Livestock Metabolome Database: Showing metabocard for Trigonelline (LMDB00270)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:06 UTC

Update Date

2018-04-30 21:14:41 UTC

Lmdb

LMDB00270

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trigonelline

Description

Trigonelline, 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. Trigonelline exists in all living organisms, ranging from bacteria to humans. Trigonelline is found, on average, in the highest concentration within a few different foods, such as arabica coffees (Coffea arabica), fenugreeks (Trigonella foenum-graecum), and grape wine and in a lower concentration in barleys (Hordeum vulgare), orange bell peppers (Capsicum annuum), and garden tomato (var.). Trigonelline has also been detected, but not quantified in, several different foods, such as eggplants (Solanum melongena), oats (Avena sativa), chickpeas (Cicer arietinum), spelts (Triticum spelta), and soy beans (Glycine max). This could make trigonelline a potential biomarker for the consumption of these foods. Trigonelline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Trigonelline.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₇H₇NO₂

Average Molecular Weight

137.136

Monoisotopic Molecular Weight

137.047678473

IUPAC Name

1-methylpyridin-1-ium-3-carboxylate

Traditional Name

trigonelline

CAS Registry Number

535-83-1

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 Key

WWNNZCOKKKDOPX-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.

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

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details