1-Methylnicotinamide (YMDB00348)

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 exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on 1-Methylnicotinamide.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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-Methyl nicotinamide
  • 1-Methylnicotinamide cation
  • 3-(Aminocarbonyl)-1-methylpyridinium
  • 3-Carbamoyl-1-methylpyridin-1-ium
  • 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-Adenosylmethionine → 1-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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-5527bd16347dfbb8af1bJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C 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 ID1-Methylnicotinamide
BioCyc IDCPD-396

Enzymes

Protein Details
1. Putative nicotinamide N-methyltransferase
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.