NCBI Taxonomy: 5402

Adenine

C5H5N5 (135.0545)

Adenine is the parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. It has a role as a human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purine nucleobase and a member of 6-aminopurines. It derives from a hydride of a 9H-purine. A purine base and a fundamental unit of adenine nucleotides. Adenine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Adenine is a natural product found in Fritillaria cirrhosa, Annona purpurea, and other organisms with data available. Adenine is a purine nucleobase with an amine group attached to the carbon at position 6. Adenine is the precursor for adenosine and deoxyadenosine nucleosides. Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (A3372, A3373). Adenine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine base and a fundamental unit of ADENINE NUCLEOTIDES. See also: adenine; dextrose, unspecified form (component of) ... View More ... Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (PMID: 17052198, 17520339). Widespread throughout animal and plant tissue, purine components of DNA, RNA, and coenzymes. Vitamin The parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. Adenine (/ˈædɪnɪn/) (symbol A or Ade) is a purine nucleobase. It is one of the four nucleobases in the nucleic acids of DNA, the other three being guanine (G), cytosine (C), and thymine (T). Adenine derivatives have various roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions in protein synthesis and as a chemical component of DNA and RNA.[2] The shape of adenine is complementary to either thymine in DNA or uracil in RNA. The adjacent image shows pure adenine, as an independent molecule. When connected into DNA, a covalent bond is formed between deoxyribose sugar and the bottom left nitrogen (thereby removing the existing hydrogen atom). The remaining structure is called an adenine residue, as part of a larger molecule. Adenosine is adenine reacted with ribose, as used in RNA and ATP; Deoxyadenosine is adenine attached to deoxyribose, as used to form DNA. Adenine forms several tautomers, compounds that can be rapidly interconverted and are often considered equivalent. However, in isolated conditions, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.[3][4] Purine metabolism involves the formation of adenine and guanine. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which in turn is synthesized from a pre-existing ribose phosphate through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as the coenzyme tetrahydrofolate. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3].

Inosine

C10H12N4O5 (268.0808)

Inosine, also known as hypoxanthosine or inotin, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Inosine is formed when hypoxanthine is attached to a ribose ring a beta-N9-glycosidic bond. Inosine is an intermediate in the degradation of purines and purine nucleosides to uric acid. Inosine is also an intermediate in the purine salvage pathway. Inosine occurs in the anticodon of certain transfer RNA molecules and is essential for proper translation of the genetic code in wobble base pairs. Inosine exists in all living species, ranging from bacteria to plants to humans. Inosine participates in a number of enzymatic reactions. In particular, inosine can be biosynthesized from inosinic acid through its interaction with the enzyme known as cytosolic purine 5-nucleotidase. In addition, inosine can be converted into hypoxanthine and ribose 1-phosphate through its interaction with the enzyme known as purine nucleoside phosphorylase. Altered levels of inosine have also been associated with purine nucleoside phosphorylase deficiency and xanthinuria type I, both of which are inborn errors of metabolism. Animal studies have suggested that inosine has neuroprotective properties. It has been proposed as a potential treatment for spinal cord injury (PMID: 16317421) and for administration after stroke, as inosine appears to induce axonal rewiring (PMID: 12084941). After ingestion, inosine is metabolized into uric acid, which has been found to be a natural antioxidant and peroxynitrite scavenger. As such, inosine may have potential benefits to patients with multiple sclerosis and Parkinson’s disease (PMID: 19425822). Inosine can also be produced by gut bacteria and appears to have a number of beneficial effects. Inosine, has been shown to activate peroxisome proliferator-activated receptor (PPAR)-gamma signaling in human colon epithelial cells. Furthermore, exogenous treatment of inosine has been found to protect against DSS-induced colitis in rodents by improving adenosine 2A receptor (A2AR)/PPAR-gamma-dependent mucosal barrier functions (PMID: 33820558). Microbiome-derived inosine has also been shown to modulate the response to checkpoint inhibitor immunotherapy in cancer models. In particular, decreased gut barrier function induced by immunotherapy increases systemic translocation of bacterially derived inosine and activates antitumor T cells. The effect of inosine is dependent on T cell expression of the adenosine A2A receptor and requires co-stimulation. Inosine appears to have other roles in non-mammalian system. For instance, it has been found to be an important feed stimulant by itself or in combination with certain amino acids in some species of farmed fish. For example, inosine and inosine-5-monophosphate have been reported as specific feeding stimulants for turbot fry, (Scophthalmus maximus) and Japanese amberjack. Inosine is a purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines D-ribonucleoside and a member of inosines. It is functionally related to a hypoxanthine and a ribofuranose. A purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed) Inosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Inosine is a natural product found in Fritillaria thunbergii, Cichorium endivia, and other organisms with data available. Inosine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed) G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals A purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Present in meat extracts and sugar beet Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Spectral] Inosine (exact mass = 268.08077) and L-Methionine (exact mass = 149.05105) and Adenosine (exact mass = 267.09675) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and L-Tyrosine (exact mass = 181.07389) and Guanosine (exact mass = 283.09167) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and Guanosine (exact mass = 283.09167) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 110 KEIO_ID I003 Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3].

Fumaric acid

C4H4O4 (116.011)

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

Ergosterol

C28H44O (396.3392)

Ergosterol is a phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. It has a role as a fungal metabolite and a Saccharomyces cerevisiae metabolite. It is a 3beta-sterol, an ergostanoid, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. Ergosterol is a natural product found in Gladiolus italicus, Ramaria formosa, and other organisms with data available. ergosterol is a metabolite found in or produced by Saccharomyces cerevisiae. A steroid occurring in FUNGI. Irradiation with ULTRAVIOLET RAYS results in formation of ERGOCALCIFEROL (vitamin D2). See also: Reishi (part of). Ergosterol, also known as provitamin D2, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. Ergosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-87-4 (retrieved 2024-07-12) (CAS RN: 57-87-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

Stearic acid

C18H36O2 (284.2715)

Stearic acid, also known as stearate or N-octadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, stearic acid is considered to be a fatty acid lipid molecule. Stearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Stearic acid can be synthesized from octadecane. Stearic acid is also a parent compound for other transformation products, including but not limited to, 3-oxooctadecanoic acid, (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid, and 16-methyloctadecanoic acid. Stearic acid can be found in a number of food items such as green bell pepper, common oregano, ucuhuba, and babassu palm, which makes stearic acid a potential biomarker for the consumption of these food products. Stearic acid can be found primarily in most biofluids, including urine, feces, cerebrospinal fluid (CSF), and sweat, as well as throughout most human tissues. Stearic acid exists in all living species, ranging from bacteria to humans. In humans, stearic acid is involved in the plasmalogen synthesis. Stearic acid is also involved in mitochondrial beta-oxidation of long chain saturated fatty acids, which is a metabolic disorder. Moreover, stearic acid is found to be associated with schizophrenia. Stearic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin . Stearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Pyroglutamic acid

C5H7NO3 (129.0426)

Pyroglutamic acid (5-oxoproline) is a cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on an L-amino acid. Elevated blood levels may be associated with problems of glutamine or glutathione metabolism. This compound is found in substantial amounts in brain tissue and other tissues in bound form, especially skin. It is also present in plant tissues. It is sold, over the counter, as a "smart drug" for improving blood circulation in the brain. Pyroglutamate in the urine is a biomarker for the consumption of cheese. When present in sufficiently high levels, pyroglutamic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of pyroglutamic acid are associated with at least five inborn errors of metabolism including 5-oxoprolinuria, 5-oxoprolinase deficiency, glutathione synthetase deficiency, hawkinsinuria, and propionic acidemia. Pyroglutamic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. It has been shown that pyroglutamic acid releases GABA from the cerebral cortex and displays anti-anxiety effects in a simple approach-avoidance conflict situation in the rat. In clinical pharmacology experiments, pyroglutamic acid significantly shortens the plasma half-life of ethanol during acute intoxication. Found in vegetables, fruits and molasses. A cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. Pyroglutamate in the urine is a biomarker for the consumption of cheese C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent

5-Amino-6-ribitylamino uracil

C9H16N4O6 (276.107)

5-Amino-6-ribitylamino uracil is an intermediate in riboflavin metabolism. It is converted from 5-amino-6-(5-phosphoribitylamino)uracil via dephosphorylation by the enzyme phosphohistidine phosphatase 1 (EC 3.1.3.-). It is considered to be the second product of the riboflavin synthase reaction (PMID: 14245407). Humans do not have all the enzymes needed to synthesize or metabolize riboflavin. However, gut microflora do have the necessary enzymatic machinery to produce and metabolize this vitamin. Riboflavin (or vitamin B2) is an easily absorbed micronutrient with a key role in maintaining health in humans and animals. It is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. Riboflavin is yellow or yellow-orange in colour and in addition to being used as a food colouring it is also used to fortify some foods including baby foods, breakfast cereals, pastas, sauces, processed cheese, fruit drinks, vitamin-enriched milk products, some energy drinks, and vitamin supplements. 5-amino-6-(d-ribitylamino)uracil, also known as 5-amino-6-ribitylamino-2,4-(1h,3h)pyrimidinedione or 5-arpd, is a member of the class of compounds known as pentoses. Pentoses are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 5-amino-6-(d-ribitylamino)uracil is soluble (in water) and a very weakly acidic compound (based on its pKa). 5-amino-6-(d-ribitylamino)uracil can be found in a number of food items such as radish (variety), chinese cabbage, common beet, and spinach, which makes 5-amino-6-(d-ribitylamino)uracil a potential biomarker for the consumption of these food products. 5-amino-6-(d-ribitylamino)uracil exists in E.coli (prokaryote) and yeast (eukaryote).

7-Hydroxy-6-methyl-8-ribityl lumazine

C12H16N4O7 (328.1019)

7-Hydroxy-6-methyl-8-ribityl lumazine is an intermediate in Riboflavin metabolism. it is converted from 6,7-Dimethyl-8-(1-D-ribityl)lumazine. [HMDB] 7-Hydroxy-6-methyl-8-ribityl lumazine is an intermediate in Riboflavin metabolism. it is converted from 6,7-Dimethyl-8-(1-D-ribityl)lumazine.

Isovelleral

C15H20O2 (232.1463)

Piperdial

C15H22O3 (250.1569)

Piperdial is found in mushrooms. Piperdial is a constituent of Lactarius piperatus Constituent of Lactarius piperatus. Piperdial is found in mushrooms.

Ergosterol peroxide

C28H44O3 (428.329)

Ergosterol peroxide is found in fruits. Ergosterol peroxide is obtained from leaves of Ananas comosus (pineapple obtained from leaves of Ananas comosus (pineapple). Ergosterol peroxide is found in pineapple and fruits.

Lactaronecatorin A

C15H22O3 (250.1569)

Lactaronecatorin A is found in mushrooms. Lactaronecatorin A is a constituent of Lactarius blennius (slimy milk cap). Constituent of Lactarius blennius (slimy milk cap). Lactaronecatorin A is found in mushrooms.

Lactapiperanol C

C16H26O4 (282.1831)

Lactapiperanol A is found in mushrooms. Lactapiperanol A is a constituent of Lactarius piperatus. Constituent of Lactarius piperatus. Lactapiperanol C is found in mushrooms.

Repandiol

C10H10O4 (194.0579)

Repandiol is found in mushrooms. Repandiol is a constituent of the edible mushrooms Hydnum repandum and Hydnum repandum var. album. Constituent of the edible mushrooms Hydnum repandum and Hydnum repandum variety album. Repandiol is found in mushrooms.

Piperalol

C15H24O3 (252.1725)

Piperalol is found in mushrooms. Piperalol is a constituent of Lactarius piperatus Constituent of Lactarius piperatus. Piperalol is found in mushrooms.

N-Nitroethylenediamine

C2H7N3O2 (105.0538)

N-Nitroethylenediamine is found in mushrooms. N-Nitroethylenediamine is isolated from Agaricus silvaticus (red staining mushroom

Baikiain

C6H9NO2 (127.0633)

Baikiain, also known as 4,5-dehydropipecolic acid, (+-)-isomer, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Baikiain is soluble (in water) and a moderately acidic compound (based on its pKa). Baikiain can be found in date, which makes baikiain a potential biomarker for the consumption of this food product.

Inosine

C10H12N4O5 (268.0808)

G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3].

L-5-Oxoproline

C5H7NO3 (129.0426)

C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent

Aristolone

C15H22O (218.1671)

Aristolone is a natural product found in Litophyton erectum, Aristolochia clematitis, and other organisms with data available. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1]. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1].

Cerevisterol

C28H46O3 (430.3447)

An ergostanoid that is (22E)-ergosta-7,22-diene substituted by hydroxy groups at positions 3, 5 and 6 (the 3beta,5alpha,6beta stereoisomer). It has been isolated from the fungus, Xylaria species. Cerevisterol is a steroid isolated from the fruiting bodies of Agaricus blazei[1]. Cerevisterol is a steroid isolated from the fruiting bodies of Agaricus blazei[1].

Ergosterol peroxide

C28H44O3 (428.329)

Russuphelol

C26H16Cl6O8 (665.8976)

Russuphelin C

C18H10Cl4O6 (461.9231)

2,6-dichloro-4-methoxyphenol

C7H6Cl2O2 (191.9745)

2-amino-7-hydroxyoctanoic acid

C8H17NO3 (175.1208)

Ergosterol

C28H44O (396.3392)

Indicator of fungal contamination, especies in cereals. Occurs in yeast and fungi. The main fungal steroidand is also found in small amts. in higher plant prods., e.g. palm oil [DFC]. D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins 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. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

Inosine

C10H12N4O5 (268.0808)

G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals Formula(Parent): C10H12N4O5; Bottle Name:Inosine; PRIME Parent Name:Inosine; PRIME in-house No.:0256, Purines COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; UGQMRVRMYYASKQ_STSL_0164_Inosine_2000fmol_180430_S2_LC02_MS02_125; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3].

Adenine

C5H5N5 (135.0545)

COVID info from PDB, Protein Data Bank, COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2357 INTERNAL_ID 2357; CONFIDENCE Reference Standard (Level 1) MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; GFFGJBXGBJISGV_STSL_0142_Adenine_0125fmol_180430_S2_LC02_MS02_16; 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. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3].

L-Pyroglutamicacid

C5H7NO3 (129.0426)

C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent

stearic acid

C18H36O2 (284.2715)

Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Fumaric Acid

C4H4O4 (116.011)

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

Pyroglutamic acid

C5H7NO3 (129.0426)

Octadecanoic acid

C18H36O2 (284.2715)

A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

N-Nitroethylenediamine

C2H7N3O2 (105.0538)

Piperalol

C15H24O3 (252.1725)

Blennin C

C15H22O3 (250.1569)

Repandiol

C10H10O4 (194.0579)

Allitol

C6H14O6 (182.079)

Allitol is a rare natural polyol that can be used as a sweetener. Allitol is an important intermediate for the preparation of the agents which against diabetes, cancer, and viral infections, including AIDS[1]. Allitol is a rare natural polyol that can be used as a sweetener. Allitol is an important intermediate for the preparation of the agents which against diabetes, cancer, and viral infections, including AIDS[1].

piperidine-2-carboxylic acid

C6H11NO2 (129.079)

Adenin

C5H5N5 (135.0545)

COVID info from PDB, Protein Data Bank, COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3]. Adenine (6-Aminopurine), a purine, is one of the four nucleobases in the nucleic acid of DNA. Adenine acts as a chemical component of DNA and RNA. Adenine also plays an important role in biochemistry involved in cellular respiration, the form of both ATP and the cofactors (NAD and FAD), and protein synthesis[1][2][3].

5-Amino-6-(D-ribitylamino)uracil

C9H16N4O6 (276.107)

An aminouracil that is D-ribitol in which the hydroxy group at position 1 is substituted by the 6-amino group of 5,6-diaminouracil. Early intermediate in bacterial riboflavin synthesis.

1-deoxy-1-(7-hydroxy-6-methyl-2,4-dioxo-3,4-dihydropteridin-8(2H)-yl)-D-ribitol

C12H16N4O7 (328.1019)

Piperdial

C15H22O3 (250.1569)

[(4as,6s,7as,7br)-6-(hydroxymethyl)-6,7b-dimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methanol

C15H24O2 (236.1776)

2-[(2s)-2-(hydroxymethyl)-2,4,6-trimethyl-1,3-dihydroinden-5-yl]ethanol

C15H22O2 (234.162)

(10r)-7,14-dihydroxy-10-methoxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-3-one

C15H10O6 (286.0477)

(2e,6s)-6-[(3r,3ar,5as,6s,7z,9ar,9bs)-6-(2-carboxyethyl)-7-(1-carboxyethylidene)-3a,5a,9b-trimethyl-octahydro-1h-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

C30H46O6 (502.3294)

1,8a-dimethyl-8-(prop-1-en-2-yl)-2,3,4,8-tetrahydro-1h-naphthalene

C15H22 (202.1721)

(3s)-5-hydroxy-4',7-bis(3-methylbut-3-en-1-yn-1-yl)-2,2',5'-trioxospiro[1-benzofuran-3,1'-cyclopentan]-3'-ene-4-carbaldehyde

C23H14O6 (386.079)

5,5,6b-trimethyl-1h,3ah,4h,6h,6ah-cyclopropa[e]indene-1a,2-dicarbaldehyde

C15H20O2 (232.1463)

13-methoxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.0¹,³.0⁴,⁸]tridecan-9-ol

C16H26O3 (266.1882)

5-[(5-amino-2,6-dihydroxypyrimidin-4-yl)amino]pentane-1,2,3,4-tetrol

C9H16N4O6 (276.107)

(4s,4ar,7as,8s)-4,8-dihydroxy-6,6,8-trimethyl-3h,4h,4ah,5h,7h,7ah,9h-azuleno[5,6-c]furan-1-one

C15H22O4 (266.1518)

(2z,4z,6r)-6-[(1r,2s,5r,6r,9r,10s)-10-(2-carboxyethyl)-2,6,9,12-tetramethyl-14-oxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-11(15),12-dien-5-yl]-2-methylhepta-2,4-dienoic acid

C30H42O5 (482.3032)

6,6,8-trimethyl-3h,4ah,5h,7h,7ah,8h-azuleno[5,6-c]furan-1-one

C15H20O2 (232.1463)

(3r,4s,8r,9s,12s)-6,6,9-trimethyl-2,13-dioxapentacyclo[9.3.0.0¹,³.0⁴,⁸.0⁹,¹¹]tetradecan-12-yl octadecanoate

C33H56O4 (516.4178)

(2s)-5-(2-hydroxyethyl)-2-(hydroxymethyl)-2,6-dimethyl-1,3-dihydroindene-4,7-diol

C14H20O4 (252.1362)

2,4-dihydroxy-6-methyl-8-[(2s,3s,4r)-2,3,4,5-tetrahydroxypentyl]pteridin-7-one

C12H16N4O7 (328.1019)

4a-hydroxy-6,6,8-trimethyl-3h,5h,7h,7ah,8h-azuleno[5,6-c]furan-1-one

C15H20O3 (248.1412)

(4ar,7ar,8r)-6,6,8-trimethyl-3h,4ah,5h,7h,7ah,8h-azuleno[5,6-c]furan-1-one

C15H20O2 (232.1463)

(1ar,2s,3s,3ar,6as,6br)-3-hydroxy-2-(hydroxymethyl)-5,5,6b-trimethyl-hexahydro-1h-cyclopropa[e]indene-1a-carbaldehyde

C15H24O3 (252.1725)

3-(2-hydroxyethyl)-8-(hydroxymethyl)-4,8-dimethyl-10-oxatricyclo[4.3.1.0¹,⁶]dec-3-ene-2,5-dione

C14H18O5 (266.1154)

2,4-dihydroxy-6-methyl-8-(2,3,4,5-tetrahydroxypentyl)pteridin-7-one

C12H16N4O7 (328.1019)

(1r,1ar,2s,3r,7r,7ar,7br)-2,3-dihydroxy-1-(hydroxymethyl)-1,7,7a-trimethyl-1ah,2h,3h,6h,7h,7bh-cyclopropa[a]naphthalen-5-one

C15H22O4 (266.1518)

(1ar,7r,7ar,7bs)-4-amino-1,1,7,7a-tetramethyl-1ah,6h,7h,7bh-cyclopropa[a]naphthalene-2,3,5-trione

C15H19NO3 (261.1365)

(1r,3r,4s,8r,9s,10r)-9-hydroxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.0¹,³.0⁴,⁸]tridecan-13-one

C15H22O3 (250.1569)

6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2a-ol

C15H24O2 (236.1776)

(1r,3ar,5r,5ar,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,5a,7-triol

C29H48O3 (444.3603)

(1s,1ar,3as,7r,7ar,7br)-1-(hydroxymethyl)-1,7,7a-trimethyl-hexahydro-1ah-cyclopropa[a]naphthalene-2,4-dione

C15H22O3 (250.1569)

(5s)-4-[(2r)-2-(4,4-dimethylcyclopent-1-en-1-yl)propyl]-5-hydroxy-2,5-dihydrofuran-3-carbaldehyde

C15H22O3 (250.1569)

(2ar,4as,6s,7as,7br)-6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2a-ol

C15H24O2 (236.1776)

(1r,3as,5r,5ar,7s,9ar,9br,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,5a,7-triol

C28H46O3 (430.3447)

(2e,6r)-6-[(3r,3ar,5as,6s,9ar,9bs)-6-(3-hydroxypropyl)-3a,5a,9b-trimethyl-7-(propan-2-ylidene)-octahydro-1h-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

C30H50O3 (458.376)

(3ar,4r,8ar)-7-(hydroxymethyl)-2,2,4-trimethyl-3,3a,4,8a-tetrahydro-1h-azulene-6-carbaldehyde

C15H22O2 (234.162)

[6-(hydroxymethyl)-6,7b-dimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-3-yl]methanol

C15H24O2 (236.1776)

9-hydroxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.0¹,³.0⁴,⁸]tridecan-13-one

C15H22O3 (250.1569)

1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,5a,7-triol

C29H48O3 (444.3603)

1-hydroxy-6,6,8-trimethyl-1h,5h,7h,7ah,8h-azuleno[5,6-c]furan-3,9-dione

C15H18O4 (262.1205)

(1s,2s,6r,7s,9s,10r,11r)-1,4,4-trimethyl-8,13-dioxatetracyclo[8.2.1.0²,⁶.0⁷,¹¹]tridecane-9,10-diol

C14H22O4 (254.1518)

6-[6-(3-hydroxypropyl)-3a,5a,9b-trimethyl-7-(propan-2-ylidene)-octahydro-1h-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

C30H50O3 (458.376)

d-allitol

C6H14O6 (182.079)

(4ar,6r,7ar,7bs)-7a-hydroxy-6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4ah,5h,7h-cyclobuta[e]inden-4-one

C15H22O3 (250.1569)

(1as,3as,6as,6br)-2-(hydroxymethyl)-5,5,6b-trimethyl-1h,3ah,4h,6h,6ah-cyclopropa[e]indene-1a-carbaldehyde

C15H22O2 (234.162)

(2ar,4ar,6s,7as,7br)-6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2a-ol

C15H24O2 (236.1776)

(1s,2s,6r,7s,9r,10r,11r)-1,4,4-trimethyl-8,13-dioxatetracyclo[8.2.1.0²,⁶.0⁷,¹¹]tridecane-9,10-diol

C14H22O4 (254.1518)

(4s,4ar,8s)-6,6,8-trimethyl-4h,4ah,5h,8h,9h-azuleno[5,6-c]furan-4-ol

C15H20O2 (232.1463)

2-[(2s)-2,6-bis(hydroxymethyl)-2,4-dimethyl-1,3-dihydroinden-5-yl]ethanol

C15H22O3 (250.1569)

(4s,4ar,7as,8r)-4,8-dihydroxy-6,6,8-trimethyl-3h,4h,4ah,5h,7h,7ah,9h-azuleno[5,6-c]furan-1-one

C15H22O4 (266.1518)

(2r)-6-(2-hydroxyethyl)-2-(hydroxymethyl)-7-(methoxymethyl)-2,5-dimethyl-1,3-dihydroinden-4-ol

C16H24O4 (280.1675)

(1as,7s,7as,7br)-1,1,7,7a-tetramethyl-1ah,5h,6h,7h,7bh-cyclopropa[a]naphthalene

C15H22 (202.1721)

3-hydroxy-2-(hydroxymethyl)-5,5,6b-trimethyl-hexahydro-1h-cyclopropa[e]indene-1a-carbaldehyde

C15H24O3 (252.1725)

2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one

C28H36O3 (420.2664)

(2e)-6-[(3r,3ar,5as,6s,9bs)-6-(3-ethoxy-3-oxopropyl)-3a,5a,9b-trimethyl-7-(propan-2-ylidene)-octahydro-1h-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

C32H52O4 (500.3865)

6-[7-(1-carboxyethylidene)-6-(3-hydroxypropyl)-3a,5a,9b-trimethyl-octahydro-1h-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

C30H48O5 (488.3502)

2-(8,8a-dimethyl-5,6,7,8-tetrahydro-1h-naphthalen-1-yl)propan-2-ol

C15H24O (220.1827)

5-hydroxy-4',7-bis(3-methylbut-3-en-1-yn-1-yl)-2,2',5'-trioxospiro[1-benzofuran-3,1'-cyclopentan]-3'-ene-4-carbaldehyde

C23H14O6 (386.079)

(1ar,7r,7ar)-4-amino-1,1,7,7a-tetramethyl-1ah,6h,7h,7bh-cyclopropa[a]naphthalene-2,3,5-trione

C15H19NO3 (261.1365)

o-phosphoethanolamine; bis(nonane)

C20H48NO4P (397.3321)

5-hydroxy-7-(3-methylbut-3-en-1-yn-1-yl)-3-[4-(3-methylbut-3-en-1-yn-1-yl)-5-oxofuran-2-ylidene]-2-oxo-1-benzofuran-4-carbaldehyde

C23H14O6 (386.079)

2-hydroxy-6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-4-one

C15H22O3 (250.1569)

(1r,2s,3r,7s,8s,9r)-2,8-dihydroxy-5,5,8-trimethyl-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridecan-10-one

C15H22O4 (266.1518)

6,6,9-trimethyl-2,13-dioxapentacyclo[9.3.0.0¹,³.0⁴,⁸.0⁹,¹¹]tetradecan-12-yl octadecanoate

C33H56O4 (516.4178)

9-hydroxy-6,6,8-trimethyl-1h,5h,7h,7ah,8h,9h-azuleno[5,6-c]furan-3-one

C15H20O3 (248.1412)

6-amino-2-({2-[(2-{[2-({2-[(2-{[2-({2-[(3-carboxy-2-{[2-({2-[(2-{[4-carboxy-2-({2-[(2-{[2-({2-[(2-{[2-({[1-(2,6-diaminohexanoyl)pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene)amino]-1,3-dihydroxybutylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-methylbutylidene)amino]-1-hydroxy-3-(4h-imidazol-4-yl)propylidene}amino)-1-hydroxybutylidene]amino}-1,3-dihydroxypropylidene)amino]-1-hydroxy-4-methylpentylidene}amino)-1-hydroxypropylidene]amino}-1-hydroxypropylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-1-hydroxy-4-(c-hydroxycarbonimidoyl)butylidene]amino}-1-hydroxypropylidene)amino]-1-hydroxy-3-methylbutylidene}amino)-1-hydroxy-3-sulfanylpropylidene]amino}-1,3-dihydroxypropylidene)amino]-1-hydroxy-4-(c-hydroxycarbonimidoyl)butylidene}amino)hexanoic acid

C100H162N28O32S (2299.163)

6,6,8-trimethyl-4h,4ah,5h,7h,7ah,9h-azuleno[5,6-c]furan-4,8-diol

C15H22O3 (250.1569)

3,5-bis(2,6-dichloro-4-hydroxyphenoxy)-2-(2,6-dichloro-4-methoxyphenoxy)-4-methoxyphenol

C26H16Cl6O8 (665.8976)

(1s,2s,3r,7s,8s,10s,13s)-2-hydroxy-8-methoxy-5,5,8-trimethyl-12,14-dioxatetracyclo[8.4.0.0¹,¹³.0³,⁷]tetradecan-11-one

C16H24O5 (296.1624)

6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-4-ol

C15H24O2 (236.1776)

6,6,9-trimethyl-2,13-dioxapentacyclo[9.3.0.0¹,³.0⁴,⁸.0⁹,¹¹]tetradecan-12-yl hexadecanoate

C31H52O4 (488.3865)

(7ar,8r)-1-hydroxy-6,6,8-trimethyl-1h,5h,7h,7ah,8h-azuleno[5,6-c]furan-3,9-dione

C15H18O4 (262.1205)

3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-4-ol

C15H24O2 (236.1776)

6-[6-(2-carboxyethyl)-3a,5a,9b-trimethyl-7-(propan-2-ylidene)-octahydro-1h-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

C30H48O4 (472.3552)

(7ar,8r,9r)-9-hydroxy-6,6,8-trimethyl-1h,5h,7h,7ah,8h,9h-azuleno[5,6-c]furan-3-one

C15H20O3 (248.1412)

1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C28H44O (396.3392)

(4s,4ar)-6,6,8-trimethyl-4h,4ah,5h,7h,9h-azuleno[5,6-c]furan-4-ol

C15H20O2 (232.1463)

(4r,4as,7ar,8r)-4,8-dihydroxy-6,6,8-trimethyl-3h,4h,4ah,5h,7h,7ah,9h-azuleno[5,6-c]furan-1-one

C15H22O4 (266.1518)

(1s,8s,9s,13r)-8,11,11-trimethyl-4,14-dioxatetracyclo[6.5.1.0²,⁶.0⁹,¹³]tetradeca-2,5-diene

C15H20O2 (232.1463)

4,8-dihydroxy-6,8-dimethyl-1-oxo-3h,4h,4ah,5h,7h,7ah,9h-azuleno[5,6-c]furan-6-carboxylic acid

C15H20O6 (296.126)

(4s,4ar,6r,7as,8s)-4,8-dihydroxy-6-(hydroxymethyl)-6,8-dimethyl-3h,4h,4ah,5h,7h,7ah,9h-azuleno[5,6-c]furan-1-one

C15H22O5 (282.1467)

[(2r,3r)-3-{4-[(2r,3r)-3-(hydroxymethyl)oxiran-2-yl]buta-1,3-diyn-1-yl}oxiran-2-yl]methanol

C10H10O4 (194.0579)

3,4,8-trihydroxy-6,6,8-trimethyl-3h,4h,4ah,5h,7h,7ah,9h-azuleno[5,6-c]furan-1-one

C15H22O5 (282.1467)

9-hydroxy-6-(hydroxymethyl)-3,6-dimethyl-12-oxatetracyclo[8.3.0.0¹,³.0⁴,⁸]tridecan-13-one

C15H22O4 (266.1518)

(1as,7s,7as,7br)-1,1,7,7a-tetramethyl-1ah,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalen-2-one

C15H22O (218.1671)

isovellerdiol

C15H24O2 (236.1776)

(1as,7s,7as,7br)-3-hydroxy-1,1,7,7a-tetramethyl-1ah,6h,7h,7bh-cyclopropa[a]naphthalen-2-one

C15H20O2 (232.1463)

(2s)-2-hydroxy-n-[(2s,3s,4r)-1,3,4-trihydroxyicosan-2-yl]docosanimidic acid

C42H85NO5 (683.6427)

6-[6-(2-carboxyethyl)-7-(1-carboxyethylidene)-3a,5a,9b-trimethyl-octahydro-1h-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

C30H46O6 (502.3294)

furan-2,3-diol

C4H4O3 (100.016)

(1s,2s,5s,6r,9s,10r,15s)-5-(5,6-dimethylhept-3-en-2-yl)-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

C28H44O3 (428.329)

1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,5a,7-triol

C28H46O3 (430.3447)

(4as,7ar,8s)-4a-hydroxy-6,6,8-trimethyl-3h,5h,7h,7ah,8h-azuleno[5,6-c]furan-1-one

C15H20O3 (248.1412)

2,6-bis(2,6-dichloro-4-hydroxyphenoxy)benzene-1,4-diol

C18H10Cl4O6 (461.9231)

2,4-dihydroxy-8-[(2s,3s,4r)-2,3,4,5-tetrahydroxypentyl]pteridin-7-one

C11H14N4O7 (314.0862)

lepidolide

C30H40O6 (496.2825)

(2r)-6-(2-ethoxyethyl)-7-(ethoxymethyl)-2-(hydroxymethyl)-2,5-dimethyl-1,3-dihydroinden-4-ol

C19H30O4 (322.2144)

(3ar,4r,5r,8s,8ar)-4-hydroxy-5-(hydroxymethyl)-2,2,8-trimethyl-3,3a,4,5,8,8a-hexahydro-1h-azulene-6-carbaldehyde

C15H24O3 (252.1725)

6-(2-hydroxyethyl)-2-(hydroxymethyl)-7-(methoxymethyl)-2,5-dimethyl-1,3-dihydroinden-4-ol

C16H24O4 (280.1675)

(3r)-5-hydroxy-4',7-bis(3-methylbut-3-en-1-yn-1-yl)-2,2',5'-trioxospiro[1-benzofuran-3,1'-cyclopentan]-3'-ene-4-carbaldehyde

C23H14O6 (386.079)

3-{2,6,9,12-tetramethyl-5-[1-(4-methyl-5-oxo-2h-furan-2-yl)propan-2-yl]-14-oxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-11(15),12-dien-10-yl}propanoic acid

C30H42O5 (482.3032)

(4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-4-ol

C15H24O2 (236.1776)

(2r,3s,4s)-5-[(5-amino-2,6-dihydroxypyrimidin-4-yl)amino]pentane-1,2,3,4-tetrol

C9H16N4O6 (276.107)

1,4,4-trimethyl-8,13-dioxatetracyclo[8.2.1.0²,⁶.0⁷,¹¹]tridecane-9,10-diol

C14H22O4 (254.1518)

4-[(2s)-2-(4,4-dimethylcyclopent-1-en-1-yl)propyl]furan-3-carbaldehyde

C15H20O2 (232.1463)

2,3-dihydroxy-1,1,7,7a-tetramethyl-1ah,2h,3h,6h,7h,7bh-cyclopropa[a]naphthalen-5-one

C15H22O3 (250.1569)

2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpent-3-en-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one

C28H38O3 (422.2821)

4a-hydroxy-6-(hydroxymethyl)-3,6,7b-trimethyl-1h,2h,4h,5h,7h,7ah-cyclobuta[e]inden-4-yl acetate

C17H26O4 (294.1831)

(3r,4s,4ar,7as,8s)-3,4,8-trihydroxy-6,6,8-trimethyl-3h,4h,4ah,5h,7h,7ah,9h-azuleno[5,6-c]furan-1-one

C15H22O5 (282.1467)