N-Methylnicotinate (BioCAD00000014752)

blood feces urine placenta

Metabolite Card

Formula: C7H7NO2 (137.0477)
SMILES: C[N+]1=CC=CC(=C1)C([O-])=O

Synonyms [en]

trigonelline; N-Methylnicotinate; Gynesine; 1-methylnicotinate; Trigenelline; Nicotinic acid N-methylbetaine

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

N-Methylnicotinate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000014752). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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. It is also found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. High amounts of trigonelline have been found in arabica coffee, fenugreeks, and common peas. Another foods such as yellow bell peppers, orange bellpeppers and muskmelons also contain trigonelline but in lower concentrations. Trigonelline has also been detected but not quantified in several different foods, such as rices, triticales, alfalfa, cereals and cereal products, and ryes. Trigonelline in the urine is a biomarker for the consumption of coffee, legumes and soy products.

Cytoplasm
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 535-83-1
  • CAS Registry Number: 6138-40-5
  • CAS Registry Number: 6138-41-6
  • PubChem: 5570
  • ChEBI: ChEBI:18123
  • HMDB: HMDB0000875
  • KEGG: C01004
  • BioCyc: METHYLNICOTINATE
  • NCBI MeSH: trigonelline
  • Wikipedia: Trigonelline
  • RefMet: RM0136017
  • MoNA: Alkaloids000099
  • MoNA: Alkaloids000126
  • MoNA: BAF_UVA_POS000069
  • MoNA: BAF_UVA_POS000070
  • MoNA: BAF_UVA_POS000071
  • MoNA: CCMSLIB00000578046
  • MoNA: CCMSLIB00003142437
  • MoNA: CCMSLIB00005464011
  • MoNA: CCMSLIB00005464012
  • MoNA: CCMSLIB00005464013
  • MoNA: CCMSLIB00005720489
  • MoNA: HMDB0000875_ms_ms_1235
  • MoNA: HMDB0000875_ms_ms_1236
  • MoNA: HMDB0000875_ms_ms_1237
  • MoNA: KO004201
  • MoNA: KO004202
  • MoNA: KO004203
  • MoNA: KO004204
  • MoNA: KO004205
  • MoNA: ML005201
  • MoNA: MoNA002136
  • MoNA: MoNA002137
  • MoNA: MoNA002138
  • MoNA: MoNA010447
  • MoNA: MoNA010448
  • MoNA: MoNA010449
  • MoNA: MoNA010450
  • MoNA: MoNA010451
  • MoNA: MoNA010452
  • MoNA: MoNA016805
  • MoNA: MoNA023989
  • MoNA: MoNA032303
  • MoNA: MoNA032304
  • MoNA: MoNA032305
  • MoNA: MoNA036208
  • MoNA: MoNA036210
  • MoNA: MoNA036211
  • MoNA: MoNA037241
  • MoNA: MoNA037959
  • MoNA: MoNA038618
  • MoNA: PM018202
  • MoNA: PR100409
  • MoNA: PR100410
  • MoNA: PS102601
  • MoNA: PS102602
  • MoNA: PS102603
  • MoNA: PT110263
  • MoNA: TOF_alkaloids_neg000036
  • MoNA: TOF_alkaloids_neg000048
  • MoNA: TOF_alkaloids_pos000085
  • MoNA: TOF_alkaloids_pos000105
  • MoNA: VF-NPL-LTQ006359
  • MoNA: VF-NPL-LTQ006360
  • MoNA: VF-NPL-QEHF003226
  • MoNA: VF-NPL-QEHF003227
  • MoNA: VF-NPL-QEHF003228
  • MoNA: VF-NPL-QEHF003229
  • MoNA: VF-NPL-QEHF003230
  • MoNA: VF-NPL-QEHF003231
  • Metlin: METLIN_273
  • Coconut NaturalProduct: CNP0337775.0
  • Coconut NaturalProduct: CNP0486406.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01721 2.1.1.7 S-adenosyl-L-methionine:nicotinate N-methyltransferase
Rhea:RHEA:17110 N-methylnicotinate + FMNH2 + O2 => (Z)-2-((N-methylformamido)methylene)-5-hydroxybutanolactone + FMN + H+
Rhea:RHEA:17111 (Z)-2-((N-methylformamido)methylene)-5-hydroxybutanolactone + FMN + H+ => N-methylnicotinate + FMNH2 + O2
Rhea:RHEA:17112 N-methylnicotinate + FMNH2 + O2 <=> (Z)-2-((N-methylformamido)methylene)-5-hydroxybutanolactone + FMN + H+
Rhea:RHEA:20242 2.1.1.7 nicotinate + S-adenosyl-L-methionine => N-methylnicotinate + S-adenosyl-L-homocysteine
Rhea:RHEA:20243 2.1.1.7 N-methylnicotinate + S-adenosyl-L-homocysteine => nicotinate + S-adenosyl-L-methionine
Rhea:RHEA:20244 2.1.1.7 nicotinate + S-adenosyl-L-methionine <=> N-methylnicotinate + S-adenosyl-L-homocysteine
Rhea:RHEA:57029 N-methylnicotinate + FADH2 + O2 => (Z)-2-((N-methylformamido)methylene)-5-hydroxybutanolactone + FAD + H+
Rhea:RHEA:57030 (Z)-2-((N-methylformamido)methylene)-5-hydroxybutanolactone + FAD + H+ => N-methylnicotinate + FADH2 + O2
Rhea:RHEA:57031 N-methylnicotinate + FADH2 + O2 <=> (Z)-2-((N-methylformamido)methylene)-5-hydroxybutanolactone + FAD + H+
BioCyc:NICOTINATE-N-METHYLTRANSFERASE-RXN 2.1.1.7 S-ADENOSYLMETHIONINE + NIACINE --> ADENOSYL-HOMO-CYS + METHYLNICOTINATE
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Organism Source

Taxonomy Source

  1. Abrus precatorius [ncbi taxid: 3816]
  2. Abrusprecatorius [ncbi taxid: ]
  3. Achillea millefolium [ncbi taxid: 13329]
  4. Achillea moschata [ncbi taxid: ]
  5. Aeschyomene indica [ncbi taxid: ]
  6. Ageratina saltillensis [ncbi taxid: 2773124]
  7. Allium cepa [ncbi taxid: 4679]
  8. Anaptychia hypoleuca [ncbi taxid: ]
  9. Apis florea [ncbi taxid: 7463]
  10. Asarum canadense [ncbi taxid: 28498]
  11. Astragalus sinicus [ncbi taxid: 47065]
  12. Astragalus wootonii [ncbi taxid: 457888]
  13. Baphicacanthus cusia [ncbi taxid: ]
  14. Bauhinia candicans [ncbi taxid: ]
  15. Bauhinia forficata [ncbi taxid: 413686]
  16. Benincasa hispida [ncbi taxid: 102211]
  17. Cacospongia scalaris [ncbi taxid: ]
  18. Campanula rotundifolia [ncbi taxid: 239422]
  19. Canavalia ensiformis [ncbi taxid: 3823]
  20. Cannabis sativa [ncbi taxid: 3483]
  21. Capsicum annuum [ncbi taxid: 4072]
  22. Cascarilla magnifolia [ncbi taxid: ]
  23. Chrysanthemoides incana [ncbi taxid: 662739]
  24. Cicer arietinum [ncbi taxid: 3827]
  25. Citropsis articulata [ncbi taxid: 1762906]
  26. Citrullus lanatus [ncbi taxid: 3654]
  27. Coffea arabica [ncbi taxid: 13443]
  28. Coffea arabica L. [ncbi taxid: ]
  29. Coffea spp. [ncbi taxid: ]
  30. Combretum indicum [ncbi taxid: 3956]
  31. Cortex mori radicis praeparata [ncbi taxid: ]
  32. Cortex phellodendri [ncbi taxid: ]
  33. Croton megistocarpus [ncbi taxid: 425923]
  34. Cucumis melo [ncbi taxid: 3656]
  35. Cucurbita moschata [ncbi taxid: 3662]
  36. Deamia testudo [ncbi taxid: 1109431]
  37. Desmodium triflorum [ncbi taxid: ]
  38. Dictamnus dasycarpus [ncbi taxid: 714465]
  39. Ecklonia kurome [ncbi taxid: ]
  40. Esenbeckia hartmanii [ncbi taxid: ]
  41. Euphorbia fidjiana [ncbi taxid: ]
  42. Eusynstyela latericius [ncbi taxid: 2795856]
  43. Fructus malvae [ncbi taxid: ]
  44. Fructus mori [ncbi taxid: ]
  45. Geranium sibiricum [ncbi taxid: 345237]
  46. Glycine max [ncbi taxid: 3847]
  47. Glycine max (L.) Merr. [ncbi taxid: ]
  48. Gnetum parvifolium [ncbi taxid: 33153]
  49. Grewia villosa [ncbi taxid: 493992]
  50. Herba lysimachiae [ncbi taxid: ]
  51. Hibiscus Rosa [ncbi taxid: ]
  52. Hibiscus rosa-sinensis L [ncbi taxid: ]
  53. Hibiscus sabdariffa [ncbi taxid: 183260]
  54. Hibiscus sabdariffa L. [ncbi taxid: ]
  55. Homo sapiens [ncbi taxid: 9606]
  56. Hordeum vulgare [ncbi taxid: 4513]
  57. Lablab purpureus [ncbi taxid: 35936]
  58. Lagerstroemia indica [ncbi taxid: 141186]
  59. Leguminosae [ncbi taxid: ]
  60. Lycopersicon esculentum [ncbi taxid: ]
  61. Lycopersicon esculentum Mill. [ncbi taxid: ]
  62. Macroptilium atropurpureum [ncbi taxid: 90550]
  63. Medicago sativa [ncbi taxid: 3879]
  64. Melilotus officinalis [ncbi taxid: 47083]
  65. Melilotus officinalis Lam. [ncbi taxid: ]
  66. Mirabilis jalapa [ncbi taxid: 3538]
  67. Morus alba [ncbi taxid: 3498]
  68. Ophiocoma dentata [ncbi taxid: ]
  69. Persea kusanoi [ncbi taxid: ]
  70. Phaseolus vulgaris [ncbi taxid: 3885]
  71. Phaseolus vulgaris L. [ncbi taxid: ]
  72. Pinellia pedatisecta [ncbi taxid: 199222]
  73. Pinellia ternata [ncbi taxid: 199225]
  74. Pisum sativum [ncbi taxid: ]
  75. Pseudolmedia laevigata [ncbi taxid: 241915]
  76. Pulicaria arabica [ncbi taxid: 119185]
  77. Quisqualis indica [ncbi taxid: ]
  78. Radix solani melongenae [ncbi taxid: ]
  79. Retama raetam [ncbi taxid: 49837]
  80. Saccharina japonica [ncbi taxid: 88149]
  81. Salta triflora [ncbi taxid: 249117]
  82. Salvia polystachya [ncbi taxid: 268922]
  83. Sarocladium strictum [ncbi taxid: 5046]
  84. Schistocerca gregaria [ncbi taxid: 7010]
  85. Semen benincasae [ncbi taxid: ]
  86. Senecio isatideus [ncbi taxid: ]
  87. Solanum lycopersicum [ncbi taxid: 4081]
  88. Solanum melongena [ncbi taxid: 4111]
  89. Solanum melongena L. [ncbi taxid: ]
  90. Streptomyces chryseus [ncbi taxid: 68186]
  91. Strophanthus sp. [ncbi taxid: ]
  92. Strophanthus spp. [ncbi taxid: ]
  93. Thalictrum simplex [ncbi taxid: 495765]
  94. Ticorea longiflora [ncbi taxid: ]
  95. Trifolium montanum [ncbi taxid: 74522]
  96. Trifolium pratense [ncbi taxid: 57577]
  97. Triglochin maritima [ncbi taxid: 55501]
  98. Trigonella foenum-graceum [ncbi taxid: ]
  99. Trigonella foenum-graecum [ncbi taxid: 78534]
  100. Vigna unguiculata [ncbi taxid: 3917]
  101. Zea mays [ncbi taxid: 4577]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5110 trigonelline biosynthesis
PlantCyc:SOY_PWY-5110 trigonelline biosynthesis
PlantCyc:PLANT_PWY-5110 trigonelline biosynthesis
PlantCyc:AHALLERI_PWY-5110 trigonelline biosynthesis
PlantCyc:CAMELINA_PWY-5110 trigonelline biosynthesis
PlantCyc:CANNUUM_PWY-5110 trigonelline biosynthesis
PlantCyc:CASHEW_PWY-5110 trigonelline biosynthesis
PlantCyc:ACOERULEA_PWY-5110 trigonelline biosynthesis
PlantCyc:ALYRATA_PWY-5110 trigonelline biosynthesis
PlantCyc:BANANA_PWY-5110 trigonelline biosynthesis
PlantCyc:BARLEY_PWY-5110 trigonelline biosynthesis
PlantCyc:CARNATION_PWY-5110 trigonelline biosynthesis
PlantCyc:CASSAVA_PWY-5110 trigonelline biosynthesis
PlantCyc:ASPARAGUS_PWY-5110 trigonelline biosynthesis
PlantCyc:BOLERACEA_CAPITATA_PWY-5110 trigonelline biosynthesis
PlantCyc:BRACHYPODIUM_PWY-5110 trigonelline biosynthesis
PlantCyc:BRAPA_FPSC_PWY-5110 trigonelline biosynthesis
PlantCyc:BREADWHEAT_PWY-5110 trigonelline biosynthesis
PlantCyc:CARIETINUM_ICC4958_PWY-5110 trigonelline biosynthesis
PlantCyc:CCAMPESTRIS_PWY-5110 trigonelline biosynthesis
View All Pathways