| Record Information |
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| Version | 1.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2020-09-11 01:33:22 UTC |
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| NP-MRD ID | NP0000018 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Trigonelline |
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| 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 is a moderately acidic compound (based on its pKa). Trigonelline exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Trigonelline is found, on average, in the highest concentration within a few different foods, such as arabica coffee, fenugreeks, and grape wines and in a lower concentration in yellow bell peppers, beers, and garden tomato (var.). Trigonelline has also been detected, but not quantified in, several different foods, such as potato, green beans, common buckwheats, tartary buckwheats, and quinoa. This could make trigonelline a potential biomarker for the consumption of these foods. An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group. |
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| Structure | |
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| Synonyms | | Value | 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 |
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| Chemical Formula | C7H7NO2 |
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| Average Molecular Weight | 137.136 |
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| Monoisotopic Molecular Weight | 137.047678473 |
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| IUPAC Name | 1-methylpyridin-1-ium-3-carboxylate |
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| Traditional Name | trigonelline |
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| CAS Registry Number | 535-83-1 |
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| SMILES | C[N+]1=CC=CC(=C1)C([O-])=O |
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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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| Spectra |
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| | | Species of Origin |
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| Species | Animalia; Plantae |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Nishina Y, Sato K, Miura R, Shiga K: Substrate recognition and activation mechanism of D-amino acid oxidase: a study using substrate analogs. J Biochem. 2000 Aug;128(2):213-23. [PubMed:10920257 ]
- Slow S, Miller WE, McGregor DO, Lee MB, Lever M, George PM, Chambers ST: Trigonelline is not responsible for the acute increase in plasma homocysteine following ingestion of instant coffee. Eur J Clin Nutr. 2004 Sep;58(9):1253-6. [PubMed:15054441 ]
- Dellow WJ, Chambers ST, Lever M, Lunt H, Robson RA: Elevated glycine betaine excretion in diabetes mellitus patients is associated with proximal tubular dysfunction and hyperglycemia. Diabetes Res Clin Pract. 1999 Feb;43(2):91-9. [PubMed:10221661 ]
- Rozan P, Kuo YH, Lambein F: Free amino acids present in commercially available seedlings sold for human consumption. A potential hazard for consumers. J Agric Food Chem. 2000 Mar;48(3):716-23. [PubMed:10725139 ]
- Daglia M, Tarsi R, Papetti A, Grisoli P, Dacarro C, Pruzzo C, Gazzani G: Antiadhesive effect of green and roasted coffee on Streptococcus mutans' adhesive properties on saliva-coated hydroxyapatite beads. J Agric Food Chem. 2002 Feb 27;50(5):1225-9. [PubMed:11853508 ]
- Tohda C, Kuboyama T, Komatsu K: Search for natural products related to regeneration of the neuronal network. Neurosignals. 2005;14(1-2):34-45. [PubMed:15956813 ]
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