5O4 (267.09674980000005)

Adenosine is a ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. It has a role as an anti-arrhythmia drug, a vasodilator agent, an analgesic, a human metabolite and a fundamental metabolite. It is a purines D-ribonucleoside and a member of adenosines. It is functionally related to an adenine. The structure of adenosine was first described in 1931, though the vasodilating effects were not described in literature until the 1940s. Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy, though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson]. Adenosine is also indicated in the treatment of supraventricular tachycardia. Adenosine was granted FDA approval on 30 October 1989. Adenosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Adenosine is an Adenosine Receptor Agonist. The mechanism of action of adenosine is as an Adenosine Receptor Agonist. Adenosine is a natural product found in Smilax bracteata, Mikania laevigata, and other organisms with data available. Adenosine is a ribonucleoside comprised of adenine bound to ribose, with vasodilatory, antiarrhythmic and analgesic activities. Phosphorylated forms of adenosine play roles in cellular energy transfer, signal transduction and the synthesis of RNA. Adenosine is a nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer - as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate, cAMP. Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously, adenosine causes transient heart block in the AV node. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Adenosine is a metabolite found in or produced by Saccharomyces cerevisiae. A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. See also: Adenosine; Niacinamide (component of); Adenosine; Glycerin (component of); Adenosine; ginsenosides (component of) ... View More ... Adenosine is a nucleoside that is composed of adenine and D-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes. Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a beta-N9-glycosidic bond. [Wikipedia]. Adenosine is found in many foods, some of which are borage, japanese persimmon, nuts, and barley. COVID info from PDB, Protein Data Bank, COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. Adenosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-61-7 (retrieved 2024-06-29) (CAS RN: 58-61-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2].

Sucrose

C12H22O11 (342.1162062)

Sucrose is a nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane (Saccharum officinarum), sugar beet (Beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is derived by crushing and extracting sugarcane with water or by extracting sugar beet with water, evaporating, and purifying with lime, carbon, and various liquids. Sucrose is also obtainable from sorghum. Sucrose occurs in low percentages in honey and maple syrup. Sucrose is used as a sweetener in foods and soft drinks, in the manufacture of syrups, in invert sugar, confectionery, preserves and jams, demulcent, pharmaceutical products, and caramel. Sucrose is also a chemical intermediate for detergents, emulsifying agents, and other sucrose derivatives. Sucrose is widespread in the seeds, leaves, fruits, flowers, and roots of plants, where it functions as an energy store for metabolism and as a carbon source for biosynthesis. The annual world production of sucrose is in excess of 90 million tons mainly from the juice of sugar cane (20\\\%) and sugar beet (17\\\%). In addition to its use as a sweetener, sucrose is used in food products as a preservative, antioxidant, moisture control agent, stabilizer, and thickening agent. BioTransformer predicts that sucrose is a product of 6-O-sinapoyl sucrose metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223). Sucrose appears as white odorless crystalline or powdery solid. Denser than water. Sucrose is a glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. It has a role as an osmolyte, a sweetening agent, a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. A nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane, sugar beet (beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Sucrose is a natural product found in Haplophyllum ramosissimum, Cyperus esculentus, and other organisms with data available. Sucrose is a metabolite found in or produced by Saccharomyces cerevisiae. A nonreducing disaccharide composed of GLUCOSE and FRUCTOSE linked via their anomeric carbons. It is obtained commercially from SUGARCANE, sugar beet (BETA VULGARIS), and other plants and used extensively as a food and a sweetener. See also: Anise; ferrous disulfide; sucrose (component of); Phosphoric acid; sucrose (component of); Sucrose caramel (related) ... View More ... In chemistry, sugar loosely refers to a number of carbohydrates, such as monosaccharides, disaccharides, or oligosaccharides. In food, sugar refers to a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose characterized by a sweet flavor. Other sugars are used in industrial food preparation, but are usually known by more specific names - glucose, fructose or fruit sugar, high fructose corn syrup, etc. Sugars is found in many foods, some of which are ucuhuba, butternut squash, common walnut, and miso. A glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula C 12H 22O 11. For human consumption, sucrose is extracted and refined from either sugarcane or sugar beet. Sugar mills – typically located in tropical regions near where sugarcane is grown – crush the cane and produce raw sugar which is shipped to other factories for refining into pure sucrose. Sugar beet factories are located in temperate climates where the beet is grown, and process the beets directly into refined sugar. The sugar-refining process involves washing the raw sugar crystals before dissolving them into a sugar syrup which is filtered and then passed over carbon to remove any residual colour. The sugar syrup is then concentrated by boiling under a vacuum and crystallized as the final purification process to produce crystals of pure sucrose that are clear, odorless, and sweet. Sugar is often an added ingredient in food production and recipes. About 185 million tonnes of sugar were produced worldwide in 2017.[6] Sucrose is particularly dangerous as a risk factor for tooth decay because Streptococcus mutans bacteria convert it into a sticky, extracellular, dextran-based polysaccharide that allows them to cohere, forming plaque. Sucrose is the only sugar that bacteria can use to form this sticky polysaccharide.[7] Sucrose. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=8030-20-4 (retrieved 2024-06-29) (CAS RN: 57-50-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

L-Tyrosine

C9H11NO3 (181.0738896)

Tyrosine (Tyr) or L-tyrosine 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 (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tyrosine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tyrosine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tyrosine is a non-essential amino acid, meaning the body can synthesize it – usually from phenylalanine. The conversion of phenylalanine to tyrosine is catalyzed by the enzyme phenylalanine hydroxylase, a monooxygenase. This enzyme catalyzes the reaction causing the addition of a hydroxyl group to the end of the 6-carbon aromatic ring of phenylalanine, such that it becomes tyrosine. Tyrosine is found in many high-protein food products such as chicken, turkey, fish, milk, yogurt, cottage cheese, cheese, peanuts, almonds, pumpkin seeds, sesame seeds, soy products, lima beans, avocados and bananas. Tyrosine is one of the few amino acids that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, including thyroid hormones (diiodotyrosine), catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism have been identified, such as hawkinsinuria and tyrosinemia I. The most common feature of these diseases is the increased amount of tyrosine in the blood, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements can help reverse these disease symptoms. Some adults also develop elevated tyrosine in their blood. This typically indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can help aleviate biochemical depression. However, tyrosine may not be good for treating psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-Dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-Dopa (http://www.dcnutrition.com). In addition to its role as a precursor for neurotransmitters, tyrosine plays an important role for the function of many proteins. Within many proteins or enzymes, certain tyrosine residues can be tagged (at the hydroxyl group) with a phosphate group (phosphorylated) by specialized protein kinases. In its phosphorylated form, tyrosine is called phosphotyrosine. Tyrosine phosphorylation is considered to be one of the key steps in signal transduction and regulation of enzymatic activity. Tyrosine (or its precursor phenylalanine) is also needed to synthesize the benzoquinone structure which forms part of coenzyme Q10. L-tyrosine is an optically active form of tyrosine having L-configuration. It has a role as an EC 1.3.1.43 (arogenate dehydrogenase) inhibitor, a nutraceutical, a micronutrient and a fundamental metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tyrosine and a L-alpha-amino acid. It is functionally related to a L-tyrosinal. It is a conjugate base of a L-tyrosinium. It is a conjugate acid of a L-tyrosinate(1-). It is an enantiomer of a D-tyrosine. It is a tautomer of a L-tyrosine zwitterion. Tyrosine is a non-essential amino acid. In animals it is synthesized from [phenylalanine]. It is also the precursor of [epinephrine], thyroid hormones, and melanin. L-Tyrosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). L-Tyrosine is the levorotatory isomer of the aromatic amino acid tyrosine. L-tyrosine is a naturally occurring tyrosine and is synthesized in vivo from L-phenylalanine. It is considered a non-essential amino acid; however, in patients with phenylketonuria who lack phenylalanine hydroxylase and cannot convert phenylalanine into tyrosine, it is considered an essential nutrient. In vivo, tyrosine plays a role in protein synthesis and serves as a precursor for the synthesis of catecholamines, thyroxine, and melanin. Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin. Dietary supplement, nutrient. Flavouring ingredient. L-Tyrosine is found in many foods, some of which are blue crab, sweet rowanberry, lemon sole, and alpine sweetvetch. An optically active form of tyrosine having L-configuration. L-Tyrosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=60-18-4 (retrieved 2024-07-01) (CAS RN: 60-18-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

L-Threonine

C4H9NO3 (119.0582404)

L-threonine is an optically active form of threonine having L-configuration. It has a role as a nutraceutical, a micronutrient, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is an aspartate family amino acid, a proteinogenic amino acid, a threonine and a L-alpha-amino acid. It is a conjugate base of a L-threoninium. It is a conjugate acid of a L-threoninate. It is an enantiomer of a D-threonine. It is a tautomer of a L-threonine zwitterion. An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins. L-Threonine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Threonine is an essential amino acid in humans (provided by food), Threonine is an important residue of many proteins, such as tooth enamel, collagen, and elastin. An important amino acid for the nervous system, threonine also plays an important role in porphyrin and fat metabolism and prevents fat buildup in the liver. Useful with intestinal disorders and indigestion, threonine has also been used to alleviate anxiety and mild depression. (NCI04) Threonine is an essential amino acid in humans. It is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 gram daily. It is highly concentrated in meat products, cottage cheese and wheat germ. The threonine content of most of the infant formulas currently on the market is approximately 20\\\\\\% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Threonine catabolism in mammals appears to be due primarily (70-80\\\\\\%) to the activity of threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate, which forms glycine and acetyl CoA, whereas threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia, is significantly less active. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (A3450). An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins. See also: Amlisimod (monomer of) ... View More ... Threonine (Thr) or L-threonine 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 (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-threonine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Threonine is found in all organisms ranging from bacteria to plants to animals. It is classified as a polar, uncharged (at physiological pH), aliphatic amino acid. Threonine is sometimes considered as a branched chain amino acid. Threonine was actually the last of the 20 amino acids to be discovered (in 1938). It was named threonine because it was similar in structure to threonic acid, a four-carbon monosaccharide. Threonine is an essential amino acid in humans, meaning the body cannot synthesize it and that it must be obtained from the diet. Foods high in threonine include cottage cheese, poultry, fish, meat, lentils, black turtle bean and sesame seeds. Adult humans require about 20 mg/kg body weight/day. In plants and microorganisms, threonine is synthesized from aspartic acid via alpha-aspartyl-semialdehyde and homoserine. In proteins, the threonine residue is susceptible to numerous posttranslational modifications. The hydroxyl side-chain can undergo O-linked glycosylation and phosphorylation through the action of a threonine kinase. Threonine is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. The threonine content of most of the infant formulas currently on the market is approximately 20\\\\\\% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (PMID 9853925). Threonine is metabolized in at least two ways. In many animals it is converted to pyruvate via threonine dehydrogenase. An intermediate in this pathway can undergo thiolysis with CoA to produce acetyl-CoA and glycine. In humans the gene for threonine dehydrogenase is an inactive pseudogene, so threonine is converted to alpha-ketobutyrate. From wide variety of protein hydrolysates. Dietary supplement, nutrient L-Threonine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=72-19-5 (retrieved 2024-07-01) (CAS RN: 72-19-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Threonine, an essential amino acid, has the potential to treat hypostatic leg ulceration[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1].

L-Leucine

C6H13NO2 (131.0946238)

Leucine (Leu) or L-leucine 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. L-leucine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Leucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Leucine is essential in humans, meaning the body cannot synthesize it, and it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-Leucine is a branched chain amino acid (BCAA). The BCAAs consist of leucine, valine and isoleucine (and occasionally threonine). BCAAs are essential amino acids whose carbon structure is marked by a branch point at the beta-carbon position. BCAAs are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. The primary metabolic end products of leucine metabolism are acetyl-CoA and acetoacetate; consequently, it is one of the two exclusively ketogenic amino acids, with lysine being the other. Leucine is the most important ketogenic amino acid in humans. The vast majority of l-leucine metabolism is initially catalyzed by the branched-chain amino acid aminotransferase enzyme, producing alpha-ketoisocaproate (alpha-KIC). alpha-KIC is metabolized by the mitochondrial enzyme branched-chain alpha-ketoacid dehydrogenase, which converts it to isovaleryl-CoA. Isovaleryl-CoA is subsequently metabolized by the enzyme isovaleryl-CoA dehydrogenase and converted to beta-methylcrotonyl-CoA (MC-CoA), which is used in the synthesis of acetyl-CoA and other compounds. During biotin deficiency, HMB can be synthesized from MC-CoA via enoyl-CoA hydratase and an unknown thioesterase enzyme, which convert MC-CoA into HMB-CoA and HMB-CoA into HMB respectively. Leucine has the capacity to directly stimulate myofibrillar muscle protein synthesis (PMID 15051860). This effect of leucine arises results from its role as an activator of the mechanistic target of rapamycin (mTOR) (PMID 23551944) a serine-threonine protein kinase that regulates protein biosynthesis and cell growth. The activation of mTOR by leucine is mediated through Rag GTPases. Leucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of leucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287). BCAAs such as leucine have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Persistently low leucine levels can result in decreased appetite, poor feeding, lethargy, poor growth, weight loss, skin rashes, hair loss, and desquamation. Many types of inborn errors of BCAA metabolism exist and these are marked by various abnormalities. The most common form is maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary res... L-leucine is the L-enantiomer of leucine. It has a role as a plant metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is a pyruvate family amino acid, a proteinogenic amino acid, a leucine and a L-alpha-amino acid. It is a conjugate base of a L-leucinium. It is a conjugate acid of a L-leucinate. It is an enantiomer of a D-leucine. It is a tautomer of a L-leucine zwitterion. An essential branched-chain amino acid important for hemoglobin formation. L-Leucine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Leucine is one of nine essential amino acids in humans (provided by food), Leucine is important for protein synthesis and many metabolic functions. Leucine contributes to regulation of blood-sugar levels; growth and repair of muscle and bone tissue; growth hormone production; and wound healing. Leucine also prevents breakdown of muscle proteins after trauma or severe stress and may be beneficial for individuals with phenylketonuria. Leucine is available in many foods and deficiency is rare. (NCI04) Leucine (abbreviated as Leu or L)[2] is a branched-chain л±-amino acid with the chemical formulaHO2CCH(NH2)CH2CH(CH3)2. Leucine is classified as a hydrophobic amino acid due to its aliphatic isobutyl side chain. It is encoded by six codons (UUA, UUG, CUU, CUC, CUA, and CUG) and is a major component of the subunits in ferritin, astacin, and other buffer proteins. Leucine is an essential amino acid, meaning that the human body cannot synthesize it, and it therefore must be ingested. It is important for hemoglobin formation. An essential branched-chain amino acid important for hemoglobin formation. See also: Isoleucine; Leucine (component of) ... View More ... Dietary supplement, nutrient [DFC]. (±)-Leucine is found in many foods, some of which are green bell pepper, italian sweet red pepper, green zucchini, and red bell pepper. L-Leucine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=61-90-5 (retrieved 2024-07-01) (CAS RN: 61-90-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1].

Uridine

C9H12N2O6 (244.0695332)

Uridine, also known as beta-uridine or 1-beta-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione, is a member of the class of compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. More specifically, uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine is soluble (in water) and a very weakly acidic compound (based on its pKa). Uridine can be synthesized from uracil. It is one of the five standard nucleosides which make up nucleic acids, the others being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their one-letter codes U, A, T, C and G respectively. Uridine is also a parent compound for other transformation products, including but not limited to, nikkomycin Z, 3-(enolpyruvyl)uridine 5-monophosphate, and 5-aminomethyl-2-thiouridine. Uridine can be found in most biofluids, including urine, breast milk, cerebrospinal fluid (CSF), and blood. Within the cell, uridine is primarily located in the mitochondria, in the nucleus and the lysosome. It can also be found in the extracellular space. As an essential nucleoside, uridine exists in all living species, ranging from bacteria to humans. In humans, uridine is involved in several metabolic disorders, some of which include dhydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and beta-ureidopropionase deficiency. Moreover, uridine is found to be associated with Lesch-Nyhan syndrome, which is an inborn error of metabolism. Uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine plays a role in the glycolysis pathway of galactose. In humans there is no catabolic process to metabolize galactose. Therefore, galactose is converted to glucose and metabolized via the normal glucose metabolism pathways. More specifically, consumed galactose is converted into galactose 1-phosphate (Gal-1-P). This molecule is a substrate for the enzyme galactose-1-phosphate uridyl transferase which transfers a UDP molecule to the galactose molecule. The end result is UDP-galactose and glucose-1-phosphate. This process is continued to allow the proper glycolysis of galactose. Uridine is found in many foods (anything containing RNA) but is destroyed in the liver and gastrointestinal tract, and so no food, when consumed, has ever been reliably shown to elevate blood uridine levels. On the other hand, consumption of RNA-rich foods may lead to high levels of purines (adenine and guanosine) in blood. High levels of purines are known to increase uric acid production and may aggravate or lead to conditions such as gout. Uridine is a ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a beta-N(1)-glycosidic bond. It has a role as a human metabolite, a fundamental metabolite and a drug metabolite. It is functionally related to a uracil. Uridine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Uridine is a Pyrimidine Analog. The chemical classification of uridine is Pyrimidines, and Analogs/Derivatives. Uridine is a natural product found in Ulva australis, Synechocystis, and other organisms with data available. Uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine has been studied as a rescue agent to reduce the toxicities associated with 5-fluorouracil (5-FU), thereby allowing the administration of higher doses of 5-FU in chemotherapy regimens. (NCI04) Uridine is a metabolite found in or produced by Saccharomyces cerevisiae. A ribonucleoside in which RIBOSE is linked to URACIL. Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a b-N1-glycosidic bond. ; Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a ?-N1-glycosidic bond. Uridine is found in many foods, some of which are celery leaves, canola, common hazelnut, and hickory nut. A ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a beta-N(1)-glycosidic bond. [Spectral] Uridine (exact mass = 244.06954) and Adenosine (exact mass = 267.09675) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Uridine (exact mass = 244.06954) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Uridine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-96-8 (retrieved 2024-06-29) (CAS RN: 58-96-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

L-Proline

C5H9NO2 (115.0633254)

Proline (Pro), also known as L-proline 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 (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Proline is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Proline is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. Proline is derived from the amino acid L-glutamate in which glutamate-5-semialdehyde is first formed by glutamate 5-kinase and glutamate-5-semialdehyde dehydrogenase (which requires NADH or NADPH). This semialdehyde can then either spontaneously cyclize to form 1-pyrroline-5-carboxylic acid, which is reduced to proline by pyrroline-5-carboxylate reductase, or turned into ornithine by ornithine aminotransferase, followed by cyclization by ornithine cyclodeaminase to form proline. L-Proline has been found to act as a weak agonist of the glycine receptor and of both NMDA and non-NMDA ionotropic glutamate receptors. It has been proposed to be a potential endogenous excitotoxin/neurotoxin. Studies in rats have shown that when injected into the brain, proline non-selectively destroys pyramidal and granule cells (PMID: 3409032 ). Therefore, under certain conditions proline can act as a neurotoxin and a metabotoxin. 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 proline are associated with at least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency. People with hyperprolinemia type I often do not show any symptoms even though they have proline levels in their blood between 3 and 10 times the normal level. Some individuals with hyperprolinemia type I exhibit seizures, intellectual disability, or other neurological or psychiatric problems. Hyperprolinemia type II results in proline levels in the blood between 10 and 15 times higher than normal, and high levels of a related compound called pyrroline-5-carboxylate. Hyperprolinemia type II has signs and symptoms that vary in severity and is more likely than type I to involve seizures or intellectual disability. L-proline is pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. It has a role as a micronutrient, a nutraceutical, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and a member of compatible osmolytes. It is a glutamine family amino acid, a proteinogenic amino acid, a proline and a L-alpha-amino acid. It is a conjugate base of a L-prolinium. It is a conjugate acid of a L-prolinate. It is an enantiomer of a D-proline. It is a tautomer of a L-proline zwitterion. Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. L-Proline is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Proline is a cyclic, nonessential amino acid (actually, an imino acid) in humans (synthesized from glutamic acid and other amino acids), Proline is a constituent of many proteins. Found in high concentrations in collagen, proline constitutes almost a third of the residues. Collagen is the main supportive protein of skin, tendons, bones, and connective tissue and promotes their health and healing. (NCI04) L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons. Pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. Flavouring ingredient; dietary supplement L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins.

Citric acid

C6H8O7 (192.0270018)

Citric acid (citrate) is a tricarboxylic acid, an organic acid with three carboxylate groups. Citrate is an intermediate in the TCA cycle (also known as the Tricarboxylic Acid cycle, the Citric Acid cycle or Krebs cycle). The TCA cycle is a central metabolic pathway for all animals, plants, and bacteria. As a result, citrate is found in all living organisms, from bacteria to plants to animals. In the TCA cycle, the enzyme citrate synthase catalyzes the condensation of oxaloacetate with acetyl CoA to form citrate. Citrate then acts as the substrate for the enzyme known as aconitase and is then converted into aconitic acid. The TCA cycle ends with regeneration of oxaloacetate. This series of chemical reactions in the TCA cycle is the source of two-thirds of the food-derived energy in higher organisms. Citrate can be transported out of the mitochondria and into the cytoplasm, then broken down into acetyl-CoA for fatty acid synthesis, and into oxaloacetate. Citrate is a positive modulator of this conversion, and allosterically regulates the enzyme acetyl-CoA carboxylase, which is the regulating enzyme in the conversion of acetyl-CoA into malonyl-CoA (the commitment step in fatty acid synthesis). In short, citrate is transported into the cytoplasm, converted into acetyl CoA, which is then converted into malonyl CoA by acetyl CoA carboxylase, which is allosterically modulated by citrate. In mammals and other vertebrates, Citrate is a vital component of bone, helping to regulate the size of apatite crystals (PMID: 21127269). Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8\\\\\% of the dry weight of the fruit. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and carbonated drinks. Because it is one of the stronger edible acids, the dominant use of citric acid is as a flavoring and preservative in food and beverages, especially soft drinks and candies. Citric acid is an excellent chelating agent, binding metals by making them soluble. It is used to remove and discourage the buildup of limescale from boilers and evaporators. It can be used to treat water, which makes it useful in improving the effectiveness of soaps and laundry detergents. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Little information is available as the condition appears to be rare, but like other types of food intolerance it is often described as a "pseudo-allergic" reaction. Citric acid appears as colorless, odorless crystals with an acid taste. Denser than water. (USCG, 1999) Citric acid is a tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms. It has a role as a food acidity regulator, a chelator, an antimicrobial agent and a fundamental metabolite. It is a conjugate acid of a citrate(1-) and a citrate anion. A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium-chelating ability. Citric acid is one of the active ingredients in Phexxi, a non-hormonal contraceptive agent that was approved by the FDA on May 2020. It is also used in combination with magnesium oxide to form magnesium citrate, an osmotic laxative. Citric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Anhydrous citric acid is a Calculi Dissolution Agent and Anti-coagulant. The mechanism of action of anhydrous citric acid is as an Acidifying Activity and Calcium Chelating Activity. The physiologic effect of anhydrous citric acid is by means of Decreased Coagulation Factor Activity. Anhydrous Citric Acid is a tricarboxylic acid found in citrus fruits. Citric acid is used as an excipient in pharmaceutical preparations due to its antioxidant properties. It maintains stability of active ingredients and is used as a preservative. It is also used as an acidulant to control pH and acts as an anticoagulant by chelating calcium in blood. A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. See also: Citric Acid Monohydrate (related). Citrate, also known as anhydrous citric acid or 2-hydroxy-1,2,3-propanetricarboxylic acid, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Citrate is soluble (in water) and a weakly acidic compound (based on its pKa). Citrate can be found in a number of food items such as ucuhuba, loquat, bayberry, and longan, which makes citrate a potential biomarker for the consumption of these food products. Citrate can be found primarily in most biofluids, including saliva, sweat, feces, and blood, as well as throughout all human tissues. Citrate exists in all living species, ranging from bacteria to humans. In humans, citrate is involved in several metabolic pathways, some of which include the oncogenic action of succinate, the oncogenic action of fumarate, the oncogenic action of 2-hydroxyglutarate, and congenital lactic acidosis. Citrate is also involved in several metabolic disorders, some of which include 2-ketoglutarate dehydrogenase complex deficiency, pyruvate dehydrogenase deficiency (E2), fumarase deficiency, and glutaminolysis and cancer. Moreover, citrate is found to be associated with lung Cancer, tyrosinemia I, maple syrup urine disease, and propionic acidemia. A citrate is a derivative of citric acid; that is, the salts, esters, and the polyatomic anion found in solution. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate. When part of a salt, the formula of the citrate ion is written as C6H5O73− or C3H5O(COO)33− . A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms. Citric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=77-92-9 (retrieved 2024-07-01) (CAS RN: 77-92-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3]. Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3].

Benzoic acid

C7H6O2 (122.0367776)

Benzoic acid appears as a white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses. Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen. It is a conjugate acid of a benzoate. A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. As the sodium salt form, sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total Positive and Negative Syndrome Scale scores dropped by 21\\\\\% compared to placebo. Benzoic acid is a Nitrogen Binding Agent. The mechanism of action of benzoic acid is as an Ammonium Ion Binding Activity. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05\\\\\%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. See also: Salicylic Acid (active moiety of); Benzoyl Peroxide (active moiety of); Sodium Benzoate (active moiety of) ... View More ... Widespread in plants especies in essential oils and fruits, mostly in esterified formand is also present in butter, cooked meats, pork fat, white wine, black and green tea, mushroom and Bourbon vanilla. It is used in foodstuffs as antimicrobial and flavouring agent and as preservative. In practical food preservation, the Na salt of benzoic acid is the most widely used form (see MDQ71-S). The antimicrobial activity comprises a wide range of microorganisms, particularly yeasts and moulds. Undissociated benzoic acid is more effective than dissociated, thus the preservative action is more efficient in acidic foodstuffs. Typical usage levels are 500-2000 ppm. Benzoic acid is found in many foods, some of which are animal foods, common grape, lovage, and fruits. Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05\\\\\%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). It can be found in Serratia (PMID:23061754). Benzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=65-85-0 (retrieved 2024-06-28) (CAS RN: 65-85-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi. Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi.

Fumaric acid

C4H4O4 (116.0109584)

Fumaric acid appears as a colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses. Fumaric acid is a butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle. It has a role as a food acidity regulator, a fundamental metabolite and a geroprotector. It is a conjugate acid of a fumarate(1-). Fumaric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. Fumarate has recently been recognized as an oncometabolite. (A15199). As a food additive, fumaric acid is used to impart a tart taste to processed foods. It is also used as an antifungal agent in boxed foods such as cake mixes and flours, as well as tortillas. Fumaric acid is also added to bread to increase the porosity of the final baked product. It is used to impart a sour taste to sourdough and rye bread. In cake mixes, it is used to maintain a low pH and prevent clumping of the flours used in the mix. In fruit drinks, fumaric acid is used to maintain a low pH which, in turn, helps to stabilize flavor and color. Fumaric acid also prevents the growth of E. coli in beverages when used in combination with sodium benzoate. When added to wines, fumaric acid helps to prevent further fermentation and yet maintain low pH and eliminate traces of metallic elements. In this fashion, it helps to stabilize the taste of wine. Fumaric acid can also be added to dairy products, sports drinks, jams, jellies and candies. Fumaric acid helps to break down bonds between gluten proteins in wheat and helps to create a more pliable dough. Fumaric acid is used in paper sizing, printer toner, and polyester resin for making molded walls. Fumaric acid is a dicarboxylic acid. It is a precursor to L-malate in the Krebs tricarboxylic acid (TCA) cycle. It is formed by the oxidation of succinic acid by succinate dehydrogenase. Fumarate is converted by the enzyme fumarase to malate. Fumaric acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by fumarate. Fumaric acid is found to be associated with fumarase deficiency, which is an inborn error of metabolism. It is also a metabolite of Aspergillus. Produced industrially by fermentation of Rhizopus nigricans, or manufactured by catalytic or thermal isomerisation of maleic anhydride or maleic acid. Used as an antioxidant, acidulant, leavening agent and flavouring agent in foods. Present in raw lean fish. Dietary supplement. Used in powdered products since fumaric acid is less hygroscopic than other acids. A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase (wikipedia). Fumaric acid is also found in garden tomato, papaya, wild celery, and star fruit. Fumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=110-17-8 (retrieved 2024-07-01) (CAS RN: 110-17-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

L-Glutamic acid

C5H9NO4 (147.0531554)

Glutamic acid (Glu), also known as L-glutamic acid or as glutamate, the name of its anion, 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. L-glutamic acid is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Glutamic acid is found in all organisms ranging from bacteria to plants to animals. It is classified as an acidic, charged (at physiological pH), aliphatic amino acid. In humans it is a non-essential amino acid and can be synthesized via alanine or aspartic acid via alpha-ketoglutarate and the action of various transaminases. Glutamate also plays an important role in the bodys disposal of excess or waste nitrogen. Glutamate undergoes deamination, an oxidative reaction catalysed by glutamate dehydrogenase leading to alpha-ketoglutarate. In many respects glutamate is a key molecule in cellular metabolism. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: Damage to mitochondria from excessively high intracellular Ca2+. Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimers disease. Glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization (http://en.wikipedia.org/wiki/Glutamic_acid). Glutamate was discovered in 1866 when it was extracted from wheat gluten (from where it got its name. Glutamate has an important role as a food additive and food flavoring agent. In 1908, Japanese researcher Kikunae Ikeda identified brown crystals left behind after the evaporation of a large amount of kombu broth (a Japanese soup) as glutamic acid. These crystals, when tasted, reproduced a salty, savory flavor detected in many foods, most especially in seaweed. Professor Ikeda termed this flavor umami. He then patented a method of mass-producing a crystalline salt of glutamic acid, monosodium glutamate. L-glutamic acid is an optically active form of glutamic acid having L-configuration. It has a role as a nutraceutical, a micronutrient, an Escherichia coli metabolite, a mouse metabolite, a ferroptosis inducer and a neurotransmitter. It is a glutamine family amino acid, a proteinogenic amino acid, a glutamic acid and a L-alpha-amino acid. It is a conjugate acid of a L-glutamate(1-). It is an enantiomer of a D-glutamic acid. A peptide that is a homopolymer of glutamic acid. L-Glutamic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimers disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM. See also: Monosodium Glutamate (active moiety of); Glatiramer Acetate (monomer of); Glatiramer (monomer of) ... View More ... obtained from acid hydrolysis of proteins. Since 1965 the industrial source of glutamic acid for MSG production has been bacterial fermentation of carbohydrate sources such as molasses and corn starch hydrolysate in the presence of a nitrogen source such as ammonium salts or urea. Annual production approx. 350000t worldwide in 1988. Seasoning additive in food manuf. (as Na, K and NH4 salts). Dietary supplement, nutrient Glutamic acid (symbol Glu or E;[4] the anionic form is known as glutamate) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can synthesize enough for its use. It is also the most abundant excitatory neurotransmitter in the vertebrate nervous system. It serves as the precursor for the synthesis of the inhibitory gamma-aminobutyric acid (GABA) in GABAergic neurons. Its molecular formula is C 5H 9NO 4. Glutamic acid exists in two optically isomeric forms; the dextrorotatory l-form is usually obtained by hydrolysis of gluten or from the waste waters of beet-sugar manufacture or by fermentation.[5][full citation needed] Its molecular structure could be idealized as HOOC−CH(NH 2)−(CH 2)2−COOH, with two carboxyl groups −COOH and one amino group −NH 2. However, in the solid state and mildly acidic water solutions, the molecule assumes an electrically neutral zwitterion structure −OOC−CH(NH+ 3)−(CH 2)2−COOH. It is encoded by the codons GAA or GAG. The acid can lose one proton from its second carboxyl group to form the conjugate base, the singly-negative anion glutamate −OOC−CH(NH+ 3)−(CH 2)2−COO−. This form of the compound is prevalent in neutral solutions. The glutamate neurotransmitter plays the principal role in neural activation.[6] This anion creates the savory umami flavor of foods and is found in glutamate flavorings such as MSG. In Europe, it is classified as food additive E620. In highly alkaline solutions the doubly negative anion −OOC−CH(NH 2)−(CH 2)2−COO− prevails. The radical corresponding to glutamate is called glutamyl. The one-letter symbol E for glutamate was assigned in alphabetical sequence to D for aspartate, being larger by one methylene –CH2– group.[7] DL-Glutamic acid is the conjugate acid of Glutamic acid, which acts as a fundamental metabolite. Comparing with the second phase of polymorphs α and β L-Glutamic acid, DL-Glutamic acid presents better stability[1]. DL-Glutamic acid is the conjugate acid of Glutamic acid, which acts as a fundamental metabolite. Comparing with the second phase of polymorphs α and β L-Glutamic acid, DL-Glutamic acid presents better stability[1]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals. L-Glutamic acid is an excitatory amino acid neurotransmitter that acts as an agonist for all subtypes of glutamate receptors (metabolic rhodophylline, NMDA, and AMPA). L-Glutamic acid has an agonist effect on the release of DA from dopaminergic nerve endings. L-Glutamic acid can be used in the study of neurological diseases[1][2][3][4][5]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals.

L-Phenylalanine

C9H11NO2 (165.0789746)

Phenylalanine (Phe), also known as L-phenylalanine 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. L-phenylalanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Phenylalanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aromatic, non-polar amino acid. In humans, phenylalanine is an essential amino acid and the precursor of the amino acid tyrosine. Like tyrosine, phenylalanine is also a precursor for catecholamines including tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper, and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in a number of high protein foods, such as meat, cottage cheese, and wheat germ. An additional dietary source of phenylalanine is artificial sweeteners containing aspartame (a methyl ester of the aspartic acid/phenylalanine dipeptide). As a general rule, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Phenylketonurics have elevated serum plasma levels of phenylalanine up to 400 times normal. High plasma concentrations of phenylalanine influence the blood-brain barrier transport of large neutral amino acids. The high plasma phenylalanine concentrations increase phenylalanine entry into the brain and restrict the entry of other large neutral amino acids (PMID: 19191004). Phenylalanine has been found to interfere with different cerebral enzyme systems. Untreated phenylketonuria (PKU) can lead to intellectual disability, seizures, behavioural problems, and mental disorders. It may also result in a musty smell and lighter skin. Classic PKU dramatically affects myelination and white matter tracts in untreated infants; this may be one major cause of neurological disorders associated with phenylketonuria. Mild phenylketonuria can act as an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. It has been recently suggested that PKU may resemble amyloid diseases, such as Alzheimers disease and Parkinsons disease, due to the formation of toxic amyloid-like assemblies of phenylalanine (PMID: 22706200). Phenylalanine also has some potential benefits. Phenylalanine can act as an effective pain reliever. Its use in premenstrual syndrome and Parkinsons may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For instance, some tumours use more phen... L-phenylalanine is an odorless white crystalline powder. Slightly bitter taste. pH (1\\\\\\% aqueous solution) 5.4 to 6. (NTP, 1992) L-phenylalanine is the L-enantiomer of phenylalanine. It has a role as a nutraceutical, a micronutrient, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an algal metabolite, a mouse metabolite, a human xenobiotic metabolite and an EC 3.1.3.1 (alkaline phosphatase) inhibitor. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a phenylalanine and a L-alpha-amino acid. It is a conjugate base of a L-phenylalaninium. It is a conjugate acid of a L-phenylalaninate. It is an enantiomer of a D-phenylalanine. It is a tautomer of a L-phenylalanine zwitterion. Phenylalanine is an essential aromatic amino acid that is a precursor of melanin, [dopamine], [noradrenalin] (norepinephrine), and [thyroxine]. L-Phenylalanine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Phenylalanine is an essential aromatic amino acid in humans (provided by food), Phenylalanine plays a key role in the biosynthesis of other amino acids and is important in the structure and function of many proteins and enzymes. Phenylalanine is converted to tyrosine, used in the biosynthesis of dopamine and norepinephrine neurotransmitters. The L-form of Phenylalanine is incorporated into proteins, while the D-form acts as a painkiller. Absorption of ultraviolet radiation by Phenylalanine is used to quantify protein amounts. (NCI04) Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in high protein foods, such as meat, cottage cheese and wheat germ. A new dietary source of phenylalanine is artificial sweeteners containing aspartame. Aspartame appears to be nutritious except in hot beverages; however, it should be avoided by phenylketonurics and pregnant women. Phenylketonurics, who have a genetic error of phenylalanine metabolism, have elevated serum plasma levels of phenylalanine up to 400 times normal. Mild phenylketonuria can be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. Phenylalanine can be an effective pain reliever. Its use in premenstrual syndrome and Parkinsons may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-dopa, produce a catecholamine effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. Some tumors use more phenylalanine (particularly melatonin-producing tumors called melanoma). One strategy is to exclude this amino acid from the diet, i.e., a Phenylketonuria (PKU) diet (compliance is a difficult issue; it is hard to quantify and is under-researched). The other strategy is just to increase phenylalanines competing amino acids, i.e., tryptophan, valine, isoleucine and leucine, but not tyrosine. An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE. See also: Plovamer (monomer of); Plovamer Acetate (monomer of) ... View More ... L-phenylalanine, also known as phe or f, belongs to phenylalanine and derivatives class of compounds. Those are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-phenylalanine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-phenylalanine can be found in watermelon, which makes L-phenylalanine a potential biomarker for the consumption of this food product. L-phenylalanine can be found primarily in most biofluids, including sweat, blood, urine, and cerebrospinal fluid (CSF), as well as throughout all human tissues. L-phenylalanine exists in all living species, ranging from bacteria to humans. In humans, L-phenylalanine is involved in a couple of metabolic pathways, which include phenylalanine and tyrosine metabolism and transcription/Translation. L-phenylalanine is also involved in few metabolic disorders, which include phenylketonuria, tyrosinemia type 2 (or richner-hanhart syndrome), and tyrosinemia type 3 (TYRO3). Moreover, L-phenylalanine is found to be associated with viral infection, dengue fever, hypothyroidism, and myocardial infarction. L-phenylalanine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Phenylalanine (Phe or F) is an α-amino acid with the formula C 9H 11NO 2. It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins, coded for by DNA. The codons for L-phenylalanine are UUU and UUC. Phenylalanine is a precursor for tyrosine; the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline); and the skin pigment melanin . Hepatic. L-phenylalanine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body, where it undergoes metabolic reactions similar to those that take place in the liver (DrugBank). If PKU is diagnosed early, an affected newborn can grow up with normal brain development, but only by managing and controlling phenylalanine levels through diet, or a combination of diet and medication. The diet requires severely restricting or eliminating foods high in phenylalanine, such as meat, chicken, fish, eggs, nuts, cheese, legumes, milk and other dairy products. Starchy foods, such as potatoes, bread, pasta, and corn, must be monitored. Optimal health ranges (or "target ranges") of serum phenylalanine are between 120 and 360 µmol/L, and aimed to be achieved during at least the first 10 years of life. Recently it has been found that a chiral isomer of L-phenylalanine (called D-phenylalanine) actually arrests the fibril formation by L-phenylalanine and gives rise to flakes. These flakes do not propagate further and prevent amyloid formation by L-phenylalanine. D-phenylalanine may qualify as a therapeutic molecule in phenylketonuria (A8161) (T3DB). L-Phenylalanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=63-91-2 (retrieved 2024-07-01) (CAS RN: 63-91-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

Cinobufagin

C26H34O6 (442.2355264)

Cinobufagin is a steroid lactone. It is functionally related to a bufanolide. Cinobufagin is a natural product found in Bufo gargarizans, Phrynoidis asper, and other organisms with data available. Cinobufagin is a bufadienolide compound extracted from the dried venom secreted by the parotid glands of toads and one of the glycosides in the traditional Chinese medicine ChanSu, with potential antineoplastic activity. Although the mechanism of action of cinobufagin is still under investigation, it has been found to suppress cancer cell proliferation and cause apoptosis in cancer cells via a sequence of apoptotic modulators that include mitochondrial Bax and cytosolic chromosome c, and caspases 3, 8, and 9. Possible upstream mediators of cinobufagin-induced apoptosis include Fas and p53. D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides Annotation level-1 Cinobufagin is an anticancer agent that can be secreted by the Asiatic toad Bufo gargarizans. Cinobufagin induces the cell cycle arrests in the G1 phase or G2/M phase, leading to apoptosis in cancer cells. Cinobufagin inhibits tumor growth in melanoma and glioblastoma multiforme xenograft mouse models[1][2][3]. Cinobufagin is an anticancer agent that can be secreted by the Asiatic toad Bufo gargarizans. Cinobufagin induces the cell cycle arrests in the G1 phase or G2/M phase, leading to apoptosis in cancer cells. Cinobufagin inhibits tumor growth in melanoma and glioblastoma multiforme xenograft mouse models[1][2][3].

Campesterol

C28H48O (400.37049579999996)

Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\\\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia. Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. Campesterol is a natural product found in Haplophyllum bucharicum, Bugula neritina, and other organisms with data available. Campesterol is a steroid derivative that is the simplest sterol, characterized by the hydroxyl group in position C-3 of the steroid skeleton, and saturated bonds throughout the sterol structure, with the exception of the 5-6 double bond in the B ring. Campesterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-62-4 (retrieved 2024-07-01) (CAS RN: 474-62-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Stigmasterol

C29H48O (412.37049579999996)

Stigmasterol is a phytosterol, meaning it is steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. Stigmasterol is a 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. It has a role as a plant metabolite. It is a 3beta-sterol, a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Stigmasterol is a natural product found in Ficus auriculata, Xylopia aromatica, and other organisms with data available. Stigmasterol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and unsaturated bonds in position 5-6 of the B ring, and position 22-23 in the alkyl substituent. Stigmasterol is found in the fats and oils of soybean, calabar bean and rape seed, as well as several other vegetables, legumes, nuts, seeds, and unpasteurized milk. See also: Comfrey Root (part of); Saw Palmetto (part of); Plantago ovata seed (part of). Stigmasterol is an unsaturated plant sterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong) and American Ginseng. Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

Galactose

C6H12O6 (180.0633852)

D-galactopyranose is a galactopyranose having D-configuration. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a D-galactose and a galactopyranose. D-Galactose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). D-Galactose is a natural product found in Vigna subterranea, Lilium tenuifolium, and other organisms with data available. An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (GALACTOSE-1-PHOSPHATE URIDYL-TRANSFERASE DEFICIENCY DISEASE) causes an error in galactose metabolism called GALACTOSEMIA, resulting in elevations of galactose in the blood. V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CE - Tests for liver functional capacity Acquisition and generation of the data is financially supported by the Max-Planck-Society

L-Isoleucine

C6H13NO2 (131.0946238)

Isoleucine (Ile) or L-isoleucine 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 (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-isolecuine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Isoleucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Isoleucine is an essential amino acid in humans, meaning the body cannot synthesize it and that it must be obtained from the diet. In plants and microorganisms, isoleucine is synthesized starting from pyruvate and alpha-ketobutyrate. Isoleucine is classified as a branched chain amino acid (BCAA). BCAAs include three amino acids: isoleucine, leucine and valine. They are alpha amino acids whose carbon structure is marked by a beta branch point. Despite their structural similarities, BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. Isoleucine is catabolized via with alpha-ketoglutarate where upon it is oxidized and split into propionyl-CoA and acetyl-CoA. Propionyl-CoA is converted into succinyl-CoA, a TCA cycle intermediate which can be converted into oxaloacetate for gluconeogenesis (hence glucogenic). The acetyl-CoA can be fed into the TCA cycle by condensing with oxaloacetate to form citrate or used in the synthesis of ketone bodies or fatty acids. The different metabolism of BCAAs accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine are required respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAAs are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia. An inability to break down isoleucine, along with other amino acids, is associated with maple syrup urine disease (MSUD) (PMID: 34125801). Isoleucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of isoleucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287). Mice fed an isoleucine deprivation diet for one day have improved insulin sensitivity, and feeding of an isoleucine deprivation diet for one week significantly decreases blood glucose levels (PMID: 24684822). L-isoleucine is the L-enantiomer of isoleucine. It has a role as a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a plant metabolite, a human metabolite, an algal metabolite and a mouse metabolite. It is an aspartate family amino acid, a proteinogenic amino acid, an isoleucine and a L-alpha-amino acid. It is a conjugate base of a L-isoleucinium. It is a conjugate acid of a L-isoleucinate. It is an enantiomer of a D-isoleucine. It is a tautomer of a L-isoleucine zwitterion. An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of leucine. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. L-Isoleucine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Isoleucine is one of nine essential amino acids in humans (present in dietary proteins), Isoleucine has diverse physiological functions, such as assisting wound healing, detoxification of nitrogenous wastes, stimulating immune function, and promoting secretion of several hormones. Necessary for hemoglobin formation and regulating blood sugar and energy levels, isoleucine is concentrated in muscle tissues in humans. Isoleucine is found especially in meats, fish, cheese, eggs, and most seeds and nuts. (NCI04) L-Isoleucine is one of the essential amino acids that cannot be made by the body and is known for its ability to help endurance and assist in the repair and rebuilding of muscle. This amino acid is important to body builders as it helps boost energy and helps the body recover from training. L-Isoleucine is also classified as a branched-chain amino acid (BCAA). It helps promote muscle recovery after exercise. Isoleucine is actually broken down for energy within the muscle tissue. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. L-Isoleucine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=73-32-5 (retrieved 2024-07-01) (CAS RN: 73-32-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid. L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid.

Putrescine

C4H12N2 (88.1000432)

Putrescine is a four-carbon alkane-alpha,omega-diamine. It is obtained by the breakdown of amino acids and is responsible for the foul odour of putrefying flesh. It has a role as a fundamental metabolite and an antioxidant. It is a conjugate base of a 1,4-butanediammonium. Putrescine is a toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine. Putrescine is a solid. This compound belongs to the polyamines. These are compounds containing more than one amine group. Known drug targets of putrescine include putrescine-binding periplasmic protein, ornithine decarboxylase, and S-adenosylmethionine decarboxylase proenzyme. Putrescine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). 1,4-Diaminobutane is a natural product found in Eupatorium cannabinum, Populus tremula, and other organisms with data available. Putrescine is a four carbon diamine produced during tissue decomposition by the decarboxylation of amino acids. Polyamines, including putrescine, may act as growth factors that promote cell division; however, putrescine is toxic at high doses. Putrescine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.Putrescine is a polyamine. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine is also found in semen. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division. Putrescine apparently has specific role in skin physiology and neuroprotection. Pharmacological interventions have demonstrated convincingly that a steady supply of polyamines is a prerequisite for cell proliferation to occur. Genetic engineering of polyamine metabolism in transgenic rodents has shown that polyamines play a role in spermatogenesis, skin physiology, promotion of tumorigenesis and organ hypertrophy as well as neuronal protection. Transgenic activation of polyamine catabolism not only profoundly disturbs polyamine homeostasis in most tissues, but also creates a complex phenotype affecting skin, female fertility, fat depots, pancreatic integrity and regenerative growth. Transgenic expression of ornithine decarboxylase antizyme has suggested that this unique protein may act as a general tumor suppressor. Homozygous deficiency of the key biosynthetic enzymes of the polyamines, ornithine and S-adenosylmethionine decarboxylase is not compatible with murine embryogenesis. (A3286, A3287). Putrescine is a metabolite found in or produced by Saccharomyces cerevisiae. A toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine. Putrescine is a polyamine. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). It is also found in semen. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division. Putrescine apparently has specific role in skin physiology and neuroprotection. (PMID:15009201, 16364196). Pharmacological interventions have demonstrated convincingly that a steady supply of polyamines is a prerequisite for cell proliferation to occur. Genetic engineering of polyamine metabolism in transgenic rodents has shown that polyamines play a role in spermatogenesis, skin physiology, promotion of tumorigenesis and organ hypertrophy as well as neuronal protection. Transgenic activation of polyamine catabolism not only profoundly disturbs polyamine homeostasis in most tissues, but also creates a complex phenotype affecting skin, female fertility, fat depots, pancreatic integrity and regenerative growth. Transgenic expression of ornithine decarboxylase antizyme has suggested that this unique protein may act as a general tumor suppressor. Homozygous deficiency of the key biosynthetic enzymes of the polyamines, ornithine and S-adenosylmethionine decarboxylase is not compatible with murine embryogenesis. Putrescine can be found in Citrobacter, Corynebacterium, Cronobacter and Enterobacter (PMID:27872963) (https://onlinelibrary.wiley.com/doi/full/10.1111/1541-4337.12099). Putrescine is an organic chemical compound related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. The two compounds are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. They are also found in semen and some microalgae, together with related molecules like spermine and spermidine. A four-carbon alkane-alpha,omega-diamine. It is obtained by the breakdown of amino acids and is responsible for the foul odour of putrefying flesh. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID B001

serin

C3H7NO3 (105.0425912)

Serine is an alpha-amino acid that is alanine substituted at position 3 by a hydroxy group. It has a role as a fundamental metabolite. It is an alpha-amino acid and a polar amino acid. It contains a hydroxymethyl group. It is a conjugate base of a serinium. It is a conjugate acid of a serinate. It is a tautomer of a serine zwitterion. DL-Serine, a fundamental metabolite, is a mixture of D-Serine and L-Serine. DL-Serine has antiviral activity against the multiplication of tobacco mosaic virus (TMV)[1]. DL-Serine, a fundamental metabolite, is a mixture of D-Serine and L-Serine. DL-Serine has antiviral activity against the multiplication of tobacco mosaic virus (TMV)[1]. D-Serine ((R)-Serine), an endogenous amino acid involved in glia-synapse interactions that has unique neurotransmitter characteristics, is a potent co-agonist at the NMDA glutamate receptor. D-Serinee has a cardinal modulatory role in major NMDAR-dependent processes including NMDAR-mediated neurotransmission, neurotoxicity, synaptic plasticity, and cell migration[1][2]. D-Serine ((R)-Serine), an endogenous amino acid involved in glia-synapse interactions that has unique neurotransmitter characteristics, is a potent co-agonist at the NMDA glutamate receptor. D-Serinee has a cardinal modulatory role in major NMDAR-dependent processes including NMDAR-mediated neurotransmission, neurotoxicity, synaptic plasticity, and cell migration[1][2]. L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation. L-Serine ((-)-Serine; (S)-Serine), one of the so-called non-essential amino acids, plays a central role in cellular proliferation.

Serotonin

C10H12N2O (176.0949582)

Serotonin or 5-hydroxytryptamine (5-HT) is a molecule that belongs to the class of compounds known as indoleamines. An indoleamine consists of an indole ring that bears an amino group or an alkyl amino group attached to the indole ring. Serotonin has an aminoethyl at position 2 and a hydroxyl group at position 5 of the indole ring. Serotonin exists in all living organisms, ranging from bacteria to plants to humans. In mammals, serotonin functions as a monoamine neurotransmitter, a biochemical messenger and regulator. It is synthesized from the essential amino acid L-Tryptophan. Approximately 90\\\\% of the human bodys total serotonin is located in the enterochromaffin cells in the GI tract, where it regulates intestinal movements. About 8\\\\% is found in platelets and 1–2\\\\% in the CNS. Serotonin in the nervous system acts as a local transmitter at synapses, and as a paracrine or hormonal modulator of circuits upon diffusion, allowing a wide variety of "state-dependent" behavioral responses to different stimuli. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. Such is the case of aggressive behavior and rhythmic motor patterns, including those responsible for feeding. In vertebrates, which display a wider and much more sophisticated behavioral repertoire, serotonin also modulates sleep, the arousal state, sexual behavior, and others. Deficiencies of the serotonergic system causes disorders such as depression, obsessive-compulsive disorder, phobias, posttraumatic stress disorder, epilepsy, and generalized anxiety disorder. Serotonin has three different modes of action in the nervous system: as transmitter, acting locally at synaptic boutons; upon diffusion at a distance from its release sites, producing paracrine (also called volume) effects, and by circulating in the blood stream, producing hormonal effects. The three modes can affect a single neuronal circuit. (PMID: 16047543). Serotonin is also a microbial metabolite that can be found in the feces and urine of mammals. Urinary serotonin is produced by Candida, Streptococcus, Escherichia, and Enterococcus (PMID: 24621061). In plants, serotonin was first found and reported in a legume called Mucuna pruriens. The greatest concentration of serotonin in plants has been found in walnuts and hickory. In pineapples, banana, kiwi fruit, plums and tomatoes the concentration of serotonin is around 3 to 30 mg/kg. Isolated from bananas and other fruitsand is also from cotton (Gossypium hirsutum) [DFC]. Serotonin is found in many foods, some of which are common pea, eggplant, swiss chard, and dill. Serotonin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=50-67-9 (retrieved 2024-07-01) (CAS RN: 50-67-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

5-Hydroxyindoleacetic acid

C10H9NO3 (191.0582404)

5-Hydroxyindoleacetic acid, also known as 5-hydroxyindole-3-acetate or 5-HIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. In humans, 5-hydroxyindoleacetic acid is a breakdown product of serotonin that is excreted in the urine and it also participates in a number of enzymatic reactions. 5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde; which is catalyzed by the mitochondrial enzyme aldehyde dehydrogenase. In addition, 5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. 5-Hydroxyindoleacetic acid is also involved in the metabolism of tryptophan. 5-Hydroxyindoleacetic acid has been found to be associated with several human diseases such as brunner syndrome, friedreichs ataxia, schizophrenia, and olivopontocerebral atrophy; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder sepiapterin reductase deficiency. Elevated levels of 5-hydroxyindoleacetic acid in urine (>20 uM) are indicative of appendicitis and gastroenteritis (PMID: 11462886). Serotonin and 5-Hydroxyindoleacetic acid are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors (NCI). 5-Hydroxyindoleacetic acid has also been found to be a product of human gut microbiota. 5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin in the human body. In chemical analysis of urine samples, 5-HIAA is used to determine the bodys levels of serotonin. 5-Hydroxyindole-3-acetic acid is found in many foods, some of which are pitanga, dandelion, coconut, and white cabbage. 5-Hydroxyindole-3-acetic acid is the main metabolite of serotonin or metanephrines, which can be used as a biomarker of neuroendocrine tumors.

Oxoglutaric acid

C5H6O5 (146.0215226)

Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207). Oxoglutaric acid has been found to be a metabolite produced by Corynebacterium and yeast (PMID: 27872963) (YMDB). [Spectral] 2-Oxoglutarate (exact mass = 146.02152) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] 2-Oxoglutarate (exact mass = 146.02152) and (S)-Malate (exact mass = 134.02152) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Flavouring ingredient

Epinephrine

C9H13NO3 (183.0895388)

Epinephrine, also known as adrenaline, is both a neurotransmitter and a hormone. It plays an important role in your body’s “fight-or-flight” response. It’s also used as a medication to treat many life-threatening conditions. Epinephrine is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. It is the active sympathomimetic hormone secreted from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. Epinephrine also constricts arterioles in the skin and gut while dilating arterioles in leg muscles. It elevates the blood sugar level by increasing hydrolysis of glycogen to glucose in the liver, and at the same time begins the breakdown of lipids in adipocytes. Epinephrine has a suppressive effect on the immune system. [HMDB] Epinephrine, also called adrenaline, is both a hormone and a neurotransmitter. As a hormone, it’s made and released by your adrenal glands, which are hat-shaped glands that sit on top of each kidney. As a central nervous system neurotransmitter, it’s a chemical messenger that helps transmit nerve signals across nerve endings to another nerve cell, muscle cell or gland cell. Epinephrine is part of your sympathetic nervous system, which is part of your body’s emergency response system to danger — the “fight-or-flight” response. Medically, the flight-or-flight response is known as the acute stress response. Epinephrine is also called a catecholamine, as are norepinephrine and dopamine. They’re given this name because of a certain molecule in its structure. As a hormone, epinephrine is made from norepinephrine inside of your adrenal gland. As a neurotransmitter, epinephrine plays a small role. Only a small amount is produced in your nerves. It plays a role in metabolism, attention, focus, panic and excitement. Abnormal levels are linked to sleep disorders, anxiety, hypertension and lowered immunity. Epinephrine’s major action is in its role as a hormone. Epinephrine is released by your adrenal glands in response to stress. This reaction causes a number of changes in your body and is known as the fight-or-flight response.

Creatine

C4H9N3O2 (131.06947340000002)

Creatine, is a naturally occurring non-protein compound. It belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Creatine is found in all vertebrates where it facilitates recycling of adenosine triphosphate (ATP). Its primary metabolic role is to combine with a phosphoryl group, via the enzyme creatine kinase, to generate phosphocreatine, which is used to regenerate ATP. Most of the human bodys total creatine and phosphocreatine stores are found in skeletal muscle (95\\\\\%), while the remainder is distributed in the blood, brain, testes, and other tissues. Creatine is not an essential nutrient as it is naturally produced in the human body from the amino acids glycine and arginine, with an additional requirement for methionine to catalyze the transformation of guanidinoacetate to creatine. In the first step of its biosynthesis glycine and arginine are combined by the enzyme arginine:glycine amidinotransferase (AGAT) to form guanidinoacetate, which is then methylated by guanidinoacetate N-methyltransferase (GAMT), using S-adenosyl methionine as the methyl donor. Creatine can also be obtained through the diet at a rate of about 1 gram per day from an omnivorous diet. A cyclic form of creatine, called creatinine, exists in equilibrium with its tautomer and with creatine. Clinically, there are three distinct disorders of creatine metabolism. Deficiencies in the two synthesis enzymes (AGAT and GAMT) can cause L-arginine:glycine amidinotransferase deficiency (caused by variants in AGAT) and guanidinoacetate methyltransferase deficiency (caused by variants in GAMT). Both disorders are inherited in an autosomal recessive manner. A third defect, creatine transporter defect, is caused by mutations in SLC6A8 and inherited in a X-linked manner. Creatine is widely used as a supplement by athletes. Its use can increase maximum power and performance in high-intensity anaerobic repetitive work (periods of work and rest) by 5 to 15\\\\\% (PMID: 24688272). Creatine has no significant effect on aerobic endurance, although it will increase power during short sessions of high-intensity aerobic exercise (PMID: 9662683). [Spectral] Creatine (exact mass = 131.06948) and L-Aspartate (exact mass = 133.03751) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Creatine (exact mass = 131.06948) and L-Cysteine (exact mass = 121.01975) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Creatine is a essential, non-proteinaceous amino acid found in all animals and in some plants. Creatine is synthesized in the kidney, liver and pancreas from L-arginine, glycine and L-methionine. Creatine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-00-1 (retrieved 2024-06-29) (CAS RN: 57-00-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

L-Lysine

C6H14N2O2 (146.1055224)

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 (–NH2) and carboxyl (–COOH) 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 α-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].

L-Methionine

C5H11NO2S (149.0510466)

Methionine (Met), also known as L-methionine, 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 (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Methionine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Methionine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. Methionine is an essential amino acid (there are 9 essential amino acids), meaning the body cannot synthesize it, and it must be obtained from the diet. It is required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, methionine is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine (PMID: 16702340 ). There is a general consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethioninemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimum recommended daily intake. Apart from some very specific indications (e.g. acetaminophen poisoning) the usefulness of SAA supplementation is not yet established (PMID: 16702341 ). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, but there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. Acute doses of methionine can lead to acute increases in plasma homocysteine, which can be used as an index of the susceptibility to cardiovascular disease. Sufficiently high doses of methionine can actually result in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times the normal amount resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid (PMID: 16702346 ). When present in sufficiently high levels, methionine can act as an atherogen and a metabotoxin. An atherogen is a compound that when present at chronically high levels causes atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methionine are associated with at least ten inborn errors of metabolism, including cystathionine beta-synthase deficiency, glycine N-methyltransferase deficiency, homocystinuria, tyrosinemia, galactosemia, homocystinuria-megaloblastic anemia due to defects in cobalamin metabolism, methionine adenosyltransferase deficiency, methylenetetrahydrofolate reductase deficiency, and S-adenosylhomocysteine (SAH) hydrolase deficiency. Chronically elevated levels of methionine in infants can lead to intellectual disability and othe... [Spectral] L-Methionine (exact mass = 149.05105) and Adenosine (exact mass = 267.09675) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Methionine (exact mass = 149.05105) and Tyramine (exact mass = 137.08406) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. l-Methionine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=63-68-3 (retrieved 2024-07-01) (CAS RN: 63-68-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant. L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant.

Cellobiose

C12H22O11 (342.11620619999997)

D-(+)-Cellobiose is an endogenous metabolite. D-(+)-Cellobiose is an endogenous metabolite. Maltose is a disaccharide formed from two units of glucose joined with an α(1→4) bond, a reducing sugar. Maltose monohydrate can be used as a energy source for bacteria. Maltose is a disaccharide formed from two units of glucose joined with an α(1→4) bond, a reducing sugar. Maltose monohydrate can be used as a energy source for bacteria.

L-Alanine

C3H7NO2 (89.0476762)

Alanine (Ala), also known as L-alanine 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 (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Alanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. In humans, alanine is a non-essential amino acid that can be easily made in the body from either the conversion of pyruvate or the breakdown of the dipeptides carnosine and anserine. Alanine can be also synthesized from branched chain amino acids such as valine, leucine, and isoleucine. Alanine is produced by reductive amination of pyruvate through a two-step process. In the first step, alpha-ketoglutarate, ammonia and NADH are converted by the enzyme known glutamate dehydrogenase to glutamate, NAD+ and water. In the second step, the amino group of the newly-formed glutamate is transferred to pyruvate by an aminotransferase enzyme, regenerating the alpha-ketoglutarate, and converting the pyruvate to alanine. The net result is that pyruvate and ammonia are converted to alanine. In mammals, alanine plays a key role in glucose–alanine cycle between tissues and liver. In muscle and other tissues that degrade amino acids for fuel, amino groups are collected in the form of glutamate by transamination. Glutamate can then transfer its amino group to pyruvate, a product of muscle glycolysis, through the action of alanine aminotransferase, forming alanine and alpha-ketoglutarate. The alanine enters the bloodstream and is transported to the liver. The alanine aminotransferase reaction takes place in reverse in the liver, where the regenerated pyruvate is used in gluconeogenesis, forming glucose which returns to the muscles through the circulation system. Alanine is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine is reduced in both severe hypoglycemia and the ketosis of diabetes. Alanine is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine, and glycine, is an inhibitory neurotransmitter in the brain (http://www.dcnutrition.com/AminoAcids/). L-Alanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-41-7 (retrieved 2024-07-01) (CAS RN: 56-41-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

Cholesterol

C27H46O (386.3548466)

Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50\\\\% of the lipid in the membrane or 60-80\\\\% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with c... Constituent either free or as esters, of fish liver oils, lard, dairy fats, egg yolk and bran Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

Brassicasterol

C28H46O (398.3548466)

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].

N-Methylserotonin

C11H14N2O (190.1106074)

N-methylserotonin is a product of the serotonin-degradative pathway, found in urine specimens of patients with psychiatric disorders (PubMed ID 8747157 ).

Pentadecane

C15H32 (212.2503872)

Pentadecane, also known as ch3-[ch2]13-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, pentadecane is considered to be a hydrocarbon lipid molecule. Pentadecane is an alkane and waxy tasting compound and can be found in a number of food items such as dill, papaya, yellow bell pepper, and pepper (c. annuum), which makes pentadecane a potential biomarker for the consumption of these food products. Pentadecane can be found primarily in saliva. Pentadecane is a non-carcinogenic (not listed by IARC) potentially toxic compound. Pentadecane is an alkane hydrocarbon with the chemical formula C15H32 . Pentadecane belongs to the family of Acyclic Alkanes. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2

Cinobufotalin

C26H34O7 (458.2304414)

Cinobufotalin is a natural product found in Bufo and Bufo bufo with data available. Cinobufotalin is a bufadienolide isolated from toad venom and utilized in traditional Chinese medicine (TCM) for its cardiotonic, diuretic and hemostatic effects, with potential cytotoxic and antineoplastic activities. Upon administration and although the exact mechanism of action(s) (MoAs) through which this agent exerts its effects have yet to be fully discovered, cinobufotalin causes DNA fragmentation, decreases mitochondrial membrane potential (MMP), increases intracellular calcium (Ca2+) ion concentrations and reactive oxygen species (ROS) production, upregulates Fas protein and activates cytochrome C, various caspases, Bid and Bax. This causes cell cycle arrest, induces apoptosis and inhibits tumor cell growth and survival. In addition, cinobufotalin inhibits the activity of sphingosine kinase 1 (SphK1) and induces pro-apoptotic ceramide production, which further promotes tumor cell apoptosis. Cinobufotalin also induces mitochondrial protein cyclophilin D (Cyp-D)-dependent opening of the mitochondrial permeability transition pore (mPTP), which may contribute to cinobufotalin-induced non-apoptotic death of certain tumor cells. D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides Cinobufotalin is a cardiotonic steroids or bufadienolides, is extracted from the skin secretions of the giant toads. Cinobufotalin has been used as a cardiotonic, diuretic and a hemostatic agent, Cinobufotalin is also a potential anti-lung cancer agent[1].

Hellebrigenin

C24H32O6 (416.2198772)

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

Turanose

C12H22O11 (342.11620619999997)

D-(+)-Turanose is a reducing disaccharide. Its systematic name is a-D-glucopyranosyl-(1-->3)-a-D-fructofuranose. It is an analog of sucrose not metabolized by higher plants, but rather acquired through the action of sucrose transporters for intracellular carbohydrate signaling. In addition to its involvement in signal transduction, D-(+)-Turanose can also be used as a carbon source by many organisms including numerous species of bacteria and fungi (Wikipedia). Isolated from honey Turanose is an isomer of Sucrose that naturally exists in honey. Turanose has anti-inflammatory and regulates adipogenesis effect. Turanose has potential for obesity and related chronic diseases research[1][2]. Turanose is an isomer of Sucrose that naturally exists in honey. Turanose has anti-inflammatory and regulates adipogenesis effect. Turanose has potential for obesity and related chronic diseases research[1][2].

Cellobiose

C12H22O11 (342.11620619999997)

Cellobiose, also known as GLCB1-4GLCB or cellose, is a disaccharide. It is also classified as a reducing sugar. In terms of its chemical structure, it is derived from the condensation of a pair beta-glucose molecules creating a beta (1‚Üí4) bond. It belongs to the class of organic compounds known as O-glycosyl compounds. These are glycosides in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Cellobiose can be obtained by enzymatic hydrolysis of cellulose and cellulose-rich materials such as cotton, jute, or paper. Cellobiose is a plant metabolite found in flowering plants, conifers and other gymnosperms. Cellobiose can also be found in vertebrates that have consumed plant foods. It has been detected, but not quantified in, several different foods, such as okra, common chokecherries, cherry tomatoes, and welsh onions. Cellobiose can be used as an indicator carbohydrate for Crohns disease and malabsorption syndrome. Intestinal permeability to detect Crohns disease and malabsorption syndrome can be measured by the sugar absorption test. This test is based on determining the ratio of the urinary excretion of a large (a disaccharide such as cellobiose) and a small carbohydrate (a monosaccharide such as lactulose or rhamnose) after oral administration. Patients with Crohns disease or with ulcerative colitis have increased permeability indices in comparison to healthy controls (PMID: 15546811). Cellobiose is a disaccharide consisting of two glucose units in a beta (1-4) glycosidic linkage. It is a microbial breakdown product from plant material (cellulose). It may be found in some food products (vegetables, fruits, corn syrups, etc.). D-(+)-Cellobiose is an endogenous metabolite. D-(+)-Cellobiose is an endogenous metabolite.

Sorbitol

C6H14O6 (182.0790344)

Sorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. It is also used in many manufacturing processes, as a pharmaceutical aid, and in several research applications. Ascorbic acid fermentation; in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, tobacco, gelatin; bodying agent for paper, textiles, and liquid pharmaceuticals; softener for candy; sugar crystallization inhibitor; surfactants; urethane resins and rigid foams; plasticizer, stabilizer for vinyl resins; food additive (sweetener, humectant, emulsifier, thickener, anticaking agent); dietary supplement. (Hawleys Condensed Chemical Dictionary) Biological Source: Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus species Use/Importance: Used for manufacturing of sorbose, propylene glycol, ascorbic acid, resins, plasticizers and as antifreeze mixtures with glycerol or glycol. Tablet diluent, sweetening agent and humectant, other food uses. Sorbitol is used in photometric determination of Ru(VI) and Ru(VIII); in acid-base titration of borate (Dictionary of Organic Compounds). Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus subspecies Sweetening agent and humectant and many other food uses. D-Glucitol is found in many foods, some of which are common salsify, other bread, wild rice, and common chokecherry. A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AD - Osmotically acting laxatives A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AG - Enemas B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CC - Tests for bile duct patency Acquisition and generation of the data is financially supported in part by CREST/JST. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D005765 - Gastrointestinal Agents > D002400 - Cathartics D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1]. D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1].

L-Threonine

C4H9NO3 (119.0582404)

An optically active form of threonine having L-configuration. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; AYFVYJQAPQTCCC_STSL_0105_Threonine_8000fmol_180506_S2_LC02_MS02_275; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. CONFIDENCE standard compound; INTERNAL_ID 10 DL-Threonine, an essential amino acid, has the potential to treat hypostatic leg ulceration[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1]. L-Threonine is a natural amino acid, can be produced by microbial fermentation, and is used in food, medicine, or feed[1].

Ornithine

C5H12N2O2 (132.0898732)

An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5. L-Ornithine ((S)-2,5-Diaminopentanoic acid) is a non-proteinogenic amino acid, is mainly used in urea cycle removing excess nitrogen in vivo. L-Ornithine shows nephroprotective[1][2]. L-Ornithine ((S)-2,5-Diaminopentanoic acid) is a non-proteinogenic amino acid, is mainly used in urea cycle removing excess nitrogen in vivo. L-Ornithine shows nephroprotective[1][2].

Docosane

C22H46 (310.3599316)

N-docosane, also known as ch3-[ch2]20-ch3 or dokosan, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, N-docosane is considered to be a hydrocarbon lipid molecule. N-docosane is an alkane and waxy tasting compound and can be found in a number of food items such as lemon balm, linden, allspice, and sunflower, which makes N-docosane a potential biomarker for the consumption of these food products. N-docosane can be found primarily in saliva. The term higher alkanes is sometimes used literally as "alkanes with a higher number of carbon atoms". One definition distinguishes the higher alkanes as the n-alkanes that are solid under natural conditions . Docosane, also known as CH3-[CH2]20-CH3 or dokosan, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Docosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, docosane is considered to be a hydrocarbon lipid molecule. Docosane is an alkane and waxy tasting compound. Docosane is found, on average, in the highest concentration within lemon balms. Docosane has also been detected, but not quantified, in several different foods, such as allspices, lindens, papaya, and sunflowers. This could make docosane a potential biomarker for the consumption of these foods. A straight-chain alkane with 22 carbon atoms. N-docosane is a solid. Insoluble in water. Used in organic synthesis, calibration, and temperature sensing equipment. Docosane is a straight-chain alkane with 22 carbon atoms. It has a role as a plant metabolite. Docosane is a natural product found in Lonicera japonica, Erucaria microcarpa, and other organisms with data available. See also: Moringa oleifera leaf oil (part of). A straight-chain alkane with 22 carbon atoms. Docosane, a straight chain alkane, can be used to synthesize structural composites with thermal energy storage/release capability[1][2]. Docosane, a straight chain alkane, can be used to synthesize structural composites with thermal energy storage/release capability[1][2].

Octacosane

C28H58 (394.4538268)

Octacosane, also known as ch3-[ch2]26-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, octacosane is considered to be a hydrocarbon lipid molecule. Octacosane can be found in a number of food items such as peach, linden, apple, and carrot, which makes octacosane a potential biomarker for the consumption of these food products. Octacosane can be found primarily in saliva. The term higher alkanes is sometimes used literally as "alkanes with a higher number of carbon atoms". One definition distinguishes the higher alkanes as the n-alkanes that are solid under natural conditions . Octacosane, also known as CH3-[CH2]26-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Octacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, octacosane is considered to be a hydrocarbon lipid molecule. Octacosane has been detected, but not quantified, in several different foods, such as peachs, coconuts, apples, sweet cherries, and lindens. This could make octacosane a potential biomarker for the consumption of these foods. A straight-chain alkane containing 28 carbon atoms.

Nonadecane

C19H40 (268.31298400000003)

Nonadecane, also known as CH3-[CH2]17-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Nonadecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, nonadecane is considered to be a hydrocarbon lipid molecule. Nonadecane is an alkane and bland tasting compound. nonadecane has been detected, but not quantified, in several different foods, such as pomes, watermelons, yellow bell peppers, allspices, and papaya. This could make nonadecane a potential biomarker for the consumption of these foods. Nonadecane has been linked to the inborn metabolic disorders including celiac disease. Isolated from apple wax. Nonadecane is found in many foods, some of which are pepper (c. annuum), red bell pepper, papaya, and dill.

scyllo-Inositol

C6H12O6 (180.0633852)

scyllo-Inositol or scyllitol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. scyllo-Inositol was first isolated from the kidneys of fish in 1858 by Staedeler and Freierchs. scyllo-Inositol is a naturally occurring plant sugar alcohol found most abundantly in the coconut palm. It appears to accumulate in a number of human tissues and biofluids through dietary consumption. It has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379). Results reported by Viola et al (PMID: 15340856) suggest that high CSF concentrations of scyllo-inositol can be induced by chronic alcoholism. scyllo-Inositol when fed to transgenic mice that exhibit a memory disease very similar to human Alzheimers disease, can block the accumulation of soluble amyloid-beta (Aβ) plaques in the brain. scyllo-Inositol was found to reverse memory deficits in the mice, reduce the amount of Aβ plaque in the brains of the mice, and reversed other symptoms associated with the presence of Aβ in the brain (PMID: 16767098). Scyllitol is an isomer of cyclohexanehexol or inositol. It was first isolated from the kidneys of fish in 1858 by Staedeler and Freierchs. Scyllitol is a naturally occurring plant sugar alcohol found most abundantly in the coconut palm. It appears to accumulate in a number of human tissues and biofluids through dietary consumption. It has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379). Results reported by Viola et al (PMID: 15340856) suggest that high CSF concentrations of scyllo-inositol can be induced by chronic alcoholism. scyllo-Inositol (also called "scyllitol") when fed to transgenic mice that exhibit a memory disease very similar to human Alzheimers disease, can block the accumulation of soluble amyloid-beta (Aβ) plaques in the brain. Scyllitol was found to reverse memory deficits in the mice, reduce the amount of Aβ plaque in the brains of the mice, and reversed other symptoms associated with the presence of Aβ in the brain (PMID: 16767098). [HMDB] C26170 - Protective Agent > C1509 - Neuroprotective Agent A - Alimentary tract and metabolism > A11 - Vitamins COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS D-chiro-Inositol is an epimer of myo-inositol found in certain mammalian glycosylphosphatidylinositol protein anchors and inositol phosphoglycans possessing insulin-like bioactivity. D-chiro-Inositol is used clinically for the treatment of polycystic ovary syndrome (PCOS) and diabetes mellitus, which can reduce hyperglycemia and ameliorate insulin resistance[1][2][3]. i-Inositol is a chemical compound related to lipids found in many foods, especially fruits such as cantaloupe and oranges. i-Inositol is a chemical compound related to lipids found in many foods, especially fruits such as cantaloupe and oranges. Scyllo-Inositol, an amyloid inhibitor, potentialy inhibits α-synuclein aggregation. Scyllo-Inositol stabilizes a non-fibrillar non-toxic form of amyloid-β peptide (Aβ42) in vitro, reverses cognitive deficits, and reduces synaptic toxicity and lowers amyloid plaques in an Alzheimer's disease mouse model[1]. Scyllo-Inositol, an amyloid inhibitor, potentialy inhibits α-synuclein aggregation. Scyllo-Inositol stabilizes a non-fibrillar non-toxic form of amyloid-β peptide (Aβ42) in vitro, reverses cognitive deficits, and reduces synaptic toxicity and lowers amyloid plaques in an Alzheimer's disease mouse model[1].

epi-Inositol

C6H12O6 (180.0633852)

epi-Inositol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. In humans, most inositol is synthesized in the kidneys, typically in amounts of a few grams per day.

allo-Inositol

C6H12O6 (180.0633852)

allo-Inositol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol.

(+)-Epibatidine

C11H13ClN2 (208.0767208)

D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics

Arenobufagin

C24H32O6 (416.2198772)

BATRACHOTOXIN

C31H42N2O6 (538.3042712)

bufalin

C24H34O4 (386.24569640000004)

Bufogenin

C24H32O4 (384.2300472)

D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides D002317 - Cardiovascular Agents

Bufotalin

C26H36O6 (444.2511756)

Cinobufagin

C26H34O6 (442.2355264)

Cinobufotalin

C26H34O7 (458.2304414)

Cinobufotalin is a cardiotonic steroids or bufadienolides, is extracted from the skin secretions of the giant toads. Cinobufotalin has been used as a cardiotonic, diuretic and a hemostatic agent, Cinobufotalin is also a potential anti-lung cancer agent[1].

Gamabufotalin

C24H34O5 (402.24061140000003)

Marinobufagenin

C24H32O5 (400.2249622)

Telocinobufagin

C24H34O5 (402.24061140000003)

Uridine

C9H12N2O6 (244.0695332)

C26170 - Protective Agent > C2459 - Chemoprotective Agent > C2080 - Cytoprotective Agent COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

creatine

C4H9N3O2 (131.06947340000002)

Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

Serotonin

C10H12N2O (176.09495819999998)

D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists

Citric Acid

C6H8O7 (192.0270018)

A - Alimentary tract and metabolism > A09 - Digestives, incl. enzymes > A09A - Digestives, incl. enzymes > A09AB - Acid preparations D064449 - Sequestering Agents > D002614 - Chelating Agents > D065096 - Calcium Chelating Agents D006401 - Hematologic Agents > D000925 - Anticoagulants C26170 - Protective Agent > C275 - Antioxidant COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3]. Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3].

Phenylalanine

C9H11NO2 (165.0789746)

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

sitosterol

C29H50O (414.386145)

A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

N-Methylserotonin

C11H14N2O (190.1106074)

A member of the class of tryptamines that is serotonin in which one of the hydrogens attached to the primary amino group is replaced by a methyl group. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053

Stigmasterol

C29H48O (412.37049579999996)

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.

Gephyrotoxin

C19H29NO (287.2249024)

Cholesterol

C27H46O (386.3548466)

A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group. 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. Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

Adenosine

C10H13N5O4 (267.09674980000005)

COVID info from PDB, Protein Data Bank, COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058913 - Purinergic Agonists D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents C - Cardiovascular system > C01 - Cardiac therapy Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Formula(Parent): C10H13N5O4; Bottle Name:Adenosine; PRIME Parent Name:Adenosine; PRIME in-house No.:0040 R0018, Purines MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OIRDTQYFTABQOQ_STSL_0143_Adenosine_0500fmol_180430_S2_LC02_MS02_33; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.113 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.109 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.097 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.096 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2621; CONFIDENCE confident structure Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2].

Phenylalanine

C9H11NO2 (165.0789746)

An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group. Annotation level-2 Acquisition and generation of the data is financially supported by the Max-Planck-Society COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS IPB_RECORD: 2701; CONFIDENCE confident structure L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

Sorbitol

C6H14O6 (182.0790344)

A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AD - Osmotically acting laxatives A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AG - Enemas B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CC - Tests for bile duct patency D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D005765 - Gastrointestinal Agents > D002400 - Cathartics CONFIDENCE standard compound; INTERNAL_ID 229 Acquisition and generation of the data is financially supported by the Max-Planck-Society D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1]. D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1].

Brassicasterol

C28H46O (398.3548466)

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].

Campesterol

C28H48O (400.37049579999996)

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. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Resibufogenin

C24H32O4 (384.2300472)

Annotation level-1 Resibufogenin is a component of cinobufogenin and has the function of inhibiting oxidative stress and tumor regeneration. Resibufogenin is a component of cinobufogenin and has the function of inhibiting oxidative stress and tumor regeneration.

Epinephrine

C9H13NO3 (183.0895388)

R - Respiratory system > R01 - Nasal preparations > R01A - Decongestants and other nasal preparations for topical use > R01AA - Sympathomimetics, plain R - Respiratory system > R03 - Drugs for obstructive airway diseases > R03A - Adrenergics, inhalants > R03AA - Alpha- and beta-adrenoreceptor agonists C - Cardiovascular system > C01 - Cardiac therapy > C01C - Cardiac stimulants excl. cardiac glycosides > C01CA - Adrenergic and dopaminergic agents S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EA - Sympathomimetics in glaucoma therapy B - Blood and blood forming organs > B02 - Antihemorrhagics > B02B - Vitamin k and other hemostatics > B02BC - Local hemostatics A - Alimentary tract and metabolism > A01 - Stomatological preparations > A01A - Stomatological preparations D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D000322 - Adrenergic Agonists C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics C78274 - Agent Affecting Cardiovascular System > C126567 - Vasopressor D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.050

Aspartic Acid

C4H7NO4 (133.0375062)

An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent COVID info from COVID-19 Disease Map, PDB, Protein Data Bank, clinicaltrial, clinicaltrials, clinical trial, clinical trials D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.051 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.050 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly. L-Aspartic acid is is an amino acid, shown to be a suitable proagent for colon-specific agent deliverly.

Serotonin

C10H12N2O (176.09495819999998)

D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists A primary amino compound that is the 5-hydroxy derivative of tryptamine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QZAYGJVTTNCVMB_STSL_0135_Serotonin_8000fmol_180506_S2_LC02_MS02_147; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053

Uridine

C9H12N2O6 (244.0695332)

C26170 - Protective Agent > C2459 - Chemoprotective Agent > C2080 - Cytoprotective Agent COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; DRTQHJPVMGBUCF_STSL_0179_Uridine_8000fmol_180506_S2_LC02_MS02_83; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.088 Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

L-Isoleucine

C6H13NO2 (131.0946238)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; AGPKZVBTJJNPAG-WHFBIAKZSA-N_STSL_0101_Isoleucine_8000fmol_180425_S2_LC02_MS02_58; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. CONFIDENCE standard compound; INTERNAL_ID 8 COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid. L-isoleucine is a nonpolar hydrophobic amino acid[1]. L-Isoleucine is an essential amino acid.

L-Methionine

C5H11NO2S (149.0510466)

The L-enantiomer of methionine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; FFEARJCKVFRZRR-BYPYZUCNSA-N_STSL_0047_Methionine_8000fmol_180416_S2_LC02_MS02_69; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant. L-Methionine is the L-isomer of Methionine, an essential amino acid for human development. Methionine acts as a hepatoprotectant.

L-alanine

C3H7NO2 (89.0476762)

The L-enantiomer of alanine. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

L-proline

C5H9NO2 (115.0633254)

A human metabolite taken as a putative food compound of mammalian origin [HMDB] MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ONIBWKKTOPOVIA_STSL_0035_Proline_2000fmol_180506_S2_LC02_MS02_282; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins.

creatine

C4H9N3O2 (131.06947340000002)

A glycine derivative having methyl and amidino groups attached to the nitrogen. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; CVSVTCORWBXHQV-UHFFFAOYSA-N_STSL_0071_Creatine_8000fmol_180416_S2_LC02_MS02_77; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

L-Lysine

C6H14N2O2 (146.1055224)

An L-alpha-amino acid; the L-isomer of lysine. 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].

Sucrose

C12H22O11 (342.11620619999997)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Cellobiose

C12H22O11 (342.11620619999997)

A glycosylglucose consisting of two glucose units linked via a beta(1->4) bond. D-(+)-Cellobiose is an endogenous metabolite. D-(+)-Cellobiose is an endogenous metabolite.

L-Leucine

C6H13NO2 (131.0946238)

Flavouring ingredient; dietary supplement, nutrient. L-Leucine is found in many foods, some of which are lettuce, common bean, pacific herring, and kefir. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ROHFNLRQFUQHCH-YFKPBYRVSA-N_STSL_0102_Leucine_8000fmol_180425_S2_LC02_MS02_19; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1]. L-Leucine is an essential branched-chain amino acid (BCAA), which activates the mTOR signaling pathway[1].

L-Phenylalanine

C9H11NO2 (165.0789746)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; COLNVLDHVKWLRT_STSL_0103_Phenylalanine_2000fmol_180506_S2_LC02_MS02_290; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

L-Tyrosine

C9H11NO3 (181.0738896)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OUYCCCASQSFEME-QMMMGPOBSA-N_STSL_0110_L-Tyrosine_0500fmol_180506_S2_LC02_MS02_57; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

putrescine

C4H12N2 (88.1000432)

L-glutamic acid

C5H9NO4 (147.0531554)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; WHUUTDBJXJRKMK-VKHMYHEASA-N_STSL_0113_Glutamic acid_8000fmol_180425_S2_LC02_MS02_66; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals. L-Glutamic acid is an excitatory amino acid neurotransmitter that acts as an agonist for all subtypes of glutamate receptors (metabolic rhodophylline, NMDA, and AMPA). L-Glutamic acid has an agonist effect on the release of DA from dopaminergic nerve endings. L-Glutamic acid can be used in the study of neurological diseases[1][2][3][4][5]. L-Glutamic acid acts as an excitatory transmitter and an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA). L-Glutamic acid shows a direct activating effect on the release of DA from dopaminergic terminals.

Citric Acid

C6H8O7 (192.0270018)

Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3]. Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3].

Benzoic Acid

C7H6O2 (122.0367776)

Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi. Benzoic acid is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products. It acts as preservatives through inhibiting both bacteria and fungi.

Bufotenine

C12H16N2O (204.12625659999998)

Fumaric Acid

C4H4O4 (116.01095839999999)

Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

Turanose

C12H22O11 (342.11620619999997)

A glycosylfructose isolated from Daphnia magna. Turanose is an isomer of Sucrose that naturally exists in honey. Turanose has anti-inflammatory and regulates adipogenesis effect. Turanose has potential for obesity and related chronic diseases research[1][2]. Turanose is an isomer of Sucrose that naturally exists in honey. Turanose has anti-inflammatory and regulates adipogenesis effect. Turanose has potential for obesity and related chronic diseases research[1][2].

4-Aminobutanoic acid

C4H9NO2 (103.0633254)

scyllo-Inositol

C6H12O6 (180.0633852)

Scyllo-Inositol, an amyloid inhibitor, potentialy inhibits α-synuclein aggregation. Scyllo-Inositol stabilizes a non-fibrillar non-toxic form of amyloid-β peptide (Aβ42) in vitro, reverses cognitive deficits, and reduces synaptic toxicity and lowers amyloid plaques in an Alzheimer's disease mouse model[1]. Scyllo-Inositol, an amyloid inhibitor, potentialy inhibits α-synuclein aggregation. Scyllo-Inositol stabilizes a non-fibrillar non-toxic form of amyloid-β peptide (Aβ42) in vitro, reverses cognitive deficits, and reduces synaptic toxicity and lowers amyloid plaques in an Alzheimer's disease mouse model[1].

Oxoglutarate

C5H6O5 (146.0215226)

Homobatrachotoxin

C32H44N2O6 (552.3199204)

D009676 - Noxae > D011042 - Poisons > D014688 - Venoms

(2R,6R,7S,8S)-7-(but-3-en-1-yl)-2-(pent-4-en-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H33NO (291.25620080000004)

Tunaxanthin I/ Chiriquixanthin A

C40H56O2 (568.4280076)

Docosane

C22H46 (310.3599316)

Docosane, a straight chain alkane, can be used to synthesize structural composites with thermal energy storage/release capability[1][2]. Docosane, a straight chain alkane, can be used to synthesize structural composites with thermal energy storage/release capability[1][2].

OCTACOSANE

C28H58 (394.4538268)

A straight-chain alkane containing 28 carbon atoms.

2,5-Diaminopentanoic acid

C5H12N2O2 (132.0898732)

Pentadecane

C15H32 (212.2503872)

A straight-chain alkane with 15 carbon atoms. It is a component of volatile oils isolated from plants species like Scandix balansae.

NONADECANE

C19H40 (268.31298400000003)

A straight-chain alkane with 19 carbon atoms. It has been found as a component of essential oils isolated from Artemisia armeniaca.

2-hydroxypropane-1,2,3-tricarboxylic acid

C6H8O7 (192.0270018)

D-Sorbitol

C6H14O6 (182.0790344)

D-(1-(13)C)glucitol

C6H14O6 (182.0790344)

2-aminopentanedioic acid

C5H9NO4 (147.0531554)

Pirod

C4H4N2O2 (112.02727639999999)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.

(2s)-2-[(8-{[(1r,2s,4r,5r,6r,7r,10s,11r,14s,16s)-5-(acetyloxy)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C40H58N4O11 (770.4101878)

(3s)-3-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C56H75N15O19S (1293.5084120000001)

3-[(1-{[1-({[(1-{[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-3-(methylsulfanyl)propyl}-c-hydroxycarbonimidoyl)-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}-2-hydroxyethyl)-c-hydroxycarbonimidoyl]methyl}-c-hydroxycarbonimidoyl)-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl)-c-hydroxycarbonimidoyl]-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C56H75N15O23S2 (1389.4601440000001)

5-methyl-3-(non-8-yn-1-yl)-octahydro-1h-pyrrolo[1,2-a]azepine

C19H33N (275.26128580000005)

(4s)-4-{[(1s)-5-amino-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}pentyl]-c-hydroxycarbonimidoyl}-4-{[(2s)-2-{[(2s,3s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-6-amino-2-{[(2s)-2-{[(2s,3s)-2-{[(2s)-2-[(2-{[(2s)-2-{[(2s)-2-[(2-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-4-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-methylbutanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxypropylidene]amino}butanoic acid

C124H206N32O28 (2591.5678556000003)

(2s)-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-n-[(1s)-1-{[(1s)-1-{[(1s)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-methylpropyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]pentanediimidic acid

C51H68N14O11S (1084.4912458000001)

(3r,5r,9ar)-5-methyl-3-(non-8-en-1-yl)-octahydro-1h-pyrrolo[1,2-a]azepine

C19H35N (277.27693500000004)

2-[(8-{[5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C40H58N4O10 (754.4152728)

(2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9as,9bs,10r,11ar)-3a,10-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C38H58N4O9 (714.4203578)

5-{3a,5a,7,10-tetrahydroxy-9a,11a-dimethyl-11-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}pyran-2-one

C24H32O7 (432.2147922)

5-[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a,7-dihydroxy-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H34O5 (402.24061140000003)

(2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid

C40H55N3O10 (737.388725)

n-[(1r,9ar)-octahydro-1h-quinolizin-1-yl]ethanimidic acid

C11H20N2O (196.157555)

4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-({2,3,6-trihydroxy-5-[(1-hydroxyethylidene)amino]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexyl}oxy)-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C25H44N2O19 (676.2538154)

(2s)-2-{[(2s)-2-({[(2r)-1-[(2s)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-4-methylpentanimidic acid

C31H40N6O4 (560.311088)

7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(6-oxopyran-3-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid

C24H30O7 (430.199143)

8-(8-hydroxy-8-methyl-hexahydroindolizin-6-ylidene)-4,7-dimethyloct-4-ene-2,3-diol

C19H33NO3 (323.2460308000001)

(2s)-2-{[(2s)-1-hydroxy-2-{[hydroxy((2s)-pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene]amino}-4-methylpentanimidic acid

C22H31N5O3 (413.2426776)

(2r,4s,5r,6r)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-{[(2r,3s,4s,5s)-2,3,6-trihydroxy-4-{[(2r,3r,4s,5s,6r)-5-hydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-[(1-hydroxyethylidene)amino]hexyl]oxy}-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

C37H64N2O28 (984.3645424)

(2r,4s,5r,6r)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-{[(2r,3s,4s,5s)-2,3,6-trihydroxy-5-[(1-hydroxyethylidene)amino]-4-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexyl]oxy}-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

C25H44N2O19 (676.2538154)

(3s)-3-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C62H73N13O21S (1367.4764448)

5-[(1r,3as,3br,5as,7s,9ar,9bs,10r,11ar)-3a,5a,7,10-tetrahydroxy-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H34O6 (418.2355264)

2-[(8-{[2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid

C41H57N3O10 (751.4043742)

5-(hept-6-en-1-yl)-8-methyl-octahydroindolizine

C16H29N (235.2299874)

5-[(1s,4r,6r,7r,10s,14s,16s,19s)-10,14,16-trihydroxy-2-methoxy-6-methyl-3-oxapentacyclo[9.7.1.0¹,¹⁴.0⁴,¹⁹.0⁶,¹⁰]nonadecan-7-yl]pyran-2-one

C25H34O7 (446.2304414)

(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}propanoic acid

C40H72N10O15 (932.5178362)

6,8-diethyl-5-pentyl-octahydroindolizine

C17H33N (251.2612858)

(2s)-2-[(4-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]-5-carbamimidamidopentanoic acid

C36H50N4O10 (698.3526760000001)

(2s)-n-[(1s)-4-carbamimidamido-1-{[(1s)-1-{[(1s,2s)-1-[({[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-methylbutyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}butyl]-2-({hydroxy[(2s)-1-[(2s)-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-3-(c-hydroxycarbonimidoyl)propanoyl]pyrrolidin-2-yl]methylidene}amino)butanediimidic acid

C52H82N16O13S (1170.5967682)

2-[(4-{[2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]-5-carbamimidamidopentanoic acid

C36H52N4O10 (700.3683252000001)

2-{[(1-{2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoyl}pyrrolidin-2-yl)(hydroxy)methylidene]amino}-n-[1-(c-hydroxycarbonimidoyl)-2-(4-hydroxyphenyl)ethyl]-3-(1h-indol-3-yl)propanimidic acid

C40H49N7O6 (723.3744134000001)

2-(6-ethyl-5-pentyl-octahydroindolizin-8-yl)ethanol

C17H33NO (267.2562008)

2-[(9-{[5-(acetyloxy)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-9-oxononylidene)amino]-5-carbamimidamidopentanoic acid

C41H60N4O11 (784.425837)

(3s)-3-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-[({[(1s)-1-{[(1s)-1-[({[(1s,2r)-2-hydroxy-1-{[(1s)-1-[({[(1s)-1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl]-c-hydroxycarbonimidoyl}propyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]propanoic acid

C52H93N13O15 (1139.6913748000002)

(3s)-3-[(2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-3-{[(1s,2s)-1-{[(1s)-1-[({[(1s)-1-{[(1s)-1-[({[(1s)-1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}propanoic acid

C48H86N12O13 (1038.6436985999999)

4-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-4-oxobutanoic acid

C28H36O8 (500.2410056)

n-[3-({6-[({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)methyl]-4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-1,4,5,6-tetrahydroxyhexan-2-yl]ethanimidic acid

C40H70N2O29 (1042.4064050000002)

4-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-4-oxobutanoic acid

C30H38O9 (542.2515698)

(2s,6r,7s,8s)-7-[(1e)-buta-1,3-dien-1-yl]-2-(penta-3,4-dien-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H29NO (287.2249024)

2-[({1-[2-({2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-3-(3h-imidazol-4-yl)propanoyl]pyrrolidin-2-yl}(hydroxy)methylidene)amino]-4-(methylsulfanyl)butanoic acid

C30H43N7O6S (629.2995378)

2-{[2-({2-[(2-{[2-({2-[(2-{[2-({2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1,3-dihydroxypropylidene}amino)-1-hydroxy-3-methylbutylidene]amino}propanoic acid

C41H74N10O13 (914.5436554)

epicholestrol

C27H46O (386.3548466)

(2s)-2-[(2-{[(2s)-2-{[(2s,3s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-4-methylpentanoic acid

C41H73N9O12 (883.5378417999999)

(4s)-4-{[(2s)-2-{[(2r)-2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-4-[(1-{[(1s)-1-[(c-hydroxycarbonimidoylmethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl)-c-hydroxycarbonimidoyl]butanoic acid

C38H54N8O10 (782.3962704)

5-[(1s,2s,4r,6r,7r,10s,11r,14s,16s,19s)-10,14,16-trihydroxy-2-methoxy-6-methyl-3-oxapentacyclo[9.7.1.0¹,¹⁴.0⁴,¹⁹.0⁶,¹⁰]nonadecan-7-yl]pyran-2-one

C25H34O7 (446.2304414)

2-[(1-hydroxy-8-{[16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-8-oxooctylidene)amino]-4-(c-hydroxycarbonimidoyl)butanoic acid

C37H52N2O10 (684.3621772)

(1r,2r,3as,3br,5ar,7s,9as,9bs,11ar)-3a,7-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate

C26H36O6 (444.2511756)

(2r,6s,7s,8r)-7-[(1e)-but-1-en-3-yn-1-yl]-2-[(2e)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol

C19H25NO (283.193604)

3-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-{[1-({1-[(1-carboxyethyl)-c-hydroxycarbonimidoyl]-2-phenylethyl}-c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}propanoic acid

C30H39N5O8 (597.2798494)

2-[(8-{[3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid

C38H53N3O9 (695.3781608)

(6z,8s)-6-[(4e,6s)-6-hydroxy-2,5-dimethyloct-4-en-1-ylidene]-8-methyl-hexahydroindolizin-8-ol

C19H33NO2 (307.25111580000004)

(2s)-5-hydroxy-n-[(2s)-1-[(2s)-2-{[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-3,4-dihydro-2h-pyrrole-2-carboximidic acid

C39H43N7O6 (705.3274658)

(1r,2s,4r,6r,7r,10s,11s,14s,16s)-14,16-dihydroxy-7-methyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-11-carbaldehyde

C24H30O6 (414.204228)

5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O5 (400.2249622)

5-[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O4 (384.2300472)

4-{[5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-4-oxobutanoic acid

C30H38O9 (542.2515698)

2-[(5r,6r,8r,8ar)-6-ethyl-5-pentyl-octahydroindolizin-8-yl]ethanol

C17H33NO (267.2562008)

(4'r,6r,6's,7s,8r,8as)-6'-[(2r)-2-hydroxypentan-2-yl]-4',8-dimethyl-hexahydrospiro[indolizine-6,2'-oxane]-7,8-diol

C19H35NO4 (341.25659500000006)

(2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

C11H13ClN2 (208.0767208)

2-{[2-({[1-(2-amino-3-phenylpropanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-4-methylpentanimidic acid

C31H40N6O4 (560.311088)

3-{[1-({1-[({[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-3-(methylsulfanyl)propyl}-c-hydroxycarbonimidoyl)-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl}-c-hydroxycarbonimidoyl)-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C58H73N13O21S2 (1351.4485168)

{3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid

C12H16N2O4S (284.0830736)

(2s)-n-[(2s,3s)-1-[(2r)-2-{[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1s)-4-carbamimidamido-1-(c-hydroxycarbonimidoyl)butyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]-5-hydroxy-3,4-dihydro-2h-pyrrole-2-carboximidic acid

C48H64N14O8 (964.5031304)

7-(but-3-en-1-yl)-2-(pent-4-en-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H33NO (291.25620080000004)

(1r,3as,3bs,7s,9bs)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C28H48O (400.37049579999996)

5-{9,14,16-trihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl}pyran-2-one

C24H32O6 (416.2198772)

(4s)-4-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-4-{[(1s)-1-{[(1s)-1-{[(1s)-1-carboxyethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}butanoic acid

C32H43N5O8 (625.3111478000001)

2-{[(1-{2-[(2-amino-1-hydroxy-4-methylpentylidene)amino]-3-(1h-indol-3-yl)propanoyl}pyrrolidin-2-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid

C31H39N5O5 (561.2951044)

1-{9,12-dihydroxy-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.1⁵,⁹.0¹,¹⁴.0²,¹¹.0⁶,¹¹]tricosa-2,21-dien-22-yl}ethyl 2-ethyl-4-methyl-1h-pyrrole-3-carboxylate

C32H44N2O6 (552.3199204)

8-methyl-5-(pent-4-en-1-yl)-octahydroindolizine

C14H25N (207.198689)

(2s,6r,7s,8r)-7-[(1e)-buta-1,3-dien-1-yl]-2-[(2z)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol

C19H27NO (285.2092532)

(2s)-2-[(4-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]-5-carbamimidamidopentanoic acid

C36H52N4O10 (700.3683252000001)

(2s)-2-{[(2s)-2-({[(2r)-1-[(2s,3s)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-4-methylpentanimidic acid

C28H42N6O4 (526.3267372)

3-[(1-{[1-({[(1-{[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-2-phenylethyl}-c-hydroxycarbonimidoyl)-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}-2-hydroxyethyl)-c-hydroxycarbonimidoyl]methyl}-c-hydroxycarbonimidoyl)-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl)-c-hydroxycarbonimidoyl]-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C60H75N15O23S (1405.488072)

(2s,6r,7s,8r)-7-[(1z)-but-1-en-3-yn-1-yl]-2-[(2z)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol

C19H25NO (283.193604)

(2s)-2-({[(2r)-1-[(2s)-2-amino-4-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-n-[(1s)-1-(c-hydroxycarbonimidoyl)-2-(4-hydroxyphenyl)ethyl]-3-(1h-indol-3-yl)propanimidic acid

C31H40N6O5 (576.306003)

(4s)-4-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-4-{[(1s)-1-{[(1s)-1-[(c-hydroxycarbonimidoylmethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}butanoic acid

C38H54N8O10 (782.3962704)

2-[(8-{[(1r,2s,3as,5ar,7s,9as,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(2-oxopyran-4-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C40H60N4O10 (756.430922)

(3s)-3-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}-2-hydroxyethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C60H75N15O23S (1405.488072)

(2r)-1-[(2s)-2-amino-3-phenylpropanoyl]-n-[(2s)-1-[(2s)-2-{[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboximidic acid

C45H56N8O6 (804.4322596)

7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

C29H38O7 (498.2617398)

(2r,3r,4e,7r)-8-[(6z,8s,8as)-8-hydroxy-8-methyl-hexahydroindolizin-6-ylidene]-4,7-dimethyloct-4-ene-2,3-diol

C19H33NO3 (323.2460308000001)

3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde

C24H32O6 (416.2198772)

5-[(1r,2s,4r,6r,7r,9r,10s,11r,14s,16s)-9,14,16-trihydroxy-11-(hydroxymethyl)-7-methyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O7 (432.2147922)

(2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid

C41H57N3O10 (751.4043742)

(2s)-2-[(6-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-6-oxohexylidene)amino]-5-carbamimidamidopentanoic acid

C38H54N4O10 (726.3839744)

(2s)-2-[(6-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16s)-5-(acetyloxy)-11-formyl-16-hydroxy-7-methyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-6-oxohexylidene)amino]-5-carbamimidamidopentanoic acid

C38H52N4O12 (756.3581552)

(1r,2s,4r,5r,6s,7r,10s,11s,14s,16r)-14-hydroxy-7,11-dimethyl-6-[(2z)-1-oxobut-2-en-2-yl]-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-5-yl acetate

C25H36O5 (416.2562606)

5-[9,14,16-trihydroxy-11-(hydroxymethyl)-7-methyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O7 (432.2147922)

(1r,5r,6s,9r,11s,12r,14r)-22-[(1s)-1-hydroxyethyl]-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.1⁵,⁹.0¹,¹⁴.0²,¹¹.0⁶,¹¹]tricosa-2,21-diene-9,12-diol

C24H35NO5 (417.25151000000005)

4-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-4-oxobutanoic acid

C28H36O7 (484.2460906)

5-hydroxy-n-(1-{2-[(1-{[1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl)-c-hydroxycarbonimidoyl]pyrrolidin-1-yl}-1-oxo-3-phenylpropan-2-yl)-3,4-dihydro-2h-pyrrole-2-carboximidic acid

C36H45N7O6 (671.3431149999999)

(2s,4as,5r,8ar)-5-methyl-2-propyl-decahydroquinoline

C13H25N (195.198689)

(1s,2r,5r,7s,10s,11s,14r,15r,20s)-16-ethenyl-7-hydroxy-10,14-dimethyl-18-oxapentacyclo[13.3.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]icos-16-en-20-yl acetate

C25H36O4 (400.2613456)

5-{5,14,16-trihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl}pyran-2-one

C24H32O6 (416.2198772)

(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

C31H40O9 (556.2672190000001)

(2s)-1-[(2r,3s)-2-({[(2r)-1-[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-5-[(diaminomethyl)amino]-1-hydroxypentylidene]amino}-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-(1h-indol-3-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-methylpentanoyl]-5-oxopyrrolidine-2-carboxylic acid

C48H65N13O9 (967.5027960000001)

(2s)-2-{[(2r)-2-({[(2r)-1-[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-3-(1h-indol-3-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-3-phenylpropanoic acid

C40H48N6O7 (724.3584298000001)

(2s)-1-[(2s)-2-({[(2r)-1-[(2s)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-(1h-indol-3-yl)propanoyl]pyrrolidine-2-carboximidic acid

C30H36N6O4 (544.2797896)

(2s,6r,7s,8s)-7-[(1z)-but-1-en-3-yn-1-yl]-2-(prop-2-en-1-yl)-1-azaspiro[5.5]undecan-8-ol

C17H25NO (259.193604)

n-(6-{[4-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1,4,5-trihydroxyhexan-2-yl)ethanimidic acid

C42H73N3O29 (1083.4329528)

(2s,6r,7s,8s)-7-[(1z)-but-1-en-3-yn-1-yl]-2-(penta-3,4-dien-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H27NO (285.2092532)

methyl 4-[(3br,5ar,7s,9as,9bs,11as)-7-hydroxy-9a,11a-dimethyl-3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-4-oxobutanoate

C24H34O4 (386.24569640000004)

n-(octahydro-1h-quinolizin-1-yl)ethanimidic acid

C11H20N2O (196.157555)

5-{10,14,16-trihydroxy-2-methoxy-6-methyl-3-oxapentacyclo[9.7.1.0¹,¹⁴.0⁴,¹⁹.0⁶,¹⁰]nonadecan-7-yl}pyran-2-one

C25H34O7 (446.2304414)

(2s,3s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-3-methylbutanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-n-[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl]-3-methylpentanimidic acid

C39H57N7O7S (767.4039972)

5-carbamimidamido-2-[(4-{[7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]pentanoic acid

C34H48N4O8 (640.3471968)

(1r,2s,4r,5s,6r,7r,10s,11s,14s,16r)-14-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-5-yl acetate

C26H34O6 (442.2355264)

(1r,5s,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1015602)

2-[(8-{[2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid

C40H55N3O10 (737.388725)

(2s)-2-{[(2s,3s)-2-{[(2s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-{[2-({[(2s)-1-[(2s)-1-[(2s)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-hydroxypropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

C65H93N17O14 (1335.7087557999998)

(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

C29H38O7 (498.2617398)

6'-(2-hydroxypentan-2-yl)-4',8-dimethyl-hexahydrospiro[indolizine-6,2'-oxane]-7,8-diol

C19H35NO4 (341.25659500000006)

(2s,6r,7s,8s)-7-(buta-1,3-dien-1-yl)-2-(penta-3,4-dien-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H29NO (287.2249024)

7-(but-1-en-3-yn-1-yl)-2-(penta-3,4-dien-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H27NO (285.2092532)

(1r,2s,4r)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

C11H13ClN2 (208.0767208)

2-[(8-{[3a,5a-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-4-(c-hydroxycarbonimidoyl)butanoic acid

C37H54N2O10 (686.3778264)

(5s,6r,8r,8as)-6,8-diethyl-5-pentyl-octahydroindolizine

C17H33N (251.2612858)

4-[(2-amino-1-hydroxy-3-methylpentylidene)amino]-4-{[1-({1-[(1-carboxyethyl)-c-hydroxycarbonimidoyl]-2-phenylethyl}-c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}butanoic acid

C32H43N5O8 (625.3111478000001)

2-[(8-{[2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(3-methylimidazol-4-yl)propanoic acid

C41H57N3O10 (751.4043742)

(3s)-3-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}-2-hydroxyethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C56H75N15O23S2 (1389.4601440000001)

(2s)-1-[(2s)-2-({[(2r)-1-[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-phenylpropanoyl]-5-oxopyrrolidine-2-carboxylic acid

C36H44N6O7 (672.3271314000001)

3-{[2-({2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-3-[({[1-({1-[({[2-hydroxy-1-({1-[({[1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)propyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]propanoic acid

C52H93N13O15 (1139.6913748000002)

(8r)-7-(but-3-en-1-yl)-2-(pent-4-en-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H33NO (291.25620080000004)

3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]propanoic acid

C9H17NO5 (219.11066720000002)

2-[(8-{[3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid

C39H55N3O9 (709.39381)

(2r,4s,5r,6r)-2-{[(2r,3s,4s,5s)-4-{[(2r,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,3,6-trihydroxy-5-[(1-hydroxyethylidene)amino]hexyl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

C31H54N2O23 (822.3117214)

5-[(1r,2s,4r,6r,7r,10s,11s,14r,16r)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O4 (384.2300472)

(2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid

C38H53N3O9 (695.3781608)

(2s)-5-carbamimidamido-2-[(4-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]pentanoic acid

C34H48N4O8 (640.3471968)

2-[(4-{[3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]-5-carbamimidamidopentanoic acid

C34H50N4O8 (642.3628460000001)

4-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-4-{[1-({1-[(1-carboxy-2-hydroxypropyl)-c-hydroxycarbonimidoyl]-2-phenylethyl}-c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}butanoic acid

C32H43N5O9 (641.3060628000001)

(3s,5r,9ar)-5-methyl-3-(non-8-yn-1-yl)-octahydro-1h-pyrrolo[1,2-a]azepine

C19H33N (275.26128580000005)

4-[(1r)-1-hydroxy-2-[c-hydroxycarbonimidoyl(methyl)amino]ethyl]phenol

C10H14N2O3 (210.1004374)

(3s)-3-{[(2s)-2-{[(2r)-2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-{[(1s)-1-{[(1s)-1-[(c-hydroxycarbonimidoylmethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}propanoic acid

C37H52N8O10 (768.3806212000001)

3-[(1-{[1-({[(1-{[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-3-(methylsulfanyl)propyl}-c-hydroxycarbonimidoyl)-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]methyl}-c-hydroxycarbonimidoyl)-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl)-c-hydroxycarbonimidoyl]-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C56H75N15O22S2 (1373.4652290000001)

(3s)-3-{[(1s)-1-[({[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C60H76N14O22S2 (1408.4699796)

3-{[2-(5-hydroxy-1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid

C14H16N2O4 (276.1110016)

2-[(8-{[2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C40H60N4O10 (756.430922)

2-{[2-({[1-(2-{[2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-3-(1h-indol-3-yl)propanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-3-phenylpropanoic acid

C40H48N6O7 (724.3584298000001)

2-({[1-(2-amino-4-methylpentanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-n-[1-(c-hydroxycarbonimidoyl)-2-(4-hydroxyphenyl)ethyl]-3-(1h-indol-3-yl)propanimidic acid

C31H40N6O5 (576.306003)

(2s)-2-({[(2r)-1-[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-3-(1h-indol-3-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-phenylpropanoic acid

C31H39N5O5 (561.2951044)

4-{[5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-4-oxobutanoic acid

C28H36O8 (500.2410056)

5-butyl-6,8-diethyl-octahydroindolizine

C16H31N (237.24563659999998)

3-[(1-{[1-({[(1-{[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-3-(methylsulfanyl)propyl}-c-hydroxycarbonimidoyl)-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]methyl}-c-hydroxycarbonimidoyl)-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl)-c-hydroxycarbonimidoyl]-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C56H75N15O19S (1293.5084120000001)

1-[2-({[1-(2-amino-3-phenylpropanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-(1h-indol-3-yl)propanoyl]pyrrolidine-2-carboxylic acid

C30H35N5O5 (545.263806)

2-[(8-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C38H56N4O10 (728.3996236)

(2s,6r,7s,8s)-7-[(1e)-buta-1,3-dien-1-yl]-2-[(2e)-penta-2,4-dien-1-yl]-1-azaspiro[5.5]undecan-8-ol

C19H29NO (287.2249024)

2-[(4-{[5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]-5-carbamimidamidopentanoic acid

C36H50N4O10 (698.3526760000001)

1-(2-amino-3-phenylpropanoyl)-n-(1-{2-[(1-{[1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl)-c-hydroxycarbonimidoyl]pyrrolidin-1-yl}-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboximidic acid

C45H56N8O6 (804.4322596)

(4s)-4-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-4-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)butanoic acid

C54H67N11O19S2 (1237.4055912000001)

(2s)-2-{[(2s)-6-amino-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxyhexylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid

C53H93N15O15 (1179.6975228000001)

(2s)-5-carbamimidamido-2-[(8-{[(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]pentanoic acid

C38H56N4O8 (696.4097936000001)

(4s)-4-{[(2s)-2-{[(2s,3s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-{[(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-6-amino-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-4-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-methylbutanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxypropylidene]amino}-4-{[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C121H203N33O29 (2582.5423708)

(1s,2r,3r,3'ar,5'ar,7's,9'as,9'bs)-7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(6-oxopyran-3-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid

C24H30O7 (430.199143)

2-[(6-{[5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-6-oxohexylidene)amino]-5-carbamimidamidopentanoic acid

C38H54N4O10 (726.3839744)

(1r,3as,3br,5as,7s,9as,9bs,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde

C24H32O6 (416.2198772)

2-{[(1-{2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-3-methylbutanoyl}pyrrolidin-2-yl)(hydroxy)methylidene]amino}-n-(1-{[1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl)-3-methylpentanimidic acid

C39H57N7O7S (767.4039972)

(1s,2r,5s,7s,10r,11s,14r,15r)-16-ethenyl-10,14-dimethyl-18-oxapentacyclo[13.3.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]icos-16-ene-5,7-diol

C23H34O3 (358.25078140000005)

(1r,2s,4r,5r,6r,7r,10s,11r,14s,16s)-14,16-dihydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-5-yl acetate

C26H34O7 (458.2304414)

(2s)-2-[(7-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-7-oxoheptylidene)amino]-5-carbamimidamidopentanoic acid

C39H56N4O10 (740.3996236)

7-[(1e)-but-1-en-3-yn-1-yl]-2-(prop-2-en-1-yl)-1-azaspiro[5.5]undecan-8-ol

C17H25NO (259.193604)

(1s,2r,3's,5s,6s,9s,11r,14r,15s,17r,19r,21r)-2,3',6-trimethyl-16,18-dioxaspiro[hexacyclo[15.3.1.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁵,¹⁹]henicosane-21,2'-oxiran]-9-ol

C23H34O4 (374.24569640000004)

2-[(5-{[3a,5a-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-5-oxopentylidene)amino]-5-carbamimidamidopentanoic acid

C35H52N4O9 (672.3734102000001)

(6z,8s,8as)-6-[(2r,4z,6r)-6-hydroxy-2,5-dimethyloct-4-en-1-ylidene]-8-methyl-hexahydroindolizin-8-ol

C19H33NO2 (307.25111580000004)

5-{3a,5a,7,10-tetrahydroxy-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}pyran-2-one

C24H34O6 (418.2355264)

(2s)-2-[(8-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C40H58N4O10 (754.4152728)

(4s)-4-{[(2s)-2-amino-1-hydroxy-3-methylbutylidene]amino}-4-{[(1s)-1-{[(1s)-1-{[(1s,2r)-1-carboxy-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}butanoic acid

C32H43N5O9 (641.3060628000001)

(2s)-2-[(9-{[(1r,2s,4r,5r,6r,7r,10s,11r,14s,16s)-5-(acetyloxy)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-9-oxononylidene)amino]-5-carbamimidamidopentanoic acid

C41H60N4O11 (784.425837)

(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-{[(2s)-2-{[(2s)-6-amino-2-{[(2s,3s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-6-amino-2-{[(2s)-6-amino-2-{[(2s)-2-{[(2s,3r)-2-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1,3-dihydroxybutylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-4-(c-hydroxycarbonimidoyl)butylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid

C123H204N36O33 (2713.5390773999998)

n-acetyl-n-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-2-methyl-1h-pyrrole-3-carboxamide

C18H19N3O3 (325.1426344)

2-[(8-{[5-(acetyloxy)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C40H58N4O11 (770.4101878)

4-{1-hydroxy-2-[c-hydroxycarbonimidoyl(methyl)amino]ethyl}phenol

C10H14N2O3 (210.1004374)

6,8-diethyl-5-propyl-octahydroindolizine

C15H29N (223.2299874)

(2r,4s,5r,6r)-2-{[(2r,3s,4s,5s)-4-{[(2r,3r,4s,5s,6r)-4-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,3,6-trihydroxy-5-[(1-hydroxyethylidene)amino]hexyl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

C43H74N2O32 (1130.4224484000001)

2-[(1-hydroxy-2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}-3-(1h-indol-3-yl)propylidene)amino]-4-methylpentanimidic acid

C22H31N5O3 (413.2426776)

(2s,4s,5r,6r)-2-{[(2r,3s,4r,5r,6r)-3-{[(2s,3r,4r,5r,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(hydroxymethyl)-6-{[(2s,3s,4s,5r)-1,4,5,6-tetrahydroxy-2-[(1-hydroxyethylidene)amino]hexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

C33H57N3O24 (879.3331842)

2-({6-amino-2-[(2-{[2-({2-[(2-{[2-({2-[(2-{[2-({2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1,3-dihydroxypropylidene}amino)-1-hydroxy-3-methylbutylidene]amino}-1-hydroxypropylidene)amino]-1-hydroxyhexylidene}amino)-3-(3h-imidazol-4-yl)propanoic acid

C53H93N15O15 (1179.6975228000001)

5-[(1r,2s,4r,5s,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O5 (400.2249622)

(2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C40H60N4O10 (756.430922)

2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-n-{2-hydroxy-1-[(1-{[1-(c-hydroxycarbonimidoyl)-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}-2-methylpropyl)-c-hydroxycarbonimidoyl]propyl}-3-methylpentanimidic acid

C30H46N8O6 (614.3540135999999)

2-{[2-({2-[(2-{[2-({2-[(2-{[2-({2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene)amino]-1,3-dihydroxypropylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene)amino]-1,3-dihydroxypropylidene}amino)-1-hydroxy-3-methylbutylidene]amino}propanoic acid

C40H72N10O15 (932.5178362)

4-[(2-amino-1-hydroxy-3-methylpentylidene)amino]-4-({1-[(1-{[2-hydroxy-1-(c-hydroxycarbonimidoyl)propyl]-c-hydroxycarbonimidoyl}-2-phenylethyl)-c-hydroxycarbonimidoyl]-2-phenylethyl}-c-hydroxycarbonimidoyl)butanoic acid

C33H46N6O8 (654.3376956000001)

2-[(4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-2,3,6-trihydroxy-5-[(1-hydroxyethylidene)amino]hexyl)oxy]-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C31H54N2O23 (822.3117214)

1-[2-({[1-(2-amino-3-phenylpropanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-(1h-indol-3-yl)propanoyl]pyrrolidine-2-carboximidic acid

C30H36N6O4 (544.2797896)

(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(3h-imidazol-4-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-4-(methylsulfanyl)butanoic acid

C30H43N7O6S (629.2995378)

3-{[1-({1-[({[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-3-(methylsulfanyl)propyl}-c-hydroxycarbonimidoyl)-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl}-c-hydroxycarbonimidoyl)-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C58H73N13O18S (1271.4916998)

1-(2-{[(1-{2-[(2-{[2-({2-amino-5-[(diaminomethyl)amino]-1-hydroxypentylidene}amino)-1-hydroxy-3-(3h-imidazol-4-yl)propylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]-3-(1h-indol-3-yl)propanoyl}pyrrolidin-2-yl)(hydroxy)methylidene]amino}-3-methylpentanoyl)-5-oxopyrrolidine-2-carboxylic acid

C48H65N13O9 (967.5027960000001)

(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

C29H38O8 (514.2566548)

2-[(4-{[3a,10-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]-5-carbamimidamidopentanoic acid

C34H50N4O9 (658.3577610000001)

5-[(1r,3as,3br,5as,7s,9ar,9bs,10s,11ar)-3a,5a,7,10-tetrahydroxy-9a,11a-dimethyl-11-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H32O7 (432.2147922)

5-{3a,5a,7,9-tetrahydroxy-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl}pyran-2-one

C24H34O6 (418.2355264)

(2s)-2-{[(2s)-2-{[(2s)-2-[(2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}propanoic acid

C41H74N10O13 (914.5436554)

(1r,5r,6r,7r,9s,11s,13s,14r)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1015602)

(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a,7-dihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthrene-9a-carbaldehyde

C24H32O5 (400.2249622)

(1r,3as,3br,5as,7r,9as,9bs,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde

C24H32O6 (416.2198772)

(3s)-3-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C58H73N13O21S2 (1351.4485168)

7-(but-1-en-3-yn-1-yl)-2-(pent-2-en-4-yn-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H25NO (283.193604)

2-[(8-{[(11s)-5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C40H58N4O10 (754.4152728)

(2s)-5-carbamimidamido-2-[(1-hydroxy-8-{[(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-8-oxooctylidene)amino]pentanoic acid

C38H56N4O9 (712.4047086)

(2s)-2-[(5-{[(1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a,5a-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-5-oxopentylidene)amino]-5-carbamimidamidopentanoic acid

C35H52N4O9 (672.3734102000001)

2-[(5-{[5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-5-oxopentylidene)amino]-5-carbamimidamidopentanoic acid

C37H52N4O10 (712.3683252000001)

(2s,6r,7s,8s)-7-(buta-1,3-dien-1-yl)-2-(penta-2,4-dien-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H29NO (287.2249024)

4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(2,3,6-trihydroxy-4-{[5-hydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-[(1-hydroxyethylidene)amino]hexyl)oxy]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C37H64N2O28 (984.3645424)

(2s)-2-[(1-hydroxy-8-{[(1r,2s,4r,6r,7r,10r,11s,14r,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-8-oxooctylidene)amino]-4-(c-hydroxycarbonimidoyl)butanoic acid

C37H52N2O10 (684.3621772)

(3s)-3-{[(2s)-2-amino-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-{[(1s)-1-{[(1s)-1-carboxyethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}propanoic acid

C30H39N5O8 (597.2798494)

4-{[7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-4-oxobutanoic acid

C28H36O7 (484.2460906)

(2s)-2-[(8-{[(1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C38H56N4O10 (728.3996236)

(2s)-2-[(8-{[(1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a,5a-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-4-(c-hydroxycarbonimidoyl)butanoic acid

C37H54N2O10 (686.3778264)

stigmast-5-en-3-ol, (3β)-

C29H50O (414.386145)

(1r,5r,6s,7s,9s,11s,12s,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1015602)

(3s)-3-{[(1s)-1-{[(1s)-1-{[(1s)-5-amino-1-{[(1s)-1-{[(1s)-5-amino-1-[({[(2s)-1-[(2s)-2-{[(1s)-1-carboxyethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-4-(c-hydroxycarbonimidoyl)-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]pentyl]-c-hydroxycarbonimidoyl}-2-hydroxyethyl]-c-hydroxycarbonimidoyl}pentyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-2-{[(2s)-2-{[(2s)-2-({2-[(2-{[(2s)-2-{[(2s)-2-{[(2s)-6-amino-2-[(2-{[(2s,3s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1,3-dihydroxypropylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyhexylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}propanoic acid

C105H185N29O32 (2364.373977)

2-({2-[(2-{[2-({2-[(2-{[2-({2-[(2-amino-1-hydroxypropylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene)amino]-3-carboxy-1-hydroxypropylidene}amino)-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene)amino]-1-hydroxyethylidene}amino)-4-methylpentanoic acid

C41H73N9O12 (883.5378417999999)

3-[(1-{[({1-[({[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-3-(methylsulfanyl)propyl}-c-hydroxycarbonimidoyl)-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl}-c-hydroxycarbonimidoyl)methyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl)-c-hydroxycarbonimidoyl]-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C60H76N14O22S2 (1408.4699796)

n-[(2s,3s,4s,5r)-6-{[(2r,3r,4r,5s,6r)-4-{[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3-{[(2r,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,4,5-trihydroxyhexan-2-yl]ethanimidic acid

C42H73N3O29 (1083.4329528)

5-hydroxy-n-(1-{2-[(1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl)-c-hydroxycarbonimidoyl]pyrrolidin-1-yl}-1-oxo-3-phenylpropan-2-yl)-3,4-dihydro-2h-pyrrole-2-carboximidic acid

C39H43N7O6 (705.3274658)

(1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1015602)

(2r,3s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1,3-dihydroxybutylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}-3-methylpentanoic acid

C33H45N5O9 (655.321712)

(2s)-5-hydroxy-n-[(2s)-1-[(2r)-2-{[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-3,4-dihydro-2h-pyrrole-2-carboximidic acid

C36H45N7O6 (671.3431149999999)

(2s)-2-({[(2s)-1-[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-4-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-n-[(1s)-1-(c-hydroxycarbonimidoyl)-2-(4-hydroxyphenyl)ethyl]-3-(1h-indol-3-yl)propanimidic acid

C40H49N7O6 (723.3744134000001)

5-methyl-3-(non-8-en-1-yl)-octahydro-1h-pyrrolo[1,2-a]azepine

C19H35N (277.27693500000004)

2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-n-[1-({1-[(1-{[({1-[(1-{[1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-phenylethyl)-c-hydroxycarbonimidoyl]-2-(3h-imidazol-4-yl)ethyl}-c-hydroxycarbonimidoyl)methyl]-c-hydroxycarbonimidoyl}-2-methylpropyl)-c-hydroxycarbonimidoyl]ethyl}-c-hydroxycarbonimidoyl)-2-(1h-indol-3-yl)ethyl]pentanediimidic acid

C51H68N14O11S (1084.4912458000001)

(2s)-2-{[(2r)-2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxypropylidene]amino}-n-({[(2s)-1-[(2s)-2-{[(1s)-2-hydroxy-1-(c-hydroxycarbonimidoyl)ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-c-hydroxycarbonimidoyl}methyl)-3-phenylpropanimidic acid

C40H50N8O10 (802.364972)

5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

C29H38O8 (514.2566548)

2-{[2-({[1-(2-amino-3-methylpentanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-4-methylpentanimidic acid

C28H42N6O4 (526.3267372)

5-[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O5 (400.2249622)

(1r,2s,4r,5r,6r,7r,10s,11s,14s,16s)-5,14,16-trihydroxy-7-methyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-11-carbaldehyde

C24H30O7 (430.199143)

5-carbamimidamido-2-[(1-hydroxy-4-{[5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-4-oxobutylidene)amino]pentanoic acid

C34H48N4O9 (656.3421118)

(2s,6r,7s,8r)-7-(buta-1,3-dien-1-yl)-2-(pent-2-en-4-yn-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H27NO (285.2092532)

3-{[2-({2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene}amino)-1-hydroxyethylidene]amino}-3-{[1-({1-[({[1-({1-[({[1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)-2-methylbutyl]-c-hydroxycarbonimidoyl}propanoic acid

C48H86N12O13 (1038.6436985999999)

(3s)-3-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C60H75N15O22S (1389.493157)

(2s)-n-[(1s)-1-{[(1s)-1-{[(1s,2r)-2-hydroxy-1-[({[(1s)-1-{[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]propyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-3-methylpentanimidic acid

C51H69N13O11S (1071.4959964)

(2r,6s,7s,8r)-7-(but-1-en-3-yn-1-yl)-2-(pent-2-en-4-yn-1-yl)-1-azaspiro[5.5]undecan-8-ol

C19H25NO (283.193604)

5-{5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl}pyran-2-one

C24H32O5 (400.2249622)

(1r,2s,4r,6r,7r,10s,11s,14s,16r)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl formate

C25H32O5 (412.2249622)

1-(2-{[(1-{2-[(2-amino-1-hydroxy-4-methylpentylidene)amino]-3-(1h-indol-3-yl)propanoyl}pyrrolidin-2-yl)(hydroxy)methylidene]amino}-3-phenylpropanoyl)-5-oxopyrrolidine-2-carboxylic acid

C36H44N6O7 (672.3271314000001)

5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

C31H40O9 (556.2672190000001)

5-[(1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a,5a,7-trihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H34O6 (418.2355264)

3-[(1-{[1-({[(1-{[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-2-phenylethyl}-c-hydroxycarbonimidoyl)-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]methyl}-c-hydroxycarbonimidoyl)-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl)-c-hydroxycarbonimidoyl]-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C60H75N15O22S (1389.493157)

5-[(1r,3as,3br,5as,7s,9r,9as,9bs,11ar)-3a,5a,7,9-tetrahydroxy-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H34O6 (418.2355264)

4-[({1-[2-({2-[(2-amino-1-hydroxy-3-methylpentylidene)amino]-1-hydroxy-3-(4-hydroxyphenyl)propylidene}amino)-4-carboxybutanoyl]pyrrolidin-2-yl}(hydroxy)methylidene)amino]-4-[(1-{[1-(c-hydroxycarbonimidoyl)ethyl]-c-hydroxycarbonimidoyl}-2-methylbutyl)-c-hydroxycarbonimidoyl]butanoic acid

C39H60N8O12 (832.433048)

2-({4-[(4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-2,3,6-trihydroxy-5-[(1-hydroxyethylidene)amino]hexyl}oxy)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C43H74N2O32 (1130.4224484000001)

(2r,3r,4e)-8-[(6z,8s,8as)-8-hydroxy-8-methyl-hexahydroindolizin-6-ylidene]-4,7-dimethyloct-4-ene-2,3-diol

C19H33NO3 (323.2460308000001)

5-[(1r,3as,3br,5as,7s,9ar,9bs,10r,11ar)-3a,5a,7,10-tetrahydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H34O7 (434.2304414)

7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid

C24H30O7 (430.199143)

n-[1-(2-{[1-({1-[(1-{[4-carbamimidamido-1-(c-hydroxycarbonimidoyl)butyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl)-c-hydroxycarbonimidoyl]-2-phenylethyl}-c-hydroxycarbonimidoyl)-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl)-3-methyl-1-oxopentan-2-yl]-5-hydroxy-3,4-dihydro-2h-pyrrole-2-carboximidic acid

C48H64N14O8 (964.5031304)

(2s,3s,4z,7r)-8-[(6z,8s,8as)-8-hydroxy-8-methyl-hexahydroindolizin-6-ylidene]-4,7-dimethyloct-4-ene-2,3-diol

C19H33NO3 (323.2460308000001)

(2s)-2-[(4-{[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]-5-carbamimidamidopentanoic acid

C34H50N4O8 (642.3628460000001)

2-[(7-{[2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-7-oxoheptylidene)amino]-5-carbamimidamidopentanoic acid

C39H58N4O10 (742.4152728)

(2s)-2-[(4-{[(1r,3as,3br,5ar,7s,9as,9bs,10r,11ar)-3a,10-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-4-oxobutylidene)amino]-5-carbamimidamidopentanoic acid

C34H50N4O9 (658.3577610000001)

5-[3a,5a,7,10-tetrahydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H34O7 (434.2304414)

2-{[3-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-5-hydroxy-2-(hydroxymethyl)-6-({1,4,5,6-tetrahydroxy-2-[(1-hydroxyethylidene)amino]hexan-3-yl}oxy)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C33H57N3O24 (879.3331842)

(1r,3as,5as,7s,9as,11ar)-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde

C24H32O6 (416.2198772)

(2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9ar,9bs,11ar)-3a-hydroxy-9a-(hydroxymethyl)-11a-methyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(1-methylimidazol-4-yl)propanoic acid

C39H55N3O9 (709.39381)

(5s,6r,8s,8ar)-6,8-diethyl-5-propyl-octahydroindolizine

C15H29N (223.2299874)

(11s,13s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1015602)

(4s)-4-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-4-{[(1s)-1-{[(1s)-1-{[(1s,2r)-2-hydroxy-1-(c-hydroxycarbonimidoyl)propyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}butanoic acid

C33H46N6O8 (654.3376956000001)

5-[(3as,3br,5ar,9as,9br,11ar)-3a,7-dihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H34O4 (386.24569640000004)

(2s)-2-[(1-hydroxy-8-{[(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-8-oxooctylidene)amino]-4-(c-hydroxycarbonimidoyl)butanoic acid

C37H52N2O10 (684.3621772)

(4s)-4-({[(2s)-1-[(2s)-2-{[(2s)-2-{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-carboxybutanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-4-{[(1s,2s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)ethyl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butanoic acid

C39H60N8O12 (832.433048)

5-[(1r,2s,4r,5r,6r,7r,10s,11r,14s,16s)-5,14,16-trihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O6 (416.2198772)

(1r,3s,11s,12s,14r,21z,24s,31r,44s)-12-hydroxy-14-(3-hydroxy-2-methylidenepropyl)-1,3,11,24,31,41,44-heptamethyl-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-39-one

C50H72O14 (896.4921812)

(2s)-2-[(7-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-7-oxoheptylidene)amino]-5-carbamimidamidopentanoic acid

C39H58N4O10 (742.4152728)

5,14,16-trihydroxy-7-methyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-11-carbaldehyde

C24H30O7 (430.199143)

n-[(1s,9as)-octahydro-1h-quinolizin-1-yl]ethanimidic acid

C11H20N2O (196.157555)

(2s)-5-carbamimidamido-2-[(1-hydroxy-4-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-4-oxobutylidene)amino]pentanoic acid

C34H48N4O9 (656.3421118)

(6z,8s,8as)-6-[(2r,4e,6s)-6-hydroxy-2,5-dimethyloct-4-en-1-ylidene]-8-methyl-hexahydroindolizin-8-ol

C19H33NO2 (307.25111580000004)

(2s,3s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-n-[(1s,2r)-2-hydroxy-1-{[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}propyl]-3-methylpentanimidic acid

C30H46N8O6 (614.3540135999999)

3-[(2-{[2-({2-[(2-amino-1-hydroxypropylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene)amino]-3-{[1-({1-[({[1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)-2-methylbutyl]-c-hydroxycarbonimidoyl}propanoic acid

C41H74N10O11 (882.5538254)

(3s)-3-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C58H73N13O18S (1271.4916998)

(1r,5r,6r,7s,9r,11s,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1015602)

2-[(8-{[3a,5a-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C38H58N4O9 (714.4203578)

(3r,5s,9ar)-5-methyl-3-(non-8-yn-1-yl)-octahydro-1h-pyrrolo[1,2-a]azepine

C19H33N (275.26128580000005)

2-[(2-{[2-({2-[(2-amino-1,3-dihydroxybutylidene)amino]-1-hydroxy-3-phenylpropylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-4-carboxy-1-hydroxybutylidene)amino]-3-methylpentanoic acid

C33H45N5O9 (655.321712)

2-[(8-{[3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C38H58N4O8 (698.4254428)

(1r,2s,7r,10s,11r,16s)-14,16-dihydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-5-yl acetate

C26H34O7 (458.2304414)

(2s)-2-[(8-{[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C38H58N4O8 (698.4254428)

(3s)-3-{[(2s)-2-{[(2s)-2-[(2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-{[(1s,2s)-1-{[(1s)-1-[({[(1s)-1-(c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-3-methylbutyl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}propanoic acid

C41H74N10O11 (882.5538254)

(2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-3-(3-methylimidazol-4-yl)propanoic acid

C41H57N3O10 (751.4043742)

22-(1-hydroxyethyl)-6,16-dimethyl-10,19-dioxa-16-azahexacyclo[12.5.3.1⁵,⁹.0¹,¹⁴.0²,¹¹.0⁶,¹¹]tricosa-2,21-diene-9,12-diol

C24H35NO5 (417.25151000000005)

5-[3a,5a,7-trihydroxy-9a-(hydroxymethyl)-11a-methyl-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]pyran-2-one

C24H34O6 (418.2355264)

(2s)-2-[(5-{[(1r,2s,4r,5r,6r,7r,10s,11s,14s,16r)-5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-5-oxopentylidene)amino]-5-carbamimidamidopentanoic acid

C37H52N4O10 (712.3683252000001)

[(1r,2s,4r,6r,7r,10s,11r,14s,16s)-16-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid

C24H32O8S (480.1817792)

(1r,2s,4r,5s,6r,7r,10s,11r,14s,16s)-14,16-dihydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-5-yl acetate

C26H34O7 (458.2304414)

(3s)-3-{[(1s)-1-{[(1s,2r)-1-[({[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1s)-2-carboxy-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}propanoic acid

C56H75N15O22S2 (1373.4652290000001)

14,16-dihydroxy-7-methyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecane-11-carbaldehyde

C24H30O6 (414.204228)

2-[(7-{[5-(acetyloxy)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-7-oxoheptylidene)amino]-5-carbamimidamidopentanoic acid

C39H56N4O10 (740.3996236)

n-[(1s)-4-carbamimidamido-1-{[(1s)-1-{[(1s,2s)-1-[({[(1s)-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-methylbutyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}butyl]-2-({hydroxy[(2s)-1-[(2s)-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoyl]pyrrolidin-2-yl]methylidene}amino)butanediimidic acid

C52H82N16O13S (1170.5967682)

(3s)-3-{[(2s)-2-{[(2r)-2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-3-[(1-{[(1s)-1-[(c-hydroxycarbonimidoylmethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl)-c-hydroxycarbonimidoyl]propanoic acid

C37H52N8O10 (768.3806212000001)

[(1r,2s,4r,6r,7r,11s,14s)-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxidanesulfonic acid

C24H32O7S (464.1868642)

5-[(1r,2s,4r,6r,7r,9r,10s,11r,14s,16s)-9,14,16-trihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl]pyran-2-one

C24H32O6 (416.2198772)

(2s)-2-[(8-{[(1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a,5a-dihydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

C38H58N4O9 (714.4203578)

3-{[1-({1-[({[1-({1-[(2-carboxy-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}ethyl)-c-hydroxycarbonimidoyl]-2-phenylethyl}-c-hydroxycarbonimidoyl)-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl}-c-hydroxycarbonimidoyl)-2-[4-(sulfooxy)phenyl]ethyl]-c-hydroxycarbonimidoyl}-3-[(1-hydroxy-2-{[hydroxy(5-hydroxy-3,4-dihydro-2h-pyrrol-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]propanoic acid

C62H73N13O21S (1367.4764448)

(5s,6r,8r,8as)-5-butyl-6,8-diethyl-octahydroindolizine

C16H31N (237.24563659999998)

(4s)-4-[({[(1s,2s)-1-{[(1s)-5-amino-1-{[(1s)-2-hydroxy-1-(c-hydroxycarbonimidoyl)ethyl]-c-hydroxycarbonimidoyl}pentyl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-4-{[(2s)-2-{[(2s,3s)-2-[(2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-{[(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-6-amino-2-{[(2s,3s)-2-{[(2s)-6-amino-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-4-(c-hydroxycarbonimidoyl)butylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-1-hydroxyhexylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}-1-hydroxyethylidene)amino]-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxypropylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-3-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}butanoic acid

C104H175N29O31 (2326.300816)

(2s)-1-[(2s)-2-({[(2r)-1-[(2s)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-(1h-indol-3-yl)propanoyl]pyrrolidine-2-carboxylic acid

C30H35N5O5 (545.263806)

n-[(2s,3s,4s,5r)-3-{[(2s,3r,4s,5s,6r)-6-({[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,4,5,6-tetrahydroxyhexan-2-yl]ethanimidic acid

C40H70N2O29 (1042.4064050000002)

2-[(6-{[5-(acetyloxy)-11-formyl-16-hydroxy-7-methyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl]oxy}-1-hydroxy-6-oxohexylidene)amino]-5-carbamimidamidopentanoic acid

C38H52N4O12 (756.3581552)