1.0 2010-04-08 22:05:17 UTC 2020-09-17 15:30:47 UTC FDB002237 Trigonelline N-Methylnicotinate or Trigonelline, also known as caffearin or gynesine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Trigonelline is a moderately acidic compound. Trigonelline exists in all living organisms, from bacteria to humans. It is a product of the metabolism of niacin (vitamin B3) and it is excreted in the urine. Trigonelline in urine is a biomarker for the consumption of coffee, legumes and soy products. Trigonelline is found in highest concentrations in arabica coffee, fenugreeks, and common pea and in lower concentrations in yellow bell peppers, orange bell peppers, and muskmelons. Trigonelline has also been detected in rices, triticales, alfalfa, cereals and cereal products, ryes fenugreek seeds, garden peas, oats and potatoes. Trigonelline may reduce dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. It also has shown anti-carcinogenic and anti-hyperglycemic effects in several studies (PMID: 22680628; PMID: 31896496; PMID: 31363374). 1-Methyl-3-pyridiniumcarboxylate 1-Methyl-3-pyridiniumcarboxylic acid 1-methylnicotinate 1-Methylnicotinic acid 1-Methylpyridinio-3-carboxylate 1-Methylpyridinio-3-carboxylic acid 1-methylpyridinium-3-carboxylate 3-carboxy-1-methyl-Pyridinium hydroxide inner salt 3-Carboxy-1-methylpyridinium hydroxide inner salt 3-Carboxy-1-methylpyridinium hydroxide, inner salt 535-83-1 (INNER SALT) Betain nicotinate Betain nicotinic acid Betaine nicotinate Betaine nicotinic acid Caffearin Caffearine Coffearin Coffearine Gynesine Gynesis N-methyl-nicotinate N-Methyl-nicotinic acid N-methylnicotinate N-methylnicotinic acid N-Methylnicotinic betaine N'-methylnicotinate N'-methylnicotinic acid Nicotinate N-methylbetaine Nicotinic acid n-methylbetaine Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt Pyridinium, 3-carboxy-1-methyl-, inner salt Trigenelline Trigenolline Trigonellin Trigonelline C7H7NO2 137.136 137.047678473 1-methylpyridin-1-ium-3-carboxylate trigonelline 535-83-1 C[N+]1=CC=CC(=C1)C([O-])=O InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3 WWNNZCOKKKDOPX-UHFFFAOYSA-N belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Alkaloids and derivatives Organic compounds Alkaloids and derivatives Aromatic heteromonocyclic compounds Azacyclic compounds Carboxylic acid salts Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives N-methylpyridinium compounds Organic oxides Organic salts Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Pyridinecarboxylic acids Pyridinium derivatives Vinylogous amides Alkaloid or derivatives Aromatic heteromonocyclic compound Azacycle Carboxylic acid Carboxylic acid derivative Carboxylic acid salt Heteroaromatic compound Hydrocarbon derivative Monocarboxylic acid or derivatives N-methylpyridinium Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyridine Pyridine carboxylic acid Pyridine carboxylic acid or derivatives Pyridinium Vinylogous amide Pyridine alkaloids a small molecule alkaloid iminium betaine Solid logp -3.30 ALOGPS logs -2.77 ALOGPS solubility 3.23e-01 g/l ALOGPS melting_point Mp 218 dec. (anhyd.) logp -3.5 ChemAxon pka_strongest_acidic 2.78 ChemAxon iupac 1-methylpyridin-1-ium-3-carboxylate ChemAxon average_mass 137.136 ChemAxon mono_mass 137.047678473 ChemAxon smiles C[N+]1=CC=CC(=C1)C([O-])=O ChemAxon formula C7H7NO2 ChemAxon inchi InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3 ChemAxon inchikey WWNNZCOKKKDOPX-UHFFFAOYSA-N ChemAxon polar_surface_area 44.01 ChemAxon refractivity 48.15 ChemAxon polarizability 13.4 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5767 Specdb::CMs 155971 Specdb::EiMs 1938 Specdb::MsIr 935 Specdb::MsIr 936 Specdb::NmrTwoD 1040 Specdb::NmrTwoD 1521 Specdb::MsMs 1235 Specdb::MsMs 1236 Specdb::MsMs 1237 Specdb::MsMs 4748 Specdb::MsMs 4749 Specdb::MsMs 4750 Specdb::MsMs 4751 Specdb::MsMs 4752 Specdb::MsMs 4753 Specdb::MsMs 4754 Specdb::MsMs 240493 Specdb::MsMs 240494 Specdb::MsMs 240495 Specdb::MsMs 242548 Specdb::MsMs 242549 Specdb::MsMs 242550 Specdb::MsMs 447129 Specdb::MsMs 447130 Specdb::MsMs 447131 Specdb::MsMs 447132 Specdb::MsMs 447133 Specdb::MsMs 447321 Specdb::MsMs 448188 Specdb::MsMs 448189 Specdb::MsMs 449866 Specdb::NmrOneD 1579 Specdb::NmrOneD 3898 Specdb::NmrOneD 4172 HMDB00875 18123 #<Reference:0x000055ce318d6d00> #<Reference:0x000055ce318d6b48> #<Reference:0x000055ce318d6990> #<Reference:0x000055ce318d67d8> #<Reference:0x000055ce318d6620> #<Reference:0x000055ce318d6468> Alfalfa Type 1 specific Medicago sativa 3879 Amaranth Type 1 specific Amaranthus 3564 Anatidae Type 1 specific Anatidae 8830 Annual wild rice Type 1 specific Zizania aquatica 75727 Arabica coffee Type 1 specific Coffea arabica 13443 800.0 800.0 800.0 mg/100 g Banana Type 1 specific Musa acuminata 4641 Barley Type 1 specific Hordeum vulgare 4513 0.89 0.89 0.89 mg/100 g Beefalo Type 1 specific Bos taurus X Bison bison 297284 Beer Type 2 specific 0.0385 0.039 0.038 mg/100 g Bison Type 1 specific Bison bison 9901 Breakfast cereal Type 2 specific Brussel sprouts Type 1 specific Brassica oleracea var. gemmifera 178616 Buffalo Type 1 specific Bubalus bubalis 89462 Bulgur Type 2 specific Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Cereals and cereal products Unknown generic Chicken Type 1 specific Gallus gallus 9031 Chickpea Type 1 specific Cicer arietinum 3827 Cocoa bean Type 1 specific Theobroma cacao 3641 Coffee Type 1 generic Coffea 13442 Coffee and coffee products Unknown generic Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Common bean Type 1 specific Phaseolus vulgaris 3885 Common buckwheat Type 1 specific Fagopyrum esculentum 3617 Common pea Type 1 specific Pisum sativum 3888 7.528571 17.75 1.25 mg/100 g Common wheat Type 1 specific Triticum aestivum 4565 Corn Type 1 specific Zea mays 4577 0.4 0.4 0.4 mg/100 g Cowpea Type 1 specific Vigna unguiculata 3917 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Eggplant Type 1 specific Solanum melongena 4111 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Fennel Type 1 specific Foeniculum vulgare 48038 Fenugreek Type 1 specific Trigonella foenum-graecum 78534 130.0 130.0 130.0 mg/100 g Flour Type 2 specific Garden onion Type 1 specific Allium cepa 4679 1.3 1.3 1.3 mg/100 g Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 4.15 4.15 4.15 mg/100 g Grape wine Type 2 specific 8.75 17.5 0.0 mg/100 g Green bean Type 1 specific Phaseolus vulgaris 3885 Green bell pepper Type 1 specific Capsicum annuum 4072 0.06 0.06 0.06 mg/100 g Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Hard wheat Type 1 specific Triticum durum 4567 Herbs and Spices Unknown generic Horse Type 1 specific Equus caballus 9796 Hyacinth bean Type 1 specific Lablab purpureus 35936 Lambsquarters Type 1 specific Chenopodium album 3559 Lentils Type 1 generic Lens culinaris 3864 Mallard duck Type 1 specific Anas platyrhynchos 8839 Millet Type 1 specific Panicum miliaceum 4540 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Muskmelon Type 1 specific Cucumis melo 3656 0.4 0.4 0.4 mg/100 g Oat Type 1 specific Avena sativa 4498 Orange bell pepper Type 1 specific Capsicum annuum 4072 0.06 0.06 0.06 mg/100 g Oriental wheat Type 1 specific Triticum turanicum 376534 Ostrich Type 1 specific Struthio camelus 8801 Parsley Type 1 specific Petroselinum crispum 4043 Pepper Type 1 specific Capsicum annuum 4072 0.06 0.06 0.06 mg/100 g Pheasant Type 1 specific Phasianus colchicus 9054 Potato Type 1 specific Solanum tuberosum 4113 Quail Type 1 specific Phasianidae 9005 Quinoa Type 1 specific Chenopodium quinoa 63459 Rabbit Type 1 specific Leporidae 9979 Red bell pepper Type 1 specific Capsicum annuum 4072 0.06 0.06 0.06 mg/100 g Red rice Type 1 specific Oryza rufipogon 4529 Rice Type 1 specific Oryza sativa 4530 Robusta coffee Type 1 specific Coffea canephora 49390 Rock ptarmigan Type 1 specific Lagopus muta 64668 Rye Type 1 specific Secale cereale 4550 Sacred lotus Type 1 specific Nelumbo nucifera 4432 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Soft-necked garlic Type 1 specific Allium sativum L. var. sativum 4682 Sorghum Type 1 specific Sorghum bicolor 4558 Soy bean Type 1 specific Glycine max 3847 Spelt Type 1 specific Triticum spelta 58933 Spinach Type 1 specific Spinacia oleracea 3562 Squab Type 1 specific Columba 8931 Tartary buckwheat Type 1 specific Fagopyrum tataricum 62330 Teff Type 1 specific Eragrostis tef 110835 Triticale Type 1 specific X Triticosecale rimpaui Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wheat Type 1 specific Triticum 4564 White lupine Type 1 specific Lupinus albus 3870 Wild boar Type 1 specific Sus scrofa 9823 Wild rice Type 1 specific Zizania 15949 Yellow bell pepper Type 1 specific Capsicum annuum 4072 0.06 0.06 0.06 mg/100 g Yellow wax bean Type 1 specific Phaseolus vulgaris 3885 Anti hyperglycemic 343 Anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. Anti-migraine 437 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Epidermal stimulant 910 Hypocholesterolemic 1016 Hypoglycemic 1017 A drug which lowers the blood glucose level. Mutagenic 1125 Osmoregulator 1176 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Tyrosine kinase inhibitor 1253