Cannabis Compound Database: Showing Compound Card for N-Methylnicotinate (CDB000121)

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Record Information

Version

1.0

Created at

2020-03-18 23:25:34 UTC

Updated at

2020-12-07 19:07:07 UTC

CannabisDB ID

CDB000121

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

N-Methylnicotinate

Description

N-Methylnicotinate or 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. 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 is a moderately acidic compound. Trigonelline exists in all living organisms, from bacteria to humans. It is a product of the metabolism of niacin (vitamin B3) and it is excreted in the urine. Trigonelline in urine is a biomarker for the consumption of coffee, legumes and soy products. Trigonelline is found in highest concentrations in arabica coffee, fenugreeks, and common pea and in lower concentrations in yellow bell peppers, orange bell peppers, and muskmelons. Trigonelline has also been detected in rices, triticales, alfalfa, cereals and cereal products, ryes fenugreek seeds, garden peas, hemp seed (Cannabis sativa; PMID: 6991645 ), oats and potatoes. Trigonelline may reduce dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. It also has shown anti-carcinogenic and anti-hyperglycemic effects in several studies (PMID: 22680628 ; PMID: 31896496 ; PMID: 31363374 ).

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

137.14

Monoisotopic Molecular Weight

137.0477

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

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Tissue and substructures:

Placenta

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Antineoplastic agent:

Anticancer agent

Household products:

Antimicrobial agent:

Antibacterial

Physical Properties

State

Solid

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0pdu-9700000000-9de70f10113aec22e7f5	2015-03-01	View Spectrum
Predicted GC-MS	N-Methylnicotinate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-9800000000-114b1e0b54ab0d6c1b04	Spectrum
Predicted GC-MS	N-Methylnicotinate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-2900000000-f7b3226615bd5e87f89b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-1900000000-a11de5552f1c306be0df	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-ee318a4f5a9d9e271a4d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-0900000000-b68b239b6e2b1aae5216	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-4eecb45261b5714a6f19	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9200000000-1f392d4e498677997436	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-2a8b2c8721614293a8f3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-016u-9000000000-0dc3b09d666ea6c7af17	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000l-6900000000-0d204e6b92b9c6b643da	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0006-9100000000-d147503f87ded3d41c26	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-b68b239b6e2b1aae5216	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-1900000000-4eecb45261b5714a6f19	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9200000000-1f392d4e498677997436	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-2a8b2c8721614293a8f3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-016u-9000000000-1638942a7b48eab1c7f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-2fd573463b73045c069a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000l-6900000000-0d204e6b92b9c6b643da	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-9100000000-d147503f87ded3d41c26	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-014i-2900000000-821723f398418c66e692	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-bdce44a0a273f61efb2b	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-1900000000-840b949e52853c7aa542	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-9500000000-71844206506e1ac6a027	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-972c1ff182d2cbcd6c30	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-8900000000-1a56824bf3a0ff0f80d0	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-9000000000-c91672f20ae7e2130b95	2017-06-28	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000875

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Trigonelline

METLIN ID

273

PubChem Compound

5570

PDB ID

Not Available

ChEBI ID

18123

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Zhou J, Chan L, Zhou S: Trigonelline: a plant alkaloid with therapeutic potential for diabetes and central nervous system disease. Curr Med Chem. 2012;19(21):3523-31. doi: 10.2174/092986712801323171. [PubMed:22680628 ]
Nugrahini AD, Ishida M, Nakagawa T, Nishi K, Sugahara T: Trigonelline: An alkaloid with anti-degranulation properties. Mol Immunol. 2020 Feb;118:201-209. doi: 10.1016/j.molimm.2019.12.020. Epub 2019 Dec 30. [PubMed:31896496 ]
Li Y, Li Q, Wang C, Lou Z, Li Q: Trigonelline reduced diabetic nephropathy and insulin resistance in type 2 diabetic rats through peroxisome proliferator-activated receptor-gamma. Exp Ther Med. 2019 Aug;18(2):1331-1337. doi: 10.3892/etm.2019.7698. Epub 2019 Jun 21. [PubMed:31363374 ]

Showing Compound Card for N-Methylnicotinate (CDB000121)

Structure for CDB000121 (N-Methylnicotinate)