Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:17 UTC |
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Update date | 2020-09-17 15:30:47 UTC |
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Primary ID | FDB002237 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Trigonelline |
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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, 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). |
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CAS Number | 535-83-1 |
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Structure | |
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Synonyms | Synonym | Source |
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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 |
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Predicted Properties | |
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Chemical Formula | C7H7NO2 |
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IUPAC name | 1-methylpyridin-1-ium-3-carboxylate |
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InChI Identifier | InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3 |
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InChI Key | WWNNZCOKKKDOPX-UHFFFAOYSA-N |
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Isomeric SMILES | C[N+]1=CC=CC(=C1)C([O-])=O |
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Average Molecular Weight | 137.136 |
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Monoisotopic Molecular Weight | 137.047678473 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Not Available |
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Sub Class | Not Available |
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Direct Parent | Alkaloids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Foods | Beverages: Nuts and legumes: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 61.31%; H 5.14%; N 10.21%; O 23.33% | DFC |
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Melting Point | Mp 218 dec. (anhyd.) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0pdu-9700000000-9de70f10113aec22e7f5 | Spectrum | Predicted GC-MS | Trigonelline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-9800000000-114b1e0b54ab0d6c1b04 | Spectrum | Predicted GC-MS | Trigonelline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-2900000000-f7b3226615bd5e87f89b | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-1900000000-a11de5552f1c306be0df | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-9000000000-ee318a4f5a9d9e271a4d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-000i-0900000000-b68b239b6e2b1aae5216 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-000i-1900000000-4eecb45261b5714a6f19 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0006-9200000000-1f392d4e498677997436 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0006-9000000000-2a8b2c8721614293a8f3 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-016u-9000000000-0dc3b09d666ea6c7af17 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-000l-6900000000-0d204e6b92b9c6b643da | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-0006-9100000000-d147503f87ded3d41c26 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-0900000000-b68b239b6e2b1aae5216 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-1900000000-4eecb45261b5714a6f19 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9200000000-1f392d4e498677997436 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-2a8b2c8721614293a8f3 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-016u-9000000000-1638942a7b48eab1c7f7 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0900000000-2fd573463b73045c069a | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000l-6900000000-0d204e6b92b9c6b643da | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0006-9100000000-d147503f87ded3d41c26 | Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-014i-2900000000-821723f398418c66e692 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-bdce44a0a273f61efb2b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004r-1900000000-840b949e52853c7aa542 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fk9-9500000000-71844206506e1ac6a027 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-972c1ff182d2cbcd6c30 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000j-8900000000-1a56824bf3a0ff0f80d0 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kb-9000000000-c91672f20ae7e2130b95 | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 5369 |
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ChEMBL ID | CHEMBL350675 |
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KEGG Compound ID | C01004 |
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Pubchem Compound ID | 5570 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18123 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00875 |
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CRC / DFC (Dictionary of Food Compounds) ID | CHH01-A:CHH01-A |
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EAFUS ID | Not Available |
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Dr. Duke ID | TRIGONELLINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001555 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Trigonelline |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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