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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:34 UTC
HMDB IDHMDB0000875
Secondary Accession Numbers
  • HMDB00875
Metabolite Identification
Common NameTrigonelline
DescriptionTrigonelline, 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. 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. It is also found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. Trigonelline is a moderately acidic compound (based on its pKa). Trigonelline exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Trigonelline is found, on average, in the highest concentration within a few different foods, such as arabica coffee, fenugreeks, and common pea and in a lower concentration in yellow bell peppers, orange bell peppers, and muskmelons. Trigonelline has also been detected, but not quantified in, several different foods, such as rices, triticales, alfalfa, cereals and cereal products, and ryes. This could make trigonelline a potential biomarker for the consumption of these foods. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. Trigonelline in the urine is a biomarker for the consumption of coffee, legumes and soy products. Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. Trigonelline occurs in many other plants, including fenugreek seeds, garden peas, hemp seed, oats and potatoes.
Structure
Data?1563860674
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 Weight137.136
Monoisotopic Molecular Weight137.047678473
IUPAC Name1-methylpyridin-1-ium-3-carboxylate
Traditional Nametrigonelline
CAS Registry Number535-83-1
SMILES
C[N+]1=CC=CC(=C1)C([O-])=O
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9800000000-114b1e0b54ab0d6c1b04Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-2900000000-f7b3226615bd5e87f89bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-a11de5552f1c306be0dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-ee318a4f5a9d9e271a4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-0900000000-b68b239b6e2b1aae5216Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-4eecb45261b5714a6f19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9200000000-1f392d4e498677997436Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-2a8b2c8721614293a8f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-016u-9000000000-0dc3b09d666ea6c7af17Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000l-6900000000-0d204e6b92b9c6b643daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0006-9100000000-d147503f87ded3d41c26Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-b68b239b6e2b1aae5216Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-4eecb45261b5714a6f19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9200000000-1f392d4e498677997436Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-2a8b2c8721614293a8f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-016u-9000000000-1638942a7b48eab1c7f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-2fd573463b73045c069aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000l-6900000000-0d204e6b92b9c6b643daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9100000000-d147503f87ded3d41c26Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-2900000000-821723f398418c66e692Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-bdce44a0a273f61efb2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-1900000000-840b949e52853c7aa542Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-9500000000-71844206506e1ac6a027Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-972c1ff182d2cbcd6c30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-8900000000-1a56824bf3a0ff0f80d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-9000000000-c91672f20ae7e2130b95Spectrum
MSMass Spectrum (Electron Ionization)splash10-0pdu-9700000000-9de70f10113aec22e7f5Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified16.08 umol/mmol creatinineAdult (>18 years old)Male
    Normal
      • Shaykhutdinov RA,...
    details
    UrineDetected and Quantified8.983 +/- 4.217 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified31.1 (5.5-109.3) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    BloodDetected but not Quantified Adult (>18 years old)Both
    Colorectal adenoma
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Bladder cancer
    details
    UrineDetected and Quantified23 +/- 19 umol/mmol creatinineNot SpecifiedBothLung cancer details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Colorectal adenoma
    details
    UrineDetected but not Quantified Adult (>18 years old)BothADPKD details
    UrineDetected and Quantified8.274 +/- 6.844 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
    Lung Cancer
    1. Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. [PubMed:22157537 ]
    Autosomal dominant polycystic kidney disease
    1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
    Eosinophilic esophagitis
    1. (). Mordechai, Hien, and David S. Wishart. .
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB002237
    KNApSAcK IDC00001555
    Chemspider ID5369
    KEGG Compound IDC01004
    BioCyc IDMETHYLNICOTINATE
    BiGG IDNot Available
    Wikipedia LinkTrigonelline
    METLIN ID273
    PubChem Compound5570
    PDB IDNot Available
    ChEBI ID18123
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceSarett, Herbert P.; Perlzweig, William A.; Levy, Edward D. Synthesis and excretion of trigonelline. Journal of Biological Chemistry (1940), 135 483-5.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. 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. [PubMed:10920257 ]
    2. 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. [PubMed:15054441 ]
    3. 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. [PubMed:10221661 ]
    4. 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. [PubMed:10725139 ]
    5. 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. [PubMed:11853508 ]
    6. Tohda C, Kuboyama T, Komatsu K: Search for natural products related to regeneration of the neuronal network. Neurosignals. 2005;14(1-2):34-45. [PubMed:15956813 ]