Record Information
Version1.0
Creation date2010-04-08 22:05:17 UTC
Update date2018-05-28 22:39:41 UTC
Primary IDFDB002237
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTrigonelline
DescriptionAlkaloid from fenugreek (Trigonella foenum-graecum) (Leguminosae), and very many other subspecies; also present in coffee beans and many animals. Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. It is 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. It is an inner salt formed by the addition of a methyl group to the nitrogen atom of niacin. 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.
CAS Number535-83-1
Structure
Thumb
Synonyms
SynonymSource
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
1-methylnicotinatebiospider
1-methylpyridinium-3-carboxylatebiospider
3-carboxy-1-methyl-Pyridinium hydroxide inner saltbiospider
3-Carboxy-1-methylpyridinium hydroxide, inner saltbiospider
535-83-1 (INNER SALT)biospider
Gynesisdb_source
N-methyl-nicotinatebiospider
N-methylnicotinatebiospider
N-methylnicotinic acidbiospider
N-Methylnicotinic betainedb_source
Nicotinic acid n-methylbetainebiospider
Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner saltbiospider
Pyridinium, 3-carboxy-1-methyl-, inner saltbiospider
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H7NO2
IUPAC name1-methylpyridin-1-ium-3-carboxylate
InChI IdentifierInChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
InChI KeyWWNNZCOKKKDOPX-UHFFFAOYSA-N
Isomeric SMILESC[N+]1=CC=CC(=C1)C([O-])=O
Average Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
Classification
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
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 61.31%; H 5.14%; N 10.21%; O 23.33%DFC
Melting PointMp 218 dec. (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9800000000-114b1e0b54ab0d6c1b04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-2900000000-f7b3226615bd5e87f89bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-a11de5552f1c306be0dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-ee318a4f5a9d9e271a4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-0900000000-b68b239b6e2b1aae5216View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-4eecb45261b5714a6f19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9200000000-1f392d4e498677997436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-2a8b2c8721614293a8f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-016u-9000000000-0dc3b09d666ea6c7af17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000l-6900000000-0d204e6b92b9c6b643daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0006-9100000000-d147503f87ded3d41c26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-b68b239b6e2b1aae5216View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-4eecb45261b5714a6f19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9200000000-1f392d4e498677997436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-2a8b2c8721614293a8f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-016u-9000000000-1638942a7b48eab1c7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-2fd573463b73045c069aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000l-6900000000-0d204e6b92b9c6b643daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9100000000-d147503f87ded3d41c26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-2900000000-821723f398418c66e692View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-bdce44a0a273f61efb2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-1900000000-840b949e52853c7aa542View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-9500000000-71844206506e1ac6a027View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-972c1ff182d2cbcd6c30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-8900000000-1a56824bf3a0ff0f80d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-9000000000-c91672f20ae7e2130b95View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0pdu-9700000000-9de70f10113aec22e7f5View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID5369
ChEMBL IDCHEMBL350675
KEGG Compound IDC01004
Pubchem Compound ID5570
Pubchem Substance IDNot Available
ChEBI ID18123
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00875
CRC / DFC (Dictionary of Food Compounds) IDCHH01-A:CHH01-A
EAFUS IDNot Available
Dr. Duke IDTRIGONELLINE
BIGG IDNot Available
KNApSAcK IDC00001555
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTrigonelline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti hyperglycemicDUKE
anti migraine52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
epidermal stimulantDUKE
hypocholesterolemicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
mutagenicDUKE
osmoregulatorDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
propecicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.