1.02010-04-08 22:05:17 UTC2020-09-17 15:30:47 UTCFDB002237TrigonellineN-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-pyridiniumcarboxylate1-Methyl-3-pyridiniumcarboxylic acid1-methylnicotinate1-Methylnicotinic acid1-Methylpyridinio-3-carboxylate1-Methylpyridinio-3-carboxylic acid1-methylpyridinium-3-carboxylate3-carboxy-1-methyl-Pyridinium hydroxide inner salt3-Carboxy-1-methylpyridinium hydroxide inner salt3-Carboxy-1-methylpyridinium hydroxide, inner salt535-83-1 (INNER SALT)Betain nicotinateBetain nicotinic acidBetaine nicotinateBetaine nicotinic acidCaffearinCaffearineCoffearinCoffearineGynesineGynesisN-methyl-nicotinateN-Methyl-nicotinic acidN-methylnicotinateN-methylnicotinic acidN-Methylnicotinic betaineN'-methylnicotinateN'-methylnicotinic acidNicotinate N-methylbetaineNicotinic acid n-methylbetainePyridinium, 3-carboxy-1-methyl-, hydroxide, inner saltPyridinium, 3-carboxy-1-methyl-, inner saltTrigenellineTrigenollineTrigonellinTrigonellineC7H7NO2137.136137.0476784731-methylpyridin-1-ium-3-carboxylatetrigonelline535-83-1C[N+]1=CC=CC(=C1)C([O-])=OInChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3WWNNZCOKKKDOPX-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 derivativesOrganic compoundsAlkaloids and derivativesAromatic heteromonocyclic compoundsAzacyclic compoundsCarboxylic acid saltsCarboxylic acidsHeteroaromatic compoundsHydrocarbon derivativesMonocarboxylic acids and derivativesN-methylpyridinium compoundsOrganic oxidesOrganic saltsOrganonitrogen compoundsOrganooxygen compoundsOrganopnictogen compoundsPyridinecarboxylic acidsPyridinium derivativesVinylogous amidesAlkaloid or derivativesAromatic heteromonocyclic compoundAzacycleCarboxylic acidCarboxylic acid derivativeCarboxylic acid saltHeteroaromatic compoundHydrocarbon derivativeMonocarboxylic acid or derivativesN-methylpyridiniumOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic saltOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPyridinePyridine carboxylic acidPyridine carboxylic acid or derivativesPyridiniumVinylogous amidePyridine alkaloidsa small moleculealkaloidiminium betaineSolidlogp-3.30logs-2.77solubility3.23e-01 g/lmelting_pointMp 218 dec. (anhyd.)logp-3.5pka_strongest_acidic2.78iupac1-methylpyridin-1-ium-3-carboxylateaverage_mass137.136mono_mass137.047678473smilesC[N+]1=CC=CC(=C1)C([O-])=OformulaC7H7NO2inchiInChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3inchikeyWWNNZCOKKKDOPX-UHFFFAOYSA-Npolar_surface_area44.01refractivity48.15polarizability13.4rotatable_bond_count1acceptor_count2donor_count0physiological_charge0formal_charge0Specdb::EiMs1938Specdb::NmrOneD1579Specdb::NmrOneD3898Specdb::NmrOneD4172Specdb::CMs5767Specdb::CMs155971Specdb::MsIr935Specdb::MsIr936Specdb::NmrTwoD1040Specdb::NmrTwoD1521Specdb::MsMs1235Specdb::MsMs1236Specdb::MsMs1237Specdb::MsMs4748Specdb::MsMs4749Specdb::MsMs4750Specdb::MsMs4751Specdb::MsMs4752Specdb::MsMs4753Specdb::MsMs4754Specdb::MsMs240493Specdb::MsMs240494Specdb::MsMs240495Specdb::MsMs242548Specdb::MsMs242549Specdb::MsMs242550Specdb::MsMs447129Specdb::MsMs447130Specdb::MsMs447131Specdb::MsMs447132Specdb::MsMs447133Specdb::MsMs447321Specdb::MsMs448188Specdb::MsMs448189Specdb::MsMs449866HMDB0087518123#<Reference:0x00005556762f6ee0>#<Reference:0x00005556762f6cb0>#<Reference:0x00005556762f6af8>#<Reference:0x00005556762f68c8>#<Reference:0x00005556762f6620>#<Reference:0x00005556762f63f0>AlfalfaType 1specificMedicago sativa3879AmaranthType 1specificAmaranthus3564AnatidaeType 1specificAnatidae8830Annual wild riceType 1specificZizania aquatica75727Arabica coffeeType 1specificCoffea arabica13443800.0800.0800.0mg/100 gBananaType 1specificMusa acuminata4641BarleyType 1specificHordeum vulgare45130.890.890.89mg/100 gBeefaloType 1specificBos taurus X Bison bison297284BeerType 2specific0.03850.0390.038mg/100 gBisonType 1specificBison bison9901Breakfast cerealType 2specificBrussel sproutsType 1specificBrassica oleracea var. gemmifera178616BuffaloType 1specificBubalus bubalis89462BulgurType 2specificCattle (Beef, Veal)Type 1specificBos taurus9913Cereals and cereal productsUnknowngenericChickenType 1specificGallus gallus9031ChickpeaType 1specificCicer arietinum3827Cocoa beanType 1specificTheobroma cacao3641CoffeeType 1genericCoffea13442Coffee and coffee productsUnknowngenericColumbidae (Dove, Pigeon)Type 1specificColumbidae8930Common beanType 1specificPhaseolus vulgaris3885Common buckwheatType 1specificFagopyrum esculentum3617Common peaType 1specificPisum sativum38887.52857117.751.25mg/100 gCommon wheatType 1specificTriticum aestivum4565CornType 1specificZea mays45770.40.40.4mg/100 gCowpeaType 1specificVigna unguiculata3917DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825EggplantType 1specificSolanum melongena4111ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984FennelType 1specificFoeniculum vulgare48038FenugreekType 1specificTrigonella foenum-graecum78534130.0130.0130.0mg/100 gFlourType 2specificGarden onionType 1specificAllium cepa46791.31.31.3mg/100 gGarden tomato (var.)Type 1specificSolanum lycopersicum var. lycopersicum3977554.154.154.15mg/100 gGrape wineType 2specific8.7517.50.0mg/100 gGreen beanType 1specificPhaseolus vulgaris3885Green bell pepperType 1specificCapsicum annuum40720.060.060.06mg/100 gGreylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996Hard wheatType 1specificTriticum durum4567Herbs and SpicesUnknowngenericHorseType 1specificEquus caballus9796Hyacinth beanType 1specificLablab purpureus35936LambsquartersType 1specificChenopodium album3559LentilsType 1genericLens culinaris3864Mallard duckType 1specificAnas platyrhynchos8839MilletType 1specificPanicum miliaceum4540Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871MuskmelonType 1specificCucumis melo36560.40.40.4mg/100 gOatType 1specificAvena sativa4498Orange bell pepperType 1specificCapsicum annuum40720.060.060.06mg/100 gOriental wheatType 1specificTriticum turanicum376534OstrichType 1specificStruthio camelus8801ParsleyType 1specificPetroselinum crispum4043PepperType 1specificCapsicum annuum40720.060.060.06mg/100 gPheasantType 1specificPhasianus colchicus9054PotatoType 1specificSolanum tuberosum4113QuailType 1specificPhasianidae9005QuinoaType 1specificChenopodium quinoa63459RabbitType 1specificLeporidae9979Red bell pepperType 1specificCapsicum annuum40720.060.060.06mg/100 gRed riceType 1specificOryza rufipogon4529RiceType 1specificOryza sativa4530Robusta coffeeType 1specificCoffea canephora49390Rock ptarmiganType 1specificLagopus muta64668RyeType 1specificSecale cereale4550Sacred lotusType 1specificNelumbo nucifera4432Sheep (Mutton, Lamb)Type 1specificOvis aries9940Soft-necked garlicType 1specificAllium sativum L. var. sativum4682SorghumType 1specificSorghum bicolor4558Soy beanType 1specificGlycine max3847SpeltType 1specificTriticum spelta58933SpinachType 1specificSpinacia oleracea3562SquabType 1specificColumba8931Tartary buckwheatType 1specificFagopyrum tataricum62330TeffType 1specificEragrostis tef110835TriticaleType 1specificX Triticosecale rimpauiTurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864WheatType 1specificTriticum4564White lupineType 1specificLupinus albus3870Wild boarType 1specificSus scrofa9823Wild riceType 1specificZizania15949Yellow bell pepperType 1specificCapsicum annuum40720.060.060.06mg/100 gYellow wax beanType 1specificPhaseolus vulgaris3885anti cancer159A substance that inhibits or prevents the proliferation of neoplasms.anti hyperglycemic343anti migraine437Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti septic603A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.antitumor672A substance that inhibits or prevents the proliferation of neoplasms.epidermal stimulant910hypocholesterolemic1016hypoglycemic1017A drug which lowers the blood glucose level.mutagenic1125osmoregulator1176pesticide1210Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.propecic1253