Trigonelline (CED0004518)

Record Information
Version1.0
Creation Date2016-05-25 18:10:07 UTC
Update Date2026-04-02 23:26:37 UTC
Accession NumberCHEM021690
Identification
Common NameTrigonelline
ClassSmall Molecule
Description
Trigonelline belongs to the alkaloids and derivatives, a superclass within the organic compounds. It has a chemical formula of C7H7NO2 and an average molecular weight of 137.14 g/mol. Biologically, the compound acts as an antioxidant (PMC12595288, PMC9826852) and has a therapeutic effect on cancer (PMC10300961). The compound is found in or released from 28 recorded sources across multiple sectors. These include electrical and electronic equipment, such as batteries, capacitors, cell phones, printed circuit boards, and wires and cables. Within household cleaning and consumer products, it is associated with soap detergents, perfumes within detergents and soaps, cigar cigarettes, pipe accessories, and other smoking requisites. In the food, food processing and cookware sector, it is linked to food preservation, food packaging, the preparation of vinegar, and fermentation processes for beer. Other sources include synthetic textiles, carpets and rugs, medical devices, and indoor air. Recorded exposure routes for trigonelline include oral, inhalation, and touch.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
1-Methyl-3-pyridiniumcarboxylateChEBI
1-MethylnicotinateChEBI
1-Methylpyridinio-3-carboxylateChEBI
3-Carboxy-1-methylpyridinium hydroxide inner saltChEBI
Betain nicotinateChEBI
Betaine nicotinateChEBI
CaffearinChEBI
CaffearineChEBI
CoffearinChEBI
GynesineChEBI
N'-methylnicotinateChEBI
N-Methyl-nicotinateChEBI
Nicotinic acid N-methylbetaineChEBI
TrigenellineChEBI
TrigonellinChEBI
1-Methyl-3-pyridiniumcarboxylic acidGenerator
1-Methylnicotinic acidGenerator
1-Methylpyridinio-3-carboxylic acidGenerator
Betain nicotinic acidGenerator
Betaine nicotinic acidGenerator
N'-methylnicotinic acidGenerator
N-Methyl-nicotinic acidGenerator
Nicotinate N-methylbetaineGenerator
N-Methylnicotinic acidHMDB
Trigonelline chlorideHMDB
Trigonelline iodideHMDB
Trigonelline tosylateHMDB
Trigonelline ionHMDB
3-Carboxy-1-methyl-pyridinium hydroxide inner saltHMDB
CoffearineHMDB
N-MethylnicotinateHMDB
TrigenollineHMDB
TrigonellineChEBI
Chemical FormulaC7H7NO2
Average Molecular Mass137.136 g/mol
Monoisotopic Mass137.048 g/mol
CAS Registry Number535-83-1
IUPAC Name1-methylpyridin-1-ium-3-carboxylate
Traditional Nametrigonelline
SMILESC[N+]1=CC(=CC=C1)C([O-])=O
InChI IdentifierInChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
InChI KeyWWNNZCOKKKDOPX-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Alkaloid or derivatives
  • Pyridine carboxylic acid or derivatives
  • N-methylpyridinium
  • Pyridinium
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP-3.3ALOGPS
logP-3.5ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.01 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.15 m³·mol⁻¹ChemAxon
Polarizability13.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-9800000000-114b1e0b54ab0d6c1b04Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-2900000000-f7b3226615bd5e87f89bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-1900000000-a11de5552f1c306be0dfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-ee318a4f5a9d9e271a4dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-b68b239b6e2b1aae5216Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-1900000000-4eecb45261b5714a6f19Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9200000000-1f392d4e498677997436Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-2a8b2c8721614293a8f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016u-9000000000-0dc3b09d666ea6c7af17Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000l-6900000000-0d204e6b92b9c6b643daNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9100000000-d147503f87ded3d41c26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-b68b239b6e2b1aae5216Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-1900000000-4eecb45261b5714a6f19Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9200000000-1f392d4e498677997436Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-2a8b2c8721614293a8f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016u-9000000000-1638942a7b48eab1c7f7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-2fd573463b73045c069aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000l-6900000000-0d204e6b92b9c6b643daNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9100000000-d147503f87ded3d41c26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-2900000000-821723f398418c66e692Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01di-0900000000-084bd5d706c5eaedceb9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-74a99451d3221944f664Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-5900000000-d144f2056f19cda10797Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000f-9400000000-8bd7fa6005fdc97f397cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0v03-9000000000-b1faecc354b988f52eb2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-8456628eef3dc643ba7eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gdl-9000000000-cb5019c3ce174a5c016fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-89a59569d6c1637ede00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000f-9300000000-360788aafbea71b6ac62Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-eb1bfedcca0bbcecf559Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00mo-9000000000-580da033f79c7e62f7d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000f-9600000000-348cd108d12033dd607eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9100000000-d147503f87ded3d41c26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-ae706efcb99799aa4f94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-bdce44a0a273f61efb2bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004r-1900000000-840b949e52853c7aa542Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-9500000000-71844206506e1ac6a027Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-972c1ff182d2cbcd6c30Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000j-8900000000-1a56824bf3a0ff0f80d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-9000000000-c91672f20ae7e2130b95Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-e9459e2f88a3c3d3b01cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-e9459e2f88a3c3d3b01cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-9300000000-05a110941d256721df76Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-4900000000-af8086d237dcbaf23b47Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-9300000000-b949cf846ba763c6b36aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fr6-9000000000-8ea1c5ea12878a66b1c2Not AvailableView Spectrum
MSMS Spectrumsplash10-0pdu-9700000000-9de70f10113aec22e7f5Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2428.0Log mg/kg[1400:4300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
cancerhas_therapeutic_effect_onNot AvailablePMC10300961
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)698.074
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)899.47
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)1137.92
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)938.784
Click to view 3D structureCocaine esteraseO00748HumansPredicted (SEA)37.9904
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)93.5748
Lysine-specific demethylase 4C structureClick to view 3D structureLysine-specific demethylase 4CQ9H3R0HumansPredicted (SEA)234.326
Click to view 3D structureSortase AQ8CM62Streptococcus mutansPredicted (SEA)39.781
Click to view 3D structureLiver carboxylesterase 1P12337Oryctolagus cuniculusPredicted (SEA)6.30579
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)1233.52
Click to view 3D structureOrganic anion transporter 3O88909Mus musculusPredicted (SEA)54.728
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)197.426
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)332.26
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)736.921
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)1428.14
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)1085.22
Click to view 3D structureLysine-specific demethylase 3AQ9Y4C1HumansPredicted (SEA)170.334
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)2469.61
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)4197.32
Click to view 3D structureProstaglandin G/H synthase 2P79208Ovis ariesPredicted (SEA)361.921
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)2910.94
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)6644.66
3-hydroxyanthranilate 3,4-dioxygenase structureClick to view 3D structure3-hydroxyanthranilate 3,4-dioxygenaseP46952HumansPredicted (SEA)6.85073
Click to view 3D structure3-hydroxyanthranilate 3,4-dioxygenaseP46953Rattus norvegicusPredicted (SEA)6.85073
Click to view 3D structureAcetylcholinesteraseP23795Bos taurusPredicted (SEA)296.761
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0000875
FooDB IDFDB002237
Phenol Explorer IDNot Available
KNApSAcK IDC00001555
BiGG IDNot Available
BioCyc IDMETHYLNICOTINATE
METLIN ID273
PDB IDNot Available
Wikipedia LinkTrigonelline
Chemspider ID5369
ChEBI ID18123
PubChem Compound ID5570
Kegg Compound IDC01004
YMDB IDNot Available
ECMDB IDM2MDB005519
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13128691
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17190852
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=185134
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22242555
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22312719
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22393699
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22559314
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24047691
9. Sarett, Herbert P.; Perlzweig, William A.; Levy, Edward D. Synthesis and excretion of trigonelline. Journal of Biological Chemistry (1940), 135 483-5.
10. Nishina Y, Sato K, Miura R, Shiga K: Substrate recognition and activation mechanism of D-amino acid oxidase: a study using substrate analogs. J Biochem. 2000 Aug;128(2):213-23.
11. Slow S, Miller WE, McGregor DO, Lee MB, Lever M, George PM, Chambers ST: Trigonelline is not responsible for the acute increase in plasma homocysteine following ingestion of instant coffee. Eur J Clin Nutr. 2004 Sep;58(9):1253-6.
12. Dellow WJ, Chambers ST, Lever M, Lunt H, Robson RA: Elevated glycine betaine excretion in diabetes mellitus patients is associated with proximal tubular dysfunction and hyperglycemia. Diabetes Res Clin Pract. 1999 Feb;43(2):91-9.
13. Rozan P, Kuo YH, Lambein F: Free amino acids present in commercially available seedlings sold for human consumption. A potential hazard for consumers. J Agric Food Chem. 2000 Mar;48(3):716-23.
14. Daglia M, Tarsi R, Papetti A, Grisoli P, Dacarro C, Pruzzo C, Gazzani G: Antiadhesive effect of green and roasted coffee on Streptococcus mutans' adhesive properties on saliva-coated hydroxyapatite beads. J Agric Food Chem. 2002 Feb 27;50(5):1225-9.
15. Tohda C, Kuboyama T, Komatsu K: Search for natural products related to regeneration of the neuronal network. Neurosignals. 2005;14(1-2):34-45.
16. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.