NCBI Taxonomy: 43879

Peganum harmala (ncbi_taxid: 43879)

found 125 associated metabolites at species taxonomy rank level.

Ancestor: Peganum

Child Taxonomies: none taxonomy data.

Harman

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

C12H10N2 (182.0844)


Harman is an indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A. It has a role as an anti-HIV agent, a plant metabolite and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It is an indole alkaloid, an indole alkaloid fundamental parent and a harmala alkaloid. Harman is a natural product found in Ophiopogon, Strychnos johnsonii, and other organisms with data available. An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A. Isolated from roots of Panax ginseng and Codonopsis lanceolata (todok). Struct. has now been shown to be identical with 1-Acetyl-b-carboline CHK59-M Harman is found in chicory. Harman is an alkaloid from the may pop (Passiflora incarnata, Passifloraceae) and many other Passiflora sp [Raw Data] CB042_Harman_pos_30eV_CB000019.txt [Raw Data] CB042_Harman_pos_20eV_CB000019.txt [Raw Data] CB042_Harman_pos_40eV_CB000019.txt [Raw Data] CB042_Harman_pos_10eV_CB000019.txt [Raw Data] CB042_Harman_pos_50eV_CB000019.txt [Raw Data] CB042_Harman_neg_50eV_000012.txt [Raw Data] CB042_Harman_neg_30eV_000012.txt [Raw Data] CB042_Harman_neg_40eV_000012.txt [Raw Data] CB042_Harman_neg_20eV_000012.txt [Raw Data] CB042_Harman_neg_10eV_000012.txt Harman. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=486-84-0 (retrieved 2024-06-29) (CAS RN: 486-84-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

   

Harmaline

3H-Pyrido[3,4-b]indole, 4,9-dihydro-7-methoxy-1-methyl-

C13H14N2O (214.1106)


Harmaline is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond. It has a role as a oneirogen. It derives from a hydride of a harman. Harmaline is a natural product found in Passiflora pilosicorona, Passiflora boenderi, and other organisms with data available. A beta-carboline alkaloid isolated from seeds of PEGANUM. A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond. Harmaline is found in fruits. Harmaline is an alkaloid from Passiflora incarnata (maypops D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants D004791 - Enzyme Inhibitors > D008996 - Monoamine Oxidase Inhibitors Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H027; [MS2] KO008994 KEIO_ID H027

   

Kaempferol

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

C15H10O6 (286.0477)


Kaempferol is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Acting as an antioxidant by reducing oxidative stress, it is currently under consideration as a possible cancer treatment. It has a role as an antibacterial agent, a plant metabolite, a human xenobiotic metabolite, a human urinary metabolite, a human blood serum metabolite and a geroprotector. It is a member of flavonols, a 7-hydroxyflavonol and a tetrahydroxyflavone. It is a conjugate acid of a kaempferol oxoanion. Kaempferol is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Kaempferol is a natural flavonoid which has been isolated from Delphinium, Witch-hazel, grapefruit, and other plant sources. Kaempferol is a yellow crystalline solid with a melting point of 276-278 degree centigrade. It is slightly soluble in water, and well soluble in hot ethanol and diethyl ether. Kaempferol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Cannabis sativa subsp. indica top (part of); Tussilago farfara flower (part of). Kaempferol, also known as rhamnolutein or c.i. 75640, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, kaempferol is considered to be a flavonoid molecule. A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol exists in all eukaryotes, ranging from yeast to humans. Kaempferol is a bitter tasting compound. Kaempferol is found, on average, in the highest concentration within a few different foods, such as saffrons, capers, and cumins and in a lower concentration in lovages, endives, and cloves. Kaempferol has also been detected, but not quantified, in several different foods, such as shallots, pine nuts, feijoa, kombus, and chicory leaves. This could make kaempferol a potential biomarker for the consumption of these foods. Kaempferol is a potentially toxic compound. Very widespread in the plant world, e.g. in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae, Leguminosae, etc. Found especies in broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon [CCD] A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Acting as an antioxidant by reducing oxidative stress, it is currently under consideration as a possible cancer treatment. CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3906; ORIGINAL_PRECURSOR_SCAN_NO 3905 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3916; ORIGINAL_PRECURSOR_SCAN_NO 3915 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3928; ORIGINAL_PRECURSOR_SCAN_NO 3927 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4291; ORIGINAL_PRECURSOR_SCAN_NO 4290 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3918; ORIGINAL_PRECURSOR_SCAN_NO 3917 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3915; ORIGINAL_PRECURSOR_SCAN_NO 3914 Acquisition and generation of the data is financially supported in part by CREST/JST. INTERNAL_ID 2358; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2358 CONFIDENCE standard compound; INTERNAL_ID 47 CONFIDENCE standard compound; ML_ID 45 Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4]. Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4].

   

Quercetin

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

C15H10O7 (302.0427)


Quercetin appears as yellow needles or yellow powder. Converts to anhydrous form at 203-207 °F. Alcoholic solutions taste very bitter. (NTP, 1992) Quercetin is a pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. It has a role as an antibacterial agent, an antioxidant, a protein kinase inhibitor, an antineoplastic agent, an EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor, a plant metabolite, a phytoestrogen, a radical scavenger, a chelator, an Aurora kinase inhibitor and a geroprotector. It is a pentahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a quercetin-7-olate. Quercetin is a flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. Quercetin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Quercetin is a flavonoid found in many foods and herbs and is a regular component of a normal diet. Extracts of quercetin have been used to treat or prevent diverse conditions including cardiovascular disease, hypercholesterolemia, rheumatic diseases, infections and cancer but have not been shown to be effective in clinical trials for any medical condition. Quercetin as a nutritional supplement is well tolerated and has not been linked to serum enzyme elevations or to episodes of clinically apparent liver injury. Quercetin is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Quercetin is a polyphenolic flavonoid with potential chemopreventive activity. Quercetin, ubiquitous in plant food sources and a major bioflavonoid in the human diet, may produce antiproliferative effects resulting from the modulation of either EGFR or estrogen-receptor mediated signal transduction pathways. Although the mechanism of action of action is not fully known, the following effects have been described with this agent in vitro: decreased expression of mutant p53 protein and p21-ras oncogene, induction of cell cycle arrest at the G1 phase and inhibition of heat shock protein synthesis. This compound also demonstrates synergy and reversal of the multidrug resistance phenotype, when combined with chemotherapeutic drugs, in vitro. Quercetin also produces anti-inflammatory and anti-allergy effects mediated through the inhibition of the lipoxygenase and cyclooxygenase pathways, thereby preventing the production of pro-inflammatory mediators. Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adju... Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercetin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions (PMID:17015250). Quercetin is isolated from many plants, especially fruits, such as Helichrysum, Euphorbia and Karwinskia spp. Present in the Solanaceae, Rhamnaceae, Passifloraceae and many other families. For example detected in almost all studied Umbelliferae. Nutriceutical with antiinflammatory props. and a positive influence on the blood lipid profile. Found in a wide variety of foods especially apples, bee pollen, blackcurrants, capers, cocoa, cranberries, dock leaves, elderberries, fennel, lovage, red onions, ancho peppers, dill weed and tarragon. A pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4014; ORIGINAL_PRECURSOR_SCAN_NO 4012 INTERNAL_ID 298; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4019; ORIGINAL_PRECURSOR_SCAN_NO 4018 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4017; ORIGINAL_PRECURSOR_SCAN_NO 4016 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4096; ORIGINAL_PRECURSOR_SCAN_NO 4094 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4024; ORIGINAL_PRECURSOR_SCAN_NO 4023 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB109_Quercetin_pos_30eV_CB000041.txt IPB_RECORD: 1761; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_pos_10eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_20eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_40eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_50eV_CB000041.txt IPB_RECORD: 161; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_neg_40eV_000027.txt [Raw Data] CB109_Quercetin_neg_50eV_000027.txt [Raw Data] CB109_Quercetin_neg_20eV_000027.txt [Raw Data] CB109_Quercetin_neg_30eV_000027.txt [Raw Data] CB109_Quercetin_neg_10eV_000027.txt CONFIDENCE standard compound; INTERNAL_ID 124 CONFIDENCE standard compound; ML_ID 54 Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

   

L-Ascorbic acid

(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

C6H8O6 (176.0321)


L-ascorbic acid is a white to very pale yellow crystalline powder with a pleasant sharp acidic taste. Almost odorless. (NTP, 1992) L-ascorbic acid is the L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate. It has a role as a coenzyme, a flour treatment agent, a food antioxidant, a plant metabolite, a cofactor, a skin lightening agent and a geroprotector. It is an ascorbic acid and a vitamin C. It is a conjugate acid of a L-ascorbate. It is an enantiomer of a D-ascorbic acid. A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. Ascorbic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Ascorbic acid is a Vitamin C. Ascorbic Acid is a natural product found in Populus tremula, Rosa platyacantha, and other organisms with data available. Ascorbic Acid is a natural water-soluble vitamin (Vitamin C). Ascorbic acid is a potent reducing and antioxidant agent that functions in fighting bacterial infections, in detoxifying reactions, and in the formation of collagen in fibrous tissue, teeth, bones, connective tissue, skin, and capillaries. Found in citrus and other fruits, and in vegetables, vitamin C cannot be produced or stored by humans and must be obtained in the diet. (NCI04) A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. See also: Sodium Ascorbate (active moiety of); D-ascorbic acid (related); Magnesium Ascorbyl Phosphate (active moiety of) ... View More ... G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids > G01AD - Organic acids A - Alimentary tract and metabolism > A11 - Vitamins > A11G - Ascorbic acid (vitamin c), incl. combinations > A11GA - Ascorbic acid (vitamin c), plain B - Blood and blood forming organs > B03 - Antianemic preparations > B03A - Iron preparations > B03AA - Iron bivalent, oral preparations COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants C26170 - Protective Agent > C275 - Antioxidant D018977 - Micronutrients > D014815 - Vitamins S - Sensory organs > S01 - Ophthalmologicals L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4]. L-Ascorbic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=50-81-7 (retrieved 2024-10-29) (CAS RN: 50-81-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Harmine

InChI=1/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H

C13H12N2O (212.095)


Harmine is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7. It has a role as a metabolite, an anti-HIV agent and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It derives from a hydride of a harman. Harmine is a natural product found in Thalictrum foetidum, Acraea andromacha, and other organisms with data available. Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920s. D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens Harmine is found in fruits. Harmine is an alkaloid from Passiflora edulis (passionfruit A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7. D004791 - Enzyme Inhibitors > D008996 - Monoamine Oxidase Inhibitors C471 - Enzyme Inhibitor > C667 - Monoamine Oxidase Inhibitor CONFIDENCE Reference Standard (Level 1); NaToxAq - Natural Toxins and Drinking Water Quality - From Source to Tap (https://natoxaq.ku.dk) [Raw Data] CB043_Harmine_pos_40eV_CB000020.txt [Raw Data] CB043_Harmine_pos_50eV_CB000020.txt [Raw Data] CB043_Harmine_pos_10eV_CB000020.txt [Raw Data] CB043_Harmine_pos_30eV_CB000020.txt [Raw Data] CB043_Harmine_pos_20eV_CB000020.txt CONFIDENCE standard compound; INTERNAL_ID 2884 [Raw Data] CB043_Harmine_neg_50eV_000013.txt [Raw Data] CB043_Harmine_neg_30eV_000013.txt [Raw Data] CB043_Harmine_neg_10eV_000013.txt [Raw Data] CB043_Harmine_neg_20eV_000013.txt [Raw Data] CB043_Harmine_neg_40eV_000013.txt Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1].

   

Vasicinone

NCGC00169472-02_C11H10N2O2_Pyrrolo[2,1-b]quinazolin-9(1H)-one, 2,3-dihydro-3-hydroxy-

C11H10N2O2 (202.0742)


Vasicinone is a member of quinazolines. Vasicinone is a natural product found in Justicia adhatoda, Anisotes trisulcus, and other organisms with data available. Vasicinone is a quinazoline alkaloid isolated from the Adhatoda vasica. Vasicinone is a potential agent for Parkinson's disease and possibly other oxidative stress-related neurodegenerative disorders[1].

   

Serotonin

3-(b-Aminoethyl)-5-hydroxyindole

C10H12N2O (176.095)


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

   

Linoleic acid

C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico

C18H32O2 (280.2402)


Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (From Stedman, 26th ed). Linoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups (−CH=CH−) are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.[5] Linoleic acid is a polyunsaturated, omega-6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents.[2] It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.[6] It is one of two essential fatty acids for humans, who must obtain it through their diet,[7] and the most essential, because the body uses it as a base to make the others. The word "linoleic" derives from Latin linum 'flax', and oleum 'oil', reflecting the fact that it was first isolated from linseed oil.

   

Tetrahydroharmine

(R)-Tetrahydroharmine

C13H16N2O (216.1263)


   

Quinoline

Quinoline Hydrochloride

C9H7N (129.0578)


Quinoline is an alkaloid from various plant species including Mentha species. Also present in cocoa, black tea and scotch whiskey. Quinoline is a flavouring ingredient Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline is found in alcoholic beverages. Quinoline is mainly used as a building block to other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[citation needed] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert" Alkaloid from various plant subspecies including Mentha subspeciesand is also present in cocoa, black tea and scotch whiskey. Flavouring ingredient CONFIDENCE standard compound; INTERNAL_ID 2526 KEIO_ID Q008

   

Deoxypeganine

3-deoxyvasicine

C11H12N2 (172.1)


   

Deoxyvasicinone

2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one

C11H10N2O (186.0793)


Annotation level-1

   

Vasicine

Vasicine

C11H12N2O (188.095)


Annotation level-1 (±)-Vasicine is the racemate of Vasicine. Vasicine (Peganine) significantly inhibits H+-K+-ATPase activity?in vitro?with an IC50 of 73.47?μg/mL. Anti-ulcer activity. Vasicine shows significant anti-secretory, antioxidant and?cytoprotective?effect[1].

   

Harmalol

1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol hydrochloride

C12H12N2O (200.095)


Harmalol is found in fruits. Harmalol is an alkaloid from Passiflora incarnata (maypops). Harmaline is a reversible inhibitor of MAO-A (RIMA). Harmine is a reversible inhibitor of MAO-A (RIMA). It is important to note that unlike synthetic pharmaceutical MAOIs such as phenelzine, harmine is reversible and selective meaning it does not have nearly as high a risk for the "cheese syndrome" caused by consuming tyramine-containing foods, which is a risk associated with monoamine oxidase A inhibitors, but not monoamine oxidase B inhibitors. Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala (also known as Harmal or Syrian Rue), including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine which was once known as Telepathine and Banisterine is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi, but not P. harmala. Dr. Alexander Shulgin has suggesed that harmaline may be a breakdown product of harmine. Harmine and harmaline are reversible MAOIs of the MAO-A isoform of the enzyme, and can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine. The harmala alkaloids occur in Peganum harmala in concentrations of roughly 3\\%, though tests have documented anywhere from 2-7\\%, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the Banisteriopsis caapi vine, the key plant ingredient in the sacramental beverage Ayahuasca, in concentrations that range between 0.31-8.43\\% for harmine, 0.03-0.83\\% for harmaline and 0.05-2.94\\% for tetrahydroharmine. Other psychoactive plants are often added to Ayahuasca to achieve visionary states of consciousness; for example leaves from Psychotria viridis, which is a source of dimethyltryptamine (DMT). The harmala alkaloids serve to potentiate these brewed compounds by preventing their breakdown in the digestive tract. The harmala alkaloids are not especially psychoactive on their own, even at high dosages, when vomiting and diarrhea become the main effect Alkaloid from Passiflora incarnata (maypops)

   

1-Hexacosanol

1-Hexacosanol, aluminum (1:3) salt

C26H54O (382.4174)


   

5-Hydroxytryptoline

5-Hydroxytryptoline

C11H12N2O (188.095)


   

Vasicine

Pyrrolo(2,1-b)quinazolin-3-ol, 1,2,3,9-tetrahydro-

C11H12N2O (188.095)


1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol is a member of quinazolines. (±)-Vasicine is the racemate of Vasicine. Vasicine (Peganine) significantly inhibits H+-K+-ATPase activity?in vitro?with an IC50 of 73.47?μg/mL. Anti-ulcer activity. Vasicine shows significant anti-secretory, antioxidant and?cytoprotective?effect[1].

   

Harmol

9H-Pyrido(3,4-b)indol-7-ol, 1-methyl- (8CI)(9CI)

C12H10N2O (198.0793)


Alkaloid from Elaeagnus angustifolia (Russian olive) and Passiflora incarnata (maypops). Harmol is found in sea-buckthornberry, herbs and spices, and fruits. Harmol is found in fruits. Harmol is an alkaloid from Elaeagnus angustifolia (Russian olive) and Passiflora incarnata (maypops). Harmol categorized as a β-carboline alkaloid. Harmol is a potent MAO inhibitor used as an analytical reference standard[1]. Harmol categorized as a β-carboline alkaloid. Harmol is a potent MAO inhibitor used as an analytical reference standard[1].

   

Harmalan

4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indole, 9ci

C12H12N2 (184.1)


Harmalan is found in fruits. Harmalan is an alkaloid from Elaeagnus angustifolia (Russian olive

   

Quinaldine

2-Methylquinoline (acd/name 4.0)

C10H9N (143.0735)


Quinaldine or 2-methylquinoline is a simple derivative of a heterocyclic compound quinoline.

   

Tetrahydroharmine

7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

C13H16N2O (216.1263)


   

5-Hydroxytryptoline

1H,2H,3H,4H,9H-pyrido[3,4-b]indol-6-ol

C11H12N2O (188.095)


   

VASICINONE

1H-Pyrrolo[2,1-b]quinazolin-9-one, 3-hydroxy-2,3-dihydro-

C11H10N2O2 (202.0742)


   

Linoleate

cis-9, cis-12-octadecadienoic acid

C18H32O2 (280.2402)


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

   

Serotonin

5-Hydroxytryptamine

C10H12N2O (176.095)


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

   

HARMINE HCl

9H-PYRIDO(3,4-B)INDOLE, 7-METHOXY-1-METHYL-, HYDROCHLORIDE (1:1)

C13H12N2O.HCl (248.0716)


Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1].

   

Harmol

1-Methyl-9H-pyrido[3,4-b]indol-7-ol Monohydrochloride Dihydrate

C12H10N2O (198.0793)


Harmol is a 9H-beta-carboline carrying a methyl substituent at C-1 and a hydroxy group at C-7; major microspecies at pH 7.3. It has a role as an antifungal agent, an apoptosis inducer and an autophagy inducer. It is a harmala alkaloid and an indole alkaloid. It is functionally related to a beta-carboline. Harmol is a natural product found in Fontinalis squamosa, Passiflora foetida, and other organisms with data available. Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.454 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.443 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.442 Harmol categorized as a β-carboline alkaloid. Harmol is a potent MAO inhibitor used as an analytical reference standard[1]. Harmol categorized as a β-carboline alkaloid. Harmol is a potent MAO inhibitor used as an analytical reference standard[1].

   

Harmine

9H-PYRIDO(3,4-B)INDOLE, 7-METHOXY-1-METHYL-, HYDROCHLORIDE (1:1)

C13H12N2O.HCl (248.0716)


Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1].

   
   

Acacetin 7-O-alpha-L-rhamnopyranoside

7- [ (6-Deoxy-alpha-L-mannopyranosyl) oxy ] -5-hydroxy-2- (4-methoxyphenyl) -4H-1-benzopyran-4-one

C22H22O9 (430.1264)


   

Acacetin 7-O-[6-O-glucosyl-2-O-(3-acetylrhamnosyl)glucoside

Acacetin 7-O-[6-O-glucosyl-2-O-(3-acetylrhamnosyl)glucoside

C36H44O20 (796.2426)


   

Deoxypeganidine

Deoxypeganidine

C14H16N2O (228.1263)


   

Ascorbic acid

(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

C6H8O6 (176.0321)


Ascorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in human diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including humans) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant (PubChem). Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants (PMID: 10799361). Moreover, ascorbic acid is found to be associated with hyperoxalemia, which is an inborn error of metabolism. Ascorbic acid is also a microbial metabolite produced by Ketogulonicigenium (PMID: 15785002). Occurs widely in animals and plants. Good sources are citrus fruits and hip berries. Isolated from ox adrenal cortex, lemons and paprika. Production industrially on a large scale from glucose. Vitamin (antiscorbutic), antioxidant, nutrient, preservative consistency enhancer. It is used to reduce discoloration, mainly browning caused by polyphenol oxidase, in fruit and vegetable products. It is used to enhance colour formn. and to reduced the formn. of nitrosamines in meat products. It is used synergistically with Sulfur dioxide HVF10-P in wine and beer as a perservative. Assists formn. of the gluten network in bread making, thus enhancing bread volume. L-Ascorbic acid is found in many foods, some of which are cabbage, hyssop, ginseng, and pancake. L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4]. L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4].

   

4-Hydroxypipecolic acid

4-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID

C6H11NO3 (145.0739)


   

Swartziol

4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-5,7,4-Trihydroxyflavonol

C15H10O6 (286.0477)


Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4]. Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4].

   

Quercetin

2- (3,4-Dihydroxyphenyl) -3,5,7-trihydroxy-4H-1-benzopyran-4-one

C15H10O7 (302.0427)


Annotation level-1 COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials relative retention time with respect to 9-anthracene Carboxylic Acid is 0.898 D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.902 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1981; CONFIDENCE confident structure IPB_RECORD: 3301; CONFIDENCE confident structure IPB_RECORD: 3283; CONFIDENCE confident structure Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

   

Harmaline

HARMALINE HYDROCHLORIDE DIHYDRATE

C13H14N2O (214.1106)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.572 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.569 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.563 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.565 D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants D004791 - Enzyme Inhibitors > D008996 - Monoamine Oxidase Inhibitors

   

Harmolol

Harmolol

C12H12N2O (200.095)


A harmala alkaloid in which the harman skeleton is hydroxy-substituted at C-7 and has been reduced across the 3,4 bond. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.398 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.395 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.387 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.386

   

Kaempferol

Kaempferol

C15H10O6 (286.0477)


Annotation level-3 Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.010 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.011 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2141; CONFIDENCE confident structure IPB_RECORD: 3341; CONFIDENCE confident structure IPB_RECORD: 3321; CONFIDENCE confident structure CONFIDENCE confident structure; IPB_RECORD: 3321 IPB_RECORD: 141; CONFIDENCE confident structure Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4]. Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4].

   

9,14-dihydroxyoctadecanoic acid

9,14-dihydroxyoctadecanoic acid

C18H36O4 (316.2613)


   

2-O-Rhamnosyl-2-O-glucosylcytisoside

2-O-Rhamnosyl-2-O-glucosylcytisoside

C34H42O19 (754.232)


   
   

SCHEMBL17100111

SCHEMBL17100111

C13H14N2O (214.1106)


   
   

Harmine

Harmine

C13H12N2O (212.095)


Origin: Plant; SubCategory_DNP: Alkaloids derived from tryptophan, beta-Carboline alkaloids, Indole alkaloids D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens D004791 - Enzyme Inhibitors > D008996 - Monoamine Oxidase Inhibitors C471 - Enzyme Inhibitor > C667 - Monoamine Oxidase Inhibitor Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.622 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.620 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.613 Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1].

   

6-Hydroxytryptamine

3-(2-aminoethyl)-1H-indol-6-ol

C10H12N2O (176.095)


   

SCHEMBL11468065

SCHEMBL11468065

C11H10N2O (186.0793)


   

Deoxypeganin

Deoxyvasicine; DesoxyPeganin; Desoxypeganine; Pegene

C11H12N2 (172.1)


Deoxypeganine is a member of quinazolines. Deoxypeganine is a natural product found in Nitraria komarovii, Peganum harmala, and Peganum nigellastrum with data available.

   

HARMINE HCl

9H-PYRIDO(3,4-B)INDOLE, 7-METHOXY-1-METHYL-, HYDROCHLORIDE (1:1)

C13H13ClN2O (248.0716)


Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine Hydrochloride (Telepathine Hydrochloride) is a natural DYRK inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1].

   

Pegenone

InChI=1/C11H10N2O/c14-11-8-4-1-2-5-9(8)12-10-6-3-7-13(10)11/h1-2,4-5H,3,6-7H

C11H10N2O (186.0793)


Deoxyvasicinone is a member of quinazolines. Deoxyvasicinone is a natural product found in Justicia adhatoda, Isatis tinctoria, and other organisms with data available.

   

Harman

Harmane

C12H10N2 (182.0844)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.504 D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens relative retention time with respect to 9-anthracene Carboxylic Acid is 0.500 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.495 IPB_RECORD: 461; CONFIDENCE confident structure Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

   

Harmane

Harmane

C12H10N2 (182.0844)


Annotation level-1 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2281; CONFIDENCE confident structure IPB_RECORD: 2961; CONFIDENCE confident structure

   

peganine

peganine

C11H12N2O (188.095)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053

   

Serotonin

5-Hydroxytryptamine

C10H12N2O (176.095)


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

   

Harmine

NCGC00016435-05!HARMINE

C13H12N2O (212.095)


   

harmalol

harmalol

C12H12N2O (200.095)


Annotation level-1

   

Nonacosanol

Nonacosan-1-ol

C29H60O (424.4644)


   

Acacetin 7-O-[2-O-rhamnosyl-2-O-glucosylglucoside

Acacetin 7-O-[2-O-rhamnosyl-2-O-glucosylglucoside

C34H42O19 (754.232)


   

Harmalan

4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indole, 9ci

C12H12N2 (184.1)


   

Khinaldin

2-Methylquinoline (acd/name 4.0)

C10H9N (143.0735)


   

Cerotin

Hexacosyl alcohol

C26H54O (382.4174)


Hexacosan-1-ol, also known as 1-hexacosanol or hexacosyl alcohol, is a member of the class of compounds known as fatty alcohols. Fatty alcohols are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, hexacosan-1-ol is considered to be a fatty alcohol lipid molecule. Hexacosan-1-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Hexacosan-1-ol can be synthesized from hexacosane. Hexacosan-1-ol can also be synthesized into 24-methylhexacosan-1-ol. Hexacosan-1-ol can be found in a number of food items such as brussel sprouts, broccoli, lemon grass, and lettuce, which makes hexacosan-1-ol a potential biomarker for the consumption of these food products. Hexacosan-1-ol is a saturated primary fatty alcohol with a carbon chain length of 26 that is a white waxy solid at room temperature. It is freely soluble in chloroform and insoluble in water. It occurs naturally in the epicuticular wax and plant cuticle of many plant species .

   

7-methoxy-9H-pyrido[3,4-b]indole

7-methoxy-9H-pyrido[3,4-b]indole

C12H10N2O (198.0793)


   

Quertin

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-

C15H10O7 (302.0427)


COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

   

Cognac oil

9,12-Octadecadienoic acid, (Z,Z)-, labeled with carbon-14

C18H32O2 (280.2402)


An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry. COVID info from PDB, Protein Data Bank, WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

530-53-0

InChI=1\C11H10N2O\c14-11-8-4-1-2-5-9(8)12-10-6-3-7-13(10)11\h1-2,4-5H,3,6-7H

C11H10N2O (186.0793)


   

linoleic

9,12-Octadecadienoic acid, (9E,12E)-

C18H32O2 (280.2402)


Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1]. Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1].

   

vitamin C

2-o-(beta-d-glucopyranosyl)-ascorbic acid_qt

C6H8O6 (176.0321)


G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids > G01AD - Organic acids A - Alimentary tract and metabolism > A11 - Vitamins > A11G - Ascorbic acid (vitamin c), incl. combinations > A11GA - Ascorbic acid (vitamin c), plain B - Blood and blood forming organs > B03 - Antianemic preparations > B03A - Iron preparations > B03AA - Iron bivalent, oral preparations COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants C26170 - Protective Agent > C275 - Antioxidant D018977 - Micronutrients > D014815 - Vitamins S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4]. L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4].

   

5-HTA

5-22-12-00016 (Beilstein Handbook Reference)

C10H12N2O (176.095)


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

   

Leucol

InChI=1\C9H7N\c1-2-6-9-8(4-1)5-3-7-10-9\h1-7

C9H7N (129.0578)


   

Aribin

InChI=1\C12H10N2\c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12\h2-7,14H,1H

C12H10N2 (182.0844)


D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

   

Deoxypeganin

Pyrrolo(2,1-b)quinazoline, 1,2,3,9-tetrahydro-

C11H12N2 (172.1)


   

Yageine

InChI=1\C13H12N2O\c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13\h3-7,15H,1-2H

C13H12N2O (212.095)


D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens D004791 - Enzyme Inhibitors > D008996 - Monoamine Oxidase Inhibitors C471 - Enzyme Inhibitor > C667 - Monoamine Oxidase Inhibitor Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1]. Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1].

   

Vitamin_C

L-Threoascorbic acid,Antiscorbutic factor,Vitamin C;(R)-5-((S)-1,2-Dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one

C6H8O6 (176.0321)


L-ascorbic acid is a white to very pale yellow crystalline powder with a pleasant sharp acidic taste. Almost odorless. (NTP, 1992) L-ascorbic acid is the L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate. It has a role as a coenzyme, a flour treatment agent, a food antioxidant, a plant metabolite, a cofactor, a skin lightening agent and a geroprotector. It is an ascorbic acid and a vitamin C. It is a conjugate acid of a L-ascorbate. It is an enantiomer of a D-ascorbic acid. A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. Ascorbic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Ascorbic acid is a Vitamin C. Ascorbic Acid is a natural product found in Populus tremula, Rosa platyacantha, and other organisms with data available. Ascorbic Acid is a natural water-soluble vitamin (Vitamin C). Ascorbic acid is a potent reducing and antioxidant agent that functions in fighting bacterial infections, in detoxifying reactions, and in the formation of collagen in fibrous tissue, teeth, bones, connective tissue, skin, and capillaries. Found in citrus and other fruits, and in vegetables, vitamin C cannot be produced or stored by humans and must be obtained in the diet. (NCI04) A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. See also: Sodium Ascorbate (active moiety of); D-ascorbic acid (related); Magnesium Ascorbyl Phosphate (active moiety of) ... View More ... G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids > G01AD - Organic acids A - Alimentary tract and metabolism > A11 - Vitamins > A11G - Ascorbic acid (vitamin c), incl. combinations > A11GA - Ascorbic acid (vitamin c), plain B - Blood and blood forming organs > B03 - Antianemic preparations > B03A - Iron preparations > B03AA - Iron bivalent, oral preparations COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants C26170 - Protective Agent > C275 - Antioxidant D018977 - Micronutrients > D014815 - Vitamins S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4]. L-Ascorbic acid (L-Ascorbate), an electron donor, is an endogenous antioxidant agent. L-Ascorbic acid inhibits selectively Cav3.2 channels with an IC50 of 6.5 μM. L-Ascorbic acid is also a collagen deposition enhancer and an elastogenesis inhibitor[1][2][3]. L-Ascorbic acid exhibits anti-cancer effects through the generation of reactive oxygen species (ROS) and selective damage to cancer cells[4].

   

leucoline

QUINOLINE

C9H7N (129.0578)


   

Quinaldine

2-METHYLQUINOLINE

C10H9N (143.0735)


   

hexacosan-1-ol

hexacosan-1-ol

C26H54O (382.4174)


A very long-chain primary fatty alcohol that is hexacosane in which a hydrogen attached to one of the terminal carbons is replaced by a hydroxy group.

   

10-methoxy-6h,7h,12h-indolo[2,3-a]quinolizin-4-one

10-methoxy-6h,7h,12h-indolo[2,3-a]quinolizin-4-one

C16H14N2O2 (266.1055)


   

7-methoxy-2h,3h,4h,9h-pyrido[3,4-b]indol-1-one

7-methoxy-2h,3h,4h,9h-pyrido[3,4-b]indol-1-one

C12H12N2O2 (216.0899)


   

8-[(2s,3r,4s,5s,6s)-3-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

8-[(2s,3r,4s,5s,6s)-3-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

C34H42O19 (754.232)


   

1h,2h,3h,4h,9h-pyrido[3,4-b]indol-5-ol

1h,2h,3h,4h,9h-pyrido[3,4-b]indol-5-ol

C11H12N2O (188.095)


   

5-methoxy-10,10-dimethyl-8,12-diazatetracyclo[6.6.1.0²,⁷.0¹¹,¹⁵]pentadeca-1(15),2,4,6,11-pentaene

5-methoxy-10,10-dimethyl-8,12-diazatetracyclo[6.6.1.0²,⁷.0¹¹,¹⁵]pentadeca-1(15),2,4,6,11-pentaene

C16H18N2O (254.1419)


   

(+-)-vasicine

(+-)-vasicine

C11H12N2O (188.095)


   

(2s,3s,4r,5s,6s)-2-{[(2s,3s,4s,5r,6s)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-({[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

(2s,3s,4r,5s,6s)-2-{[(2s,3s,4s,5r,6s)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-({[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

C36H44O20 (796.2426)


   

1-{1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl}propan-2-one

1-{1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl}propan-2-one

C14H16N2O (228.1263)


   

7-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one

7-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one

C34H42O19 (754.232)


   

1h,2h,3h,4h-pyrrolo[3,4-b]quinolin-9-one

1h,2h,3h,4h-pyrrolo[3,4-b]quinolin-9-one

C11H10N2O (186.0793)


   

(3r)-3-hydroxy-1h,2h,3h-pyrrolo[2,1-b]quinazolin-9-one

(3r)-3-hydroxy-1h,2h,3h-pyrrolo[2,1-b]quinazolin-9-one

C11H10N2O2 (202.0742)


   

7-methoxy-9-methyl-3h,4h-pyrido[3,4-b]indole

7-methoxy-9-methyl-3h,4h-pyrido[3,4-b]indole

C13H14N2O (214.1106)


   

1-[(1r,3s,4ar,8as)-3-hydroxy-1,2,3,4,4a,8a-hexahydroisoquinolin-1-yl]propan-2-one

1-[(1r,3s,4ar,8as)-3-hydroxy-1,2,3,4,4a,8a-hexahydroisoquinolin-1-yl]propan-2-one

C12H17NO2 (207.1259)


   

1-{3-hydroxy-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl}propan-2-one

1-{3-hydroxy-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl}propan-2-one

C14H16N2O2 (244.1212)


   

7-methoxy-1h,2h,3h,4h,9h-pyrido[3,4-b]indole-1-carbaldehyde

7-methoxy-1h,2h,3h,4h,9h-pyrido[3,4-b]indole-1-carbaldehyde

C13H14N2O2 (230.1055)


   

2,5-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})benzoic acid

2,5-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})benzoic acid

C19H26O14 (478.1322)


   

1-{1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl}-1h,2h,3h-pyrrolo[2,1-b]quinazolin-9-one

1-{1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl}-1h,2h,3h-pyrrolo[2,1-b]quinazolin-9-one

C22H20N4O (356.1637)


   

7-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3s,4r,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one

7-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3s,4r,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one

C34H42O19 (754.232)


   

n,n'-bis(3-hydroxy-5-methylphenyl)ethanediamide

n,n'-bis(3-hydroxy-5-methylphenyl)ethanediamide

C16H16N2O4 (300.111)


   

(9r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-ol

(9r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-ol

C11H12N2O (188.095)


   

5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

C22H22O9 (430.1264)


   

(2s,3r,4r,5s,6r)-2-(hydroxymethyl)-6-({7-methoxy-1-methyl-9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

(2s,3r,4r,5s,6r)-2-(hydroxymethyl)-6-({7-methoxy-1-methyl-9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

C19H22N2O7 (390.1427)


   

2,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})benzoic acid

2,5-bis({[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})benzoic acid

C19H26O14 (478.1322)


   

(2r,3s,4r,5r,6s)-2-(hydroxymethyl)-6-({7-methoxy-1-methyl-3h,4h,9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

(2r,3s,4r,5r,6s)-2-(hydroxymethyl)-6-({7-methoxy-1-methyl-3h,4h,9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

C19H24N2O7 (392.1583)


   

(2s,4r)-4-hydroxypiperidine-2-carboxylic acid

(2s,4r)-4-hydroxypiperidine-2-carboxylic acid

C6H11NO3 (145.0739)


   

(3r)-1-[(2-aminophenyl)methyl]-3-hydroxypyrrolidin-2-one

(3r)-1-[(2-aminophenyl)methyl]-3-hydroxypyrrolidin-2-one

C11H14N2O2 (206.1055)


   

8-(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

8-(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

C34H42O19 (754.232)


   

(1s)-1-[(9r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl]-1h,2h,3h-pyrrolo[2,1-b]quinazolin-9-one

(1s)-1-[(9r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl]-1h,2h,3h-pyrrolo[2,1-b]quinazolin-9-one

C22H20N4O (356.1637)


   

(3s)-3-[(9r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl]-1h,2h,3h-pyrrolo[2,1-b]quinazolin-9-one

(3s)-3-[(9r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl]-1h,2h,3h-pyrrolo[2,1-b]quinazolin-9-one

C22H20N4O (356.1637)


   

1-[(9r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl]propan-2-one

1-[(9r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl]propan-2-one

C14H16N2O (228.1263)


   

1-[(3s,9r)-3-hydroxy-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl]propan-2-one

1-[(3s,9r)-3-hydroxy-1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-yl]propan-2-one

C14H16N2O2 (244.1212)


   

(9r,14s)-9,14-dihydroxyoctadecanoic acid

(9r,14s)-9,14-dihydroxyoctadecanoic acid

C18H36O4 (316.2613)


   

2-(hydroxymethyl)-6-({7-methoxy-1-methyl-9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

2-(hydroxymethyl)-6-({7-methoxy-1-methyl-9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

C19H22N2O7 (390.1427)


   

(-)-peganine

(-)-peganine

C11H12N2O (188.095)


   

{3,4,5-trihydroxy-6-[(4-hydroxy-2-{[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl)oxy]oxan-2-yl}methyl acetate

{3,4,5-trihydroxy-6-[(4-hydroxy-2-{[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl)oxy]oxan-2-yl}methyl acetate

C42H54O25 (958.2954)


   

2-[(4,5-dihydroxy-2-{[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl)oxy]-3,5-dihydroxy-6-methyloxan-4-yl acetate

2-[(4,5-dihydroxy-2-{[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl)oxy]-3,5-dihydroxy-6-methyloxan-4-yl acetate

C36H44O20 (796.2426)


   

1-(3-hydroxy-1,2,3,4,4a,8a-hexahydroisoquinolin-1-yl)propan-2-one

1-(3-hydroxy-1,2,3,4,4a,8a-hexahydroisoquinolin-1-yl)propan-2-one

C12H17NO2 (207.1259)


   

5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

C22H22O9 (430.1264)


   

1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-ol

1h,2h,3h,9h-pyrrolo[2,1-b]quinazolin-9-ol

C11H12N2O (188.095)


   

5-hydroxy-2-(4-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one

5-hydroxy-2-(4-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one

C22H22O9 (430.1264)


   

7-methoxy-1h,2h,3h,4h-pyrido[3,4-b]indole-9-carbaldehyde

7-methoxy-1h,2h,3h,4h-pyrido[3,4-b]indole-9-carbaldehyde

C13H14N2O2 (230.1055)


   

10-methoxy-2-methyl-6h,7h,12h-indolo[2,3-a]quinolizin-4-one

10-methoxy-2-methyl-6h,7h,12h-indolo[2,3-a]quinolizin-4-one

C17H16N2O2 (280.1212)


   

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-({7-methoxy-1-methyl-9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-({7-methoxy-1-methyl-9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

C19H22N2O7 (390.1427)


   

8-[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

8-[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

C34H42O19 (754.232)


   

2-(hydroxymethyl)-6-({7-methoxy-1-methyl-3h,4h,9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

2-(hydroxymethyl)-6-({7-methoxy-1-methyl-3h,4h,9h-pyrido[3,4-b]indol-8-yl}oxy)oxane-3,4,5-triol

C19H24N2O7 (392.1583)


   

2-(3-hydroxypropyl)quinazolin-4-ol

2-(3-hydroxypropyl)quinazolin-4-ol

C11H12N2O2 (204.0899)


   

(2s,3r,4r,5s,6s)-2-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

(2s,3r,4r,5s,6s)-2-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

C36H44O20 (796.2426)


   

7-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one

7-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one

C34H42O19 (754.232)