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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:06 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 an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. High amounts of trigonelline have been found in arabica coffee, fenugreeks, and common peas. Another foods such as yellow bell peppers, orange bellpeppers and muskmelons also contain trigonelline but in lower concentrations. Trigonelline has also been detected but not quantified in several different foods, such as rices, triticales, alfalfa, cereals and cereal products, and ryes. Trigonelline in the urine is a biomarker for the consumption of coffee, legumes and soy products.
Structure
Data?1582752161
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

Adverse health effect

Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-3.910 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker126.36730932474
[M+H]+Not Available124.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00001380
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+125.78932859911
AllCCS[M-H]-123.7832859911
DeepCCS[M+H]+122.92430932474
DeepCCS[M-H]-119.43530932474
DeepCCS[M-2H]-156.45330932474
DeepCCS[M+Na]+131.54530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrigonellineC[N+]1=CC=CC(=C1)C([O-])=O1923.8Standard polar33892256
TrigonellineC[N+]1=CC=CC(=C1)C([O-])=O1127.0Standard non polar33892256
TrigonellineC[N+]1=CC=CC(=C1)C([O-])=O1209.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trigonelline GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9800000000-114b1e0b54ab0d6c1b042017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trigonelline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0pdu-9700000000-9de70f10113aec22e7f52015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-2900000000-f7b3226615bd5e87f89b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-1900000000-a11de5552f1c306be0df2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014i-9000000000-ee318a4f5a9d9e271a4d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-000i-0900000000-b68b239b6e2b1aae52162012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-000i-1900000000-4eecb45261b5714a6f192012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0006-9200000000-1f392d4e4986779974362012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0006-9000000000-2a8b2c8721614293a8f32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-016u-9000000000-0dc3b09d666ea6c7af172012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-000l-6900000000-0d204e6b92b9c6b643da2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-0006-9100000000-d147503f87ded3d41c262012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ , positive-QTOFsplash10-000i-0900000000-b68b239b6e2b1aae52162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ , positive-QTOFsplash10-000i-1900000000-4eecb45261b5714a6f192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ , positive-QTOFsplash10-0006-9200000000-1f392d4e4986779974362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-2a8b2c8721614293a8f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QQ , positive-QTOFsplash10-016u-9000000000-1638942a7b48eab1c7f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-2fd573463b73045c069a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QTOF , positive-QTOFsplash10-000l-6900000000-0d204e6b92b9c6b643da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline LC-ESI-QTOF , positive-QTOFsplash10-0006-9100000000-d147503f87ded3d41c262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trigonelline Linear Ion Trap , positive-QTOFsplash10-014i-2900000000-821723f398418c66e6922017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trigonelline 10V, Positive-QTOFsplash10-000i-0900000000-bdce44a0a273f61efb2b2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trigonelline 20V, Positive-QTOFsplash10-004r-1900000000-840b949e52853c7aa5422017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trigonelline 40V, Positive-QTOFsplash10-0fk9-9500000000-71844206506e1ac6a0272017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trigonelline 10V, Negative-QTOFsplash10-000i-0900000000-972c1ff182d2cbcd6c302017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trigonelline 20V, Negative-QTOFsplash10-000j-8900000000-1a56824bf3a0ff0f80d02017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trigonelline 40V, Negative-QTOFsplash10-00kb-9000000000-c91672f20ae7e2130b952017-06-28Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
    • Analysis of 30 no...
details
UrineDetected and Quantified31.1 (5.5-109.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
UrineDetected and Quantified23 +/- 19 umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothADPKD details
UrineDetected and Quantified8.274 +/- 6.844 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
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. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1698551
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 ]
  7. 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. [PubMed:32033212 ]