Showing Compound Trigonelline (FDB002237)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:17 UTC

Update date

2019-11-26 02:57:12 UTC

Primary ID

FDB002237

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Trigonelline

Description

Alkaloid 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 Number

535-83-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Methyl-3-pyridiniumcarboxylate	ChEBI
1-Methylnicotinate	ChEBI
1-Methylpyridinio-3-carboxylate	ChEBI
3-Carboxy-1-methylpyridinium hydroxide inner salt	ChEBI
Betain nicotinate	ChEBI
Betaine nicotinate	ChEBI
Caffearin	ChEBI
Caffearine	ChEBI
Coffearin	ChEBI
Gynesine	ChEBI
N'-methylnicotinate	ChEBI
N-Methyl-nicotinate	ChEBI
Nicotinic acid N-methylbetaine	ChEBI
Trigenelline	ChEBI
Trigonellin	ChEBI
1-Methyl-3-pyridiniumcarboxylic acid	Generator
1-Methylnicotinic acid	Generator
1-Methylpyridinio-3-carboxylic acid	Generator
Betain nicotinic acid	Generator
Betaine nicotinic acid	Generator
N'-methylnicotinic acid	Generator
N-Methyl-nicotinic acid	Generator
Nicotinate N-methylbetaine	Generator
N-Methylnicotinic acid	HMDB
Trigonelline chloride	HMDB
Trigonelline iodide	HMDB
Trigonelline tosylate	HMDB
Trigonelline ion	HMDB
3-Carboxy-1-methyl-pyridinium hydroxide inner salt	HMDB
Coffearine	HMDB
N-Methylnicotinate	HMDB
Trigenolline	HMDB
Trigonelline	ChEBI
1-methylnicotinate	biospider
1-methylpyridinium-3-carboxylate	biospider
3-carboxy-1-methyl-Pyridinium hydroxide inner salt	biospider
3-Carboxy-1-methylpyridinium hydroxide, inner salt	biospider
535-83-1 (INNER SALT)	biospider
Gynesis	db_source
N-methyl-nicotinate	biospider
N-methylnicotinate	biospider
N-methylnicotinic acid	biospider
N-Methylnicotinic betaine	db_source
Nicotinic acid n-methylbetaine	biospider
Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt	biospider
Pyridinium, 3-carboxy-1-methyl-, inner salt	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.5	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.01 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.15 m³·mol⁻¹	ChemAxon
Polarizability	13.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C7H7NO2

IUPAC name

1-methylpyridin-1-ium-3-carboxylate

InChI Identifier

InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3

InChI Key

WWNNZCOKKKDOPX-UHFFFAOYSA-N

Isomeric SMILES

C[N+]1=CC=CC(=C1)C([O-])=O

Average Molecular Weight

137.136

Monoisotopic Molecular Weight

137.047678473

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

iminium betaine (CHEBI:18123 )
alkaloid (CHEBI:18123 )
Pyridine alkaloids (C01004 )
a small molecule (METHYLNICOTINATE )

Ontology

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Biofluid and excreta:

Foods

Beverages:

Coffee products

Nuts and legumes:

Legumes

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 61.31%; H 5.14%; N 10.21%; O 23.33%	DFC
Melting Point	Mp 218 dec. (anhyd.)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9800000000-114b1e0b54ab0d6c1b04	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-2900000000-f7b3226615bd5e87f89b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-1900000000-a11de5552f1c306be0df	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-ee318a4f5a9d9e271a4d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-0900000000-b68b239b6e2b1aae5216	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-4eecb45261b5714a6f19	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9200000000-1f392d4e498677997436	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-2a8b2c8721614293a8f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-016u-9000000000-0dc3b09d666ea6c7af17	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000l-6900000000-0d204e6b92b9c6b643da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0006-9100000000-d147503f87ded3d41c26	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-b68b239b6e2b1aae5216	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-1900000000-4eecb45261b5714a6f19	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9200000000-1f392d4e498677997436	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-2a8b2c8721614293a8f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-016u-9000000000-1638942a7b48eab1c7f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-2fd573463b73045c069a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000l-6900000000-0d204e6b92b9c6b643da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-9100000000-d147503f87ded3d41c26	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-014i-2900000000-821723f398418c66e692	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-bdce44a0a273f61efb2b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-1900000000-840b949e52853c7aa542	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-9500000000-71844206506e1ac6a027	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-972c1ff182d2cbcd6c30	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-8900000000-1a56824bf3a0ff0f80d0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-9000000000-c91672f20ae7e2130b95	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0pdu-9700000000-9de70f10113aec22e7f5	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18123

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00875

CRC / DFC (Dictionary of Food Compounds) ID

CHH01-A:CHH01-A

EAFUS ID

Not Available

Dr. Duke ID

TRIGONELLINE

BIGG ID

Not Available

KNApSAcK ID

C00001555

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Trigonelline

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti hyperglycemic			DUKE
anti migraine	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
epidermal stimulant			DUKE
hypocholesterolemic			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
mutagenic			DUKE
osmoregulator			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
propecic			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.

Showing Compound Trigonelline (FDB002237)

Structure for FDB002237 (Trigonelline)