NCBI Taxonomy: 7599

Thymidine

C10H14N2O5 (242.0902674)

Deoxythymidine, also known as 2-deoxy-5-methyluridine or 5-methyl-2-deoxyuridine, is a member of the class of compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxythymidine is soluble (in water) and a very weakly acidic compound (based on its pKa). Deoxythymidine can be synthesized from thymine. Deoxythymidine is also a parent compound for other transformation products, including but not limited to, tritiated thymidine, alpha-tritiated thymidine, and 5,6-dihydrothymidine. Deoxythymidine can be found in a number of food items such as butternut squash, mammee apple, catjang pea, and climbing bean, which makes deoxythymidine a potential biomarker for the consumption of these food products. Deoxythymidine can be found primarily in most biofluids, including blood, amniotic fluid, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Deoxythymidine exists in all living species, ranging from bacteria to humans. In humans, deoxythymidine is involved in the pyrimidine metabolism. Deoxythymidine is also involved in few metabolic disorders, which include beta ureidopropionase deficiency, dihydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and UMP synthase deficiency (orotic aciduria). Moreover, deoxythymidine is found to be associated with canavan disease and degenerative disc disease. Thymidine (deoxythymidine; other names deoxyribosylthymine, thymine deoxyriboside) is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase . Thymidine, also known as deoxythymidine or deoxyribosylthymine or thymine deoxyriboside, is a pyrimidine deoxynucleoside. It consists of the nucleobase thymine attached to deoxyribose through a beta N- glycosidic bond. Thymidine also belongs to the class of organic compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxythymidine (or thymidine) is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. Therefore, thymidine is essential to all life. Indeed, thymidine exists in all living species, ranging from bacteria to plants to humans. Within humans, thymidine participates in a number of enzymatic reactions. In particular, thymidine can be biosynthesized from 5-thymidylic acid through its interaction with the enzyme cytosolic purine 5-nucleotidase. In addition, thymidine can be converted into 5-thymidylic acid; which is catalyzed by the enzyme thymidine kinase. Deoxythymidine can be phosphorylated with one, two or three phosphoric acid groups, creating dTMP (deoxythymidine monophosphate), dTDP, or dTTP (for the di- and tri- phosphates, respectively). dTMP can be incorporated into DNA via DNA polymerases. In cell biology, thymidine can be used to synchronize the cells in S phase. Derivatives of thymidine are used in a number of drugs, including Azidothymidine (AZT), which is used in the treatment of HIV infection. AZT inhibits the process of reverse transcription in the human immunodeficiency virus. Thymidine is a pyrimidine 2-deoxyribonucleoside having thymine as the nucleobase. It has a role as a metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a thymine. It is an enantiomer of a telbivudine. Thymidine is a pyrimidine deoxynucleoside. Thymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in S phase. Thymidine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Thymidine is a natural product found in Fritillaria thunbergii, Saussurea medusa, and other organisms with data available. Thymidine is a pyrimidine nucleoside that is composed of the pyrimidine base thymine attached to the sugar deoxyribose. As a constituent of DNA, thymidine pairs with adenine in the DNA double helix. (NCI04) Thymidine is a metabolite found in or produced by Saccharomyces cerevisiae. A nucleoside in which THYMINE is linked to DEOXYRIBOSE. A pyrimidine 2-deoxyribonucleoside having thymine as the nucleobase. KEIO_ID T014; [MS2] KO009272 KEIO_ID T014 Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3]. Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3].

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].

L-Tryptophan

C11H12N2O2 (204.0898732)

Tryptophan (Trp) or L-tryptophan 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-tryptophan is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tryptophan 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. Tryptophan is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. The requirement for tryptophan and protein decreases with age. The minimum daily requirement for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ. A cup of low-fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://www.dcnutrition.com). Tryptophan is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Tryptophan is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of conditions or diseases that are characterized by tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn diets or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia. Hartnups disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnups disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnups disease. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin by the pineal gland, which promotes sleep. Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed th... L-tryptophan is a white powder with a flat taste. An essential amino acid; occurs in isomeric forms. (NTP, 1992) L-tryptophan is the L-enantiomer of tryptophan. It has a role as an antidepressant, a nutraceutical, a micronutrient, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tryptophan and a L-alpha-amino acid. It is a conjugate base of a L-tryptophanium. It is a conjugate acid of a L-tryptophanate. It is an enantiomer of a D-tryptophan. It is a tautomer of a L-tryptophan zwitterion. An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals. L-Tryptophan is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Tryptophan is the least plentiful of all 22 amino acids and an essential amino acid in humans (provided by food), Tryptophan is found in most proteins and a precursor of serotonin. Tryptophan is converted to 5-hydroxy-tryptophan (5-HTP), converted in turn to serotonin, a neurotransmitter essential in regulating appetite, sleep, mood, and pain. Tryptophan is a natural sedative and present in dairy products, meats, brown rice, fish, and soybeans. (NCI04) Tryptophan is an essential amino acid which is the precursor of serotonin. Serotonin is a brain neurotransmitter, platelet clotting factor and neurohormone found in organs throughout the body. Metabolism of tryptophan to serotonin requires nutrients such as vitamin B6, niacin and glutathione. Niacin is an important metabolite of tryptophan. High corn or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea and dementia. Inborn errors of tryptophan metabolism exist where a tumor (carcinoid) makes excess serotonin. Hartnups disease is a disease where tryptophan and other amino acids are not absorbed properly. Tryptophan supplements may be useful in each condition, in carcinoid replacing the over-metabolized nutrient and in Hartnups supplementing a malabsorbed nutrient. Some disorders of excess tryptophan in the blood may contribute to mental retardation. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan fragments correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension and anxiety states. The requirement for tryptophan and protein decreases with age. Adults minimum daily requirement is 3 mg/kg/day or about 200 mg a day. This may be an underestimation, for there are 400 mg of tryptophan in just a cup of wheat germ. A cup of low fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg per pound. An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals. See also: Serotonin; tryptophan (component of); Chamomile; ginger; melatonin; thiamine; tryptophan (component of) ... View More ... Constituent of many plants. Enzymatic hydrolysis production of most plant and animal proteins. Dietary supplement, nutrient D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants COVID info from PDB, Protein Data Bank The L-enantiomer of tryptophan. Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA09_Tryptophan_pos_30eV_1-1_01_662.txt [Raw Data] CBA09_Tryptophan_pos_20eV_1-1_01_661.txt [Raw Data] CBA09_Tryptophan_neg_30eV_1-1_01_716.txt [Raw Data] CBA09_Tryptophan_pos_10eV_1-1_01_660.txt [Raw Data] CBA09_Tryptophan_neg_10eV_1-1_01_714.txt [Raw Data] CBA09_Tryptophan_neg_40eV_1-1_01_717.txt [Raw Data] CBA09_Tryptophan_neg_20eV_1-1_01_715.txt [Raw Data] CBA09_Tryptophan_pos_50eV_1-1_01_664.txt [Raw Data] CBA09_Tryptophan_neg_50eV_1-1_01_718.txt [Raw Data] CBA09_Tryptophan_pos_40eV_1-1_01_663.txt IPB_RECORD: 253; CONFIDENCE confident structure KEIO_ID T003 DL-Tryptophan is an endogenous metabolite. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1]. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[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].

beta-Carotene

C40H56 (536.4381776)

Beta-carotene is a cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. It has a role as a biological pigment, a provitamin A, a plant metabolite, a human metabolite, a mouse metabolite, a cofactor, a ferroptosis inhibitor and an antioxidant. It is a cyclic carotene and a carotenoid beta-end derivative. Beta-carotene, with the molecular formula C40H56, belongs to the group of carotenoids consisting of isoprene units. The presence of long chains of conjugated double bonds donates beta-carotene with specific colors. It is the most abundant form of carotenoid and it is a precursor of the vitamin A. Beta-carotene is composed of two retinyl groups. It is an antioxidant that can be found in yellow, orange and green leafy vegetables and fruits. Under the FDA, beta-carotene is considered as a generally recognized as safe substance (GRAS). Beta-Carotene is a natural product found in Epicoccum nigrum, Lonicera japonica, and other organisms with data available. Beta-Carotene is a naturally-occurring retinol (vitamin A) precursor obtained from certain fruits and vegetables with potential antineoplastic and chemopreventive activities. As an anti-oxidant, beta carotene inhibits free-radical damage to DNA. This agent also induces cell differentiation and apoptosis of some tumor cell types, particularly in early stages of tumorigenesis, and enhances immune system activity by stimulating the release of natural killer cells, lymphocytes, and monocytes. (NCI04) beta-Carotene is a metabolite found in or produced by Saccharomyces cerevisiae. A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC). See also: Lycopene (part of); Broccoli (part of); Lycium barbarum fruit (part of). Beta-Carotene belongs to the class of organic compounds known as carotenes. These are a type of polyunsaturated hydrocarbon molecules containing eight consecutive isoprene units. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Beta-carotene is therefore considered to be an isoprenoid lipid molecule. Beta-carotene is a strongly coloured red-orange pigment abundant in fungi, plants, and fruits. It is synthesized biochemically from eight isoprene units and therefore has 40 carbons. Among the carotenes, beta-carotene is distinguished by having beta-rings at both ends of the molecule. Beta-Carotene is biosynthesized from geranylgeranyl pyrophosphate. It is the most common form of carotene in plants. In nature, Beta-carotene is a precursor (inactive form) to vitamin A. Vitamin A is produed via the action of beta-carotene 15,15-monooxygenase on carotenes. In mammals, carotenoid absorption is restricted to the duodenum of the small intestine and dependent on a class B scavenger receptor (SR-B1) membrane protein, which is also responsible for the absorption of vitamin E. One molecule of beta-carotene can be cleaved by the intestinal enzyme Beta-Beta-carotene 15,15-monooxygenase into two molecules of vitamin A. Beta-Carotene contributes to the orange color of many different fruits and vegetables. Vietnamese gac and crude palm oil are particularly rich sources, as are yellow and orange fruits, such as cantaloupe, mangoes, pumpkin, and papayas, and orange root vegetables such as carrots and sweet potatoes. Excess beta-carotene is predominantly stored in the fat tissues of the body. The most common side effect of excessive beta-carotene consumption is carotenodermia, a physically harmless condition that presents as a conspicuous orange skin tint arising from deposition of the carotenoid in the outermost layer of the epidermis. Yellow food colour, dietary supplement, nutrient, Vitamin A precursor. Nutriceutical with antioxidation props. beta-Carotene is found in many foods, some of which are summer savory, gram bean, sunburst squash (pattypan squash), and other bread product. A cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BB - Protectives against uv-radiation for systemic use A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins

beta-Cryptoxanthin

C40H56O (552.4330926)

beta-Cryptoxanthin has been isolated from abalone, fish eggs, and many higher plants. beta-Cryptoxanthin is a major source of vitamin A, often second only to beta-carotene, and is present in fruits such as oranges, tangerines, and papayas (PMID: 8554331). Frequent intake of tropical fruits that are rich in beta-cryptoxanthin is associated with higher plasma beta-cryptoxanthin concentrations in Costa Rican adolescents. Papaya intake was the best food predictor of plasma beta-cryptoxanthin concentrations. Subjects that frequently consumed (i.e. greater or equal to 3 times/day) tropical fruits with at least 50 micro g/100 g beta-cryptoxanthin (e.g. papaya, tangerine, orange, watermelon) had twofold the plasma beta-cryptoxanthin concentrations of those with intakes of less than 4 times/week (PMID: 12368412). A modest increase in beta-cryptoxanthin intake, equivalent to one glass of freshly squeezed orange juice per day, is associated with a reduced risk of developing inflammatory disorders such as rheumatoid arthritis (PMID: 16087992). Higher prediagnostic serum levels of total carotenoids and beta-cryptoxanthin were associated with lower smoking-related lung cancer risk in middle-aged and older men in Shanghai, China (PMID: 11440962). Consistent with inhibition of the lung cancer cell growth, beta-cryptoxanthin induced the mRNA levels of retinoic acid receptor beta (RAR-beta) in BEAS-2B cells, although this effect was less pronounced in A549 cells. Furthermore, beta-cryptoxanthin transactivated the RAR-mediated transcription activity of the retinoic acid response element. These findings suggest a mechanism of anti-proliferative action of beta-cryptoxanthin and indicate that beta-cryptoxanthin may be a promising chemopreventive agent against lung cancer (PMID: 16841329). Cryptoxanthin is a natural carotenoid pigment. It has been isolated from a variety of sources including the petals and flowers of plants in the genus Physalis, orange rind, papaya, egg yolk, butter, apples, and bovine blood serum. In a pure form, cryptoxanthin is a red crystalline solid with a metallic lustre. It is freely soluble in chloroform, benzene, pyridine, and carbon disulfide. In the human body, cryptoxanthin is converted into vitamin A (retinol) and is therefore considered a provitamin A. As with other carotenoids, cryptoxanthin is an antioxidant and may help prevent free radical damage to cells and DNA, as well as stimulate the repair of oxidative damage to DNA. Structurally, cryptoxanthin is closely related to beta-carotene, with only the addition of a hydroxyl group. It is a member of the class of carotenoids known as xanthophylls. Beta-cryptoxanthin is a carotenol that exhibits antioxidant activity. It has been isolated from fruits such as papaya and oranges. It has a role as a provitamin A, an antioxidant, a biomarker and a plant metabolite. It derives from a hydride of a beta-carotene. beta-Cryptoxanthin is a natural product found in Hibiscus syriacus, Cladonia gracilis, and other organisms with data available. A mono-hydroxylated xanthophyll that is a provitamin A precursor. See also: Corn (part of). A carotenol that exhibits antioxidant activity. It has been isolated from fruits such as papaya and oranges. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Cryptoxanthin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=472-70-8 (retrieved 2024-10-31) (CAS RN: 472-70-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Zeaxanthin

C40H56O2 (568.4280076)

Zeaxanthin is a carotenoid xanthophyll and is one of the most common carotenoid found in nature. It is the pigment that gives corn, saffron, and many other plants their characteristic color. Zeaxanthin breaks down to form picrocrocin and safranal, which are responsible for the taste and aroma of saffron Carotenoids are among the most common pigments in nature and are natural lipid soluble antioxidants. Zeaxanthin is one of the two carotenoids (the other is lutein) that accumulate in the eye lens and macular region of the retina with concentrations in the macula greater than those found in plasma and other tissues. Lutein and zeaxanthin have identical chemical formulas and are isomers, but they are not stereoisomers. The main difference between them is in the location of a double bond in one of the end rings. This difference gives lutein three chiral centers whereas zeaxanthin has two. A relationship between macular pigment optical density, a marker of lutein and zeaxanthin concentration in the macula, and lens optical density, an antecedent of cataractous changes, has been suggested. The xanthophylls may act to protect the eye from ultraviolet phototoxicity via quenching reactive oxygen species and/or other mechanisms. Some observational studies have shown that generous intakes of lutein and zeaxanthin, particularly from certain xanthophyll-rich foods like spinach, broccoli and eggs, are associated with a significant reduction in the risk for cataract (up to 20\\%) and for age-related macular degeneration (up to 40\\%). While the pathophysiology of cataract and age-related macular degeneration is complex and contains both environmental and genetic components, research studies suggest dietary factors including antioxidant vitamins and xanthophylls may contribute to a reduction in the risk of these degenerative eye diseases. Further research is necessary to confirm these observations. (PMID: 11023002). Zeaxanthin has been found to be a microbial metabolite, it can be produced by Algibacter, Aquibacter, Escherichia, Flavobacterium, Formosa, Gramella, Hyunsoonleella, Kordia, Mesoflavibacter, Muricauda, Nubsella, Paracoccus, Siansivirga, Sphingomonas, Zeaxanthinibacter and yeast (https://reader.elsevier.com/reader/sd/pii/S0924224417302571?token=DE6BC6CC7DCDEA6150497AA3E375097A00F8E0C12AE03A8E420D85D1AC8855E62103143B5AE0B57E9C5828671F226801). It is a marker for the activity of Bacillus subtilis and/or Pseudomonas aeruginosa in the intestine. Higher levels are associated with higher levels of Bacillus or Pseudomonas. (PMID: 17555270; PMID: 12147474) Zeaxanthin is a carotenol. It has a role as a bacterial metabolite, a cofactor and an antioxidant. It derives from a hydride of a beta-carotene. Zeaxanthin is a most common carotenoid alcohols found in nature that is involved in the xanthophyll cycle. As a coexistent isomer of lutein, zeaxanthin is synthesized in plants and some micro-organisms. It gives the distinct yellow color to many vegetables and other plants including paprika, corn, saffron and wolfberries. Zeaxanthin is one of the two primary xanthophyll carotenoids contained within the retina of the eye and plays a predominant component in the central macula. It is available as a dietary supplement for eye health benefits and potential prevention of age-related macular degeneration. Zeaxanthin is also added as a food dye. Zeaxanthin is a natural product found in Bangia fuscopurpurea, Erythrobacter longus, and other organisms with data available. Carotenoids found in fruits and vegetables. Zeaxanthin accumulates in the MACULA LUTEA. See also: Saffron (part of); Corn (part of); Lycium barbarum fruit (part of). D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

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.

Deoxyguanosine

C10H13N5O4 (267.09674980000005)

Deoxyguanosine, also known as dG, belongs to the class of organic compounds known as purine 2-deoxyribonucleosides. Purine 2-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2‚Äô. Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. Deoxyguanosine is one of the four deoxyribonucleosides that make up DNA. Deoxyguanosine exists in all living species, ranging from bacteria to plants to humans. Deoxyguanosine participates in a number of enzymatic reactions. In particular, deoxyguanosine can be biosynthesized from 2-deoxyguanosine 5-monophosphate through the enzyme known as cytosolic purine 5-nucleotidase. In addition, deoxyguanosine can be converted into 2-deoxyguanosine 5-monophosphate (dGMP); which is mediated by the enzyme deoxyguanosine kinase. Deoxyguanosine is involved in the rare, inherited metabolic disorder called the purine nucleoside phosphorylase deficiency (PNP deficiency). In particular PNP deficiency is characterized by elevated levels of dGTP (deoxyguanosine triphosphate). PNP accounts for approximately 4\\\\% of patients with severe combined immunodeficiency (PMID: 1931007). PNP-deficient patients suffer from recurrent infections, usually beginning in the first year of life. Two thirds of patients have evidence of neurologic disorders with spasticity, developmental delay and mental retardation. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-hydroxy-deoxyguanosine is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion. Isolated from plants, e.g. Phaseolus vulgaris (kidney bean) COVID info from COVID-19 Disease Map KEIO_ID D057; [MS2] KO008942 KEIO_ID D057 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2’-Deoxyguanosine (Deoxyguanosine) is a purine nucleoside with a variety of biological activities. 2’-Deoxyguanosine can induce DNA division in mouse thymus cells. 2’-Deoxyguanosine is a potent cell division inhibitor in plant cells[1][2][3]. 2'-Deoxyguanosine (Deoxyguanosine) is deoxyguanosine.

Tyramine

C8H11NO (137.0840596)

Tyramine is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals. Tyramine is a biomarker for the consumption of cheese [Spectral] Tyramine (exact mass = 137.08406) and L-Methionine (exact mass = 149.05105) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Tyramine (exact mass = 137.08406) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics Acquisition and generation of the data is financially supported in part by CREST/JST. D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents IPB_RECORD: 267; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 5105 D049990 - Membrane Transport Modulators KEIO_ID T008 Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1]. Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1].

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].

Canthaxanthin

C40H52O2 (564.3967092)

Canthaxanthin, also known as Cantaxanthin, Cantaxanthine, or Canthaxanthine is a keto-carotenoid, a pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. Canthaxanin is also classified as a xanthophyll. Xanthophylls are yellow pigments and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. Both are carotenoids. Xanthophylls and carotenes are similar in structure, but xanthophylls contain oxygen atoms while carotenes are purely hydrocarbons, which do not contain oxygen. Their content of oxygen causes xanthophylls to be more polar (in molecular structure) than carotenes and causes their separation from carotenes in many types of chromatography. (Carotenes are usually more orange in color than xanthophylls. Canthaxanthin is naturally found in bacteria, algae and some fungi. Canthaxanthin is associated with E number E161g and is approved for use as a food coloring agent in different countries, including the United States and the EU. Canthaxanthin is used as poultry feed additive to yield red color in skin and yolks. The European Union permits the use of canthaxanthin in feedstuff at a maximum content of 25 mg/kg of final feedstuff while the United States allows the use of this pigment in broiler chicken and salmonid fish feeds. Canthoxanthin was first isolated in edible chanterelle mushroom (Cantharellus cinnabarinus), from which it derived its name. It has also been found in green algae, bacteria, archea (a halophilic archaeon called Haloferax alexandrines), fungi and bioaccumulates in tissues and egg yolk from wild birds and at low levels in crustaceans and fish such as carp, golden grey mullet, and seabream. Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in Pacific Salmon. Canthaxanthin is used in farm-raised trout to give a red/orange color to their flesh similar to wild trout. Canthaxanthin has been used as a food additive for egg yolk, in cosmetics and as a pigmenting agent for human skin applications. It has also been used as a feed additive in fish and crustacean farms. Canthaxanthin is a potent lipid-soluble antioxidant (PMID: 2505240). Canthaxanthin increases resistance to lipid peroxidation primarily by enhancing membrane alpha-tocopherol levels and secondarily by providing weak direct antioxidant activity. Canthaxanthin biosynthesis in bacteria and algae proceeds from beta-carotene via the action of an enzyme known as a beta-carotene ketolase, that is able to add a carbonyl group to carbon 4 and 4 of the beta carotene molecule. Food colouring. Constituent of the edible mushroom (Cantharellus cinnabarinus), sea trout, salmon and brine shrimp. It is used in broiler chicken feed to enhance the yellow colour of chicken skin D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

echinenone

C40H54O (550.4174434)

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

Lutein 5,6-epoxide

C40H56O3 (584.4229226)

Lutein; 5,6-Epoxide is found in common grape. Paprika oleoresin (also known as paprika extract) is an oil soluble extract from the fruits of Capsicum Annum Linn or Capsicum Frutescens(Indian red chillies), and is primarily used as a colouring and/or flavouring in food products. It is composed of capsaicin, the main flavouring compound giving pungency in higher concentrations, and capsanthin and capsorubin, the main colouring compounds (among other carotenoids). Isolated from a variety of higher plants and from algae. Taraxanthin was a mixture with lutein epoxide as the main component. [CCD]. Lutein 5,6-epoxide is found in many foods, some of which are rice, swamp cabbage, garden tomato (variety), and common grape.

Lathosterol

C27H46O (386.3548466)

Lathosterol is a 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. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID: 8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O [HMDB] Lathosterol is a 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. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID:8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis.

D-Alanine

C3H7NO2 (89.0476762)

Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It 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 regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It 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. Alanine can be found in some Gram-positive bacteria (PMID:24752840). Amino acids are one of the most important molecules in living organisms, and most of them have a chiral carbon at a -position. In the higher animals, a large part of the naturally occurring amino acids is the L-form, and the stereoisomers (D-amino acids) had been believed to be rare. However, several D-amino acids have been found in mammals including humans, and their distributions, functions and origins have gradually been clarified. The D-alanine (D-Ala) amounts have also been reported to change in the case of diseases. Proteins of the frontal lobe white and gray matter of human brains, both normal and Alzheimer subjects, contain D-alanine at concentrations between 0.50 and 1.28 mumol/g of wet tissue, 50-70-times lower than the concentration of L-alanine. D-Alanine have been detected in the sera of both normal subjects and patients with renal dysfunction, and their concentrations were higher in the patients than in the normal subjects. (PMID: 16141519, 1450921, 8535409, 1426150, 1933416) [HMDB] KEIO_ID A011 D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR.

D-Phenylalanine

C9H11NO2 (165.0789746)

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

D-methionine

C5H11NO2S (149.0510466)

V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AB - Antidotes An optically active form of methionine having D-configuration. C26170 - Protective Agent > C275 - Antioxidant C78284 - Agent Affecting Integumentary System Methionine (MRX-1024; D-Methionine) is an effective chemoprotective agent which can also inhibit the neuronal activity through GABAA receptor activation.

D-phenylalanine

C9H11NO2 (165.0789746)

The D-enantiomer of phenylalanine. D-Phenylalanine is the synthetic dextro isomer of phenylalanine. D-Phenylalanine inhibits biofilm development of Pseudoalteromonas sp. SC2014[1]. D-Phenylalanine is the synthetic dextro isomer of phenylalanine. D-Phenylalanine inhibits biofilm development of Pseudoalteromonas sp. SC2014[1].

Alloxanthin

C40H52O2 (564.3967092)

Alloxanthin is found in channel catfish. Alloxanthin is a constituent of many shellfish including the giant scallop (Pecten maximus) and edible mussel (Mytilus edulis). Constituent of many shellfish including the giant scallop (Pecten maximus) and edible mussel (Mytilus edulis). Alloxanthin is found in channel catfish and mollusks.

Mytiloxanthin

C40H54O4 (598.4021884)

Mytiloxanthin is found in blue mussel. Mytiloxanthin is isolated from the mussels Mytilus edulis. Isolated from the mussels Mytilus edulis. Mytiloxanthin is found in blue mussel and mollusks.

Pectenolone

C40H52O3 (580.3916242)

Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.

4-Hydroxymytiloxanthin

C40H54O5 (614.3971034)

4-Ketoalloxanthin

C40H50O3 (578.3759749999999)

Pectenol B

C40H54O3 (582.4072734)

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].

Tyramine

C8H11NO (137.0840596)

D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics A primary amino compound obtained by formal decarboxylation of the amino acid tyrosine. D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators Annotation level-2 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2741; CONFIDENCE confident structure Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1]. Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1].

Thymidine

C10H14N2O5 (242.09026740000002)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.220 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.211 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.213 Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3]. Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3].

L-Tryptophan

C11H12N2O2 (204.0898732)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QIVBCDIJIAJPQS-VIFPVBQESA-N_STSL_0010_L-Tryptophan_8000fmol_180410_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. CONFIDENCE standard compound; INTERNAL_ID 5 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.178 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.176 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.170 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.171 L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1]. L-Tryptophan (Tryptophan) is an essential amino acid that is the precursor of serotonin, melatonin, and vitamin B3[1].

2-Deoxyadenosine

C10H13N5O3 (251.10183480000003)

A purine 2-deoxyribonucleoside having adenine as the nucleobase. D000890 - Anti-Infective Agents > D000998 - Antiviral Agents COVID info from COVID-19 Disease Map D009676 - Noxae > D009153 - Mutagens Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Formula(Parent): C10H13N5O3; Bottle Name:2-Deoxyadenosine monohydrate; PRIME Parent Name:2-Deoxyadenosine; PRIME in-house No.:0140, Purines relative retention time with respect to 9-anthracene Carboxylic Acid is 0.265 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.269 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.261 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.263 2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA. 2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA. 2'-Deoxyadenosine is a nucleoside adenosine derivative, pairing with deoxythymidine (T) in double-stranded DNA.

β-Carotene

C40H56 (536.4381776)

The novel carbohydrate-derived b-carboline, 1-pentahydroxypentyl-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid, was identified in fruit- and vegetable-derived products such as juices, jams, and tomato sauces. This compound occurred as two diastereoisomers, a cis isomer (the major compound) and a trans isomer, ranging from undetectable amounts to 6.5 ug/g. Grape, tomato, pineapple, and tropical juices exhibited the highest amount of this alkaloid (up to 3.8 mg/L), whereas apple, banana, and peach juices showed very low or nondetectable levels. This tetrahydro-b-carboline was also found in jams (up to 0.45 ug/g), and a relative high amount was present in tomato concentrate (6.5 ug/g) and sauce (up to 1.8 ug/g). This b-carboline occurred in fruit-derived products as a glycoconjugate from a chemical condensation of d-glucose and l-tryptophan that is highly favored at low pH values and high temperature. Production, processing treatments, and storage of fruit juices and jams can then release this b-carboline. Fruit-derived products and other foods containing this compound might be an exogenous dietary source of this glucose-derived tetrahydro-b-carboline.(PMID: 12137498) [HMDB] Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE is 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BB - Protectives against uv-radiation for systemic use A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE is 10 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.

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.

D-Alanine

C3H7NO2 (89.0476762)

The D-enantiomer of alanine. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR.

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].

Cryptoxanthin

C40H56O (552.4330926)

Isolated from papaya (Carica papaya) and many other higher plants, also from fish eggs [DFC]. beta-Cryptoxanthin is found in many foods, some of which are smelt, soy yogurt, common carp, and rose hip.

Zeaxanthin

C40H56O2 (568.4280076)

Meso-zeaxanthin (3R,3´S-zeaxanthin) is a xanthophyll carotenoid, as it contains oxygen and hydrocarbons, and is one of the three stereoisomers of zeaxanthin. Of the three stereoisomers, meso-zeaxanthin is the second most abundant in nature after 3R,3´R-zeaxanthin, which is produced by plants and algae. To date, meso-zeaxanthin has been identified in specific tissues of marine organisms and in the macula lutea, also known as the "yellow spot", of the human retina . Meso-zeaxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Meso-zeaxanthin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Meso-zeaxanthin can be found in channel catfish, crustaceans, and fishes, which makes meso-zeaxanthin a potential biomarker for the consumption of these food products. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan.

Deoxyguanosine

C10H13N5O4 (267.09674980000005)

2’-Deoxyguanosine (Deoxyguanosine) is a purine nucleoside with a variety of biological activities. 2’-Deoxyguanosine can induce DNA division in mouse thymus cells. 2’-Deoxyguanosine is a potent cell division inhibitor in plant cells[1][2][3]. 2'-Deoxyguanosine (Deoxyguanosine) is deoxyguanosine.

5-Methyluridine

C10H14N2O6 (258.0851824)

CONFIDENCE standard compound; INTERNAL_ID 320 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids. 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids.

5-Methyluridine

C10H15N3O5 (257.101166)

Alloxanthin

C40H52O2 (564.3967092)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan.

Mytiloxanthin

C40H54O4 (598.4021884)

Pectenol A/ (Pectenol)

C40H54O3 (582.4072734)

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

C13H14N2O2 (230.1055224)

Lathosterol

C27H46O (386.3548466)

Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis.

canthaxanthin

C40H52O2 (564.3967092)

A carotenone that consists of beta,beta-carotene bearing two oxo substituents at positions 4 and 4. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

(2R)-2-aminopropanoic acid

C3H7NO2 (89.0476762)

Ovothiol A

C7H11N3O2S (201.0571946)

A L-histidine derivative that is L-histidine substituted at positions N3 and C5 on the imidazole ring by methyl and mercapto groups respectively.

[(E,2S,5R)-2-propan-2-yl-5-[(3S,5S,6R,8S,9R,10S,13R,14S,15S,17R)-6,8,15-trihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]hex-3-enyl] hydrogen sulfate

C33H56O12S (676.3492296000001)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(2r,5r)-2-hydroxy-5,6-dimethyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C57H94O28S (1258.5652043999999)

2-hydroxy-n-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docosa-4,13-dien-2-yl)hexadecanimidic acid

C44H83NO9 (769.6067508)

9a,11a-dimethyl-1-{6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]heptan-2-yl}-tetradecahydrocyclopenta[a]phenanthrene-3,5,5a,7-tetrol

C32H56O9 (584.3924126000001)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-5-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C56H92O28S (1244.5495552)

(2r)-n-[(2s,3s,4r,16r)-3,4-dihydroxy-16-methyl-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]-2-hydroxyhexadecanimidic acid

C42H83NO10 (761.6016658)

2-hydroxy-n-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docosa-4,13-dien-2-yl)tetradecanimidic acid

C42H79NO9 (741.5754524)

n-(3,4-dihydroxy-16-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl)-2-hydroxyhexadecanimidic acid

C42H83NO10 (761.6016658)

4-keto-4'-hydroxyalloxanthin

C40H50O4 (594.3708899999999)

(2r)-2-hydroxy-n-[(2s,3r,4e,13z)-3-hydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docosa-4,13-dien-2-yl]hexadecanimidic acid

C44H83NO9 (769.6067508)

6-{3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-3-isopropylheptanoic acid

C29H50O6 (494.36072)

[(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-1-[(2r)-5-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H44O7S (512.2807594)

(1r,2r,3s,3as,3bs,5s,5as,7s,9as,9br,11ar)-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydrocyclopenta[a]phenanthrene-2,3,3b,5,7-pentol

C32H56O10 (600.3873276)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C56H92O28S (1244.5495552)

1-(7-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,5,5a,7-tetrol

C27H48O5 (452.3501558)

2-hydroxy-n-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docosa-4,13-dien-2-yl)pentadecanimidic acid

C43H81NO9 (755.5911016)

{1-acetyl-5-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl}oxidanesulfonic acid

C21H32O6S (412.1919492)

(2s,3r,4e,6r)-6-[(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-3,3b,5-trihydroxy-9a,11a-dimethyl-7-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethyl-n-(2-sulfoethyl)hept-4-enimidic acid

C35H59NO12S (717.3757774000001)

[(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-{[(2s,3s,4s,5r,6s)-3,4-dihydroxy-6-methyl-5-(sulfooxy)oxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C33H54O14S2 (738.2954824000001)

6-hydroxy-3-[(9e,11e,13e,15e)-18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-1,17-diyn-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H48O4 (592.3552407999999)

(1r,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2s,5r)-5-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-diol

C27H46O3 (418.34467659999996)

2-[(3,3b,5-trihydroxy-9a,11a-dimethyl-1-{6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]hept-3-en-2-yl}-tetradecahydrocyclopenta[a]phenanthren-7-yl)oxy]oxane-3,4,5-triol

C37H62O13 (714.4190202)

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docos-9-en-2-yl)-2-hydroxypentadecanimidic acid

C43H83NO10 (773.6016658)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3r,4s,5r,6r)-3-{[(2s,3r,4s,5s,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C62H102O33S (1406.6023762)

(2s,3r,4s,5r)-2-{[(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-3,3b,5-trihydroxy-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}oxane-3,4,5-triol

C37H64O13 (716.4346694000001)

(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,7-tetrol

C32H56O9 (584.3924126000001)

7-[(4,5-dihydroxy-3-methoxyoxan-2-yl)oxy]-1-(7-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol

C33H56O10 (612.3873276)

(2r)-n-[(2s,3s,4r,13z)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docos-13-en-2-yl]-2-hydroxypentadecanimidic acid

C43H83NO10 (773.6016658)

1-(1-hydroxyethyl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthrene-5,7-diol

C21H34O3 (334.25078140000005)

(2s)-2-[(1s,3as,3bs,5s,5as,7s,9as,11as)-5,7-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-hydroxy-6-methylheptan-4-one

C27H44O4 (432.3239424)

(2r,3s,5s)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

C10H13N5O3 (251.10183480000003)

(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,6s)-7-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,5,5a,7-tetrol

C27H48O5 (452.3501558)

[(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-1-[(2r,5r)-5-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H44O7S (512.2807594)

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docos-13-en-2-yl)-2-hydroxypentadecanimidic acid

C43H83NO10 (773.6016658)

9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-imino-3h-purin-6-ol

C10H13N5O4 (267.09674980000005)

(1r,2r,3r,3as,3br,5r,5as,7s,9ar,9bs,11ar)-1-[(2r,6s)-7-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-2,3,5,7-tetrol

C27H48O5 (452.3501558)

(2s,3r,4s,5r)-2-{[(1r,3s,3as,3bs,5r,5as,7s,9as,9br,11ar)-3,3b,5-trihydroxy-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}oxane-3,4,5-triol

C37H64O13 (716.4346694000001)

[(1s,3as,3bs,5s,5as,7s,9as,11ar)-1-acetyl-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3s,4s,5r,6r)-3-{[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C56H90O32S (1306.513566)

9a,11a-dimethyl-1-{6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]heptan-2-yl}-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,7-tetrol

C32H56O9 (584.3924126000001)

(2r,15z)-n-[(2s,3s,4r)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptadecan-2-yl]-2-hydroxytetracos-15-enimidic acid

C47H91NO10 (829.6642626)

[(1s,3s,3as,3bs,5s,5as,7s,9as,9br,11ar)-5,7-dihydroxy-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2r,3r,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxidanesulfonic acid

C32H56O11S (648.3543146000001)

bis(estradiol)

C36H48O4 (544.3552407999999)

6-{3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-3-methylhept-4-enoic acid

C27H44O6 (464.3137724)

(1r,2r,3r,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,6s)-7-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol

C33H56O10 (612.3873276)

(2r)-n-[(2s,3s,4r,9z)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docos-9-en-2-yl]-2-hydroxypentadecanimidic acid

C43H83NO10 (773.6016658)

(2s,3r,4s,5r)-2-{[(3s,6r)-6-[(1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-3,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-3-yl]oxy}oxane-3,4,5-triol

C32H56O8 (568.3974976000001)

(1s,3as,3bs,5s,5as,7s,9as,11as)-1-(1-hydroxyethyl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthrene-5,7-diol

C21H34O3 (334.25078140000005)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-hydroxy-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H44O7S (512.2807594)

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

C21H32O3 (332.23513219999995)

(2r)-2-hydroxy-n-[(2s,3r,4e,9z)-3-hydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docosa-4,9-dien-2-yl]hexadecanimidic acid

C44H83NO9 (769.6067508)

9a,11a-dimethyl-1-[6-methyl-5-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)heptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol

C35H62O11 (658.4291902)

(6s)-6-hydroxy-2,3,4,4-tetramethylcyclohex-2-en-1-one

C10H16O2 (168.1150236)

(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydrocyclopenta[a]phenanthrene-3,5,5a,7-tetrol

C32H56O9 (584.3924126000001)

2-[(6-{3,3b,5-trihydroxy-9a,11a-dimethyl-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthren-1-yl}-2-methylheptan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C38H66O14 (746.4452336)

[(1r,3ar,3br,5r,5ar,7s,9ar,11ar)-5-{[(2s,3s,4r,5r,6r)-4-{[(2s,3r,4s,5s)-5-{[(2r,3s,4r,5r,6r)-3-{[(2s,3s,4s,5r,6s)-3,5-dihydroxy-6-methyl-4-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(2r)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C62H102O33S (1406.6023762)

2'-deoxy-inosine

C10H12N4O4 (252.08585119999998)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C55H90O27S (1214.538991)

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

C21H32O6S (412.1919492)

(3r,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-isopropylheptanoic acid

C29H50O6 (494.36072)

(2r)-n-[(2s,3s,4r,13z)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docos-13-en-2-yl]-2-hydroxyhexadecanimidic acid

C44H85NO10 (787.617315)

(6s)-6-hydroxy-3-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4s)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15,17-octaen-1-yn-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H50O4 (594.3708899999999)

(6s)-6-hydroxy-3-[(3e,5e,7e,9e,11e,13e,15e)-18-[(4s)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-1,17-diyn-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H48O4 (592.3552407999999)

9a,11a-dimethyl-1-{6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]hept-3-en-2-yl}-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,7-tetrol

C32H54O9 (582.3767634)

(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2r,3s,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydrocyclopenta[a]phenanthrene-3,5,5a,7-tetrol

C32H56O9 (584.3924126000001)

1-(7-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-2,3,3b,5,7-pentol

C27H48O6 (468.3450708)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(1s)-1-hydroxy-1-[(2r,3s)-3-(2-methylpropyl)oxiran-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C56H92O28S (1244.5495552)

9a,11a-dimethyl-1-{6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]heptan-2-yl}-tetradecahydrocyclopenta[a]phenanthrene-2,3,3b,5,7-pentol

C32H56O10 (600.3873276)

(2r)-2-hydroxy-n-[(2s,3s,4r,13z)-1,3,4-trihydroxydocos-13-en-2-yl]hexadecanimidic acid

C38H75NO5 (625.564494)

{5-[(4-{[5-({4,5-dihydroxy-6-methyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-4-hydroxy-6-methyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl)oxy]-1-(2-hydroxy-6-methyl-4-oxoheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl}oxidanesulfonic acid

C57H94O27S (1242.5702894)

[(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H42O6S (494.27019520000005)

(1s,3s)-1-methyl-1h,2h,3h,4h,9h-pyrido[3,4-b]indole-3-carboxylic acid

C13H14N2O2 (230.1055224)

2-[(2-methyl-6-{3,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl}heptan-3-yl)oxy]oxane-3,4,5-triol

C32H56O8 (568.3974976000001)

ossipurinolo

C5H4N4O2 (152.0334244)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4r,6r)-4-{[(2s,3r,4s,5s,6r)-5-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-methyl-3-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-6-methyl-5-oxooxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C57H92O27S (1240.5546402)

1-(5-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-diol

C27H46O3 (418.34467659999996)

[(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-{[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-methyl-5-(sulfooxy)oxan-2-yl]oxy}-1-[(2r,5s)-5-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C33H54O14S2 (738.2954824000001)

[(1r,3s,3as,3br,5s,7s,9ar,9bs,11ar)-5,7-dihydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxidanesulfonic acid

C32H56O11S (648.3543146000001)

(1r,2r,3s,3as,3bs,5s,5as,7s,9as,9br,11ar)-1-[(2r,6s)-7-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-2,3,3b,5,7-pentol

C27H48O6 (468.3450708)

9a,11a-dimethyl-1-(6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptan-2-yl)-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,7-tetrol

C33H58O10 (614.4029768)

(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-9a,11a-dimethyl-1-[(2r,3e,5r)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}hept-3-en-2-yl]-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,7-tetrol

C32H54O9 (582.3767634)

(1r)-4-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15,17-octaen-1-yn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

C40H54O2 (566.4123584)

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docos-13-en-2-yl)-2-hydroxyhexadecanimidic acid

C44H85NO10 (787.617315)

doradexanthin

C40H54O3 (582.4072734)

(2s)-2-(phenylamino)propanoic acid

C9H11NO2 (165.0789746)

1-{5,7-dihydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}ethanone

C21H32O3 (332.23513219999995)

[5-({4-[(5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-3,5-dihydroxy-6-methyloxan-2-yl}oxy)-1-(2-hydroxy-6-methylhept-5-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C56H92O27S (1228.5546402)

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

C27H44O3 (416.3290274)

1-(7-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-2,3,5,7-tetrol

C27H48O5 (452.3501558)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C44H72O19S (936.4388282)

[(1s,5s,7s,9ar,11as)-5-({4-[(5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-3,5-dihydroxy-6-methyloxan-2-yl}oxy)-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C56H92O28S (1244.5495552)

[(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-3,3b,5-trihydroxy-9a,11a-dimethyl-1-[(2r,3e,5r)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}hept-3-en-2-yl]-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C32H54O12S (662.3335804000001)

2-[(3,3b,5-trihydroxy-9a,11a-dimethyl-1-{6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]heptan-2-yl}-tetradecahydrocyclopenta[a]phenanthren-7-yl)oxy]oxane-3,4,5-triol

C37H64O13 (716.4346694000001)

9a,11a-dimethyl-1-{6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]heptan-2-yl}-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,4,5,7-tetrol

C32H56O9 (584.3924126000001)

(2s,3r,4s,5r)-2-{[(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-3,3b,5-trihydroxy-9a,11a-dimethyl-1-[(2r,3e,5r)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}hept-3-en-2-yl]-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}oxane-3,4,5-triol

C37H62O13 (714.4190202)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-1-acetyl-5-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C21H32O6S (412.1919492)

(2r,3r,4s,5s,6r)-2-{[(3s,6r)-6-[(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-3,3b,5-trihydroxy-9a,11a-dimethyl-7-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methylheptan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C38H66O14 (746.4452336)

[(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3r,4s,5r,6r)-3-{[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-methyl-4-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxoheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C62H102O32S (1390.6074612)

(1r,2r,3r,3as,3bs,4r,5r,5ar,6r,7s,9as,9br,11ar)-1-[(2r,6s)-7-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-2,3,3b,4,5,6,7-heptol

C27H48O8 (500.33490079999996)

[(1e,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5s,6r)-5-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-methyl-3-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-1-(6-methyl-4-oxohept-5-en-2-ylidene)-2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C57H90O26S (1222.5440760000001)

{5-[(4-{[5-({3-[(3,5-dihydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)-4-hydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl)oxy]-1-(2-hydroxy-6-methyl-4-oxoheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl}oxidanesulfonic acid

C62H102O33S (1406.6023762)

(2r)-2-hydroxy-n-[(2s,3r,4e,13z)-3-hydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docosa-4,13-dien-2-yl]tetradecanimidic acid

C42H79NO9 (741.5754524)

(1r,2r,3r,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,6s)-7-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-2,3,5,5a,7-pentol

C27H48O6 (468.3450708)

(2s)-2-hydroxy-n-[(2s,3s,4e,12e)-3-hydroxy-1-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}henicosa-4,12-dien-2-yl]hexadecanimidic acid

C43H81NO9 (755.5911016)

1-(7-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-2,3,3b,4,5,6,7-heptol

C27H48O8 (500.33490079999996)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C56H92O27S (1228.5546402)

[(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-3,3b,5-trihydroxy-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C32H56O12S (664.3492296000001)

(1r,3r,3as,3bs,5s,5as,7s,9as,9br,11ar)-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptan-2-yl]-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,7-tetrol

C33H58O10 (614.4029768)

(2s,3r,4r,5r)-2-{[(3s,6r)-6-[(1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-3,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-3-yl]oxy}oxane-3,4,5-triol

C32H56O8 (568.3974976000001)

(1r,2r,3s,3as,3bs,4r,5r,5ar,6r,7s,9as,9br,11ar)-1-[(2r,6s)-7-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-2,3,3b,4,5,6,7-heptol

C27H48O8 (500.33490079999996)

2-hydroxy-n-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docosa-4,9-dien-2-yl)hexadecanimidic acid

C44H83NO9 (769.6067508)

adenosine, 2'-deoxy-

C10H13N5O3 (251.10183480000003)

(2s,3r,4s,5r)-2-{[(1r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-3,3b,5-trihydroxy-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}oxane-3,4,5-triol

C37H62O13 (714.4190202)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5s,6r)-5-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-methyl-3-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C57H94O27S (1242.5702894)

(1r,3r,3as,3bs,4s,5r,5as,7s,9ar,9bs,11ar)-9a,11a-dimethyl-1-[(2r,5s)-6-methyl-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,4,5,7-tetrol

C32H56O9 (584.3924126000001)

[(3r,4r,5r,6s)-6-{[(3s,6r)-6-[(1r,3s,5s,5ar,7s,9as,11ar)-3,3b,5,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methylheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxidanesulfonic acid

C32H56O12S (664.3492296000001)

{5-[(4-{[5-({4,5-dihydroxy-6-methyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-4-hydroxy-6-methyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl)oxy]-9a,11a-dimethyl-1-(6-methyl-4-oxohept-5-en-2-ylidene)-2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl}oxidanesulfonic acid

C57H90O26S (1222.5440760000001)

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptadecan-2-yl)-2-hydroxytetracos-15-enimidic acid

C47H91NO10 (829.6642626)

[(1s,3as,3bs,5s,5as,7s,9as,11as)-5-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-4-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-1-[(2s)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C49H80O23S (1068.4810850000001)

[5-hydroxy-1-(2-hydroxy-6-methyl-4-oxoheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H44O7S (512.2807594)

(1r,3s,3as,3bs,5r,5ar,7s,9ar,9br,11ar)-9a,11a-dimethyl-1-[(2r,5r)-6-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)heptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol

C35H62O11 (658.4291902)

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

C21H32O3 (332.23513219999995)

(2r)-2-hydroxy-n-[(2s,3r,4e,13z)-3-hydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docosa-4,13-dien-2-yl]pentadecanimidic acid

C43H81NO9 (755.5911016)

1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-5-methylpyrimidin-2-one

C10H14N2O6 (258.0851824)

2-hydroxy-n-(1,3,4-trihydroxydocos-13-en-2-yl)hexadecanimidic acid

C38H75NO5 (625.564494)

2-[(3,3b,5-trihydroxy-9a,11a-dimethyl-1-{6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]heptan-2-yl}-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl)oxy]oxane-3,4,5-triol

C37H62O13 (714.4190202)

[(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-{[(2r,3r,4s,5r,6r)-4-{[(2s,3r,4s,5r)-5-{[(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C56H90O27S (1226.538991)

(3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid

C27H44O6 (464.3137724)

(1s,3as,3bs,5s,5as,7s,9as,11as)-1-[(1r)-1-hydroxyethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthrene-5,7-diol

C21H34O3 (334.25078140000005)

1-(7-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-2,3,5,5a,7-pentol

C27H48O6 (468.3450708)