Compound: Trigonelline
SMILES: O=C([O-])c1c[n+](ccc1)C
InChIKey: WWNNZCOKKKDOPX-UHFFFAOYSA-N
Synonyms: Trigonelline, 535-83-1, Gynesine, Caffearine, N-Methylnicotinate, Coffearine, Trigonellin, 1-methylpyridin-1-ium-3-carboxylate, Betain nicotinate, Coffearin, Betaine nicotinate, Nicotinic acid N-methylbetaine, 1-Methylpyridinio-3-carboxylate, Trigenelline, Caffearin, 3-Carboxy-1-methylpyridinium hydroxide inner salt, 1-methylnicotinate, CHEBI:18123, 3NQ9N60I00, Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt, DTXSID2026230, 3-Carboxy-1-methylpyridinium hydroxide, inner salt, RefChem:52089, DTXCID906230, 208-620-5, Trigenolline, 1-methylpyridinium-3-carboxylate, 1-Methyl-3-pyridiniumcarboxylate, N'-Methylnicotinate, MFCD00054262, 1-methylpyridine-3-carboxylic acid, CCRIS 1332, EINECS 208-620-5, BRN 3905114, Trigonelline?, UNII-3NQ9N60I00, HSDB 7684, N-methyl-nicotinate, 3-Carboxy-1-methylpyridinium inner salt, N'-Methylnicotinic acid, Trigonelline (Standard), 6138-40-5, TRIGONELLINE [MI], TRIGONELLINE [HSDB], 5-22-02-00143 (Beilstein Handbook Reference), MLS002153895, N-Methylnicotinic acid betaine, SCHEMBL195666, SPECTRUM1500880, TRIGONELLINE [USP-RS], CHEMBL350675, orb1304887, SCHEMBL29561369, HY-N0414R, HMS2096H08, HMS2234K22, HMS3371K21, HMS5086O06, HY-N0414, MSK40340, BDBM50480286, BDBM50548713, CCG-38517, NSC714350, SBB085963, AKOS005067859, FT32681, NSC-714350, SDCCGMLS-0066739.P001, NCGC00095649-01, NCGC00095649-02, NCGC00095649-03, NCGC00095649-04, NCGC00095649-07, NCGC00095649-09, AC-34290, AS-17722, SMR001233244, 1-Methyl-Nicotinic Acid Anion(Trigonelline), AB00052974, CS-0008944, NS00014578, Pyridinium, 3-carboxy-1-methyl-, inner salt, C01004, 3-carboxy-1-methyl-Pyridinium hydroxide inner salt, AP-163/40806827, Q928965, 3-Carboxy-1-methylpyridinium, Hydroxide, Inner salt, TrigonellineN-Methylnicotinate; Caffearine; Gynesine, TRIGONELLINE (CONSTITUENT OF FENUGREEK SEED) [DSC]
Theoretical properties:
molecular_formula: C7H7NO2
molecular_weight: 137.14 g/mol
exact_mass: 137.047678466 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 10
topological_polar_surface_area: 44 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Prisms, aqueous, from alcohol + water
color: Prisms, aqueous, from alcohol + water
melting_point: Colorless prisms. MP: 218 °C (decomposes). Very soluble in water. Soluble in alcohol; nearly insoluble in ether, benzene, and chloroform /Trigonelline anhydrous/
Descriptions:
pubchem: N-methylnicotinate is an iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group. It has a role as a plant metabolite, a food component and a human urinary metabolite. It is an alkaloid and an iminium betaine. It is functionally related to a nicotinate. It is a conjugate base of a N-methylnicotinic acid.
chebi: An iminium betaine that is the conjugate base of <em>N</em>-methylnicotinic acid, arising from deprotonation of the carboxy group.
chembl: TRIGONELLINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Trigonelline is an alkaloid with chemical formula C7H7NO2. It is a zwitterion formed by the methylation of the nitrogen atom of niacin (vitamin B3). Trigonelline is a product of niacin metabolism that is excreted in the urine of mammals.
Trigonelline occurs in many plants. It has been isolated from the Japanese radish (Raphanus sativus cv. Sakurajima Daikon), fenugreek seeds (Trigonella foenum-graecum, hence the name), garden peas, hemp seed, oats, potatoes, Stachys species, dahlia, Strophanthus species, and Dichapetalum cymosum.  Trigonelline is also found in coffee. Higher levels of trigonelline are found in arabica coffee.
Holtz, Kutscher, and Theilmann have recorded its presence in a number of animals.