Trigonelline (CHEM021690)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:07 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021690
Identification
Common NameTrigonelline
ClassSmall Molecule
DescriptionAn iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9800000000-114b1e0b54ab0d6c1b04Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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.