NCBI Taxonomy: 458531

Eurycoma longifolia (ncbi_taxid: 458531)

found 206 associated metabolites at species taxonomy rank level.

Ancestor: Eurycoma

Child Taxonomies: none taxonomy data.

Scopoletin

7-hydroxy-6-methoxy-2H-chromen-2-one

C10H8O4 (192.0422568)


Scopoletin is a hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. It has a role as a plant growth regulator and a plant metabolite. It is functionally related to an umbelliferone. Scopoletin is a natural product found in Ficus auriculata, Haplophyllum cappadocicum, and other organisms with data available. Scopoletin is a coumarin compound found in several plants including those in the genus Scopolia and the genus Brunfelsia, as well as chicory (Cichorium), redstem wormwood (Artemisia scoparia), stinging nettle (Urtica dioica), passion flower (Passiflora), noni (Morinda citrifolia fruit) and European black nightshade (Solanum nigrum) that is comprised of umbelliferone with a methoxy group substituent at position 6. Scopoletin is used to standardize and establish pharmacokinetic properties for products derived from the plants that produce it, such as noni extract. Although the mechanism(s) of action have not yet been established, this agent has potential antineoplastic, antidopaminergic, antioxidant, anti-inflammatory and anticholinesterase effects. Plant growth factor derived from the root of Scopolia carniolica or Scopolia japonica. See also: Arnica montana Flower (part of); Lycium barbarum fruit (part of); Viburnum opulus root (part of). Isolated from Angelica acutiloba (Dong Dang Gui). Scopoletin is found in many foods, some of which are lambsquarters, lemon, sunflower, and sherry. Scopoletin is found in anise. Scopoletin is isolated from Angelica acutiloba (Dong Dang Gui A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA72_Scopoletin_pos_20eV.txt [Raw Data] CBA72_Scopoletin_pos_40eV.txt [Raw Data] CBA72_Scopoletin_neg_30eV.txt [Raw Data] CBA72_Scopoletin_neg_50eV.txt [Raw Data] CBA72_Scopoletin_pos_50eV.txt [Raw Data] CBA72_Scopoletin_pos_10eV.txt [Raw Data] CBA72_Scopoletin_neg_40eV.txt [Raw Data] CBA72_Scopoletin_neg_10eV.txt [Raw Data] CBA72_Scopoletin_pos_30eV.txt [Raw Data] CBA72_Scopoletin_neg_20eV.txt Scopoletin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=92-61-5 (retrieved 2024-07-12) (CAS RN: 92-61-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

Thymidine

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

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].

   

Vanillic acid

4-hydroxy-3-methoxybenzoic acid

C8H8O4 (168.0422568)


Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity (PMID: 16899266). Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072, 10543794, 11728709, 9579070). Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity. (PMID: 16899266). Vanillic acid is a monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. It has a role as a plant metabolite. It is a monohydroxybenzoic acid and a methoxybenzoic acid. It is a conjugate acid of a vanillate. Vanillic acid is a natural product found in Ficus septica, Haplophyllum cappadocicum, and other organisms with data available. Vanillic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. Vanillic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=121-34-6 (retrieved 2024-06-29) (CAS RN: 121-34-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

   

Adenosine

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

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].

   

Protocatechuic acid

3,4-dihydroxybenzoic acid

C7H6O4 (154.0266076)


Protocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment. 3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies . 3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as a human xenobiotic metabolite, a plant metabolite, an antineoplastic agent, an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor and an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor. It is a member of catechols and a dihydroxybenzoic acid. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate. 3,4-Dihydroxybenzoic acid is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. Protocatechuic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Vaccinium myrtillus Leaf (part of); Menyanthes trifoliata leaf (part of) ... View More ... A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-50-3 (retrieved 2024-06-29) (CAS RN: 99-50-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

   

Nicotinic acid

pyridine-3-carboxylic acid

C6H5NO2 (123.032027)


Nicotinic acid is an odorless white crystalline powder with a feebly acid taste. pH (saturated aqueous solution) 2.7. pH (1.3\\\\\% solution) 3-3.5. (NTP, 1992) Nicotinic acid is a pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group. It has a role as an antidote, an antilipemic drug, a vasodilator agent, a metabolite, an EC 3.5.1.19 (nicotinamidase) inhibitor, an Escherichia coli metabolite, a mouse metabolite, a human urinary metabolite and a plant metabolite. It is a vitamin B3, a pyridinemonocarboxylic acid and a pyridine alkaloid. It is a conjugate acid of a nicotinate. Niacin is a B vitamin used to treat vitamin deficiencies as well as hyperlipidemia, dyslipidemia, hypertriglyceridemia, and to reduce the risk of myocardial infarctions. Nicotinic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Niacin is a Nicotinic Acid. Niacin, also known as nicotinic acid and vitamin B3, is a water soluble, essential B vitamin that, when given in high doses, is effective in lowering low density lipoprotein (LDL) cholesterol and raising high density lipoprotein (HDL) cholesterol, which makes this agent of unique value in the therapy of dyslipidemia. Niacin can cause mild-to-moderate serum aminotransferase elevations and high doses and certain formulations of niacin have been linked to clinically apparent, acute liver injury which can be severe as well as fatal. Niacin is a water-soluble vitamin belonging to the vitamin B family, which occurs in many animal and plant tissues, with antihyperlipidemic activity. Niacin is converted to its active form niacinamide, which is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and its phosphate form, NADP. These coenzymes play an important role in tissue respiration and in glycogen, lipid, amino acid, protein, and purine metabolism. Although the exact mechanism of action by which niacin lowers cholesterol is not fully understood, it may act by inhibiting the synthesis of very low density lipoproteins (VLDL), inhibiting the release of free fatty acids from adipose tissue, increasing lipoprotein lipase activity, and reducing the hepatic synthesis of VLDL-C and LDL-C. Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan (see below), but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient. A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties. Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan, but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient. Nicotinic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=59-67-6 (retrieved 2024-06-29) (CAS RN: 59-67-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Niacin (Vitamin B3) is an orally active water-soluble B3 vitamin that is an essential nutrient for humans. Niacin (Vitamin B3) plays a key role in energy metabolism, cell signaling cascades regulating gene expression and apoptosis. Niacin (Vitamin B3) is also used in the study of cardiovascular diseases[1][2]. Niacin (Vitamin B3) is an orally active water-soluble B3 vitamin that is an essential nutrient for humans. Niacin (Vitamin B3) plays a key role in energy metabolism, cell signaling cascades regulating gene expression and apoptosis. Niacin (Vitamin B3) is also used in the study of cardiovascular diseases[1][2].

   

Guanosine

2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

C10H13N5O5 (283.0916648)


Guanosine (G), also known as 2-amino-inosine, 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 sugar moiety. Guanosine consists of a guanine base attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine is a white, crystalline powder with no odor and mild saline taste. It is very soluble in acetic acid, and slightly soluble in water, but insoluble in ethanol, diethyl ether, benzene, and chloroform. Guanosine exists in all living species, ranging from bacteria to plants to humans. High levels of guanosine can be found in clovers, coffee plants, and the pollen of pines. It has been detected, but not quantified in, several different foods, such as leeks, garlic, chicory roots, green bell peppers, and black-eyed peas. Guanosine plays an important role in various biochemical processes including the synthesis of nucleic acids such as RNA and intracellular signal transduction (cGMP). The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are both structurally similar to guanosine. Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP). In humans, guanosine is involved in intracellular signalling through the adenosine receptors A1R and A2AR (PMID: 31847113). Evidence from rodent and cell models has shown a number of important neurotrophic and neuroprotective effects of guanosine. In particular, it is effective in preventing deleterious consequences of seizures, spinal cord injury, pain, mood disorders and aging-related diseases, such as ischemia, Parkinson‚Äôs and Alzheimer‚Äôs diseases (PMID: 27699087). Studies with rodent models of Parkinson‚Äôs disease have shown that guanosine decreases neuronal apoptotic cell death and increases dopaminergic neurons at substantia nigra pars compacta, accompanied by an improvement of motor symptoms in Parkinson‚Äôs disease (i.e. a reduction of bradykinesia). Guanosine promotes neurite arborization, outgrowth, proliferation and differentiation. Systemic administration of guanosine for eight weeks (8 mg/kg) has been shown to stimulate neuroprogenitors proliferation in the subventricular zone (SVZ) in a mouse model of Parkinsonism (PMID: 27699087). The effect of guanosine treatment is accompanied by an increased number of fibroblast growth factor (FGF-2)-positive cells which is an important regulator of neuroprogenitor/stem cell proliferation, survival and differentiation (PMID: 27699087). Guanosine prevents reactive oxygen species (ROS) generation and cell death in hippocampal slices subjected to the oxygen/glucose deprivation (PMID: 31847113). Guanosine is a purine nucleoside in which guanine is attached to ribofuranose via a beta-N(9)-glycosidic bond. It has a role as a fundamental metabolite. It is a purines D-ribonucleoside and a member of guanosines. It is functionally related to a guanine. Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate) which are factors in signal transduction pathways. Guanosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Guanosine is a natural product found in Ulva australis, Allium chinense, and other organisms with data available. Guanosine is a purine nucleoside formed from a beta-N9-glycosidic bond between guanine and a ribose ring and is essential for metabolism. Guanosine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine nucleoside that has guanine linked by its N9 nitrogen to the C1 carbon of ribose. It is a component of ribonucleic acid and its nucleotides play important roles in metabolism. (From Dorland, 28th ed) Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate). ; The nucleoside guanosine exert important neuroprotective and neuromodulator roles in the central nervous system, which may be related to inhibition of the glutamatergic neurotransmission activity. Guanosine is the specific extracellular guanine-based purines effector and indicate that its conversion occurs not only in the central nervous system but also peripherally. (PMID: 16325434); Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a ?-N9-glycosidic bond. Guanosine is found in many foods, some of which are elderberry, malus (crab apple), acerola, and arrowhead. A purine nucleoside in which guanine is attached to ribofuranose via a beta-N(9)-glycosidic bond. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Spectral] Guanosine (exact mass = 283.09167) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) and Glutathione disulfide (exact mass = 612.15196) and AMP (exact mass = 347.06308) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Guanosine (exact mass = 283.09167) and Guanine (exact mass = 151.04941) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) were not completely separated on HPLC under the present analytical conditions as described in AC$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. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.125 CONFIDENCE standard compound; INTERNAL_ID 317 KEIO_ID G015; [MS2] KO008966 Annotation level-2 KEIO_ID G015 Guanosine (DL-Guanosine) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine possesses anti-HSV activity. Guanosine (DL-Guanosine) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine possesses anti-HSV activity. Guanosine (DL-Guanosine) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine possesses anti-HSV activity.

   

4-Hydroxybenzaldehyde

4-hydroxybenzaldehyde

C7H6O2 (122.0367776)


4-Hydroxybenzaldehyde, also known as 4-formylphenol or 4-hydroxybenzenecarbonal, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and oats. 4-Hydroxybenzaldehyde has also been detected, but not quantified, in several different foods, such as cardoons, colorado pinyons, oyster mushrooms, common chokecherries, and potato. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. 4-hydroxybenzaldehyde is a hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. It has a role as a plant metabolite, a mouse metabolite and an EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor. 4-Hydroxybenzaldehyde is a natural product found in Ficus septica, Visnea mocanera, and other organisms with data available. Occurs naturally combined in many glycosides. Constituent of vanillin. Isol. in free state from opium poppy (Papaver somniferum) A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=123-08-0 (retrieved 2024-07-02) (CAS RN: 123-08-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

   

Scopolin

6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one

C16H18O9 (354.0950778)


Scopolin is a member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a monosaccharide derivative, a member of coumarins and a beta-D-glucoside. It is functionally related to a scopoletin. Scopolin is a natural product found in Artemisia ordosica, Astragalus onobrychis, and other organisms with data available. See also: Chamaemelum nobile flower (part of). A member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].

   

Eurycomalactone

(1S,2R,5S,9S,10S,11R,12R,13R,16R)-9,12-dihydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.02,11.05,10]hexadec-6-ene-3,8,15-trione

C19H24O6 (348.1572804)


Eurycomalactone is a steroid lactone. Eurycomalactone is a natural product found in Eurycoma longifolia with data available. Eurycomalactone is an active quassinoid could be isolated from Eurycoma longifolia Jack. Eurycomalactone is a potent NF-κB inhibitor with an IC50 value of 0.5 μM. Eurycomalactone inhibits protein synthesis and depletes cyclin D1. Eurycomalactone enhances radiosensitivity through arrest cell cycle at G2/M phase and delayed DNA double-strand break repair. Eurycomalactone inhibits the activation of AKT/NF-κB signaling, induces apoptosis and enhances chemosensitivity to Cisplatin (HY-17394)[1][2][3].

   

Stigmasterol

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

C29H48O (412.37049579999996)


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

   

beta-Sitosterol 3-O-beta-D-galactopyranoside

(2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C35H60O6 (576.4389659999999)


Daucosterol is a steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. It has a role as a plant metabolite. It is a steroid saponin, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a sitosterol. It derives from a hydride of a stigmastane. Sitogluside is a natural product found in Ophiopogon intermedius, Ophiopogon jaburan, and other organisms with data available. beta-Sitosterol 3-O-beta-D-galactopyranoside is found in herbs and spices. beta-Sitosterol 3-O-beta-D-galactopyranoside is a constituent of Hibiscus sabdariffa (roselle) leaves. C308 - Immunotherapeutic Agent Daucosterol is a natural sterol compound. Daucosterol is a natural sterol compound.

   

Amalorin

11-hydroxy-1,6-diazatetracyclo[7.6.1.0?,??.0??,??]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

C14H8N2O2 (236.0585748)


Amalorin is an organic heterotetracyclic compound and an alkaloid. 11-Hydroxycanthin-6-one is a natural product found in Brucea javanica, Amaroria soulameoides, and other organisms with data available.

   

Methyl nigakinone

3,4-dimethoxy-1,6-diazatetracyclo[7.6.1.0^{5,16.0^{10,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one

C16H12N2O3 (280.0847882)


Methyl nigakinone is a member of beta-carbolines. 4,5-Dimethoxycanthin-6-one is a natural product found in Alangium chinense, Picrasma quassioides, and Eurycoma longifolia with data available. 4,5-Dimethoxycanthin-6-one is a potent and uncompetitive inhibitor of CYP1A2-mediated phenacetin O-deethylation with an IC50 value of 1.7μM and a Ki value of 2.6 μM. 4,5-Dimethoxycanthin-6-one, as an alkaloid, is isolated from the wood of Picrasma quassioides BENNET (Simaroubaceae)[1][2]. 4,5-Dimethoxycanthin-6-one is a potent and uncompetitive inhibitor of CYP1A2-mediated phenacetin O-deethylation with an IC50 value of 1.7μM and a Ki value of 2.6 μM. 4,5-Dimethoxycanthin-6-one, as an alkaloid, is isolated from the wood of Picrasma quassioides BENNET (Simaroubaceae)[1][2].

   

Canthin-6-one

1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

C14H8N2O (220.06365979999998)


Canthin-6-one is an indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6. It has a role as a metabolite and an antimycobacterial drug. It is an indole alkaloid, an organic heterotetracyclic compound and an enone. Canthin-6-one is a natural product found in Zanthoxylum mayu, Zanthoxylum ovalifolium, and other organisms with data available. D016573 - Agrochemicals D010575 - Pesticides Canthin-6-one displays a wide range of biological activities, such as antimycobacterial activity[1]. Canthin-6-one displays a wide range of biological activities, such as antimycobacterial activity[1].

   

Fraxidin

InChI=1/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)9(13)11(7)15-2/h3-5,13H,1-2H

C11H10O5 (222.052821)


Fraxidin is a hydroxycoumarin. Fraxidin is a natural product found in Artemisia minor, Melilotus messanensis, and other organisms with data available. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2344 Fraxidin is a class of coumarin isolated from the roots of Jatropha podagrica, exhibits antibacterial activity against Bacillus subtilis with an inhibition zone of 12 mm at a concentration of 20 μg/disk[1][2]. Fraxidin is a class of coumarin isolated from the roots of Jatropha podagrica, exhibits antibacterial activity against Bacillus subtilis with an inhibition zone of 12 mm at a concentration of 20 μg/disk[1][2].

   

Syringic acid

InChI=1/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12

C9H10O5 (198.052821)


Syringic acid, also known as syringate or cedar acid, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Outside of the human body, Syringic acid is found, on average, in the highest concentration within a few different foods, such as common walnuts, swiss chards, and olives and in a lower concentration in apples, tarragons, and peanuts. Syringic acid has also been detected, but not quantified in several different foods, such as sweet marjorams, silver lindens, bulgurs, annual wild rices, and barley. This could make syringic acid a potential biomarker for the consumption of these foods. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Research suggests that phenolics from wine may play a positive role against oxidation of low-density lipoprotein (LDL), which is a key step in the development of atherosclerosis. Syringic acid is a phenol present in some distilled alcohol beverages. It is also a product of microbial (gut) metabolism of anthocyanins and other polyphenols that have been consumed (in fruits and alcoholic beverages - PMID:18767860). Syringic acid is also a microbial metabolite that can be found in Bifidobacterium (PMID:24958563). Syringic acid is a dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. It has a role as a plant metabolite. It is a member of benzoic acids, a dimethoxybenzene and a member of phenols. It is functionally related to a gallic acid. It is a conjugate acid of a syringate. Syringic acid is a natural product found in Visnea mocanera, Pittosporum illicioides, and other organisms with data available. Syringic acid is a metabolite found in or produced by Saccharomyces cerevisiae. Present in various plants free and combined, e.g. principal phenolic constituent of soyabean meal (Glycine max) A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents KEIO_ID S018 Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation.

   

beta-Carboline

Norharman hydrochloride

C11H8N2 (168.0687448)


beta-Carboline, also known as norharmane, is an organic amine and is the prototype of a class of compounds known as beta-carbolines. beta-Carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. beta-Carboline is a very strong basic compound (based on its pKa). beta-Carboline alkaloids are widely distributed in plants and animals and many are inverse agonists of the GABA-A receptor complex (PMID: 17334612). Other biological activities demonstrated by these compounds include intercalation; inhibition of CDK, topoisomerase, and monoamine oxidase; and interaction with 5-hydroxy serotonin receptors. These compounds have also exhibited sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial activities (PMID: 17305548). b-Carboline (9H-pyrido[3,4-b]indole) is an organic amine that is the prototype of a class of compounds known as b-carbolines. [HMDB]. Norharman is found in chicory. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 75 CONFIDENCE standard compound; INTERNAL_ID 2883 D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6]. Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6].

   

Syringaldehyde

InChI=1/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H

C9H10O4 (182.057906)


Syringaldehyde is a hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity. It has a role as a hypoglycemic agent and a plant metabolite. It is a hydroxybenzaldehyde and a dimethoxybenzene. Syringaldehyde is a natural product found in Ficus septica, Mikania laevigata, and other organisms with data available. Syringaldehyde is a metabolite found in or produced by Saccharomyces cerevisiae. A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

   

5-Methoxycanthin-6-one

3-methoxy-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one

C15H10N2O2 (250.07422400000002)


5-Methoxycanthin-6-one is an alkaloid and an organic heterotetracyclic compound. 5-Methoxycanthin-6-one is a natural product found in Zanthoxylum caribaeum, Fagaropsis angolensis, and other organisms with data available. 5-Methoxycanthin-6-one is an alkaloid from the wood of Picrasma excelsa (Jamaican quassiawood

   

14,15β-dihydroxyklaineanone

(1R,2S,3S,7S,9R,12R,13R,14S,15R,16R,17S)-3,12,13,15,16-pentahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-5-ene-4,11-dione

C20H28O8 (396.1784088)


14,15beta-Dihydroxyklaineanone is a natural product found in Eurycoma longifolia with data available.

   

n-pentyl beta-carboline-1-propionate

n-pentyl beta-carboline-1-propionate

C19H22N2O2 (310.1681192)


   

Guaiacylglycerol

(1R,2S)-1-(4-hydroxy-3-methoxyphenyl)propane-1,2,3-triol

C10H14O5 (214.08411940000002)


   

9-Hydroxycanthin-6-one

9-Hydroxycanthin-6-one

C14H8N2O2 (236.0585748)


An indole alkaloid that is canthin-6-one substituted by a hydroxy group at position 9. Isolated from the roots of Eurycoma longifolia, it exhibits antineoplastic activity.

   

7-Methoxy-beta-Carboline 1-propionic acid

3-(7-methoxy-9H-pyrido[3,4-b]indol-1-yl)propanoic acid

C15H14N2O3 (270.10043740000003)


   

11-Hydroxycanthin-6-one

11-Hydroxycanthin-6-one

C14H8N2O2 (236.0585748)


   

9-Methoxycanthin-6-one

9-Methoxycanthin-6-one

C15H10N2O2 (250.07422400000002)


D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams 9-Methoxycanthin-6-one, a canthin-6-one alkaloid, is present in intact plant parts and in callus tissues of different explants. 9-Methoxycanthin-6-one shows anti-tumor activity[1][2]. 9-Methoxycanthin-6-one, a canthin-6-one alkaloid, is present in intact plant parts and in callus tissues of different explants. 9-Methoxycanthin-6-one shows anti-tumor activity[1][2].

   

Syringaldehyde

Syringaldehyde

C9H10O4 (182.057906)


Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 303; CONFIDENCE confident structure Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

   
   

Daucosterol

(2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C35H60O6 (576.4389659999999)


Daucosterol is a steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. It has a role as a plant metabolite. It is a steroid saponin, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a sitosterol. It derives from a hydride of a stigmastane. Sitogluside is a natural product found in Ophiopogon intermedius, Ophiopogon jaburan, and other organisms with data available. A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa. C308 - Immunotherapeutic Agent Daucosterol is a natural sterol compound. Daucosterol is a natural sterol compound.

   

9,10-Dimethoxycanthin-6-one

9,10-Dimethoxycanthin-6-one

C16H12N2O3 (280.0847882)


   

5-hydroxymethyl-9-methoxycanthin-6-one

5-hydroxymethyl-9-methoxycanthin-6-one

C16H12N2O3 (280.0847882)


   

1-Hydroxy-9-medroxycanthin-6-one

1-Hydroxy-9-medroxycanthin-6-one

C15H10N2O3 (266.069139)


   

8-Methoxycanthin-6-one

13-METHOXY-1,6-DIAZATETRACYCLO[7.6.1.0?,(1)?.0(1)?,(1)?]HEXADECA-3,5,7,9(16),10(15),11,13-HEPTAEN-2-ONE

C15H10N2O2 (250.07422400000002)


9-methoxycanthin-6-one is an indole alkaloid that is the 9-methoxy derivative of canthin-6-one. Isolated from Eurycoma longifolia and Simaba multiflora, it exhibits cytotoxic activity towards human cancer cell lines. It has a role as a metabolite, an antineoplastic agent and an antiplasmodial drug. It is an indole alkaloid, an aromatic ether and an organic heterotetracyclic compound. It is functionally related to a canthin-6-one. 9-Methoxycanthin-6-one is a natural product found in Simarouba glauca, Eurycoma longifolia, and other organisms with data available. An indole alkaloid that is the 9-methoxy derivative of canthin-6-one. Isolated from Eurycoma longifolia and Simaba multiflora, it exhibits cytotoxic activity towards human cancer cell lines. D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams 9-Methoxycanthin-6-one, a canthin-6-one alkaloid, is present in intact plant parts and in callus tissues of different explants. 9-Methoxycanthin-6-one shows anti-tumor activity[1][2]. 9-Methoxycanthin-6-one, a canthin-6-one alkaloid, is present in intact plant parts and in callus tissues of different explants. 9-Methoxycanthin-6-one shows anti-tumor activity[1][2].

   

14,15 β-Dihydroxyklaineanone

(1R,2S,3S,7S,9R,12R,13R,14S,15R,16R,17S)-3,12,13,15,16-pentahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-5-ene-4,11-dione

C20H28O8 (396.1784088)


14,15beta-Dihydroxyklaineanone is a natural product found in Eurycoma longifolia with data available.

   

7-Methoxy-b-carboline-1-propionicacid

3-(7-methoxy-9H-pyrido[3,4-b]indol-1-yl)propanoic acid

C15H14N2O3 (270.10043740000003)


7-Methoxy-beta-carboline-1-propionic acid is a natural product found in Eurycoma longifolia with data available.

   

Scopoletin

Scopoletin

C10H8O4 (192.0422568)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.637 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.629 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.631 IPB_RECORD: 1582; CONFIDENCE confident structure Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

Norharmane

9H-Pyrido[3,4-B]indole

C11H8N2 (168.0687448)


D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens IPB_RECORD: 2981; CONFIDENCE confident structure Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6]. Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6].

   

Adenosine

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].

   

Thymidine

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].

   

Vanillic Acid

Vanillic acid hexoside

C8H8O4 (168.0422568)


Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

   

Fraxidin

InChI=1/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)9(13)11(7)15-2/h3-5,13H,1-2H

C11H10O5 (222.052821)


Fraxidin is a hydroxycoumarin. Fraxidin is a natural product found in Artemisia minor, Melilotus messanensis, and other organisms with data available. Fraxidin, also known as 8-hydroxy-6,7-dimethoxy-2h-1-benzopyran-2-one, is a member of the class of compounds known as hydroxycoumarins. Hydroxycoumarins are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. Fraxidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Fraxidin can be found in durian and watermelon, which makes fraxidin a potential biomarker for the consumption of these food products. Fraxidin is a class of coumarin isolated from the roots of Jatropha podagrica, exhibits antibacterial activity against Bacillus subtilis with an inhibition zone of 12 mm at a concentration of 20 μg/disk[1][2]. Fraxidin is a class of coumarin isolated from the roots of Jatropha podagrica, exhibits antibacterial activity against Bacillus subtilis with an inhibition zone of 12 mm at a concentration of 20 μg/disk[1][2]. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2]. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2].

   

4-Hydroxybenzaldehyde

4-Hydroxybenzaldehyde

C7H6O2 (122.0367776)


p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

   

3,4-Dihydroxybenzoic acid

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266076)


   
   

Norharman

InChI=1\C11H8N2\c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10\h1-7,13

C11H8N2 (168.0687448)


D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens Annotation level-1 Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6]. Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6].

   

5-Methoxycanthin-6-one

3-methoxy-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one

C15H10N2O2 (250.07422400000002)


   

2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

C10H13N5O4 (267.09674980000005)


   

Scopoletol

2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy- (9CI)

C10H8O4 (192.0422568)


Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

99-50-3

InChI=1\C7H6O4\c8-5-2-1-4(7(10)11)3-6(5)9\h1-3,8-9H,(H,10,11

C7H6O4 (154.0266076)


D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

   

Vanillate

4-Hydroxy-3-methoxybenzoic acid

C8H8O4 (168.0422568)


Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

   

Stigmasterin

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

C29H48O (412.37049579999996)


C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

   

Cedar acid

InChI=1\C9H10O5\c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10\h3-4,10H,1-2H3,(H,11,12

C9H10O5 (198.052821)


D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation.

   

FR-0985

4-08-00-00251 (Beilstein Handbook Reference)

C7H6O2 (122.0367776)


p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

   

AI3-28796

InChI=1\C9H10O4\c1-12-7-3-6(5-10)4-8(13-2)9(7)11\h3-5,11H,1-2H

C9H10O4 (182.057906)


Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

   

canthinone

1,6-diazatetracyclo[7.6.1.0^{5,16.0^{10,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one

C14H8N2O (220.06365979999998)


Canthin-6-one is an indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6. It has a role as a metabolite and an antimycobacterial drug. It is an indole alkaloid, an organic heterotetracyclic compound and an enone. Canthin-6-one is a natural product found in Zanthoxylum mayu, Zanthoxylum ovalifolium, and other organisms with data available. An indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6. D016573 - Agrochemicals D010575 - Pesticides Canthin-6-one displays a wide range of biological activities, such as antimycobacterial activity[1]. Canthin-6-one displays a wide range of biological activities, such as antimycobacterial activity[1].

   

methyl 8,11-dihydroxy-2,6,9,15-tetramethyl-3,14-dioxo-13-oxatetracyclo[10.2.1.0²,¹⁰.0⁵,⁹]pentadeca-4,6-diene-8-carboxylate

methyl 8,11-dihydroxy-2,6,9,15-tetramethyl-3,14-dioxo-13-oxatetracyclo[10.2.1.0²,¹⁰.0⁵,⁹]pentadeca-4,6-diene-8-carboxylate

C20H24O7 (376.1521954)


   

4,5,7,8,17-pentahydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione

4,5,7,8,17-pentahydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione

C20H26O9 (410.15767460000006)


   

(1r,2s,5r,8r,9r,10r,11s,12s,13s,16s)-8,9,12-trihydroxy-2,10,16-trimethyl-6-methylidene-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-3,15-dione

(1r,2s,5r,8r,9r,10r,11s,12s,13s,16s)-8,9,12-trihydroxy-2,10,16-trimethyl-6-methylidene-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-3,15-dione

C19H26O6 (350.1729296)


   

(1'r,2s,5'r,7'r,8'r,11'r,13's,17's,18's,19'r)-4',5',7',8',17'-pentahydroxy-14',18'-dimethyl-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-ene-9',16'-dione

(1'r,2s,5'r,7'r,8'r,11'r,13's,17's,18's,19'r)-4',5',7',8',17'-pentahydroxy-14',18'-dimethyl-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-ene-9',16'-dione

C20H24O10 (424.13694039999996)


   

(1r,3ar,3br,7s,9ar,9br,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

(1r,3ar,3br,7s,9ar,9br,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O (412.37049579999996)


   

(1s,2r,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,14,15-trihydroxy-2,6,13,16-tetramethyl-4,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-en-8-yl acetate

(1s,2r,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,14,15-trihydroxy-2,6,13,16-tetramethyl-4,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-en-8-yl acetate

C21H28O8 (408.1784088)


   

(1s,2r,6r,8s,9s,10r,12r,13r,16r)-8,9,12-trihydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadec-4-ene-3,15-dione

(1s,2r,6r,8s,9s,10r,12r,13r,16r)-8,9,12-trihydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadec-4-ene-3,15-dione

C19H26O6 (350.1729296)


   

3-(hydroxymethyl)-13-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-5,7,9(16),10(15),11,13-hexaen-2-one

3-(hydroxymethyl)-13-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-5,7,9(16),10(15),11,13-hexaen-2-one

C16H14N2O3 (282.10043740000003)


   

(1s,4r)-4-hydroxy-1-[(2r,5r)-5-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]-4-[(2s,5r)-5-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]butyl acetate

(1s,4r)-4-hydroxy-1-[(2r,5r)-5-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]-4-[(2s,5r)-5-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-2-methyloxolan-2-yl]butyl acetate

C32H56O7 (552.4025826)


   

(1r,4r,5r,6r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,6,7,8,16,17-heptahydroxy-6-(hydroxymethyl)-14,18-dimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one

(1r,4r,5r,6r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,6,7,8,16,17-heptahydroxy-6-(hydroxymethyl)-14,18-dimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one

C20H28O11 (444.16315380000003)


   

(1r,2s,3s,7s,8r,9s,12r,13r,14s,15r,16r,17s)-3,8,12,13,15,16-hexahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-5-ene-4,11-dione

(1r,2s,3s,7s,8r,9s,12r,13r,14s,15r,16r,17s)-3,8,12,13,15,16-hexahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-5-ene-4,11-dione

C20H28O9 (412.17332380000005)


   

1-[4-(3,3-dimethyloxiran-2-yl)-4-hydroxybutan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

1-[4-(3,3-dimethyloxiran-2-yl)-4-hydroxybutan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C30H50O3 (458.37597500000004)


   

(1s,2r,5r,9s,10s,11r,12r,15r)-11-hydroxy-2,6,9,15-tetramethyl-13-oxatetracyclo[10.2.1.0²,¹⁰.0⁵,⁹]pentadec-6-ene-3,8,14-trione

(1s,2r,5r,9s,10s,11r,12r,15r)-11-hydroxy-2,6,9,15-tetramethyl-13-oxatetracyclo[10.2.1.0²,¹⁰.0⁵,⁹]pentadec-6-ene-3,8,14-trione

C18H22O5 (318.1467162)


   

4,8,9,12-tetrahydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadec-6-ene-3,15-dione

4,8,9,12-tetrahydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadec-6-ene-3,15-dione

C19H26O7 (366.16784459999997)


   

(1s,2r,3s,5r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-7-one

(1s,2r,3s,5r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-7-one

C19H24O7 (364.1521954)


   

3,12,15,16-tetrahydroxy-2,6,14,17-tetramethyl-4,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-5-en-8-yl acetate

3,12,15,16-tetrahydroxy-2,6,14,17-tetramethyl-4,11-dioxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-5-en-8-yl acetate

C22H30O9 (438.18897300000003)


   

(2r)-2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one

(2r)-2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one

C10H12O5 (212.06847019999998)


   

11-hydroxy-2,6,9,15-tetramethyl-13-oxatetracyclo[10.2.1.0²,¹⁰.0⁵,⁹]pentadeca-4,6-diene-3,8,14-trione

11-hydroxy-2,6,9,15-tetramethyl-13-oxatetracyclo[10.2.1.0²,¹⁰.0⁵,⁹]pentadeca-4,6-diene-3,8,14-trione

C18H20O5 (316.13106700000003)


   

(1s,4s,5s,6r,7s,8s,11s,13r,17r,18r,19s)-4,5,7,8,17-pentahydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione

(1s,4s,5s,6r,7s,8s,11s,13r,17r,18r,19s)-4,5,7,8,17-pentahydroxy-6,14,18-trimethyl-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-ene-9,16-dione

C20H26O9 (410.15767460000006)


   

3-{7-methoxy-9h-pyrido[3,4-b]indol-1-yl}propanoic acid

3-{7-methoxy-9h-pyrido[3,4-b]indol-1-yl}propanoic acid

C15H14N2O3 (270.10043740000003)


   

(3s)-3-(hydroxymethyl)-13-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-5,7,9(16),10(15),11,13-hexaen-2-one

(3s)-3-(hydroxymethyl)-13-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-5,7,9(16),10(15),11,13-hexaen-2-one

C16H14N2O3 (282.10043740000003)


   

3a,6,6,9a,11a-pentamethyl-1-(4,5,6-trihydroxy-6-methylheptan-2-yl)-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

3a,6,6,9a,11a-pentamethyl-1-(4,5,6-trihydroxy-6-methylheptan-2-yl)-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

C30H50O4 (474.37089000000003)


   

(2s,4r,7r,8r,9s,12r)-7,8,11-trihydroxy-12-(hydroxymethyl)-2,9-dimethyl-2-[(2r)-3-methyl-5-oxo-2h-furan-2-yl]-5-oxatricyclo[6.3.1.0⁴,¹²]dodec-1(11)-ene-6,10-dione

(2s,4r,7r,8r,9s,12r)-7,8,11-trihydroxy-12-(hydroxymethyl)-2,9-dimethyl-2-[(2r)-3-methyl-5-oxo-2h-furan-2-yl]-5-oxatricyclo[6.3.1.0⁴,¹²]dodec-1(11)-ene-6,10-dione

C19H22O9 (394.1263762)


   

(1s,2r,9s,11r,12r,15r)-11-hydroxy-2,6,9,15-tetramethyl-13-oxatetracyclo[10.2.1.0²,¹⁰.0⁵,⁹]pentadec-6-ene-3,8,14-trione

(1s,2r,9s,11r,12r,15r)-11-hydroxy-2,6,9,15-tetramethyl-13-oxatetracyclo[10.2.1.0²,¹⁰.0⁵,⁹]pentadec-6-ene-3,8,14-trione

C18H22O5 (318.1467162)


   

4-hydroxy-3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-5,7,9(16),10(15),11,13-hexaen-2-one

4-hydroxy-3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-5,7,9(16),10(15),11,13-hexaen-2-one

C15H12N2O3 (268.0847882)


   

(1r,2s,4r,7r,8r,9s,10r,11r,12s)-7,8,10,11-tetrahydroxy-2,9,12-trimethyl-2-[(2r)-3-methyl-5-oxo-2h-furan-2-yl]-5-oxatricyclo[6.3.1.0⁴,¹²]dodecan-6-one

(1r,2s,4r,7r,8r,9s,10r,11r,12s)-7,8,10,11-tetrahydroxy-2,9,12-trimethyl-2-[(2r)-3-methyl-5-oxo-2h-furan-2-yl]-5-oxatricyclo[6.3.1.0⁴,¹²]dodecan-6-one

C19H26O8 (382.1627596)


   

13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

C20H18N2O7 (398.11139579999997)


   

(3s,4s)-4-hydroxy-3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-5,7,9(16),10(15),11,13-hexaen-2-one

(3s,4s)-4-hydroxy-3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-5,7,9(16),10(15),11,13-hexaen-2-one

C15H12N2O3 (268.0847882)


   

3,15-dihydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-5-ene-4,11,16-trione

3,15-dihydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-5-ene-4,11,16-trione

C20H26O6 (362.17292960000003)


   

3,14,15-trihydroxy-2,6,13,16-tetramethyl-4,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-en-8-yl acetate

3,14,15-trihydroxy-2,6,13,16-tetramethyl-4,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-en-8-yl acetate

C21H28O8 (408.1784088)


   

2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)ethanone

2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)ethanone

C9H10O4 (182.057906)


   

3,8,9,12-tetrahydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadec-5-ene-4,15-dione

3,8,9,12-tetrahydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadec-5-ene-4,15-dione

C19H26O7 (366.16784459999997)


   

3,12,13,15,16-pentahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-5-ene-4,11-dione

3,12,13,15,16-pentahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-5-ene-4,11-dione

C20H28O8 (396.1784088)


   

8,9,12-trihydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadeca-4,6-diene-3,15-dione

8,9,12-trihydroxy-2,6,10,16-tetramethyl-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadeca-4,6-diene-3,15-dione

C19H24O6 (348.1572804)


   

(1s,3as,5as,9ar,9br,11as)-3a,6,6,9a,11a-pentamethyl-1-[(2s,4r,5s)-4,5,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

(1s,3as,5as,9ar,9br,11as)-3a,6,6,9a,11a-pentamethyl-1-[(2s,4r,5s)-4,5,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

C30H50O4 (474.37089000000003)


   

4'-[hydroxy(oxiran-2-yl)methyl]-5-(3-hydroxyprop-1-en-1-yl)-2',3,6'-trimethoxy-[1,1'-biphenyl]-2-ol

4'-[hydroxy(oxiran-2-yl)methyl]-5-(3-hydroxyprop-1-en-1-yl)-2',3,6'-trimethoxy-[1,1'-biphenyl]-2-ol

C21H24O7 (388.1521954)