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Identification
YMDB IDYMDB00348
Name1-Methylnicotinamide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1-Methylnicotinamide, also known as trigonellinamide or trigonellamide chloride, belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. 1-Methylnicotinamide is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methylnicotinamide exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 1-Methyl-3-carbamoylpyridinium
  • 1-Methyl-3-carbamoylpyridinium cation
  • 1-Methylnicotinamide
  • 3-Amido-N-methylpyridinium: 1-methyl-3-Pyridinecarboxamide
  • 3-carbamoyl-1-methyl-Pyridinium
  • I-methyl nicotinamide
  • N-1-methylnicotinamide
  • N-Methyl-3-carbamidopyridinium
  • N-Methyl-3-carbamoylpyridinium ion
  • N'-methylnicotinamide
  • N'methylnicotinamide
  • N1-Methylnicotinamide
  • Trigonellinamide
  • 1-Methylnicotinamide cation
  • 3-(Aminocarbonyl)-1-methylpyridinium
  • N(1)-Methylnicotinamide
  • N(1)-Methylnicotinamide chloride
  • N(1)-Methylnicotinamide cyanide
  • N(1)-Methylnicotinamide fluoride
  • N(1)-Methylnicotinamide iodide, 3-(aminocarbonyl-13C)-labeled
  • N(1)-Methylnicotinamide methylsulfate
  • N(1)-Methylnicotinamide perchlorate
  • N(1)-Methylnicotinamide bromide
  • N(1)-Methylnicotinamide iodide
  • N(1)-Methylnicotinamide tetrafluoroborate (1-)
  • Trigonellamide chloride
CAS number3106-60-3
WeightAverage: 137.1592
Monoisotopic: 137.07148792
InChI KeyLDHMAVIPBRSVRG-UHFFFAOYSA-O
InChIInChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1
IUPAC Name3-carbamoyl-1-methylpyridin-1-ium
Traditional IUPAC Name1-methylnicotinamide
Chemical FormulaC7H9N2O
SMILES[H]N([H])C(=O)C1=C([H])[N+](=C([H])C([H])=C1[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
Alternative Parents
Substituents
  • Nicotinamide
  • N-methylpyridinium
  • Pyridinium
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility855 mg/mL [Chloride salt, HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP-3.7ALOGPS
logP-4.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)12.24ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.97 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.13 m³·mol⁻¹ChemAxon
Polarizability14.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
SMPDB ReactionsNot Available
KEGG Reactions
Niacinamide + S-Adenosylmethionine1-Methylnicotinamide + S-Adenosylhomocysteine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-5900000000-5a5fd45836c387d92371JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-c99e0e70357eb6fa74bbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-93675f2b9efbaba4d471JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fvl-9000000000-b1e908db583e418c2545JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-0900000000-9c3104d60f21f6375b0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-e500f262d42edb9b3ad7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9200000000-496b2cf62a07bea4f746JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-002f-9000000000-a17b3a63979577f6fa9eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00ou-9000000000-46a856cd097a7a14dc90JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000l-6900000000-360fb882a925f7e9edc9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0006-9000000000-babd4e89db309a5c74cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-9c3104d60f21f6375b0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-e500f262d42edb9b3ad7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9200000000-052c844f974abba065ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-002f-9000000000-a17b3a63979577f6fa9eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00ou-9000000000-2fe6c195129f32a62a3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000l-6900000000-360fb882a925f7e9edc9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9000000000-babd4e89db309a5c74cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-08a578fa81c8d41a4fe6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-d889aade6d1014ffb393JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-1900000000-8052aba6067c868e594fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9500000000-579bc8310420ec3d8786JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-141e3a418b748abf9e1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-33499eeb5abff5a8b53bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e45f804a013c97310f00JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Anderson, R. M., Bitterman, K. J., Wood, J. G., Medvedik, O., Sinclair, D. A. (2003). "Nicotinamide and PNC1 govern lifespan extension by calorie restriction in Saccharomyces cerevisiae." Nature 423:181-185.12736687
Synthesis Reference:Nelis, Hans J. C. F.; Airy, Subhash C.; Sinsheimer, J. E. Comparison of the alkylation of nicotinamide and 4-(p-nitrobenzyl)pyridine for the determination of aliphatic epoxides. Analytical Chemistry (1982), 54(2), 213-16.
External Links:
ResourceLink
CHEBI ID16797
HMDB IDHMDB00699
Pubchem Compound ID457
Kegg IDC02918
ChemSpider ID73580
FOODB IDFDB022188
Wikipedia IDNot Available
BioCyc IDCPD-396

Enzymes

General function:
Involved in nicotinamide N-methyltransferase activity
Specific function:
Putative nicotinamide N-methyltransferase involved in rDNA silencing and in lifespan determination
Gene Name:
NNT1
Uniprot ID:
Q05874
Molecular weight:
29632.30078
Reactions
S-adenosyl-L-methionine + nicotinamide → S-adenosyl-L-homocysteine + 1-methylnicotinamide.